DEF 14A of CarGurus, Inc., Apr 26, 2024

DEF 14A of CarGurus, Inc.

Filed Apr 26, 2024 · FY20230000950170-24-049120

Open on EDGAR

  1. A. Proposal 1 – Election of Class I Directors

    A. Proposal 1 – Election of Class I Directors The three nominees for Class I director receiving the highest number of votes FOR election will be elected as director. This is called a plurality. Proposal 1 is a non-discretionary matter. Therefore, if your shares are held in street name and you do not instruct your broker or other nominee how to vote your shares on Proposal 1, your broker or other nominee cannot vote your shares on Proposal 1. Shares held in street name by brokers or other nominees who indicate on their proxies that they do not have authority to vote the shares on Proposal 1 will not be counted as votes FOR or WITHHELD from any nominee and will be treated as “broker non-votes.” Broker non-votes will have no effect on the voting on Proposal 1. With respect to Proposal 1, you may: • vote FOR all nominees; • vote FOR any nominee(s) and WITHHOLD your vote from the other nominee(s); or • WITHHOLD your vote from all nominees. Votes that are withheld will not be included in the vote tally for Proposal 1 and will not affect the results of the vote.

  2. BOARD OF DIRECTORS

    BOARD OF DIRECTORS

  3. Information Regarding Directors and Director Nominees

    Information Regarding Directors and Director Nominees Our Fourth Amended and Restated Certificate of Incorporation provides for the classification of our Board of Directors into three classes, with the terms of service of the three classes staggered so that the term of one class expires each year. As a result, only one class of our directors is elected at each annual meeting of stockholders, with the other classes continuing for the remainder of their respective three-year terms. Our Board of Directors currently consists of seven directors. The members of the classes are divided as follows: • the Class I directors are Lori Hickok, Greg Schwartz, and Jason Trevisan, each with a term expiring at the Annual Meeting; • the Class II directors are Steven Conine and Stephen Kaufer, each with a term expiring at the annual meeting of stockholders to be held in 2025; and • the Class III directors are Manik Gupta and Langley Steinert, each with a term expiring at the annual meeting of stockholders to be held in 2026. At each annual meeting of stockholders, directors are elected for a full term of three years to continue or succeed those directors whose terms are expiring. Our Board of Directors has nominated Ms. Hickok and Messrs. Schwartz and Trevisan for election at the Annual Meeting as Class I directors, to serve for a term expiring at the annual meeting of stockholders to be held in 2027, or until their respective successors have been duly elected and qualified. Each of Ms. Hickok and Messrs. Schwartz and Trevisan is presently a director and has indicated a willingness to continue to serve as a director, if elected. Unless otherwise instructed, proxies will be voted for Ms. Hickok and Messrs. Schwartz and Trevisan. In the event that any of Ms. Hickok or Messrs. Schwartz and Trevisan is not a candidate or is unable to serve as a director at the time of the election (which is not currently expected), your proxy will be voted for any nominee who is designated by our Board of Directors to fill the vacancy.

  4. Director Qualifications

    Director Qualifications The following table and biographical descriptions provide information as of April 1, 2024, relating to each director and the director nominees, including each director’s age and period of service as a member of our Board of Directors; Board of Directors committee memberships; business experience during the past five years, including directorships at other public companies; and the other experience, qualifications, attributes, or skills that led our Board of Directors to conclude such person should serve as a director of CarGurus:

  5. Director Qualifications

    | | BOARD OF DIRECTORS | | | | | | | | | Steven Conine | Manik Gupta | Lori Hickok | Stephen Kaufer | Greg Schwartz | Langley Steinert | Jason Trevisan | | Current Occupation | Co-Founder at Wayfair Inc. | Corporate VP, Microsoft Teams at Microsoft Corporation | N/A | Co-Founder and Chief Executive Officer at Give Freely, LLC | CEO, Co-Founder and Chairman of the Board at Tomo Networks, Inc. | Founder and Executive Chair at CarGurus, Inc. | CEO at CarGurus, Inc. | | Skills & Experience | | | | | | | | | Independent | ✓ | ✓ | ✓ | ✓ | ✓ | | | | Additional Board of Directors Experience | ✓ | ✓ | ✓ | ✓ | ✓ | ✓ | ✓ | | Executive Leadership | ✓ | ✓ | ✓ | ✓ | ✓ | ✓ | ✓ | | Online Marketplace Industry | ✓ | ✓ | ✓ | ✓ | ✓ | ✓ | ✓ | | Innovation & Technology | ✓ | ✓ | ✓ | ✓ | ✓ | ✓ | ✓ | | Strategic Planning | ✓ | ✓ | ✓ | ✓ | ✓ | ✓ | ✓ | | Corporate Governance | ✓ | ✓ | ✓ | ✓ | ✓ | ✓ | ✓ | | Financial Reporting; Accounting; Taxation | | | ✓ | | | | ✓ | | Internet & Media | ✓ | ✓ | ✓ | ✓ | ✓ | ✓ | ✓ | | Finance & Investment Management | ✓ | | ✓ | ✓ | ✓ | ✓ | ✓ | | Oversight of Data Privacy & Cybersecurity | ✓ | ✓ | ✓ | ✓ | ✓ | ✓ | ✓ | | Human Capital Management | ✓ | ✓ | ✓ | ✓ | ✓ | ✓ | ✓ | | Audit Committee Financial Expert | | | ✓ | | | | | | Additional Information | | | | | | | | | Board Class/ Term Ends | Class II 2025 | Class III 2026 | Class I 2027* | Class II 2025 | Class I 2027* | Class III 2026 | Class I 2027* | | Age | 51 | 47 | 60 | 61 | 51 | 60 | 49 | | Tenure | 5 | >1 | 5 | 16 | 6 | 18 | 3 | | Current Other Public Company Directorships | Wayfair Inc. (Co-Chairman) | None | 1stDibs.com, Inc. | None | None | None | None |

  6. Director Qualifications

    | Director Nominee | | Continuing Director | | * If elected at the Annual Meeting | | The ✓ indicates that the item is a specific experience, qualification, attribute, or skill that the director or director nominee brings to our Board of Directors. The lack of ✓ for a particular item does not mean that the director or director nominee does not possess that experience, qualification, attribute, or skill. We expect each director to be knowledgeable in several of these areas. | | For the Nasdaq Board Diversity Matrix, see “Board Diversity Matrix” on page 17. |

  7. Director Qualifications

    | BOARD OF DIRECTORS | | | Class I Directors to be Elected at the Annual Meeting (term expiring 2027) | | | Lori Hickok Director Since: August 2018 Age: 60 Committees Audit – Chair Other Public Company Boards 1stdibs.com, Inc. | Key Skills and Experience Independent Additional Board of Directors Experience Executive Leadership Online Marketplace Industry Innovation & Technology Strategic Planning Corporate Governance Financial Reporting; Accounting; Taxation Internet & Media Finance & Investment Management Oversight of Data Privacy & Cybersecurity Human Capital Management Audit Committee Financial Expert | | Ms. Hickok has served as a member of our Board of Directors since August 2018. Ms. Hickok was the Executive Vice President, Chief Financial and Development Officer for Scripps Networks Interactive, Inc. (Scripps), a leading developer of engaging lifestyle content in the home, food, and travel categories for television, the internet, and emerging platforms, from July 2017 until April 2018. Prior to that, she served as Scripps’s Executive Vice President, Chief Financial Officer from March 2015 until June 2017, and Executive Vice President, Finance from July 2008 until February 2015. Prior to Scripps’s spin off from The E.W. Scripps Company (E.W. Scripps) on July 1, 2008, Ms. Hickok served for six years as E.W. Scripps’s Vice President and Corporate Controller. She first joined E.W. Scripps in 1988 as a financial analyst in the corporate finance department, and held positions as the Chief Analyst for Corporate Development, New Media Operations Controller, and Divisional Controller for E.W. Scripps’s former cable television systems division, which merged in 1996 with Comcast Corporation. Ms. Hickok serves on the board of directors of 1stdibs.com, Inc., an online marketplace for luxury design products, a position she has held since June 2021. She also serves on the board of directors of the Second Harvest Food Bank of East Tennessee. A retired Certified Public Accountant, Ms. Hickok received a Bachelor of Science degree in Accounting & Finance from Miami University. We believe Ms. Hickok is qualified to serve as a member of our Board of Directors because of her extensive finance and accounting background, including as an executive officer at a public company, and her experience as an executive in the media and internet industries. | |

  8. Director Qualifications

    | Greg Schwartz Director Since: March 2018 Age: 51 Committees Audit | Key Skills and Experience Independent Additional Board of Directors Experience Executive Leadership Online Marketplace Industry Innovation & Technology Strategic Planning Corporate Governance Internet & Media Finance & Investment Management Oversight of Data Privacy & Cybersecurity Human Capital Management | | Mr. Schwartz has served as a member of our Board of Directors since March 2018. Mr. Schwartz is the co-founder of Tomo Networks, Inc. (Tomo), an internet-based mortgage and real estate company, and has served as Tomo’s Chief Executive Officer and Chairman of its Board of Directors since June 2020. Prior to founding and joining Tomo, from June 2018 to December 2019, Mr. Schwartz served as the President Media & Marketplaces of Zillow Group, Inc. (Zillow), an online real estate marketplace, prior to which he served as Zillow’s Chief Business Officer from August 2015 to June 2018, Chief Revenue Officer from September 2010 to August 2015, and Vice President of Sales from March 2007 to September 2010. Prior to joining Zillow, Mr. Schwartz was Vice President of Advertising Sales at CNNMoney.com, a financial media company, from July 2005 to March 2007. From August 2001 to July 2005 Mr. Schwartz served as National Accounts Director for the Automotive and Finance Properties of Yahoo!, Inc., an online search company. Mr. Schwartz held various positions at DoubleClick, Inc., an online advertising company, from 1998 to 2000, including Director of Business Development. Mr. Schwartz holds a Bachelor of Arts degree in Government from Hamilton College. We believe Mr. Schwartz is qualified to serve as a member of our Board of Directors because of his extensive experience as an executive in the online marketplace industry and as an executive officer at a public company. | | | Jason Trevisan Director Since: January 2021 Age: 49 | Key Skills and Experience Additional Board of Directors Experience Executive Leadership Online Marketplace Industry Innovation & Technology Strategic Planning Corporate Governance Financial Reporting; Accounting; Taxation Internet & Media Finance & Investment Management Oversight of Data Privacy & Cybersecurity Human Capital Management | | Mr. Trevisan has served as our Chief Executive Officer and a member of our Board of Directors since January 2021. Prior to such appointments, he served as our Chief Financial Officer from September 2015 to January 2021, as our Treasurer from July 2016 to January 2021, and as our President, International from January 2020 to January 2021. He served as our interim Principal Financial Officer and Treasurer from October 2022 to December 2023. Prior to joining CarGurus, Mr. Trevisan was a General Partner with Polaris Partners (Polaris), a venture capital firm, from September 2003 to August 2015. While at Polaris, Mr. Trevisan led investments in and served as a director of numerous consumer internet and software companies including LegalZoom, PartsSource, Shoedazzle, and The Roberts Group. Prior to joining Polaris, from September 1999 to June 2001, Mr. Trevisan held management roles in analytics and client services at aQuantive, a digital marketing service and technology company, which was acquired by Microsoft Corporation in 2007. Earlier in his career, from July 1996 to August 1999, he served as a consultant with Bain & Company, a management consulting company. Mr. Trevisan received a Master of Business Administration degree from the Tuck School of Business at Dartmouth College and a Bachelor of Arts degree from Duke University. We believe Mr. Trevisan is qualified to serve as a member of our Board of Directors because of his extensive experience in the online marketplace industry and his deep understanding of our business as it has evolved over time. | |

  9. Director Qualifications

    | Class II Directors (term expiring 2025) | | | Steven Conine Director Since: June 2018 Age: 51 Committees Compensation Other Public Company Boards Wayfair Inc. | Key Skills and Experience Independent Additional Board of Directors Experience Executive Leadership Online Marketplace Industry Innovation & Technology Strategic Planning Corporate Governance Internet & Media Finance & Investment Management Oversight of Data Privacy & Cybersecurity Human Capital Management | | Mr. Conine has served as a member of our Board of Directors since June 2018. Mr. Conine is the co-founder of Wayfair Inc. (Wayfair) and has served as a director of Wayfair since 2002. He previously served as Wayfair’s Chief Technology Officer from 2002 until 2015. Prior to founding Wayfair, Mr. Conine served as Chief Technology Officer for Simplify Mobile Corporation, an enterprise software company he co-founded in 2001, Chief Operating Officer for the London office of iXL Enterprises, Inc. from 1999 to 2000, and Chief Technology Officer of Spinners Incorporated, an IT consulting company he co-founded, from 1995 to 1998. Mr. Conine received a Bachelor of Science degree from Cornell University. We believe Mr. Conine is qualified to serve as a member of our Board of Directors because of his extensive experience as a co-founder, director, and executive in technology and internet marketplaces, as well as serving as an executive and member of the board of directors at a public company. | | | Stephen Kaufer Director Since: June 2007 Age: 61 Committees Compensation – Chair Former Public Company Boards TripAdvisor, Inc. | Key Skills and Experience Independent Additional Board of Directors Experience Executive Leadership Online Marketplace Industry Innovation & Technology Strategic Planning Corporate Governance Internet & Media Finance & Investment Management Oversight of Data Privacy & Cybersecurity Human Capital Management | | Mr. Kaufer has served as a member of our Board of Directors since June 2007. He is Co-founder and Chief Executive Officer of Give Freely, LLC., a mission driven company that helps users save money when shopping online while also generating donations to the users’ favorite charity. Prior to that, he co-founded TripAdvisor, Inc. (TripAdvisor), an online marketplace for travel-related content, in February 2000 and served as the President and Chief Executive Officer of TripAdvisor until July 2022. Mr. Kaufer was a director of TripAdvisor since the completion of its spin-off from Expedia, Inc. in December 2011 through July 2022. Prior to co-founding TripAdvisor, Mr. Kaufer served as President of CDS, Inc., an independent software vendor specializing in programming and testing tools. Prior to joining CDS, Inc., Mr. Kaufer co-founded CenterLine Software in 1985 and served as its Vice President of Engineering until 1998. Mr. Kaufer has served on the boards of several privately held companies, including LiveData, Inc. and GlassDoor, Inc., and currently serves as a member of the board of directors at the Neuroendocrine Tumor Research Foundation. Mr. Kaufer holds a Bachelor of Arts degree from Harvard University. We believe Mr. Kaufer is qualified to serve as a member of our Board of Directors because of his extensive experience as an executive in the online marketplace industry. Mr. Kaufer also possesses strategic and governance skills gained through his service as an executive and member of the board of directors of a public company and with several private companies. | |

  10. Director Qualifications

    | Class III Directors (term expiring 2026) | | | Manik Gupta Director Since: July 2023 Age: 47 Committees Audit Former Public Company Boards Gores Technology Partners, Inc. | Key Skills and Experience Independent Additional Board of Directors Experience Executive Leadership Online Marketplace Industry Innovation & Technology Strategic Planning Corporate Governance Internet & Media Oversight of Data Privacy & Cybersecurity Human Capital Management | | Mr. Gupta has served as a member of our Board of Directors since July 2023. He has served as the Corporate Vice President, Microsoft Teams at Microsoft Corporation, a technology corporation, since November 2022 and served as Corporate Vice President, Microsoft Teams, Consumer Communications and Communities at Microsoft from August 2021 to November 2022. From January 2020 onwards Mr. Gupta has served as an advisor and investor to startups based in the U.S. and India. Mr. Gupta served as the Chief Product Officer at Uber Technologies, Inc. (Uber), a transportation marketplace technology company, from November 2018 to December 2019. From March 2018 to November 2018 Mr. Gupta served as Vice President, Product Management, Maps and Marketplace at Uber and from September 2017 to March 2018 he served as Senior Director, Product, Maps and Marketplace at Uber. Mr. Gupta joined Uber in November 2015 as Director, Product Management, Maps. From December 2014 to November 2015 Mr. Gupta served as Director, Product Management, Google Maps at Google Inc., a technology company. From June 2008 to December 2014 Mr. Gupta served in a variety of product leadership roles within Google Maps across Asia and the U.S. Mr. Gupta was a Project Manager and Solutions Architect at Hewlett Packard, a multinational enterprise information technology company, from June 2003 to April 2007. Mr. Gupta co-founded BuyItTogether.com, an e-commerce startup, where he served as the founding head of engineering and product and held various technical leadership roles from June 1999 to April 2003. Mr. Gupta previously served on the board of directors of Gores Technology Partners, Inc., a capital market company, from February 2021 to December 2022 where he also served on the audit committee. Mr. Gupta holds a Master of Business Administration, Analytical Finance and Strategic Marketing, degree from the Indian School of Business, Hyderabad, India and a Bachelor of Applied Science in Computer Engineering degree from the Nanyang Technological University, Singapore. We believe Mr. Gupta is qualified to serve as a member of our Board of Directors because of his significant public company experience and his deep knowledge of the technology industry. | | | Langley Steinert Director Since: March 2006 Chair Since: September 2017 Executive Chair Since: January 2021 Age: 59 | Key Skills and Experience Additional Board of Directors Experience Executive Leadership Online Marketplace Industry Innovation & Technology Strategic Planning Corporate Governance Internet & Media Finance & Investment Management Oversight of Data Privacy & Cybersecurity Human Capital Management | | Mr. Steinert is our founder and has served as our Executive Chair since January 2021 and as a member of our Board of Directors since our founding. Mr. Steinert has served as our Chair since September 2017, and served as our Chief Executive Officer from our founding to January 2021 and as our President from June 2015 to February 2019. Mr. Steinert is also the co-founder of ApartmentAdvisor, Inc., an apartment rental marketplace, and has served as Chairman of its board of directors since October 2020. Mr. Steinert also serves as a board member at the Tuck School of Business at Dartmouth College. From February 2000 through February 2006 Mr. Steinert was Chairman and co-founder of TripAdvisor. Mr. Steinert holds a Master of Business Administration degree from the Tuck School of Business at Dartmouth College and a Bachelor of Arts degree from Georgetown University. | |

  11. Director Qualifications

    | We believe Mr. Steinert is qualified to serve as a member of our Board of Directors because of his extensive experience in the online marketplace industry. As our founder and Executive Chair, we also value his deep understanding of our business as it has evolved over time. |

  12. Director Qualifications

    There are no family relationships among any of our directors or executive officers.

  13. EXECUTIVE AND DIRECTOR COMPENSATION AND RELATED MATTERS

    EXECUTIVE AND DIRECTOR COMPENSATION AND RELATED MATTERS

  14. Compensation Philosophy and Objectives

    Compensation Philosophy and Objectives We believe in providing a competitive total compensation package to our executive officers, including our Named Executive Officers, through a combination of annual base salary, annual cash incentive award opportunities, long-term incentive compensation opportunities in the form of equity awards, and broad-based health and welfare benefit plans. Our executive compensation program is designed to achieve the following objectives: Attract, motivate, and retain executive officers of outstanding ability and potential; reward the achievement of key performance measures; and ensure that executive compensation is meaningfully related to the creation of stockholder value. We believe that our executive compensation program should generally include short-term and long-term elements, including cash and equity compensation, and should reward consistent performance that meets or exceeds expectations. We evaluate the compensation provided to our executive officers to ensure it remains competitive relative to compensation paid by companies of similar size and geographic location operating in our industry, taking into account our relative performance, our financial and strategic objectives, and the performance of each individual executive officer.

  15. Compensation-Setting Process

    Compensation-Setting Process Role of the Compensation Committee The Compensation Committee is responsible for reviewing and approving the compensation of our executive officers, including our Named Executive Officers, subject to any approval of our Board of Directors that the Compensation Committee determines to be desirable or is required by applicable law or Nasdaq listing standards. Specifically, the Compensation Committee oversees our compensation and benefit plans and policies, administers our equity compensation plans, and reviews and approves (or makes recommendations to our Board of Directors regarding) the compensation of our executive officers. Role of our Chief Executive Officer Our Chief Executive Officer evaluates at least annually the performance of each of our executive officers and makes recommendations to the Compensation Committee with respect to annual base salary adjustments, target annual cash incentive award opportunities, actual award payments, and equity awards for each such executive officer. While the Compensation Committee takes these recommendations into consideration in its deliberations, it exercises its own independent judgment in approving the executive compensation of our executive officers. Our Chief Executive Officer does not make recommendations regarding his own compensation, and he does not participate in any discussions regarding his own compensation. Role of Compensation Consultant The Compensation Committee has the authority under the Compensation Committee Charter to engage the services of a compensation consultant to assist it in carrying out its responsibilities. In each of the past four years, the Compensation Committee formally retained Compensia to assist it in developing and overseeing the Company’s executive compensation program and non-employee director compensation program and practices and to provide an analysis of competitive market data. To assist the Compensation Committee with its consideration of 2023 executive compensation decisions, Compensia provided the Compensation Committee with compensation data and an updated competitive market analysis for similarly situated executive officers at our peer group companies. Similarly, to assist the Compensation Committee with its consideration of 2023 non-employee director compensation program, Compensia provided the Compensation Committee with compensation data and an updated competitive market analysis for similarly situated directors at our peer group companies. Compensia also provided consulting services to the Company on an ad hoc basis regarding equity compensation matters and assisted with review of the “Compensation Discussion and Analysis” section of the Company’s proxy statement for the 2023 annual meeting of stockholders. Compensia maintains a policy that is specifically designed to prevent any conflicts of interest. In addition, the Compensation Committee has assessed the independence of Compensia taking into account, among other things, the factors set forth in Exchange Act Rule 10C-1 and the applicable Nasdaq listing standards and concluded that no conflict of interest has arisen with respect to the work that Compensia performs for the Compensation Committee. Competitive Positioning The Compensation Committee has established and maintains a compensation peer group consisting of publicly traded companies, which the Compensation Committee reviews and modifies from time to time to consist of the following set of peers for purposes of reviewing and considering our executive officers’ 2023 base salaries, target annual cash incentive award opportunities, and annual equity awards. The Compensation Committee believes that this compensation peer group accurately reflected the Company’s growth, opportunities, and current market positioning. This group consisted of technology companies that the Compensation Committee determined operate within our industry, compete with us for talent, or are located in the same general geographic area. Other factors considered include comparable revenues, market capitalization, and projected revenue growth. In connection with its review, the Compensation Committee removed seven peer companies for 2023 – Bottomline Technologies, Inc., Cerence, Inc., EverQuote, Inc., HubSpot, Inc., LendingTree, Inc., Wayfair Inc., and Yext, Inc. – because they either were acquired or fell outside of the comparable revenue and market capitalization ranges. The following companies were used by the Compensation Committee during 2023 as our compensation peer group:

  16. Compensation-Setting Process

    *Represents new addition to peer group. The Compensation Committee considered both Compensia’s competitive market analysis and compensation data drawn internally from publicly-available proxy statements and industry-specific survey data for this compensation peer group as reference points for its 2023 executive compensation decisions. While the Compensation Committee takes into account peer company compensation practices, the Compensation Committee uses this information as one of many factors in its deliberations on compensation matters and does not set compensation levels to meet specific percentiles. The Compensation Committee reviews the analyses prepared internally and by Compensia based on the compensation data drawn from a compensation peer group to develop a subjective representation of the “competitive market” with respect to current executive compensation levels and related policies and practices. The Compensation Committee then evaluates how our pay practices and the compensation levels of our executive officers compare to the competitive market. As part of this evaluation, the Compensation Committee also reviews the performance measures and performance goals generally used within the competitive market to reward performance. Management and the Compensation Committee strive to incorporate flexibility into our executive compensation program and the assessment process to respond to and adjust for the evolving business environment and the value delivered by our executive officers, including our Named Executive Officers.

  17. Elements of Executive Compensation

    These annual base salaries were effective as of April 1, 2023, except for Ms. Palazzo, who commenced employment with the Company on December 4, 2023, and Mr. Hallowell, who commenced employment with the Company on October 16, 2023. (2) The Compensation Committee awarded base merit salary increases for 2023 to certain of our Named Executive Officers after its annual review of our executive compensation program. Mr. Quinn received a 16.9% increase based on a market adjustment. (3) At Mr. Steinert’s request, to demonstrate his confidence in the Company and to continue to align his interests with those of our stockholders, the Compensation Committee maintained Mr. Steinert’s annual base salary of $10,000 for 2023. The actual base salaries paid to our Named Executive Officers in 2023 and the amounts of the transition awards, as discussed above, are set forth in the “Summary Compensation Table” below. Cash Incentive Awards In 2023 we provided our executive officers, including our Named Executive Officers other than Mr. Steinert, with the opportunity to earn cash incentive awards to encourage the achievement of our corporate performance objectives and to reward those individuals who significantly impact our corporate results based on the objectives set forth in our annual operating plan. The Compensation Committee determines and approves cash incentive award decisions for our executive officers including whether to exercise discretion to modify the calculated payouts. In February 2018 the Compensation Committee approved the CarGurus, Inc. Annual Incentive Plan (the Annual Incentive Plan), providing an opportunity for certain of our salaried employees, including our Named Executive Officers, to earn annual cash incentive awards, as described below. Pursuant to the Annual Incentive Plan, each participant is eligible to receive a cash incentive award for the relevant year based on our level of achievement of one or more pre-established strategic objectives and financial performance goals and the participant’s individual performance goals, if applicable, during such year. The amount actually paid to a participant may be more or less than the participant’s target award opportunity, depending on the extent to which applicable performance goals were satisfied. Participants, including our Named Executive Officers, will not receive a payout for any performance measure that fails to achieve target level criteria. In February 2023 the Compensation Committee established the 2023 performance measures and related target performance levels, as well as the corresponding weighting for each measure, for our executive officers, including our Named Executive Officers other than Mr. Steinert, under the Annual Incentive Plan (the 2023 Annual Incentive Plan). Target Cash Incentive Award Opportunities Under the Annual Incentive Plan, each participant’s actual annual cash incentive award is calculated, in part, by reference to a target annual cash incentive award opportunity based on either a percentage of the participant’s annual base salary for the year or a specified dollar amount, in the case of our executive officers, as determined by the Compensation Committee. To set the target annual cash incentive award opportunities of our Named Executive Officers for 2023, the Compensation Committee considered Compensia’s competitive market analysis, including a comparison of our Named Executive Officers’ target cash incentive award opportunities to those executives holding comparable positions at the companies in our compensation peer group as well as its own assessment of our 2022 performance and the other factors described in “Elements of Executive Compensation – Base Salary” above. The target annual cash incentive award opportunities of our Named Executive Officers for 2023 was as follows:

  18. Elements of Executive Compensation

    | Named Executive Officer | Target Cash Incentive Award Opportunity | Target Cash Incentive Award Opportunity (as a percentage of annual base salary) | Percentage Change from 2022 Target Cash Incentive Award Opportunity(1) | | Mr. Trevisan | $525,000 | 93% | 5.0% | | Ms. Palazzo(2) | $250,000 | 64% | N/A | | Mr. Steinert(3) | — | — | — | | Mr. Hallowell(4) | $325,000 | 76% | N/A | | Mr. Quinn(5) | $225,000 | 59% | 12.5% |

  19. Elements of Executive Compensation

    The Compensation Committee determined our Named Executive Officers target annual incentive award opportunities for 2023 as a part of its annual practice of conducting a market review of peer group executive pay practices. The Compensation Committee considered that higher target cash incentive award opportunities means more at-risk compensation. The target cash incentive awards for each of Ms. Palazzo and Mr. Hallowell were determined following the Compensation Committee’s evaluation of peer group data on others in similar positions (2) Ms. Palazzo was appointed as our Chief Financial Officer effective December 4, 2023. Amount represents the target annual cash incentive opportunity for Ms. Palazzo. Based on her hire date, Ms. Palazzo was eligible for a prorated payout under the 2023 Annual Incentive Plan. (3) At Mr. Steinert’s request, to demonstrate his confidence in the Company and to continue to align his interests with those of our stockholders, the Compensation Committee continued to consider Mr. Steinert ineligible to receive an annual cash incentive award for his 2023 performance. (4) Mr. Hallowell was appointed as the Chief Executive Officer, CarOffer on December 1, 2023, and served as our Head of Industry Transformation from October 16, 2023 to December 1, 2023. Amount represents the target annual cash incentive opportunity for Mr. Hallowell. Based on his hire date, Mr. Hallowell was eligible for a prorated payout under the 2023 Annual Incentive Plan. (5) Mr. Quinn received a 12.5% increase based on a market adjustment. The amount actually paid to a participant could be more or less than the participant’s target annual cash incentive award opportunity, depending on the extent to which applicable performance goals were satisfied. Consistent with prior years, for 2023 the Compensation Committee determined that annual cash incentive awards for such year would be paid to our executive officers in two installments rather than in one lump sum, whereby (i) 40% of each executive officer’s target annual cash incentive award opportunity would be made in an initial lump sum payment following completion of our second fiscal quarter of 2023 (the First Half 2023 Payment) and (ii) the remainder of each executive officer’s full-year annual cash incentive award would be paid in a lump sum payment following the end of 2023 based on the Compensation Committee’s evaluation of our actual performance for the full year as measured against the achievement of the pre-established corporate and individual performance goals described below (the Second Half 2023 Payment). The Compensation Committee has traditionally determined that annual cash incentive awards would be paid in two installments to align with the incentive plan for our broader employee base, which awards a portion of employees’ bonuses mid-year for retention purposes. Corporate Strategic Objectives Our Board of Directors approves annual strategic objectives for the Company, which are formulated by management to reflect the Company’s goals for that year, and the Compensation Committee utilizes these initiatives as the business performance goals upon which annual cash incentive award payments are based. The 2023 strategic objectives involved optimizing marketplace growth, driving customer centricity, enabling our strategic transition to digital transactions, and activities related to employee engagement and enablement. Each of these initiative categories involved one or more quantitative and qualitative metrics as established by our management that had to be successfully completed for that portion of the initiative to be considered achieved. For 2023 the threshold, target, and maximum performance levels for the strategic objectives actually achieved and the corresponding payout levels on a sliding scale under the 2023 Annual Incentive Plan were established as follows:

  20. Elements of Executive Compensation

    | Performance Measure | Performance Level | Payout Percentage | | Strategic Objectives | Threshold (33%)(1) | 0% | | | Target (70%) | 100% | | | Maximum (100%) | 150% |

  21. Elements of Executive Compensation

    There is no payout under the strategic objective performance measure for performance that does not meet the target level criteria. Corporate Financial Performance Goals The Compensation Committee selected gross profit and adjusted earnings before interest and taxes (EBIT), a non-GAAP financial measure, as the financial performance measurements for 2023. The threshold, target, and maximum performance levels for gross profit and adjusted EBIT, as set forth in our annual operating plan, and the corresponding payout levels on a sliding scale for achievement of such measures under the 2023 Annual Incentive Plan, were established as follows:

  22. Elements of Executive Compensation

    | Performance Measure | Performance Level | Payout Percentage | | Gross Profit | Threshold (95%)(1) | 0% | | | Target (100%) | 100% | | | Maximum (105%) | 200% | | Adjusted EBIT | Threshold (90%)(1) | 0% | | | Target (100%) | 100% | | | Maximum (110%) | 150% |

  23. Elements of Executive Compensation

    (1) There is no payout under the gross profit or adjusted EBIT performance measure for performance that does not meet the target level criteria. We calculate adjusted EBIT as GAAP consolidated net income, adjusted to exclude: depreciation and amortization, impairment of long-lived assets, stock-based compensation expense, transaction-related expenses, other income, net, the provision for income taxes, and net income attributable to redeemable noncontrolling interest. The Compensation Committee determined that, for purposes of the 2023 Annual Incentive Plan, these corporate financial measures were the most appropriate performance measures to use in determining annual cash incentive awards because, in its view, they were the best indicators of our successful execution of our annual operating plan. Thus, the target performance levels for these corporate performance goals were the minimum performance levels that had to be achieved before participants could earn any annual cash incentive awards relating to this measure. If the target performance goal for a particular measure was not achieved, then no award payments would be made under the 2023 Annual Incentive Plan with respect to such measure. The above-referenced performance objectives should not be interpreted as a prediction of how we will perform in future periods. As described above, the purpose of these objectives was to establish a method for determining the payment of annual cash incentive compensation in 2023. You are cautioned not to rely on these performance goals as a prediction of our future performance. Individual Performance Goals For purposes of the 2023 Annual Incentive Plan, the Compensation Committee authorized (i) Mr. Steinert to establish one or more individual performance goals for Mr. Trevisan’s annual cash incentive award opportunity and (ii) Mr. Trevisan to establish one or more individual performance goals for each executive officer, including each Named Executive Officer other than Mr. Steinert and himself, as part of the executive officer’s annual cash incentive award opportunity. As part of our annual performance evaluation process, Messrs. Steinert and Trevisan, after consultation with Mr. Trevisan or each other executive officer, respectively, established the executive officer’s performance goals for the year. These performance goals were not intended to be formulaic, but rather to serve as the framework upon which Messrs. Steinert and Trevisan could evaluate the applicable executive officer’s overall performance. Such performance goals were established with reference to each individual executive officer’s position or function within the Company and included operational metrics that could reflect corporate or departmental goals or could include specific operational goals with respect to the executive officer’s area of responsibility. These performance goals also included the demonstration of leadership and effective decision-making, effective communication, promotion of our strategic objectives and values, and commitment to excellence and work ethic and could include more specific objectives for the executive officer, such as the successful completion of major projects and organization capability building. For our executive officers other than Mr. Steinert in 2023 the Compensation Committee established performance ratings for the individual performance goals achieved and the corresponding payout levels under the 2023 Annual Incentive Plan as follows:

  24. Elements of Executive Compensation

    | Performance Measure | Performance Rating | Payout Percentage | | Individual Performance Goals | Partially Met Expectations | 50 – 95% | | | Met Expectations | 95 – 115% | | | Exceeded Expectations | 115 – 130% | | | Far Exceeded Expectations | 130 – 150% |

  25. Elements of Executive Compensation

    | Performance Measure | Weighting | | Strategic Objectives | 25% | | Gross Profit | 30% | | Adjusted EBIT | 15% | | Individual Performance Goals | 30% |

  26. Elements of Executive Compensation

    | Named Executive Officer | Actual Cash Incentive Award for First Half of 2023 Payment (40% of Annual Target Award) | | Mr. Trevisan | $205,028 | | Ms. Palazzo(1) | N/A | | Mr. Steinert(2) | — | | Mr. Hallowell(3) | N/A | | Mr. Quinn | $85,028 |

  27. Elements of Executive Compensation

    (1) Ms. Palazzo was appointed as our Chief Financial Officer effective December 4, 2023. (2) At Mr. Steinert’s request, to demonstrate his confidence in the Company and to continue to align his interests with those of our stockholders, the Compensation Committee continued to consider Mr. Steinert ineligible to receive an annual cash incentive award for his 2023 performance. (3) Mr. Hallowell was appointed as the Chief Executive Officer, CarOffer on December 1, 2023, and served as our Head of Industry Transformation from October 16, 2023 to December 1, 2023. In February 2024 the Compensation Committee determined the Second Half 2023 Payments based on the appropriate total amounts to be paid to our executive officers, including our Named Executive Officers other than Mr. Steinert, under the 2023 Annual Incentive Plan based on our actual performance for 2023 with respect to each corporate performance goal and each executive officer’s individual performance against the executive officer’s distinct performance goals. For 2023 the actual results against the targets set for the corporate components under the 2023 Annual Incentive Plan were as follows:

  28. Elements of Executive Compensation

    | Performance Measure | Achievement Percentage or Rating | Payout Percentage | | Strategic Objectives | 75.0% | 106.7% | | Gross Profit | 98.4% | 84.0% | | Adjusted EBIT | 107.9% | 139.5% | | Individual Performance Goals | (1) | (1) |

  29. Elements of Executive Compensation

    (1) Performance ratings and corresponding payout percentages for each Named Executive Officer varied based on the 2023 performance reviews conducted for each such individual. The target annual cash incentive award opportunities and the actual cash incentive award payments (inclusive of the First Half 2023 Payments) made to our Named Executive Officers (other than Mr. Steinert) for 2023 were as follows:

  30. Elements of Executive Compensation

    | Named Executive Officer | Target Annual Cash Incentive Award | Actual Annual Cash Incentive Award | Percentage of Target Annual Cash Incentive Award Actually Paid | | Mr. Trevisan | $525,000 | $595,187 | 114.7% | | Ms. Palazzo(1) | $19,178 | $19,699 | 102.7% | | Mr. Steinert(2) | — | — | — | | Mr. Hallowell(3) | $68,562 | $70,424 | 102.7% | | Mr. Quinn | $225,000 | $234,627 | 107.2% |

  31. Elements of Executive Compensation

    Ms. Palazzo’s employment with the Company began effective as of December 4, 2023. Her annual cash incentive target and award for 2023 performance was prorated. (2) At Mr. Steinert’s request, to demonstrate his confidence in the Company and to continue to align his interests with those of our stockholders, the Compensation Committee continue to consider Mr. Steinert ineligible to receive an annual cash incentive award for 2023 performance. (3) Mr. Hallowell’s employment with the Company began effective as of October 16, 2023. His annual cash incentive target and award for 2023 performance was prorated. The annual cash incentive award payments made to our Named Executive Officers for 2023 are set forth in the “Summary Compensation Table” below. One-Time Cash Bonus In February 2024 the Compensation Committee approved a special one-time cash bonus of $20,000 to Mr. Hallowell in recognition of his transition to the role of Chief Executive Officer, CarOffer in December 2023 and the associated increased responsibilities. In consideration of the foregoing, the Compensation Committee made the determination that the special one-time cash bonus was in the best interest of stockholders and would facilitate long-term value creation. Long-Term Incentive Compensation Historically and during 2023 we have used RSU awards with time-based vesting requirements to retain, motivate, and reward our executive officers, including our Named Executive Officers, for long-term increases in the value of our Class A common stock and, thereby, to align their interests with those of our stockholders. Typically, the size and form of the equity awards granted to our existing or newly-hired executive officers are determined in the discretion of the Compensation Committee at a level that it believes is competitive with current market practices (with reference to our compensation peer group) and after taking into consideration each individual executive officer’s role and the scope of responsibilities, qualifications, experience, past performance and expected future contributions, current equity holdings, and the potential equity awards to be granted to our other executive officers. For its determination of the size and form of equity awards to be granted to our executive officers in 2023, the Compensation Committee considered Compensia’s competitive market analysis, including a review of equity awards granted to executives holding comparable positions at the companies in our compensation peer group, as well as its own assessment of our 2022 performance and the other factors described in “Elements of Executive Compensation – Base Salary” above. Additionally, while we typically grant equity awards to our executive officers on an annual basis, the Compensation Committee previously determined to increase the size of the 2021 equity award granted to Mr. Trevisan to cover the value of awards he would otherwise receive through 2024. As a result, the Compensation Committee had indicated at that time that it did not contemplate that Mr. Trevisan would be eligible for an equity grant in respect of long-term incentive compensation until 2025. Mr. Trevisan did not receive an equity grant in 2022 but, as discussed below, did receive a special one-time retention award in 2023. The Compensation Committee also approved an annual equity grant of RSUs to Mr. Trevisan in February 2024. In deciding to grant the RSU award to Mr. Trevisan in 2024, the Compensation Committee considered the retentive power of Mr. Trevisan’s previous equity awards, market conditions impacting the Company’s stock price, and the incentive power of such grant to Mr. Trevisan to continue to focus on creating long-term stockholder value and align his interests with those of our stockholders. In addition, in February 2023 the Company granted special one-time retention award grants of RSUs under the 2017 Plan to its executive officers, including Messrs. Trevisan and Quinn. In granting these retention awards, the Compensation Committee evaluated the retentive power of previous equity awards and market conditions impacting the Company’s stock price. In consideration of the foregoing, the Compensation Committee made the determination that the retention awards were in the best interests of our stockholders and would facilitate long-term value creation. The Compensation Committee granted the following equity awards to our Named Executive Officers in 2023:

  32. Elements of Executive Compensation

    | Named Executive Officer | RSU Award (number of shares) | RSU Award (grant date fair value)(1) | | Mr. Trevisan | 153,364(2) | $2,564,246 | | Ms. Palazzo | 91,575(3) | $1,999,998 | | Mr. Steinert | 149,521(4) | $2,499,991 | | Mr. Hallowell | 156,075(5) | $2,799,986 | | Mr. Quinn | 119,616(6) | $1,999,980 |

  33. Elements of Executive Compensation

    (1) The amounts reported represent the grant date fair value of the time-based RSU awards, as computed in accordance with the Financial Accounting Standard Board’s ASC Topic 718 (FASB ASC Topic 718), which excludes the impact of estimated forfeitures related to service-based vesting conditions, reflects the accounting cost for the equity awards, and does not correspond to the actual economic value that may be received by our Named Executive Officers from the equity awards. (2) One-time retention award, vesting as follows: 12.5% of the RSUs subject to the award vests on the date that is three months following the vesting commencement date of January 1, 2023, and 12.25% of the RSUs subject to the award vests on the first day of each three-month period thereafter until the second anniversary of the vesting commencement date, contingent upon Mr. Trevisan remaining continuously employed by us through each applicable vesting date. (3) New hire award, vesting as follows: 25% of the RSUs subject to the award vests on December 4, 2024, and 6.25% of the RSUs subject to the award vests on the last day of each three-month period thereafter until December 31, 2027, contingent upon Ms. Palazzo remaining continuously employed by us through each applicable vesting date. (4) Annual retention award, vesting as follows: 6.25% of the RSUs subject to the award vests on the date that is three months following the vesting commencement date of January 1, 2023, and 6.25% of the RSUs subject to the award vests on the first day of each three-month period thereafter until the fourth anniversary of the vesting commencement date, contingent upon Mr. Steinert remaining continuously employed by us through each applicable vesting date. (5) Includes (i) a new hire award of 100,334 RSUs, vesting as follows: 25% of the RSUs subject to the award vests on the date that is one year following the vesting commencement date of October 16, 2023, and 6.25% of the RSUs subject to the award vests on the last day of each three-month period thereafter until October 31, 2027, and (ii) in connection with his hiring, a one-time award of 55,741 RSUs, vesting as follows: 12.5% of the RSUs subject to the award vests January 1, 2024, and then 12.5% of the RSUs subject to the award vests on the first day of each three-month period thereafter until October 1, 2025, in each case contingent upon Mr. Hallowell remaining continuously employed by us through each applicable vesting date. (6) Includes (i) an annual retention award of 101,674 RSUs vesting as follows: 6.25% of the RSUs subject to the award vests on the date that is three months following the vesting commencement date of January 1, 2023, and 6.25% of the RSUs subject to the award vests on the first day of each three-month period thereafter until the fourth anniversary of the vesting commencement date and (ii) a one-time retention award of 17,942 RSUs vesting as follows: 12.5% of the RSUs subject to the award vests on the date that is three months following the vesting commencement date of January 1, 2023, and 12.25% of the RSUs subject to the award vests on the first day of each three-month period thereafter until the second anniversary of the vesting commencement date, in each case contingent upon Mr. Quinn remaining continuously employed by us through each applicable vesting date. Upon vesting, all of the RSU awards presented in the table above will be settled by issuing the number of shares of our Class A common stock underlying the RSUs that vested on such date. In addition, as described above, all such RSU awards provide for acceleration of vesting in the event the executive officer’s employment is terminated by us without cause or by the executive officer for good reason within 12 months following a Change of Control (as defined in the 2017 Plan). The equity awards granted to our Named Executive Officers in 2023 are set forth in the “Summary Compensation Table” and the “Grants of Plan-Based Awards Table” below. Welfare and Health Benefits We have established a broad-based tax-qualified savings plan under Section 401(k) of the Code for our eligible U.S. employees, including our executive officers, who satisfy certain eligibility requirements, including requirements relating to age and length of service. Currently, we match contributions made to the plan by our employees as follows: 50% of an employee’s calendar-year contributions, up to a maximum of 8% of the employee’s cash compensation paid during the period. Mandatory matching contributions may be subject to vesting based on an employee’s employment start date and length of service. Employees can designate the investment of their Section 401(k) accounts into a broad range of mutual funds. We do not allow investment in our Class A common stock through the Section 401(k) plan. We intend for the plan to qualify under Section 401(a) of the Code so that contributions by employees to the plan, and income earned on plan contributions, are not taxable to employees until withdrawn from the plan. In addition, our executive officers, including our Named Executive Officers, are eligible to receive the same employee benefits that are generally available to all of our U.S. CarGurus employees, subject to the satisfaction of certain eligibility requirements. These benefits include: medical, dental, and vision coverage; health savings and flexible spending accounts; paid time off; flexible hybrid work schedules or remote work on a case-by-case basis; employee assistance programs; short-term and long-term disability insurance; term life insurance; and fertility health and family-forming benefits, as well as paid access to certain wellness and family care resources. In structuring our employee benefit programs, we seek to provide an aggregate level of benefits that are competitive with those provided by similar companies, compliant with applicable laws and practices, and affordable to our employees. We adjust these programs as needed based upon regular monitoring of applicable laws and practices, the competitive market, and our employees’ needs. Perquisites and Other Personal Benefits We do not view perquisites or other personal benefits as a significant element of our executive compensation program. Accordingly, we do not provide significant perquisites or other personal benefits to our executive officers, including our Named Executive Officers, except as generally made available to our employees, or in situations where we believe it is appropriate to assist an executive officer in the performance of the individual’s duties, to make our executive officers more efficient and effective, and for recruitment and retention purposes. During 2023 we provided Mr. Trevisan with a supplemental commuting benefit to and from our offices in Cambridge, Massachusetts to allow him to more efficiently use commuting hours for business purposes. The amounts associated with this benefit are reflected in the “Summary Compensation Table” below. In the future, we may provide perquisites or other personal benefits in limited circumstances, such as those described in the preceding paragraph. All future practices with respect to perquisites or other personal benefits for our executive officers will be approved and subject to periodic review by the Compensation Committee.

  34. Post-Employment Compensation Arrangements

    Post-Employment Compensation Arrangements The employment offer letters with certain of our executive officers, including our Named Executive Officers, provide for certain protections in the event of their termination of employment under specified circumstances. We believe that these protections were necessary to induce these individuals to forego other opportunities or leave their then-current employment for the uncertainty of a demanding position in a new and unfamiliar organization. We also believe that these arrangements continue to serve our executive retention objectives by helping these executive officers maintain continued focus and dedication to their responsibility to maximize stockholder value. For a summary of the material terms and conditions of the post-employment compensation arrangements with our Named Executive Officers, see “Executive Employment Arrangements” below. For an estimate of the value of payments and benefits that our Named Executive Officers would have been eligible to receive if a hypothetical change of control or other trigger event had occurred on December 31, 2023, see “Potential Payments upon Termination of Employment or Change in Control” below.

  35. Tax and Accounting Considerations

    Tax and Accounting Considerations Deductibility of Executive Compensation In determining executive compensation, the Compensation Committee considers the possible income tax consequences to the Company and to our executive officers. To maintain maximum flexibility in designing our executive compensation program, the Compensation Committee, while considering tax deductibility as one factor in determining compensation, does not limit compensation to those levels or types of compensation that are intended to be deductible. Generally, Section 162(m) of the Code disallows a federal income tax deduction for public corporations of remuneration in excess of $1 million paid for any fiscal year to certain current or former executive officers. To maintain flexibility to compensate our executive officers in a manner designed to promote our short-term and long-term corporate goals and objectives, the Compensation Committee has not adopted a policy that all compensation must be deductible. Therefore, the Compensation Committee may approve base salaries and other compensation awards for our executive officers that may not be fully deductible because of the deduction limit of Section 162(m). Accounting for Stock-Based Compensation We follow FASB ASC Topic 718 for our stock-based compensation awards. FASB ASC Topic 718 requires us to measure the compensation expense for all share-based payment awards made to our employees and non-employee members of our Board of Directors, including RSU awards that may be settled in shares of our Class A common stock, options to purchase shares of our Class A common stock, and other stock awards, based on the grant date “fair value” of these awards. For RSU awards that may be settled in shares of our Class A common stock, the grant date fair value is determined using the closing price of our Class A common stock. For options to purchase shares of our Class A common stock, the grant date fair value is determined utilizing the Black-Scholes option-pricing model, a generally accepted option valuation methodology. FASB ASC Topic 718 also requires us to recognize the compensation cost of our stock-based compensation awards in our income statements over the period that an employee or director is required to render service in exchange for an RSU award, stock option, or other stock award. This calculation is performed for accounting purposes and reported in the executive compensation tables required by the federal securities laws, even though the recipient of the awards may never realize any value from their awards.

  36. Summary Compensation Table

    Summary Compensation Table The following table presents for the years ended December 31, 2023, 2022, and 2021, the compensation paid or awarded to, or earned by, our Named Executive Officers.

  37. Summary Compensation Table

    | Name and Principal Position | Year | Salary ($) | Bonus ($) | Stock Awards ($)(1) | NQSO Awards ($)(2) | Non-Equity Incentive Plan Compensation ($)(3) | All Other Compensation ($) | Total ($) | | Jason Trevisan Chief Executive Officer | 2023 | 565,000(4) | — | 2,564,246 | — | 595,187 | 28,780(5) | 3,753,213 | | | 2022 | 556,200 | — | 545,278(6) | — | 432,480 | 13,158 | 1,547,116 | | | 2021 | 540,000 | — | 13,512,566 | 4,499,992 | 640,882 | 17,810 | 19,211,250 | | Elisa Palazzo(7) Chief Financial Officer | 2023 | 31,023 | 50,000(8) | 1,999,998 | — | 19,699 | — | 2,100,720 | | Langley Steinert Executive Chair | 2023 | 10,000 | — | 2,499,991 | — | — | — | 2,509,991 | | | 2022 | 10,000 | — | 2,575,722(9) | — | — | — | 2,585,722 | | | 2021 | 10,000 | — | 1,876,728 | 625,000 | — | — | 2,511,728 | | Zachary Hallowell(10) Chief Executive Officer, CarOffer | 2023 | 88,542 | 320,000(11) | 2,799,986 | — | 70,424 | — | 3,278,952 | | Matthew Quinn Chief Technology Officer | 2023 | 369,500(12) | 7,500(13) | 1,999,980 | — | 234,627 | 12,329(14) | 2,623,936 | | | 2022 | 325,000 | 22,500(15) | 1,700,235 | 499,994 | 175,028 | 11,069(15) | 2,733,826 |

  38. Summary Compensation Table

    (1) Represents the aggregate grant date fair value of the time-based RSU awards based on the closing market price of our Class A common stock on the date of grant computed in accordance with FASB ASC Topic 718. See Notes 2 and 11 to the consolidated financial statements in our Annual Report for the assumptions regarding the valuation of these equity awards. For performance-based RSUs granted in 2021, the value reported reflects the value of the awards at the grant date based upon the grant date fair value determined utilizing a Monte Carlo simulation model, a generally accepted statistical technique used, in this instance, to simulate a range of possible future prices for the Company and the companies that comprise the S&P 500 Index as of the day before the applicable performance period (PSU Peer Group Companies) over the applicable performance periods under the performance-based RSU awards. If the performance-based RSU awards granted in 2021 and, with respect to Mr. Quinn, granted in 2022, were earned at the maximum level, the grant date fair value of the performance-based RSUs would be as follows: Mr. Trevisan, $5,650,752; Mr. Steinert, $783,432; and Mr. Quinn, $1,400,499 utilizing a Monte Carlo simulation model, a generally accepted statistical technique used, in this instance, to simulate a range of possible future prices for the Company and the PSU Peer Group Companies over the applicable performance periods under the performance-based RSU award. The vesting terms of such performance-based RSUs were subsequently amended in February 2022 to time-based RSUs (the 2022 PSU Amendment). The amounts listed in the table above for the 2022 awards include the modification expense associated with the 2022 PSU Amendment. For more information regarding the amended performance-based RSU awards, see the “Modification of 2021 and 2022 Performance-Based Equity Grants” section of our 2023 Proxy Statement. (2) Represents the aggregate grant date fair value of the NQSO awards, which is determined utilizing the Black-Scholes option-pricing model, a generally accepted option valuation methodology. See Notes 2 and 11 to the consolidated financial statements in our Annual Report for the assumptions regarding the valuation of these equity awards. (3) The amounts this column reflect cash incentive awards under our Annual Incentive Plan for the applicable year determined by the Compensation Committee based on our achievement of certain strategic objectives, financial performance goals, and the individual Named Executive Officer’s performance goals, as applicable. (4) Includes $2,200 for the one-time cash transition payment discussed above in “Transition Awards.” (5) Consists of (i) $15,362 attributable to Mr. Trevisan for his use of a limited supplemental shared commuting benefit, (ii) $11,250 for the Company’s Section 401(k) matching contribution, and (iii) $2,168 for the purchase of a vehicle at a CarGurus dealer pursuant to the Company’s auto perk benefit, which is offered to all employees after two years of employment at CarGurus and every four years thereafter. Due to the aggregate size of Mr. Trevisan’s 2021 equity award package upon his appointment to Chief Executive Officer, he did not receive an award in 2022. The amount reflected in the table above is related to the modification expense associated with the 2022 PSU Amendment. For more information regarding the amended performance-based RSU awards, see the “Modification of 2021 and 2022 Performance-Based Equity Grants” section of our 2023 Proxy Statement. Ms. Palazzo was appointed as our Chief Financial Officer effective December 4, 2023. Her base salary for 2023 was $390,000, of which she received a pro rata share from December 4, 2023 to December 31, 2023. Pursuant to a Relocation Repayment Agreement dated October 16, 2023, between Ms. Palazzo and the Company, Ms. Palazzo is entitled to the payment of relocation expenses of up to $150,000 in connection with her relocation from New York to the Cambridge, Massachusetts area (the Relocation Expenses). No Relocation Expenses were paid to Ms. Palazzo in 2023. See “Executive Employment Arrangements” for more information. (8) This amount reflects the cash sign-on bonus paid to Ms. Palazzo in connection with her hire. (9) Includes $75,733 related to the modification expense associated with the 2022 PSU Amendment. For more information regarding the amended performance-based RSU awards, see the “Modification of 2021 and 2022 Performance-Based Equity Grants” section of our 2023 Proxy Statement. (10) Mr. Hallowell was appointed as the Chief Executive Officer, CarOffer on December 1, 2023, and served as our Head of Industry Transformation from October 16, 2023 to December 1, 2023. His base salary for 2023 was $425,000, of which he received a pro rata share from October 16, 2023 to December 31, 2023. (11) Consists of (i) the cash sign-on bonus of $300,000 paid to Mr. Hallowell in connection with his hire and (ii) the one-time cash bonus of $20,000 discussed above in “Cash Incentive Awards – One Time Cash Bonus.” (12) Includes $3,250 for the one-time cash transition payment discussed above in “Transition Awards.” (13) In connection with the commencement of his employment, Mr. Quinn received a $30,000 cash sign-on bonus, which was paid in three installments. This amount reflects the remaining installment of the cash sign-on bonus paid to Mr. Quinn in connection with his hire. See “Executive Employment Arrangements” for more information. (14) Consists of $12,329 for the Company’s Section 401(k) matching contribution. (15) In connection with the commencement of his employment, Mr. Quinn received a $30,000 cash sign-on bonus, which was paid in three installments. Mr. Quinn received the first two installments, totaling $22,500, in 2022 (the 2022 Bonus Payment). The 2022 Bonus Payment was inadvertently included in the “All Other Compensation” column of the “Summary Compensation Table” in our 2023 Proxy Statement. The presentation of Mr. Quinn’s 2022 compensation has been updated to include the 2022 Cash Bonus Payment in the “Bonus” column. The amount in the “All Other Compensation” column for 2022 represents the Company’s Section 401(k) matching contribution.

  39. Grants of Plan-Based Awards Table

    Grants of Plan-Based Awards Table The following table presents, for each of our Named Executive Officers, information concerning each grant of a cash or equity award made during the year ended December 31, 2023.

  40. Grants of Plan-Based Awards Table

    | | | | Estimated Future Payouts Under Non-Equity Incentive Plan Awards(1) | | | | | | | | Name | Approval Date | Grant Date | Threshold ($) | Target ($) | Maximum ($) | All Other Stock Awards: Number of Shares of Stock or Units (#) | All Other Option Awards: Number of Securities Underlying Options(#) | Exercise or Base Price of Option Awards ($/sh) | Grant Date Fair Value of Stock and Option Awards ($)(2) | | Jason Trevisan | 02/16/2023 | 02/16/2023 | — | — | — | 153,364 | — | — | 2,564,246 | | | — | — | 0 | 518,835 | 866,250 | — | — | — | — | | Elisa Palazzo | 09/26/2023 | 12/04/2023 | — | — | — | 91,575 | — | — | 1,999,998 | | | — | — | 0 | 19,178(3) | 30,938(3) | — | — | — | — | | Langley Steinert | 02/16/2023 | 02/16/2023 | — | — | — | 149,521 | — | — | 2,499,991 | | Zachary Hallowell | 09/26/2023 | 10/16/2023 | — | — | — | 156,075 | — | — | 2,799,986 | | | — | — | 0 | 68,562(3) | 111,719(3) | — | — | — | — | | Matthew Quinn | 02/16/2023 | 02/16/2023 | — | — | — | 119,616 | — | — | 1,999,980 | | | — | — | 0 | 218,835 | 371,250 | — | — | — | — |

  41. Grants of Plan-Based Awards Table

    The amounts reported in the “Target” sub-column reflect the minimum payment level of non-equity incentive plan compensation for each of our Named Executive Officers assuming a target level of performance under the 2023 Annual Incentive Plan. The amounts reported in the “Maximum” sub-column reflect that for 2023, the program provided each Named Executive Officer with the potential to earn a maximum of 165% of the target cash incentive award opportunity. The design and operation of the 2023 Annual Incentive Plan are described in the “Compensation Discussion and Analysis” section of this Proxy Statement. Non-equity incentive plan awards actually paid by us for services rendered in 2023 are reported in the “Non-Equity Incentive Plan Compensation” column of the “Summary Compensation Table” above. Represents the aggregate grant date fair value of the time-based RSU awards under the 2017 Plan based on the closing market price of our Class A common stock on the date of grant computed in accordance with FASB ASC Topic 718. See Notes 2 and 11 to the consolidated financial statements in our Annual Report for the assumptions regarding the valuation of these equity awards. (3) 2023 target and maximum annual cash incentive opportunity pro-rated for service time provided in 2023.

  42. Outstanding Equity Awards at Fiscal Year-End Table

    Outstanding Equity Awards at Fiscal Year-End Table The following table presents, for each of our Named Executive Officers, information regarding outstanding equity awards held as of December 31, 2023.

  43. Outstanding Equity Awards at Fiscal Year-End Table

    | | | | Option Awards | | | | Stock Awards | | | Name | Grant Date | Vesting Commencement Date | Number of securities underlying unexercised options (#) exercisable | Number of securities underlying unexercised options (#) unexercisable | Option exercise price($) | Option expiration date | Number of shares or units of stock that have not vested (#) | Market value of shares or units of stock that have not vested ($)(1) | | Jason Trevisan | 02/12/2020 | 01/01/2021 | — | — | — | — | 4,852(2) | 117,224 | | | 02/10/2021 | 01/01/2021 | — | — | — | — | 78,981(3) | 1,908,181 | | | 02/10/2021 | 01/01/2021 | 180,709(4) | 82,141(4) | 35.61 | 02/10/2031 | — | — | | | 02/08/2022 | 01/01/2021 | — | — | — | — | 39,490(5)(6) | 954,078 | | | 02/16/2023 | 01/01/2023 | — | — | — | — | 95,853(7)) | 2,315,808 | | Elisa Palazzo | 12/04/2023 | 12/04/2023 | —) | — | — | —) | 91,575(8) | 2,212,452 | | Langley Steinert | 02/12/2020 | 01/01/2021 | — | — | — | — | 4,159(2) | 100,481 | | | 02/10/2021 | 01/01/2021 | — | — | — | — | 10,970(3) | 265,035 | | | 02/10/2021 | 01/01/2021 | 25,098(4) | 11,409(4) | 35.61 | 02/10/2031 | — | — | | | 02/08/2022 | 01/01/2022 | — | — | — | — | 40,317(9) | 974,059 | | | 02/08/2022 | 01/01/2021 | — | — | — | — | 5,484(5)(6) | 132,493 | | | 02/16/2023 | 01/01/2023 | — | — | — | — | 121,486(10) | 2,935,102 | | Zachary Hallowell | 10/16/2023 | 10/16/2023 | — | — | — | — | 55,741(11) | 1,346,703 | | | 10/16/2023 | 10/16/2023 | — | — | — | — | 100,334(12) | 2,424,069 | | Matthew Quinn | 01/03/2022 | 01/01/2022 | — | — | — | — | 16,072(13) | 388,300 | | | 01/03/2022 | 01/01/2022 | 13,270(14) | 17,026(14) | 35.00 | 01/03/2032 | — | — | | | 02/08/2022 | 01/01/2022 | — | — | — | — | 8,034(6)(13) | 194,101 | | | 02/16/2023 | 01/01/2023 | — | — | — | — | 11,214(7) | 270,930 | | | 02/16/2023 | 01/01/2023 | — | — | — | — | 82,611(10) | 1,995,882 |

  44. Outstanding Equity Awards at Fiscal Year-End Table

    (1) The market price for our Class A common stock is based on $24.16 per share, the closing market price of our Class A common stock on December 29, 2023, the last trading day of 2023. Our Class B common stock is valued the same as our Class A common stock. (2) 6.25% of the shares of our Class A common stock subject to this RSU award vested on April 1, 2020, and 6.25% of the shares subject to the award will vest (or have vested, as applicable) on the first day of each three-month period thereafter until January 1, 2024, contingent upon the Named Executive Officer remaining continuously employed by us through each applicable vesting date. (3) 6.25% of the shares of our Class A common stock subject to this RSU award vested on April 1, 2021, and 6.25% of the shares subject to the award will vest (or have vested, as applicable) on the first day of each three-month period thereafter until January 1, 2025, contingent upon the Named Executive Officer remaining continuously employed by us through each applicable vesting date. 6.25% of the shares of our Class A common stock underlying this NQSO award vested on April 1, 2021, and 6.25% of the shares of our Class A common stock underlying the award will vest (or have vested, as applicable) on the first day of each three-month period thereafter until January 1, 2025, contingent upon the Named Executive Officer remaining continuously employed by us through each applicable vesting date. 6.25% of the shares of our Class A common stock subject to this RSU award vested on April 1, 2021, and 6.25% of the shares subject to the award will vest (or have vested, as applicable) on the first day of each three-month period thereafter until January 1, 2025, contingent upon the Named Executive Officer remaining continuously employed by us through each applicable vesting date. (6) In February 2022 the Compensation Committee amended the vesting provisions of the performance-based RSU awards granted to our executive officers in 2021 and 2022, as applicable, from performance-based to time-based. See the “Modification of 2021 and 2022 Performance-Based Equity Grants” section of our 2023 Proxy Statement for more information. This table gives effect to the 2022 PSU Amendment. (7) 12.5% of the shares of our Class A common stock subject to this RSU award vested on April 1, 2023, and 12.5% of the shares subject to the award will vest (or have vested, as applicable) on the first day of each three-month period thereafter until January 1, 2025, contingent upon the Named Executive Officer remaining continuously employed by us through each applicable vesting date. (8) 25% of the shares of our Class A common stock underlying this RSU award will vest on December 4, 2024, and 6.25% of the shares of our Class A common stock underlying the award will vest on the last day of each three-month period thereafter until December 31, 2027, contingent upon Ms. Palazzo remaining continuously employed by us through each applicable vesting date. (9) 6.25% of the shares of our Class A common stock subject to this RSU award vested on April 1, 2022, and 6.25% of the shares subject to the award will vest (or have vested, as applicable) on the first day of each three-month period thereafter until January 1, 2026, contingent upon Mr. Steinert remaining continuously employed by us through each applicable vesting date. (10) 6.25% of the shares of our Class A common stock subject to this RSU award vested on April 1, 2023, and 6.25% of the shares subject to the award will vest (or have vested, as applicable) on the first day of each three-month period thereafter until January 1, 2027, contingent upon the Named Executive Officer remaining continuously employed by us through each applicable vesting date. (11) 12.5% of the shares of our Class A common stock subject to this RSU award vested on January 1, 2024, and 12.5% of the shares subject to the award will vest (or have vested, as applicable) on the first day of each three-month period thereafter until October 1, 2025, contingent upon Mr. Hallowell remaining continuously employed by us through each applicable vesting date. (12) 25% of the shares of our Class A common stock underlying this RSU award will vest on October 16, 2024, and 6.25% of the shares of our Class A common stock underlying the award will vest on the last day of each three-month period thereafter until October 31, 2027, contingent upon Mr. Hallowell remaining continuously employed by us through each applicable vesting date. (13) 25% of the shares of our Class A common stock subject to this RSU award vested on January 3, 2023, and 6.25% of the shares of our Class A common stock underlying the award will vest on the first day of each three-month period thereafter until January 1, 2026, contingent upon Mr. Quinn remaining continuously employed by us through each applicable vesting date. 25% of the shares of our Class A common stock underlying this NQSO award vested on January 3, 2023, and 6.25% of the shares of our Class A common stock underlying the award will vest (or have vested, as applicable) on the first day of each three-month period thereafter until January 1, 2026, contingent upon Mr. Quinn remaining continuously employed by us through each applicable vesting date.

  45. Option Exercises and Stock Vested Table

    Option Exercises and Stock Vested Table The following table presents, for each of our Named Executive Officers, the number of shares of our Class A common stock acquired upon the vesting of RSU awards during the year ended December 31, 2023, and the aggregate value realized upon the vesting of such awards. None of our Named Executive Officers exercised stock options during the year ended December 31, 2023.

  46. Option Exercises and Stock Vested Table

    | Name | Stock Awards – number of shares acquired on vesting (#)(1) | Stock Awards – value realized on vesting ($)(2) | | Jason Trevisan | 210,809 | 3,755,072 | | Elisa Palazzo | — | — | | Langley Steinert | 79,767 | 1,474,942 | | Zachary Hallowell | — | — | | Matthew Quinn | 44,541 | 813,457 |

  47. Option Exercises and Stock Vested Table

    (1) The amounts reported in this column represent the gross number of shares of our Class A common stock acquired upon the vesting of RSU awards without taking into account any shares that may have been withheld to satisfy applicable tax withholding obligations. Upon vesting of these awards, the Company withheld a portion of distributable shares in respect of taxes. The number of shares received after taking into account any shares withheld are as follows: 121,150 for Mr. Trevisan, 50,852 for Mr. Steinert, and 28,749 for Mr. Quinn. (2) The amounts reported in this column represent the taxable income recognized upon the vesting of RSU awards calculated by multiplying the gross number of RSUs vested by the closing market price of our Class A common stock on the vesting date or, if the vesting occurred on a day on which Nasdaq was closed for trading, the prior trading day.

  48. Potential Payments upon Termination of Employment or Change in Control

    Potential Payments upon Termination of Employment or Change in Control The following table sets forth the potential (estimated) payments and benefits to which our Named Executive Officers would have been entitled, as specified under their respective employment offer letter or equity award agreement, as applicable, assuming an employment termination date of December 31, 2023, on which the market price for our Class A common stock was $24.16 per share (the closing price on December 29, 2023, the last trading day of the year).

  49. Potential Payments upon Termination of Employment or Change in Control

    | Name and Benefit | Termination without Cause ($) | Resignation for Good Reason ($) | Change of Control ($) | Termination without Cause or for Good Reason in connection with Change of Control ($) | | Jason Trevisan | | | | | | Base Salary | — | — | — | — | | Bonus | — | — | — | — | | Equity Awards (Accelerated Vesting)(1) | — | — | — | 5,295,292 | | Health & Benefits | — | — | — | — | | Other(2) | 100,000 | 100,000 | — | 100,000 | | Total Estimated Value | 100,000 | 100,000 | — | 5,395,292 | | Elisa Palazzo | | | — | | | Base Salary(3) | 292,500 | 292,500 | — | 292,500 | | Bonus | — | — | — | — | | Equity Awards (Accelerated Vesting)(1) | — | — | — | 2,212,452 | | Health & Benefits(3) | 5,839 | 5,839 | — | 5,839 | | Other | — | — | — | — | | Total Estimated Value | 298,339 | 298,339 | — | 2,510,791 | | Langley Steinert | | | | | | Base Salary | — | — | — | — | | Bonus | — | — | — | — | | Equity Awards (Accelerated Vesting)(1) | — | — | — | 4,407,171 | | Health & Benefits | — | — | — | — | | Other | — | — | — | — | | Total Estimated Value | — | — | — | 4,407,171 |

  50. Potential Payments upon Termination of Employment or Change in Control

    | Name and Benefit | Termination without Cause ($) | Resignation for Good Reason ($) | Change of Control ($) | Termination without Cause or for Good Reason in connection with Change of Control ($) | | Zachary Hallowell | | | | | | Base Salary(4) | 356,250 | 356,250 | — | 356,250 | | Bonus | — | — | — | — | | Equity Awards (Accelerated Vesting)(1) | — | — | — | 3,770,772 | | Health & Benefits(4) | 15,642 | 15,642 | — | 15,642 | | Other | — | — | — | — | | Total Estimated Value | 371,892 | 371,892 | — | 4,142,664 | | Matthew Quinn | | | | | | Base Salary(5) | 285,000 | 285,000 | — | 285,000 | | Bonus | — | — | — | — | | Equity Awards (Accelerated Vesting)(1) | — | — | — | 2,849,213 | | Health & Benefits(5) | 17,518 | 17,518 | — | 17,518 | | Other | — | — | — | — | | Total Estimated Value | 302,518 | 302,518 | — | 3,151,731 |

  51. Potential Payments upon Termination of Employment or Change in Control

    Our forms of time-based RSU award agreement and NQSO award agreement provide for acceleration of unvested RSUs or NQSOs, as applicable, under such award in the event that such executive officer is terminated by us without Cause or by such executive officer for Good Reason (each as defined in the Company’s standard time-based RSU award agreement and NQSO award agreement, as applicable, for executive officers, the forms of which have been previously filed with the SEC) within 12 months following a Change of Control (as defined in the 2017 Plan). For all purposes above, a Change of Control under the 2017 Plan generally occurs if: (i) a person, entity, or affiliated group, with certain exceptions, acquires more than 50% of our then outstanding voting securities; (ii) we merge into another entity unless the holders of our voting shares immediately prior to the merger have at least 50% of the combined voting power of the securities in the merged entity or its parent; (iii) we merge into another entity and the members of our Board of Directors prior to the merger would not constitute a majority of the board of directors of the merged entity or its parent; (iv) we sell or dispose of all or substantially all of our assets; (v) our stockholders approve a plan of complete liquidation or dissolution; or (vi) a majority of the members of our Board of Directors is replaced during any 12-month period by directors whose appointment or election is not endorsed by a majority of the incumbent directors. (2) Pursuant to an employment offer letter between the Company and Mr. Trevisan dated August 10, 2015, if we terminate Mr. Trevisan’s employment without cause, or Mr. Trevisan terminates his employment for good reason, subject to him signing and not revoking a release of any and all claims against the Company, he will be entitled to a lump-sum cash severance payment in the amount of $100,000. See “Executive Employment Arrangements” for more information. (3) Pursuant to an employment offer letter between the Company and Ms. Palazzo dated October 16, 2023, if we terminate Ms. Palazzo’s employment without cause, or Ms. Palazzo terminates her employment for good reason, subject to her signing and not revoking a release of any and all claims against the Company and a reaffirmation of all her post-employment obligations under her nondisclosure agreement, and in the Company’s sole discretion, a one-year post-employment noncompetition agreement, she will be entitled to (i) a severance payment of an amount equal to nine months of her base salary, which will be paid in substantially equal installments in accordance with the Company’s payroll practices over six months commencing within 60 days following her termination of employment and (ii) reimbursement on a monthly basis for the COBRA premiums that Ms. Palazzo would pay for continued health care coverage under our group health plans for herself and her dependents until the earlier of nine months, until she becomes eligible under another employer’s group coverage, or until she ceases to be eligible for COBRA coverage for any reason. See “Executive Employment Arrangements” for more information. Pursuant to an employment offer letter between the Company and Mr. Hallowell dated September 29, 2023, if we terminate Mr. Hallowell’s employment without cause, or Mr. Hallowell terminates his employment for good reason, subject to his signing and not revoking a release of any and all claims against the Company and a reaffirmation of all his post-employment obligations under his nondisclosure agreement, and in the Company’s sole discretion, a one-year post-employment noncompetition agreement, he will be entitled to (i) a severance payment of an amount equal to nine months of his base salary, which will be paid in substantially equal installments in accordance with the Company’s payroll practices over six months commencing within 60 days following his termination of employment and (ii) reimbursement on a monthly basis for the COBRA premiums that Mr. Hallowell would pay for continued health care coverage under our group health plans for himself and his dependents until the earlier of nine months, until he becomes eligible under another employer’s group coverage, or until he ceases to be eligible for COBRA coverage for any reason. See “Executive Employment Arrangements” for more information. Pursuant to an employment offer letter between the Company and Mr. Quinn dated December 21, 2022, if we terminate Mr. Quinn’s employment without cause, or Mr. Quinn terminates his employment for good reason, subject to his signing and not revoking a release of any and all claims against the Company and a reaffirmation of all his post-employment obligations under his nondisclosure agreement, and in the Company’s sole discretion, a one-year post-employment noncompetition agreement, he will be entitled to (i) a severance payment of an amount equal to nine months of his base salary, which will be paid in substantially equal installments in accordance with the Company’s payroll practices over six months commencing within 60 days following his termination of employment and (ii) reimbursement on a monthly basis for the COBRA premiums that Mr. Quinn would pay for continued health care coverage under our group health plans for himself and his dependents until the earlier of nine months, until he becomes eligible under another employer’s group coverage, or until he ceases to be eligible for COBRA coverage for any reason. See “Executive Employment Arrangements” for more information.

  52. CEO Pay Ratio Disclosure

    CEO Pay Ratio Disclosure As required by Item 402(u) of Regulation S-K, we are providing disclosure regarding the ratio of the annual total compensation of Mr. Trevisan, our Chief Executive Officer, to the median of the annual total compensation of all our employees, other than our Chief Executive Officer. We consider the pay ratio set forth below to be a reasonable estimate, calculated in a manner in accordance with applicable SEC rules. We identified our median employee for 2023 using a consistently applied compensation measure, annualized base salary, for all of our 1,343 active employees (236 of whom were employed through CarOffer) as of December 31, 2023, excluding Mr. Trevisan. Compensation data for our employees outside the U.S. was converted to U.S. dollars using the currency exchange rates used for organizational planning purposes, which consider factors including historic and forecasted rates. We did not make any cost-of-living adjustments. We identified employees within $1,000 of the calculated median base salary amount for 2023 and selected the employee from that group most representative of our consolidated employee population. We annualized the compensation of all newly-hired employees in 2023. Other than Mr. Trevisan, we included all of our employees and those of our consolidated subsidiaries as of December 31, 2023, whether employed on a full-time or part-time basis. We selected December 31, 2023, as the date as of which we would identify the “median employee” because it enabled us to make such identification in a reasonably efficient and economical manner. For 2023 the annual total compensation of Mr. Trevisan, calculated pursuant to Item 402 of Regulation S-K, was $3,753,213, as set forth in the “Summary Compensation Table” above, approximately 68% of such amount was equity-based. After identifying our median employee, we calculated that employee’s annual total compensation for 2023 utilizing the same methodology used to calculate the total compensation of Mr. Trevisan as reflected in the “Summary Compensation Table” above. Based on such calculation, our median employee’s annual total compensation was $167,361, which amount is inclusive of the individual’s annualized base salary for 2023, the grant date value of an RSU award granted in 2023, actual short-term incentive cash payment, and the Company’s Section 401(k) matching contribution. The resulting ratio of our Chief Executive Officer’s annual total compensation to the median of the annual total compensation of all of our employees is approximately 22.43:1.

  53. Pay versus Performance

    Pay versus Performance The following information is presented to disclose the relationship between compensation actually paid (CAP), as calculated under Item 402(v) of Regulation S-K, and the financial performance of the Company. As required by Item 402(v) of Regulation S-K, the table presented below discloses CAP for (i) the Company’s principal executive officer (PEO) and (ii) the Company’s Named Executive Officers other than the PEO (the Non-PEO NEOs), on an average basis, for 2023, 2022, 2021, and 2020. The methodology for calculating amounts presented in the columns “CAP to PEO (Former)”, “CAP to PEO (Current),” and “Average CAP to Non-PEO NEOs,” including details regarding the amounts that were deducted from, and added to, the Summary Compensation Table (SCT) totals to arrive at the values presented for CAP, are provided in the footnotes to the table. A narrative discussion of the relationship between CAP and the Company performance measures (i) listed in the table and (ii) that the Company has deemed most important in linking CAP during 2023 to Company performance is also presented below. Consistent with Item 402(v) of Regulation S-K, the Company has identified gross profit as its “Company-Selected Measure.” The Company believes that this measure represents the most important financial performance measure used to link CAP to Company performance. Gross profit is a key component of the Company’s executive compensation program, as described in the Compensation Discussion and Analysis. Compensation decisions at the Company are made independently of the Pay versus Performance disclosure requirements and this disclosure is intended to be supplemental to the compensation program objectives and strategy discussed in the Compensation Discussion and Analysis, not in replacement.

  54. Pay versus Performance Table

    Pay versus Performance Table In accordance with Item 402(v) of Regulation S-K, the following table sets forth information concerning SCT total compensation and CAP for the Company’s PEO and Non-PEO NEOs for 2023, 2022, 2021, and 2020 and the corresponding financial performance of the Company in each year.

  55. Pay versus Performance Table

    | | | | | | | | Value of Initial Fixed $100 Investment Based on: | | | | | Year | SCT Total for PEO (Former)(1) | SCT Total for PEO (Current)(1) | CAP(2) to PEO (Former) (1)(3) | CAP(2) to PEO (Current)(1)(3) | Average SCT Total for Non-PEO NEOs(1) | Average CAP(2) to Non-PEO NEOs(1)(4) | Total Shareholder Return | 2023 Peer Group Total Shareholder Return(5) | Net Income (in thousands) | Gross Profit (in thousands)(6) | | (a) | (b) | (b) | (c) | (c) | (d) | (e) | (f) | (g) | (h) | (i) | | 2023 | — | $3,753,213 | — | $6,878,427 | $2,628,399 | $3,685,780 | $68.68 | $94.85 | $22,053 | $651,454 | | 2022 | — | $1,547,116 | — | $(5,908,845) | $2,550,688 | $236,663 | $39.82 | $70.27 | $78,954 | $657,553 | | 2021 | $2,511,728 | $19,211,250 | $2,146,098 | $16,797,283 | $5,174,391 | $3,598,175 | $95.62 | $133.53 | $110,373 | $657,358 | | 2020 | $2,301,672 | — | $1,503,671 | — | $4,062,953 | $2,984,557 | $90.19 | $149.36 | $77,553 | $508,745 |

  56. Pay versus Performance Table

    (1) As a result of a PEO transition that occurred in 2021, two PEOs are reported in the above table. In 2020 and 2021 Mr. Steinert was the PEO (listed as “Former PEO”). On January 21, 2021, Mr. Steinert ceased to serve as PEO and Mr. Trevisan was appointed PEO (listed as “Current PEO”). The Company’s Non-PEO NEOs for the applicable years are as follows: a. 2023: Elisa Palazzo, Langley Steinert, Zachary Hallowell, and Matthew Quinn b. 2022: Langley Steinert, Scot Fredo, Matthew Quinn, and Andrea Eldridge c. 2021: Samuel Zales, Andrea Eldridge, Scot Fredo, Dafna Sarnoff, and Sarah Welch d. 2020: Jason Trevisan, Samuel Zales, Thomas Caputo, and Sarah Welch (2) CAP does not mean that our executive officers were actually paid these amounts in the listed year, but this is a dollar amount derived from the starting point of SCT total compensation under the methodology prescribed under Item 402(v) of Regulation S-K. a. Consistent with SEC rules, we calculated CAP amounts for the Named Executive Officers as follows: (i) Total compensation from the SCT, (ii) deduct the total amounts reported in the Stock Awards and Option Awards columns of the SCT, (iii) add the fair value as of the end of the covered fiscal year of all awards granted during the covered fiscal year that are outstanding and unvested as of the end of the covered fiscal year, (iv) add the amount equal to the change as of the end of the covered fiscal year (from the end of the prior year) in fair value of any awards granted in any prior fiscal years that are outstanding and unvested as of the end of the covered fiscal year, (v) add, for awards that are granted and vest in the same year, the fair value as of the vesting date, (vi) add the amount equal to the change as of the vesting date (from the end of the prior fiscal year) in fair value of any awards granted in any prior fiscal year for which all applicable vesting conditions were satisfied at the end of or during the covered fiscal year, and (vii) deduct, for awards granted in any prior fiscal year that fail to meet the applicable vesting conditions during the covered year, the amount equal to the fair value at the end of the prior fiscal year. (3) The following table sets forth the adjustments made to SCT total compensation pursuant to Item 402(v) of Regulation S-K to determine CAP for the Current PEO and Former PEO in 2023, 2022, 2021, and 2020:

  57. Pay versus Performance Table

    | PEO SCT Total to CAP Adjustments | 2023 | 2022 | 2021 – PEO (Current) | 2021 – PEO (Former) | 2020 | | Total Reported in SCT | $3,753,213 | $1,547,116 | $19,211,250 | $2,511,728 | $2,301,672 | | Less Grant Date Fair Value of Stock Awards and Option Awards Reported in SCT | $(2,564,246) | $(545,278) | $(18,012,558) | $(2,501,728) | $(2,291,672) |

  58. Pay versus Performance Table

    | PEO SCT Total to CAP Adjustments | 2023 | 2022 | 2021 – PEO (Current) | 2021 – PEO (Former) | 2020 | | Year-End Fair Value of Equity Awards Granted During Covered Year That Remained Unvested as of Last Day of Covered Year | $2,315,808 | $0 | $13,651,861 | $1,896,098 | $1,715,482 | | Change in Fair Value from Last Day of Prior Year to Last Day of Covered Year of Unvested Equity Awards | $1,628,283 | $(7,994,953) | $191,487 | $116,789 | -$187,524 | | Vesting-Date Fair Value of Equity Awards Granted During Year that Vested During Year | $1,127,794 | $0 | $1,891,757 | $262,730 | $272,397 | | Change in Fair Value from Last Day of Prior Year to Vesting Date of Unvested Equity Awards that Vested During Covered Year | $617,575 | $1,084,270 | $(136,514) | $(139,519) | $(306,684) | | Fair Value at Last Day of Prior Year of Equity Awards Forfeited During Covered Year | $0 | $0 | $0 | $0 | $0 | | Total Adjustments | $3,125,214 | $(7,455,961) | $(2,413,967) | $(365,630) | $(798,001) | | CAP | $6,878,427 | $(5,908,845) | $16,797,283 | $2,146,098 | $1,503,671 |

  59. Pay versus Performance Table

    The following table sets forth the adjustments made to SCT total compensation pursuant to Item 402(v) of Regulation S-K to determine CAP for the Non-PEO NEOs in 2023, 2022, 2021, and 2020:

  60. Pay versus Performance Table

    | Non-PEO NEOs Average SCT to CAP Adjustments | 2023 | 2022 | 2021 | 2020 | | Total Reported in SCT | $2,628,399 | $2,550,688 | $5,174,391 | $4,062,953 | | Less Grant Date Fair Value of Stock Awards and Option Awards Reported in SCT | $(2,324,989) | $(2,181,475) | $(4,225,087) | $(3,437,517) | | Year-End Fair Value of Equity Awards Granted During Covered Year That Remained Unvested as of Last Day of Covered Year | $2,796,285 | $537,561 | $3,027,728 | $2,771,171 | | Change in Fair Value from Last Day of Prior Year to Last Day of Year of Unvested Equity Awards | $249,270 | $(960,465) | $53,440 | $(311,807) | | Vesting-Date Fair Value of Equity Awards Granted During Covered Year that Vested During Covered Year | $263,883 | $231,449 | $342,600 | $272,391 | | Change in Fair Value from Last Day of Prior Year to Vesting Date of Unvested Equity Awards that Vested During Covered Year | $72,932 | $58,906 | $(57,775) | $(373,634) | | Fair Value at Last Day of Prior Year of Equity Awards Forfeited During Covered Year | $0 | $0 | $(717,123) | $0 | | Total Adjustments | $1,057,381 | $(2,314,024) | $(1,576,217) | $(1,078,396) | | CAP | $3,685,780 | $236,663 | $3,598,175 | $2,984,557 |

  61. Pay versus Performance Table

    Total Shareholder Return is determined based on the value of an initial fixed investment of $100 in our Class A common stock on December 31, 2019, assuming the reinvestment of any dividends. The peer group Total Shareholder Return represents the Total Shareholder Return of our Compensation Discussion and Analysis peer group companies, weighted by market capitalization at each fiscal year end. Our Compensation Discussion and Analysis peer group companies for 2020 – 2023 were as follows: 2023 Compensation Discussion and Analysis peer companies: ACI Worldwide, Inc., ACV Auctions Inc., Alarm.com Holdings, Inc., Angi Inc., Cars.com Inc., Commvault Systems, Inc., Envestnet, Inc., Everbridge, Inc., Flywire Corp., NetScout Systems, Inc., New Relic, Inc., Pegasystems Inc., Qualys, Inc., Rapid7, Inc., Redfin Corporation, Shutterstock, Inc., TripAdvisor, Inc., Upwork, Inc., Yelp Inc. b. 2022 Compensation Discussion and Analysis peer companies: Alarm.com, Inc., Bottomline Technologies Inc., Cars.com Inc., Cerence Inc., Everbridge, Inc., EverQuote, Inc. HubSpot, Inc., LendingTree, Inc., New Relic, Inc., Pegasystems Inc., Qualys, Inc. Rapid7, Inc., Redfin Corporation, Shutterstock, Inc., TripAdvisor, Inc., Wayfair Inc, Yelp Inc., Yext, Inc. c. 2021 Compensation Discussion and Analysis peer companies: Alarm.com, Inc., Bottomline Technologies Inc., Cars.com Inc., Etsy Inc., Everbridge, Inc., EverQuote, Inc. HubSpot, Inc., LendingTree, Inc., New Relic, Inc., Paylocity Holding Corporation, Pegasystems Inc., Qualys, Inc. Rapid7, Inc., Redfin Corporation, TripAdvisor, Inc., TrueCar, Inc. Wayfair Inc, Yelp Inc., Yext, Inc d. 2020 Compensation Discussion and Analysis peer companies: Alarm.com, Inc., Cars.com Inc., Etsy Inc., GrubHub, Inc., HubSpot, Inc., LendingTree, Inc., New Relic, Inc., Paylocity Holding Corporation, Pegasystems Inc., Qualys, Inc. Rapid7, Inc., TripAdvisor, Inc., TrueCar, Inc., Varonis Systems, Inc., Wayfair Inc, Yelp Inc., Yext, Inc., Zillow Group, Inc. (6) Gross Profit is the financial performance measure, which, in the Company’s assessment, represents for 2023 as the most important performance measure used to link compensation actually paid to our PEOs and Non-PEO NEOs to the Company’s performance.

  62. Analysis of the Information Presented in the Pay versus Performance Table

    Analysis of the Information Presented in the Pay versus Performance Table The charts below show the relationship between the CAP to our Current PEO and Former PEO and Average CAP to our Non-PEO NEOs in 2023, 2022, 2021, and 2020 to each of (1) the Company’s cumulative Total Shareholder Return, (2) Net Income, and (3) Gross Profit. A chart comparing the Company’s cumulative Total Shareholder Return and the Company’s Peer Group Total Shareholder Return is also provided below. As described in greater detail in “Compensation Discussion and Analysis,” the Compensation Committee’s philosophy is to provide a competitive total compensation package to our executive officers, including our Named Executive Officers, through a combination of annual base salary, annual cash incentive award opportunities, long-term incentive compensation opportunities in the form of equity awards, and broad-based health and welfare benefit plans. The objectives of our philosophy are to attract, motivate, and retain executive officers of outstanding ability and potential, reward the achievement of key performance measures, and ensure that executive compensation is meaningfully related to the creation of stockholder value. While the Compensation Committee utilizes several performance measures to align executive compensation with Company performance, all of those measures are not presented in the Pay versus Performance table. Moreover, the Compensation Committee generally seeks to incentivize long-term performance, and therefore does not specifically align the Company’s performance measures with CAP for a particular year. In accordance with Item 402(v) of Regulation S-K, we are providing the following charts displaying the relationships between information presented in the Pay versus Performance table. Description of Relationship Between PEO, Former PEO, and Non-PEO NEOs CAP and Company Total Shareholder Return The following chart sets forth the relationship between CAP to our PEO, CAP to our Former PEO, the average of CAP to our Non-PEO NEOs, and the Company’s cumulative Total Shareholder Return over the four most recently completed fiscal years. Our executive compensation program emphasizes long-term incentives tied to our stock price. We believe that the CAP to the Former PEO, Current PEO, and Non-PEO NEOs is aligned to our stock price performance, as shown in the chart above. For the three-year period ended December 31, 2023, the CAP to the Current PEO decreased by 59%, and for the four-year period ended December 31, 2023, the average CAP to the Non-PEO NEOs decreased by 9%. We believe the foregoing is aligned with the Company’s Total Shareholder Return, which for the four-year period ended December 31, 2023, decreased by 31.32%. Description of Relationship Between PEO, Former PEO, and Non-PEO NEO CAP and Net Income The following chart sets forth the relationship between CAP to our PEO, CAP to our former PEO, the average of CAP to our Non-PEO NEOs, and our Net Income during the four most recently completed fiscal years. As shown in the chart above, the CAP to the Former PEO and Current PEO and the average CAP to the Non-PEO NEOs is generally aligned with the Company’s performance on Net Income. For the three-year period ended December 31, 2023, the CAP to the Current PEO decreased by 59%, and for the four-year period ended December 31, 2023, the average CAP to the Non-PEO NEOs decreased by 9%. For the four-year period ended December 31, 2023, the Company’s Net Income decreased by 72%. Description of Relationship Between PEO, Former PEO, and Non-PEO NEO CAP and Gross Profit The following chart sets forth the relationship between CAP to our PEO, CAP to our former PEO, the average of CAP to our Non-PEO NEOs, and our Gross Profit during the four most recently completed fiscal years. Aside from our stock price performance, we believe that Gross Profit is the most important financial metric that ties our executives’ compensation to our performance. Our Gross Profit has remained relatively steady from 2021 to 2023, as reflected in the Pay versus Performance table and the chart above. Our year-over-year CAP outcomes do not always align directionally with the year-over-year Gross Profit outcomes because the greatest sensitivity to our executives’ compensation is tied to our stock price. As such, we expect that our stock price will continue to have a much larger impact on CAP than Gross Profit. For the four-year period ended December 31, 2023, the Company’s Gross Profit increased by 28%, whereas for the three-year period ended December 31, 2023, the CAP to the Current PEO decreased by 59%, and for the four-year period ended December 31, 2023, the average CAP to the Non-PEO NEOs decreased by 9%. Description of Relationship Between Company Total Shareholder Return and Peer Group Total Shareholder Return The following chart compares our cumulative Total Shareholder Return over the four most recently completed fiscal years to that of our peer group total shareholder return over the same period. 1Represents values based on an initial fixed $100 investment made on December 31, 2019. For the four-year period ended December 31, 2023, based on a fixed $100 investment made on December 31, 2019, the Total Shareholder Return for the Company’s peer group disclosed in the chart above decreased by 5.15%, compared to the Company’s Total Shareholder Return, which decreased by 31.32% over the same period.

  63. Director Compensation

    Director Compensation During 2023 we compensated our non-employee directors for their service as directors. Accordingly, neither Mr. Steinert, our Executive Chair and Chair of our Board of Directors, nor Mr. Trevisan, our Chief Executive Officer, received any additional compensation for their service as directors. The Compensation Committee periodically reviews the compensation of our non-employee directors and, as applicable, makes recommendations to our Board of Directors for its consideration of changes to our non-employee director compensation program. The Compensation Committee compares the compensation of the non-employee members of our Board of Directors to the compensation paid to the non-employee directors of the companies in our compensation peer group. The Compensation Committee also considers the responsibilities we ask from the members of our Board of Directors along with the amount of time required to perform those responsibilities. In 2022 the Compensation Committee recommended and the Board of Directors approved a modification to our non-employee director compensation program to increase compensation for all non-employee directors and the Compensation Committee Chair, effective as of January 1, 2023, by $5,000 and $3,000, respectively. These changes were made based on a competitive analysis prepared by Compensia of our non-employee director compensation program as compared to our peers and were made to ensure our program remained aligned with the market.

  64. Director Compensation Table

    Director Compensation Table

  65. Director Compensation Table

    | Name | Fees Earned or Paid in Cash ($) | Stock Awards ($)(1)(2) | Total ($) | | Steven Conine | 55,000 | 175,000 | 230,000 | | Manik Gupta(3) | 23,506 | 82,192 | 105,698 | | Yvonne Hao(4) | — | — | — | | Lori Hickok | 60,000 | 175,000 | 235,000 | | Stephen Kaufer | 55,000 | 175,000 | 230,000 | | Greg Schwartz | 50,000 | 175,000 | 225,000 | | Ian Smith(5) | 23,506 | — | 23,506 |

  66. Director Compensation Table

    (1) The amount reported in this column represents the aggregate grant date fair value of the RSU award based on the closing market price of our Class A common stock on the date of grant computed in accordance with FASB ASC Topic 718. See Notes 2 and 11 to the consolidated financial statements in our Annual Report for the assumptions regarding the valuation of these equity awards. (2) As of December 31, 2023, our non-employee directors held the following aggregate number of shares of our Class A common stock under unvested RSU awards:

  67. Director Compensation Table

    | Name | Aggregate Number of Shares Underlying 2023 Stock Awards | | Steven Conine | 8,750 | | Yvonne Hao | — | | Manik Gupta | 3,517 | | Lori Hickok | 8,750 | | Stephen Kaufer | 8,750 | | Greg Schwartz | 8,750 | | Ian Smith | — |

  68. Director Compensation Table

    (3) Mr. Gupta’s fees and stock award were prorated based on his service during the year, which commenced July 14, 2023. (4) Ms. Hao resigned from our Board of Directors effective January 11, 2023. Mr. Smith retired from our Board of Directors effective June 6, 2023, and his fees were prorated based on his service during the fiscal year.

  69. ELECTION OF DIRECTORS

    ELECTION OF DIRECTORS Our Board of Directors may establish the authorized number of directors from time to time by resolution. Our Fourth Amended and Restated Certificate of Incorporation provides for a classified Board of Directors. This means our Board of Directors is divided into three classes, with the term of service of each class of directors staggered so that the term of one class expires at each annual meeting of the stockholders. Our Board of Directors currently consists of seven members, divided into three classes as follows: • the Class I directors are Lori Hickok, Greg Schwartz, and Jason Trevisan, each with a term expiring at the Annual Meeting; • the Class II directors are Steven Conine and Stephen Kaufer, each with a term expiring at the annual meeting of stockholders to be held in 2025; and • the Class III directors are Manik Gupta and Langley Steinert, each with a term expiring at the annual meeting of stockholders to be held in 2026. At each annual meeting of stockholders, director nominees are elected for a full term of three years to succeed those directors whose terms are expiring. Ms. Hickok and Messrs. Schwartz and Trevisan are current directors whose terms expire at the Annual Meeting. Our Board of Directors has nominated Ms. Hickok and Messrs. Schwartz and Trevisan for election as the Class I directors, each to serve for a three-year term expiring at the 2027 annual meeting of stockholders, or until their respective successors have been duly elected and qualified. OUR BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS A VOTE “FOR” THE CLASS I NOMINEES NAMED ABOVE.