Maya Prosor
LemonadeAbout Maya Prosor
Maya Prosor is a founding team member of Lemonade and has served as Chief Business Officer since July 2022; she is 40 years old and holds a BA in Business Administration and Entrepreneurship from Reichman University’s Zell Entrepreneurship Program . Company performance during her tenure shows 2024 total revenue up 22% to $526.5M, gross written premium up 26% to $929.0M, and net loss improved to $(202.2)M from $(236.9)M; the company-reported TSR value for a fixed $100 investment stood at $45 in 2024 and Adjusted EBITDA was $(150)M .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Lemonade | Chief Business Officer | Since Jul 2022 | Leads business development and growth initiatives across products/geographies . |
| Lemonade | Homeowners Company Lead | Jul 2020 – Jul 2022 | Drove product expansion and performance in homeowners segment . |
| Lemonade | VP, Business Development | Aug 2015 – Jul 2020 | Built partnerships and market entry capabilities for early scaling . |
External Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Duracell–Powermat JV | Assistant Vice President, Market Development | 2010 – 2015 | Advanced commercialization and market development for wireless charging JV . |
Fixed Compensation
| Year | Base Salary (USD) | Cash Incentive (Annual) | All Other Compensation |
|---|---|---|---|
| 2023 | $400,000 | None (company does not provide annual cash incentives to NEOs) | — |
| 2024 | $400,000 | None (company does not provide annual cash incentives to NEOs) | — |
Performance Compensation
Equity Grants (2023–2024)
| Grant Date | Award Type | Shares/Options | Exercise Price | Grant-Date Fair Value |
|---|---|---|---|---|
| Feb 7, 2023 | Stock Options | 100,000 | $18.17 | $1,197,695 |
| Aug 11, 2023 | Stock Options | 83,700 | $15.13 | $864,089 |
| Mar 1, 2024 | RSUs | 7,576 | — | $128,186 |
| Jun 23, 2024 | Stock Options | 95,408 | $15.90 | $1,029,452 |
| Sep 8, 2024 | Stock Options | 45,000 | $18.14 | $562,050 |
Vesting and Realization
| Metric | FY 2024 |
|---|---|
| Shares acquired on vesting | 2,642 |
| Value realized on vesting | $68,557 |
| Option exercises | None |
Outstanding Equity (as of Dec 31, 2024)
| Grant Date | Exercisable Options | Unexercisable Options | Exercise Price | Option Expiration | Unvested RSUs | RSU Market Value |
|---|---|---|---|---|---|---|
| Feb 7, 2023 | 50,000 | 50,000 | $18.17 | Feb 7, 2033 | — | — |
| Aug 11, 2023 | 26,159 | 57,541 | $15.13 | Aug 11, 2033 | — | — |
| Jun 23, 2024 | 23,852 | 71,556 | $15.90 | Jun 23, 2034 | — | — |
| Sep 8, 2024 | 2,813 | 42,187 | $18.14 | Sep 8, 2034 | — | — |
| Mar 1, 2024 (RSUs) | — | — | — | — | 5,682 | $208,416 (based on $36.68 on 12/31/24) |
Vesting schedules: Options generally vest in 16 equal quarterly installments over 4 years; certain 2024 options vest in 8 equal quarterly installments over 2 years; RSUs vest in 16 equal quarterly installments over 4 years .
Equity Ownership & Alignment
| Component | Amount |
|---|---|
| Common shares directly owned | 34,298 |
| RSUs vesting within 60 days of Apr 10, 2025 | 661 |
| Options exercisable or becoming exercisable within 60 days | 350,049 |
| Total beneficial ownership | 385,008 |
| Shares outstanding (Record Date) | 73,266,170 |
| Ownership as % of shares outstanding | ~0.53% (385,008 ÷ 73,266,170) |
| Hedging/Pledging | Prohibited by Insider Trading Compliance Policy |
Insider trading plans:
- Adopted Rule 10b5-1 plan to sell up to 50,000 shares (through March 1, 2025) via Cohen Holdings 2021 LLC on March 13, 2024 .
- Adopted Rule 10b5-1 plan to sell up to 10,000 shares (through May 30, 2026) on September 12, 2025 .
Employment Terms
| Provision | Normal Termination (Without Cause) | Change-in-Control Window (3 months before to 12 months after) |
|---|---|---|
| Base salary continuity | 6 months of base salary | 12 months of base salary |
| Target bonus payout | 50% of target annual bonus | 100% of target annual bonus |
| Equity acceleration | 6 months of vesting acceleration | Full acceleration of all outstanding equity |
| At-will employment | Yes | Yes |
| Definition of “Cause” | Includes unauthorized disclosure, refusal to follow lawful directives, embezzlement, felony, gross negligence/willful misconduct, materially detrimental acts/statements | |
| Clawback policy | Company-wide policy compliant with Rule 10D-1; recovers erroneously awarded incentive comp for prior 3 fiscal years upon required restatement |
Estimated aggregate payments (hypothetical event on Dec 31, 2024):
- Termination without cause (no CIC): Total $251,005; includes $200,000 cash, $37,256 equity acceleration, $13,749 healthcare .
- Termination without cause in connection with CIC: Total $602,195; includes $400,000 cash, $174,698 equity acceleration, $27,497 healthcare .
Compensation Structure Notes
- Pay mix is equity-heavy; the company does not provide annual cash incentive compensation to NEOs, emphasizing stock options and RSUs with service-based vesting .
- Company-selected performance measures reported for pay-versus-performance disclosure include In Force Premium (IFP) and Adjusted EBITDA; however, Prosor’s reported awards are time-vested without explicit PSU metrics or weightings .
Compensation Trend (Summary Compensation Table)
| Year | Salary | Options | Stock Awards | All Other Comp | Total |
|---|---|---|---|---|---|
| 2023 | $400,000 | $2,061,784 | — | — | $2,461,784 |
| 2024 | $400,000 | $1,591,502 | $128,186 | — | $2,119,688 |
Governance & Market Context
- Say-on-Pay support improved: 2024 vote ~87.5% “For” the NEO compensation program .
- Compensation peer group used in 2024 spans fintech/insurtech (e.g., Affirm, Hippo, Oscar Health, Root, Trupanion), with selection criteria based on sector, revenue ($250M–$2B), and market cap ($200M–$3.6B) .
Investment Implications
- Retention risk appears moderate: severance provides salary/bonus continuity and equity acceleration (6 months; full upon CIC), which can aid retention through strategic events but also create CIC windfalls; this is a standard double-trigger construct with generous equity acceleration .
- Alignment: Prosor holds a meaningful option stack and time-vested RSUs; hedging/pledging are prohibited, supporting alignment; total beneficial ownership ~0.53% as of the 2025 record date .
- Near-term selling pressure: disclosed Rule 10b5-1 plans for up to 50,000 shares through March 1, 2025 and 10,000 shares through May 30, 2026 imply scheduled supply into the market, though actual sales depend on execution and trading windows .
- Pay-for-performance signaling: reliance on time-vested equity (no cash bonus plan, no explicit PSUs for Prosor) means realizable pay is driven by stock price performance and continued service; company-level PVP disclosure emphasizes IFP and Adjusted EBITDA, but individual award metrics for Prosor are time-based .