Shai Wininger
LemonadeAbout Shai Wininger
Shai Wininger, age 51, is Co‑Founder, President, and a non‑independent director of Lemonade (LMND). He has served on the board since June 2015 and returned to the President role effective January 1, 2024 after a period as Co‑CEO, focusing on strategy, operations, product/technology, and customer experience . 2024 operating performance showed gross written premium +26% YoY to $929.0M, total revenue +22% to $526.5M, and net loss improved to $(202.2)M from $(236.9)M; pay programs are heavily equity‑based with no annual cash bonus, aligning incentives with long‑term value creation . Pay‑versus‑performance data shows cumulative TSR since IPO translating a $100 initial investment to $45 in 2024 and peer index at $190, with Adjusted EBITDA at $(150)M and In‑Force Premium at $944M .
Key performance metrics (context)
| Metric | 2023 | 2024 |
|---|---|---|
| Gross Written Premium ($M) | 738.4 | 929.0 |
| Total Revenue ($M) | 429.8 | 526.5 |
| Net Loss ($M) | (236.9) | (202.2) |
Pay vs Performance highlights
| Measure | 2022 | 2023 | 2024 |
|---|---|---|---|
| Company TSR ($100 initial) | 17 | 20 | 45 |
| Peer Group TSR ($100 initial) | 141 | 153 | 190 |
| Net Income ($M) | (297.8) | (236.9) | (202.2) |
| In‑Force Premium ($M) | 625 | 747 | 944 |
| Adjusted EBITDA ($M) | (225) | (173) | (150) |
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Lemonade, Inc. | Co‑Founder; various roles incl. Co‑CEO, CTO, Secretary, Treasurer; currently President | 2015–present | Foundational leadership across product/tech and operations; board service since 2015 |
| Fiverr Ltd. | Founder; Chief Technology Officer | 2009–2010s (founded in 2009) | Built engineering, design, product; scaled marketplace platform |
| Mobideo Aerospace | Senior Management | 2005–2010 | Led industrial analytics/control platform development |
| Handsmart Software | Senior Management | 2003–2005 | Built mobile licensing platform for content apps |
| Trimus Inc. | Senior Management | 1999–2003 | Built virtual reality web browser; early tech innovation |
| Neri Bloomfield Academy of Design and Education | Resident Faculty (Computer Graphics) | 2002–2007 | Academic leadership; technical instruction |
External Roles
The proxy does not disclose current public company board service for Shai Wininger beyond Lemonade directorship .
Fixed Compensation
| Component | 2022 | 2023 | 2024 |
|---|---|---|---|
| Base Salary ($) | 375,225 | 392,732 | 492,887 |
| Bonus ($) | — | — | — (no annual cash incentive) |
| Options (Grant‑date fair value, $) | 7,541,200 | 1,209,932 | 3,175,367 |
| Stock Awards (RSUs, Grant‑date fair value, $) | — | — | 149,698 |
| All Other Compensation ($) | 159,088 | 148,885 | 173,070 |
| Total ($) | 8,075,513 | 1,751,549 | 3,991,022 |
Notes:
- All other compensation includes Israeli pension, severance, disability, education fund contributions and car allowance; 2024 detail for Wininger totals $173,070 .
- The company states NEOs currently do not receive annual cash incentives .
Performance Compensation
2024 equity grants and vesting
| Grant Date | Award Type | Shares/Options | Exercise Price | Vesting |
|---|---|---|---|---|
| 02/02/2024 | RSUs | 9,327 | — | 16 equal quarterly installments over 4 years |
| 06/23/2024 | Stock Options | 133,572 | $15.90 | 16 equal quarterly installments over 4 years |
| 08/12/2024 | Stock Options | 167,130 | $15.02 | 16 equal quarterly installments over 4 years |
- 2024 executive equity awards largely time‑based; the company emphasizes equity as ~80% of target compensation and no cash bonus program in 2024 .
Notable performance‑conditioned legacy option (exercisability gates)
| Award | Metric | Targets (Average Closing Price for any 30 consecutive days) | Exercisability | Forfeiture Provision |
|---|---|---|---|---|
| 04/21/2021 options (PEOs) | Stock price hurdles | $126, $162, $198, $234 (each gate = 25%) | Portions become exercisable upon meeting price gates by April 21, 2025 | Any portion not exercisable by Apr 21, 2025 automatically forfeited |
2024 realized activity
| Item | Quantity | Value |
|---|---|---|
| RSUs vested in 2024 | 2,331 shares | $60,481 (at vest dates) |
| Options exercised in 2024 | 0 | $0 |
Equity Ownership & Alignment
| Holder | Beneficial Shares | % of Outstanding | Breakdown within 60 days (as of Apr 10, 2025) |
|---|---|---|---|
| Shai Wininger | 4,457,356 | 6.1% | 583 RSUs to vest; 1,073,114 options exercisable/will become exercisable |
- Shares outstanding: 73,266,170 as of the Record Date (Apr 10, 2025) .
- Insider trading policy prohibits short sales, hedging, margin purchases, and pledging LMND stock; no pledges disclosed and pledging prohibited, reducing alignment risk .
- 2024 RSU vest cadence implies modest, regular supply; options are time‑vested but require exercise to create sellable shares; Wininger did not exercise options in 2024, indicating limited near‑term selling from options .
Employment Terms
| Term | Summary |
|---|---|
| Employment agreement | Amended & Restated July 7, 2020; at‑will; original agreement July 1, 2015 |
| Base salary history | NIS 55,000/mo → NIS 80,000 (Mar 2018) → NIS 105,000 (May 2021) → NIS 152,000 (Sep 2023) |
| Benefits | Company contributions to Managers Insurance Plan (13.3%), provident fund, and 7.5% to education fund (employee contributes 2.5%) |
| Severance (no CIC) | 6 months base salary + 50% of target bonus + acceleration of 6 months’ vesting (subject to release) |
| Severance (CIC window) | 12 months base salary + 100% of target bonus + full acceleration of outstanding equity (subject to release) |
| “Cause” definition | Includes breach of agreement/fiduciary duties (with 7‑day cure), felony involving moral turpitude, willful failure to perform causing significant adverse effect |
Estimated potential payments (as of Dec 31, 2024):
| Scenario | Cash | Equity Acceleration | Healthcare/Other | Total |
|---|---|---|---|---|
| Termination w/o Cause (no CIC) | $246,444 | $69,497 | — | $315,941 |
| Termination w/o Cause in CIC window | $492,887 | $389,077 | — | $881,964 |
Governance protections:
- Clawback policy compliant with SEC Rule 10D‑1/NYSE listing standards for restatements; recovers erroneously awarded incentive compensation over prior 3 fiscal years .
- No tax gross‑ups for compensation or parachute excise taxes .
Board Governance
- Role: Class II Director; up for election to serve through 2028 Annual Meeting .
- Independence: Not independent (executive officer); independent directors are Eisenberg, Haj‑Yehia, Schwartz, Angelidis‑Smith .
- Committees: Standing committees (Audit; Compensation; Nominating & Corporate Governance) comprised of independent directors; Wininger does not serve on committees .
- Board leadership: Combined CEO/Chair (Daniel Schreiber) with Lead Independent Director (Michael Eisenberg) providing counterbalance .
- Executive sessions: Non‑management directors meet without management at least twice per year; presided by Lead Independent Director .
- Attendance: Six board meetings in 2024; each director attended ≥75% of board and committee meetings during their service period .
Director Compensation
Non‑employee director policy (not applicable to Wininger as an employee director):
- Annual cash fees: Board $20,000; Audit Chair $20,000/Audit member $7,500; Comp Chair $10,000/Comp member $5,000; Nominating Chair $7,500/Nominating member $3,500 .
- Equity: Initial RSU grant $175,000 (3‑year annual vesting); annual RSU $150,000 (1‑year vesting); accelerated upon change in control .
Compensation Peer Group (2024)
Companies used for benchmarking include Affirm, Alteryx, Enova, Envestnet, EverQuote, Fiverr International, Hippo, LendingClub, LendingTree, MoneyLion, nCino, NerdWallet, Oscar Health, PagerDuty, Q2 Holdings, Root, SelectQuote, SoFi, Trupanion, Upstart; selected based on fintech/insurtech focus, revenue $250M–$2B, market cap $200M–$3.6B .
Say‑on‑Pay & Shareholder Feedback
- 2024 advisory vote approval: ~87.5% “For,” an improvement vs. 2023, indicating shareholder support for program design .
- Annual say‑on‑pay cadence adopted; next vote expected at 2026 meeting .
Additional Compensation Program Features
- Equity plan capacity: 2020 Plan with evergreen up to 5% of outstanding shares annually through 2030; legacy 2015 Plan maintained for outstanding awards; assumed Metromile plans with 404,207 awards settled in LMND stock .
- Outstanding equity at 12/31/2024 across plans: 9,376,193 options and 4,278,383 RSUs outstanding .
- Grant timing: Committee grants RSUs annually post‑meeting for non‑employee directors; off‑cycle grants possible; no timing of MNPI to affect award values .
Trading Signal Considerations
- Near‑term supply from vesting: Wininger has 583 RSUs scheduled to vest within 60 days of Apr 10, 2025 and significant options scheduled to become exercisable within 60 days (1,073,114), but options require voluntary exercise; policy prohibits hedging/pledging which reduces forced selling risk .
- 2024 realized sales pressure: No option exercises by Wininger; RSU vesting relatively small (2,331 shares, $60,481) .
Investment Implications
- Alignment: Heavy equity mix (no annual cash bonus) and prohibitions on hedging/pledging align Wininger’s incentives with long‑term equity value; performance‑gated legacy options reinforce stock price discipline .
- Retention/Change‑in‑Control: Moderate severance (6 months) and robust CIC protection (12 months salary + 100% bonus + full acceleration) indicate balanced retention economics; acceleration terms could increase share supply in a transaction scenario .
- Selling pressure: 2024 activity shows limited realized selling from Wininger (no option exercises), suggesting low near‑term insider sell pressure absent significant option exercises; regular RSU vesting is small and predictable .
- Governance: Dual executive/director role (non‑independent) mitigated by independent committees, Lead Independent Director, and executive sessions; combined CEO/Chair persists, but board asserts appropriateness given strategy execution needs .
- Performance vector: Strong growth in GWP and revenue with improving net loss; yet TSR since IPO lags insurance peer index, making equity‑heavy pay sensitive to stock recovery; monitoring Adjusted EBITDA trajectory and price‑gate outcomes on legacy options informs confidence signals .