Shai Wininger compensation by year
Lemonade Summary Compensation Table · all 7 fiscal years held| Component | FY2019 | FY2020 | FY2021 | FY2022 | FY2023 | FY2024 | FY2025 |
|---|---|---|---|---|---|---|---|
| Salary | $266,667 | $278,969 | $359,128 | $375,225 | $392,732 | $492,887 | $528,242 |
| Bonus | $0 | $0 | — | $0 | — | $0 | $0 |
| Stock awards | $0 | $0 | — | $0 | — | $149,698 | $0 |
| Option awards | $0 | $0 | $21,031,500 | $7,541,200 | $1,209,932 | $3,175,367 | $5,398,705 |
| Non-equity incentive | $0 | $0 | — | $0 | — | $0 | $0 |
| Pension and deferred compensation | $0 | $0 | — | $0 | — | $0 | $0 |
| All other | $93,168 | $98,284 | $143,902 | $159,088 | $148,885 | $173,070 | $185,786 |
| Total | $359,835 | $377,253 | $21,534,530 | $8,075,513 | $1,751,549 | $3,991,022 | $6,112,733 |
Each year as stated in that year's proxy. A dash means the company reported no figure in that column. Source: Lemonade, Inc. DEF 14A filed April 22, 2026, accession 0001691421-26-000024, and prior-year filings. Open the filing on EDGAR.
How this page was built: the Lemonade, Inc. filed document, accession 0001691421-26-000024. Every figure is read from that document and cited to the page and table it appears in. Filed April 22, 2026.
Equity holdings
unvested awards at FY2025 year-end| Type | Unvested units | Value at year-end | Exercise price |
|---|---|---|---|
| RSU | 4,664 | $331,984 | — |
| Option | 117,132 | — | $59.74 |
| Option | 97,493 | — | $15.02 |
| Option | 93,750 | — | $30.89 |
| Option | 51,275 | — | $15.13 |
| Option | 66,786 | — | $15.90 |
Per the Outstanding Equity Awards at Fiscal Year-End table in Lemonade, Inc.'s FY2025 proxy; value at the fiscal year-end close, as the company printed it.
Insider transactions since the last proxy
1 Form 4 line since the FY2025 proxy (filed April 22, 2026)current to 2026-11-10 · updated nightly
| Date | Transaction | Plan | Shares | Price | Held after |
|---|---|---|---|---|---|
| 2026-09-02 | Gift | — | 1,876 | $0.00 | 4,416,873 |
The 1 most recent of 1 lines, each as reported on the Form 4. "10b5-1" marks a trade the filing reports under a pre-arranged trading plan. View every Form 4 filing on EDGAR →
Change-in-control & termination
estimated payments Lemonade discloses, by trigger · FY2025| Trigger | Cash severance | Accelerated equity | Benefits continuation | Total as disclosed |
|---|---|---|---|---|
| Change in control, no termination | $0 | $0 | $0 | $0 |
| Change in control and involuntary termination | $528,242 | $17,490,262 | $0 | $18,018,504 |
| Involuntary termination without cause | $264,121 | $7,190,466 | $0 | $7,454,587 |
Per the Potential Payments Upon Termination or Change in Control table in Lemonade, Inc.'s FY2025 proxy. Estimates as the company printed them; a dash means it printed no figure.
Lemonade’s named executive officers, FY2025
as the company reported each| Named executive officer | Role | FY2025 total |
|---|---|---|
| Shai Wininger · this page | Co-Founder and President | $6,112,733 |
| Tim Bixby | Chief Financial Officer and Treasurer | $6,097,705 |
| Daniel Schreiber | Co-Founder and Chief Executive Officer | $6,076,514 |
| Maya Prosor | Chief Business Officer | $3,639,223 |
| Adina Eckstein | Chief Operating Officer | $2,796,689 |
| John Peters | Chief Insurance Officer | $1,298,453 |
Board service
Lemonade board · FY2021–FY2025How this board is paid
Company policy: Lemonade pays directors a $30,000 cash retainer and $150,000 in equity. As stated in Lemonade's FY2025 proxy.
Shai Wininger's compensation dossier, Lemonade
You have read Shai Wininger's totals and holdings. The dossier adds each equity grant Lemonade disclosed for Shai Wininger and Lemonade's own disclosed peer group, where the company discloses them, with every row in a PDF and a CSV cited to its filing.
See an example →The full Lemonade compensation record
free company briefThis page is one person within Lemonade's record. The company brief lists every named executive, each linking to their own page.
Peer companies
named in the Lemonade proxy · each links to its own free briefCompensation, the day it’s disclosed
The CompBrief Daily Digest lists the newest executive and director compensation disclosures as companies file them. Or order Lemonade's full Executive Compensation Report with peer benchmarking.
How this record is built
Every figure on this page is one figure from a public SEC filing, printed as the filing states it and cited to the document. Compensation totals are Lemonade's own disclosed totals, not summed by Velarion. Insider transactions are read from Form 4 filings and cover every line filed since the most recent proxy. Nothing is estimated by Velarion; where the company does not disclose a value the cell reads "—", and a section appears only where the company discloses the data. Corrections: records@velarion.ai.
Order LMND
Add the email the receipt and the PDF go to, then press the report you want. Each button opens its own card payment on Stripe.