LMND insider ownership: who sold, why, and what they still hold

What stands out

Maria Angelidis-Smith bought 8.7K shares for $485K, first on Mar 10, 2026.Purchase, Mar 10, 2026

Timothy Bixby sold $2.3M of stock with no disclosed trading plan. The filings don't state a reason.Largest such sale, Nov 11, 2025

A share of stake is shown for 0 of the 6 officers and directors who sold. 12 are left out

Left out: Shai Wininger, Daniel Schreiber, Michael Eisenberg, Timothy Bixby, Adina Eckstein, John Peters, Maria Angelidis-Smith, Maya Prosor, Debra Schwartz, Samer Haj-Yehia, Prashant Ratanchandani and Geoff Seeley (share of stake is being verified).

Disclosed company stock is not an insider's whole wealth.

Who sold, and how much of their stake

Officers and directors, past 12 months. Their share of stake is being verified and is not shown yet; amounts and trading plans are below.

Daniel Schreiber

Chief Executive Officer, Director

Not confirmed

Share of stake not shown: share of stake is being verified. Why

$12.9MDisclosed plan

Adina Eckstein

Chief Operating Officer

Not confirmed

Share of stake not shown: share of stake is being verified. Why

$10.2MDisclosed plan

Timothy Bixby

Chief Financial Officer

Not confirmed

Share of stake not shown: share of stake is being verified. Why

$8.6M67% planned, 6% to cover taxes 26% no plan disclosed

John Peters

Chief Insurance Officer

Not confirmed

Share of stake not shown: share of stake is being verified. Why

$5.5M84% planned 16% no plan disclosed

Debra Schwartz

Director

Not confirmed

Share of stake not shown: share of stake is being verified. Why

$351KNo plan disclosed

All 6 sellers

Selling by month

Officers and directors, Oct 2025 to Oct 2026. Each sale is counted once: under a disclosed plan, else to cover taxes, else no plan disclosed.

Disclosed planTo cover taxesNo plan disclosedOne dollar scale for every month; the tallest bar is labeled

Recent activity

Past 30 days, Sep 17, 2026 to Oct 16, 2026

No officer or director trades were reported for the past 30 days. The most recent before that:

Sep 4, 2026John Peters sold 2.2K shares ($122K) under a disclosed trading plan.

Who	Shares	Price	% of total stake	Total stake after	Trade date	Filed
John Peters Chief Insurance Officer	2,249	$54.45	n/a	n/a	Sep 4, 2026	Sep 8, 2026

Outside holders, reported separately

SoftBank Group Capital Ltd reported no open-market sales in the past 12 months. Large shareholders and the funds or companies that board members represent are not part of management, so they are left out of the figures above.

Details

Common questions

Is the Lemonade, Inc. CEO selling stock?

Yes. Daniel Schreiber sold 136K shares ($12.9M) in the past 12 months, all of it under a trading plan disclosed in the filings.

Why are Lemonade, Inc. insiders selling?

Filings rarely give a reason, and we don't guess at one. What they show is how the sales were made: 89% of sales by value ran under 10b5-1 trading plans disclosed in the filings, 2% were to cover taxes and 9% had no disclosed plan. A trading plan schedules sales in advance.

Are any Lemonade, Inc. insiders buying?

Yes. 1 officer or director reported 2 purchases in the past 12 months (Form 4 code P; rows the filings describe as reinvested dividends, plan purchases, private deals or moves into the person's own trust are not counted).

The evidence

Who sold6 officers and directors: amount, % of holdings, trading plan

Who sold	Amount	% of holdings	Trading plan
Daniel Schreiber Chief Executive Officer, Director	$12.9M 136K shares	Not confirmed share of stake is being verified. Why	Disclosed plan
Adina Eckstein Chief Operating Officer	$10.2M 133K shares	Not confirmed share of stake is being verified. Why	Disclosed plan
Timothy Bixby Chief Financial Officer	$8.6M 112K shares	Not confirmed share of stake is being verified. Why	67% under a disclosed plan, 6% to cover taxes 26% no plan disclosed
John Peters Chief Insurance Officer	$5.5M 79K shares	Not confirmed share of stake is being verified. Why	84% under a disclosed plan 16% no plan disclosed
Debra Schwartz Director	$351K 4.2K shares	Not confirmed share of stake is being verified. Why	No plan disclosed
Maya Prosor Chief Business Officer	$147K 2.7K shares	Not confirmed share of stake is being verified. Why	To cover taxes

Outside holder, reported separately: SoftBank Group Capital Ltd (a 10% owner, not part of management). No open-market sales reported in the period. Latest filing

The full ownership picture0 of 12 officers and directors confirmed

Vested shares across all share classes, held directly and through trusts, LLCs and family members, as reported on SEC Forms 3, 4 and 5. Unvested awards and options are never counted as owned shares.

Insider

Held Oct 16, 2025

Sold

Held Oct 16, 2026

Still held

Shai Wininger

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Shai Wininger are complete.

President, Director

n/a

Vesting, gifts, unvested awards and holding lines for Shai Wininger

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Shai Wininger are complete; balances and unit counts will be added when the check is finished.

−1.9Kgifted (net of own trusts)

Stock options (not counted as shares):

Options held	Strike price	Expires	Intrinsic value (estimate)
133,572	$15.90	Jun 23, 2034	$5.1M
167,130	$15.02	Aug 12, 2034	$6.6M
127,780	$59.74	Aug 18, 2035	$0

Estimate: options held × ($54.45 − strike price), using the most recent insider trade price on Form 4 (Sep 4, 2026), not a market close.

Daniel Schreiber

Chief Executive Officer, Director

n/a

−136K

n/a

Vesting, gifts, unvested awards and holding lines for Daniel Schreiber

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Daniel Schreiber are complete; balances and unit counts will be added when the check is finished.

−35Kgifted (net of own trusts)

Stock options (not counted as shares):

Options held	Strike price	Expires	Intrinsic value (estimate)
133,572	$15.90	Jun 23, 2034	$5.1M
167,130	$15.02	Aug 12, 2034	$6.6M
127,780	$59.74	Aug 18, 2035	$0

Estimate: options held × ($54.45 − strike price), using the most recent insider trade price on Form 4 (Sep 4, 2026), not a market close.

Michael Eisenberg

Director

n/a

Vesting, gifts, unvested awards and holding lines for Michael Eisenberg

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Michael Eisenberg are complete; balances and unit counts will be added when the check is finished.

−5Kgifted (net of own trusts)

Timothy Bixby

Chief Financial Officer

n/a

−112K

n/a

Vesting, gifts, unvested awards and holding lines for Timothy Bixby

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Timothy Bixby are complete; balances and unit counts will be added when the check is finished.

−6Kgifted (net of own trusts)

Stock options (not counted as shares):

Options held	Strike price	Expires	Intrinsic value (estimate)
277,300	$23.69	Sep 25, 2029	$8.5M
178,890	$15.90	Jun 23, 2034	$6.9M
127,780	$59.74	Aug 18, 2035	$0

Estimate: options held × ($54.45 − strike price), using the most recent insider trade price on Form 4 (Sep 4, 2026), not a market close.

Adina Eckstein

Chief Operating Officer

n/a

−133K

n/a

Vesting, gifts, unvested awards and holding lines for Adina Eckstein

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Adina Eckstein are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Stock options (not counted as shares):

Options held	Strike price	Expires	Intrinsic value (estimate)
4,514	$44.57	Dec 6, 2031	$45K
7,074	$27.35	Apr 5, 2032	$192K
71,556	$15.90	Jun 23, 2034	$2.8M
54,417	$55.13	Mar 8, 2036	$0

Estimate: options held × ($54.45 − strike price), using the most recent insider trade price on Form 4 (Sep 4, 2026), not a market close.

John Peters

Chief Insurance Officer

n/a

−79K

n/a

Vesting, gifts, unvested awards and holding lines for John Peters

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for John Peters are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Stock options (not counted as shares):

Options held	Strike price	Expires	Intrinsic value (estimate)
10,000	$5.26	Mar 27, 2028	$492K
25,556	$59.74	Aug 18, 2035	$0

Estimate: options held × ($54.45 − strike price), using the most recent insider trade price on Form 4 (Sep 4, 2026), not a market close.

Maria Angelidis-Smith

Director

n/a

Vesting, gifts, unvested awards and holding lines for Maria Angelidis-Smith

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Maria Angelidis-Smith are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Maya Prosor

Chief Business Officer

n/a

−2.7K

n/a

Vesting, gifts, unvested awards and holding lines for Maya Prosor

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Maya Prosor are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Stock options (not counted as shares):

Options held	Strike price	Expires	Intrinsic value (estimate)
80,000	$23.69	Dec 1, 2029	$2.5M
100,000	$18.17	Feb 7, 2033	$3.6M
49,800	$27.35	Apr 5, 2032	$1.3M
83,700	$15.13	Aug 11, 2033	$3.3M
28,500	$79.30	Sep 2, 2031	$0
65,000	$19.03	Jul 14, 2032	$2.3M
14,800	$44.57	Dec 6, 2031	$146K
5,000	$94.07	Mar 10, 2031	$0
95,408	$15.90	Jun 23, 2034	$3.7M
45,000	$18.14	Sep 9, 2034	$1.6M
76,668	$59.74	Aug 18, 2035	$0

Estimate: options held × ($54.45 − strike price), using the most recent insider trade price on Form 4 (Sep 4, 2026), not a market close.

Debra Schwartz

Director

n/a

−4.2K

n/a

Vesting, gifts, unvested awards and holding lines for Debra Schwartz

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Debra Schwartz are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Samer Haj-Yehia

Director

n/a

Vesting, gifts, unvested awards and holding lines for Samer Haj-Yehia

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Samer Haj-Yehia are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Prashant Ratanchandani

Director

n/a

Vesting, gifts, unvested awards and holding lines for Prashant Ratanchandani

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Prashant Ratanchandani are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Geoff Seeley

Director

n/a

Vesting, gifts, unvested awards and holding lines for Geoff Seeley

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Geoff Seeley are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Holdings and share of stake for Lemonade, Inc. are being verified, so no balances, unit counts or percentages are shown. Sales, proceeds, plan and tax status, titles and dates come straight from individual filings.

What explains the selling$37.7M of sales by plan status, purpose, seller and month

Officer and director open-market sales: $37.7M across 466,216 shares. Plan status and stated purpose are separate questions, and a sale can have both.

By plan status

Disclosed plan · $33.6M · 89%

11%

The lighter segment is sales with no plan disclosed in the filing ($4.2M), including tax-related sales outside a plan.

No plan disclosed · $3.5M

Sales with no 10b5-1 plan and no tax reference in the filing. $2.3M of it is Timothy Bixby. No plan disclosed is a statement about the filing, not about why the sale happened. Largest such sale: Timothy Bixby, Nov 11, 2025

Taxes

$1.1M of sales (2.9%) cite tax obligations in their footnotes, $423K of them also under a plan. Example: Maya Prosor, Sep 3, 2026

Purchases · 1 buyer (2 trades)

1 officer or director bought shares in this period, in 2 trades(Form 4 code P, leaving out rows the filings describe as reinvested dividends, plan purchases, private deals or moves into the person's own trust). Across all their filings on record there are 7 purchase trades.

Charitable gifts · 6K shares

Gifts the filings describe as charitable. Gifts are not sales and are not included in the sale totals.

Seller	Shares sold	Proceeds	Under a disclosed plan	Share of total	Sales dates
Daniel Schreiber Chief Executive Officer, Director	136K	$12.9M	100%	34%	Jan 22, 2026 to Jan 23, 2026
Adina Eckstein Chief Operating Officer	133K	$10.2M	100%	27%	Nov 7, 2025 to Dec 11, 2025
Timothy Bixby Chief Financial Officer	112K	$8.6M	67%	23%	Nov 11, 2025 to Sep 3, 2026
John Peters Chief Insurance Officer	79K	$5.5M	84%	15%	Nov 20, 2025 to Sep 4, 2026
Debra Schwartz Director	4.2K	$351K	0%	0.9%	Dec 11, 2025 to Dec 11, 2025
Maya Prosor Chief Business Officer	2.7K	$147K	0%	0.4%	Dec 2, 2025 to Sep 3, 2026

Sales by month

Month	Sale proceeds	Disclosed plan	To cover taxes	No plan disclosed
Oct 2025	$0	$0	$0	$0
Nov 2025	$7.3M	$5.0M	$0	$2.3M
Dec 2025	$8.1M	$7.2M	$223K	$639K
Jan 2026	$14.5M	$14.5M	$0	$0
Feb 2026	$0	$0	$0	$0
Mar 2026	$395K	$276K	$118K	$0
Apr 2026	$0	$0	$0	$0
May 2026	$0	$0	$0	$0
Jun 2026	$467K	$283K	$183K	$0
Jul 2026	$6.1M	$6.1M	$0	$0
Aug 2026	$578K	$0	$0	$578K
Sep 2026	$330K	$169K	$160K	$0
Oct 2026	$0	$0	$0	$0

Is this normal? Selling year by year5 earlier years to compare with

In line with the past 5 years. 6 insiders sold; the average is 4 a year.

12 months ending	Shares sold	Insiders who sold	Proceeds
Oct 16, 2026 Latest 12 months	466K	6	$37.7M
Oct 16, 2025 1 year earlier	295K	5	$13.2M
Oct 16, 2024 2 years earlier	13K	3	$231K
Oct 17, 2023 3 years earlier	16K	2	$317K
Oct 17, 2022 4 years earlier	49K	3	$2.4M
Oct 17, 2021 5 years earlier	1.94M	8	$217M

Open-market sales (Form 4 code S) by people who were officers or directors, in split-adjusted shares. Earlier years include people who have since left. A sale that an outside holder also reports (a family trust, a fund) is counted with outside holders in every year. Shares, not dollars, are compared, so a change in the stock price doesn't look like a change in selling. Years the filings don't fully cover are shown but left out of the average.

Known gaps and uncertainty12 officers and directors not confirmed

Holdings and share of stake are being verified. Balances, unit counts and every share-of-stake figure for Lemonade, Inc. are held back until that check is finished. Sales, proceeds, plan and tax status, titles and dates come straight from individual filings and are complete.

External context: we only cite outside events when a documented connection exists. None is shown for this period.

Sources and methodology256 filings on record, 48 filed in the 12-month period, and how we read them

All 256 Forms 3, 4 and 5 on record for Lemonade, Inc. (SEC CIK 1691421), filed from Jul 2, 2020 to Sep 8, 2026; 48 of them were filed in the 12 months this page covers, retrieved from SEC EDGAR on Oct 16, 2026. Prices are the ones reported in each filing, often weighted averages.

Holdings. Each holding line (a share class plus an owner, such as a trust or LLC) carries its last reported balance forward. Entities first reported during the period start at zero, so transfers between an insider's own trusts don't count as selling. Lines not reported for three years or more are listed separately and left out of totals.

Sales. A sale counts as under a 10b5-1 plan if its footnote cites one or the filing's Rule 10b5-1 box is checked, and as tax-related if its footnote cites tax obligations or sell-to-cover. Shares withheld by the company for taxes are listed separately. Sales with neither attribute are labeled "no plan disclosed".

Full methodology

Former or inactive filers (14)No filing in 18 months; last reported balances, not in any total

Name	Last filed	Last reported balance
Mwashuma Nyatta	Jun 26, 2024	23,989,957 shares, last reported balance as of Jun 24, 2024
Silvija Martincevic	Jun 9, 2023	18,462 shares, last reported balance as of Jun 7, 2023
Irina Novoselsky	Jun 9, 2023	18,462 shares, last reported balance as of Jun 7, 2023
Alex Clavel	Apr 4, 2023	No balance on record
Jorge Espinel	Dec 8, 2021	No balance on record
Joel Cutler	Jun 4, 2021	12,868 shares, last reported balance as of Jun 2, 2021
Joel Cutler	Jun 4, 2021	1,506,722 shares, last reported balance as of Jun 2, 2021
Becker Seidman	Mar 17, 2021	No balance on record
Haim Sadger	Mar 12, 2021	386,688 shares, last reported balance as of Mar 10, 2021
Haim Sadger	Mar 12, 2021	No balance on record
George Hutton	Jan 21, 2021	15,000 shares, last reported balance as of Jan 19, 2021
Aleph, L.P.	Jul 8, 2020	4,539,063 shares, last reported balance as of Jul 7, 2020
SC ISRAEL VENTURE V (TTGP), LTD.	Jul 8, 2020	4,539,063 shares, last reported balance as of Jul 7, 2020
General Catalyst Group Management Holdings GP, LLC	Jul 8, 2020	3,222,313 shares, last reported balance as of Jul 7, 2020

Spotted something wrong on this page? Report an error. We check every report against the SEC filing and list what we fix in the corrections log.

Lemonade, Inc. insiders sold $37.7M in the past 12 months. How much of their stake is that?

What stands out

Who sold, and how much of their stake

Selling by month

Recent activity

Outside holders, reported separately

Common questions

Is the Lemonade, Inc. CEO selling stock?

Why are Lemonade, Inc. insiders selling?

Are any Lemonade, Inc. insiders buying?

The evidence

No plan disclosed · $3.5M

Taxes

Purchases · 1 buyer (2 trades)

Charitable gifts · 6K shares

Sales by month