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Lemonade, Inc. planned insider sales

In the last twelve months insiders at Lemonade, Inc. filed 33 Form 144 notices of planned sales, 474,483 shares worth $38.7 million at the time of filing, from 6 sellers. The latest, filed 4 September 2026: Peters John Sheldon (officer), 2,249 shares worth $122,458, planned for around 4 September 2026 through Fidelity Brokerage Services LLC.

FiledSellerRelationshipSharesValuePlanned saleSold, per Form 4BrokerHow acquiredFiling
4 September 2026Peters John SheldonOfficer2,249$122,4584 September 20263,108 shares from 3 September 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
3 September 2026Peters John SheldonOfficer859$46,9283 September 2026None on Form 4 yetFidelity Brokerage Services LLCRestricted Stock VestingForm 144
3 September 2026Prosor MayaOfficer1,040$56,8163 September 20261,040 shares from 3 September 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
3 September 2026Bixby Timothy EOfficer1,893$103,4163 September 20261,893 shares from 3 September 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
13 August 2026Peters John SheldonOfficer11,000$578,00013 August 202611,000 shares from 13 August 2026Fidelity Brokerage Services LLCStock Option ExerciseForm 144
7 July 2026Bixby Timothy EOfficer73,000$5.8 million7 July 202673,000 shares from 7 July 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
6 July 2026Peters John SheldonOfficer3,444$272,0766 July 20263,444 shares from 6 July 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
4 June 2026Peters John SheldonOfficer3,608$191,0084 June 20265,343 shares from 3 June 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
3 June 2026Prosor MayaOfficer1,220$64,8713 June 20261,220 shares from 3 June 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
3 June 2026Peters John SheldonOfficer1,735$92,2563 June 2026No matching Form 4 saleFidelity Brokerage Services LLCRestricted Stock VestingForm 144
3 June 2026Bixby Timothy EOfficer2,227$118,4173 June 20262,227 shares from 3 June 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
4 March 2026Peters John SheldonOfficer3,571$187,4784 March 20265,344 shares from 3 March 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
3 March 2026Prosor MayaOfficer223$11,1773 March 2026223 shares from 3 March 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
3 March 2026Peters John SheldonOfficer1,773$88,8673 March 2026No matching Form 4 saleFidelity Brokerage Services LLCRestricted Stock VestingForm 144
3 March 2026Bixby Timothy EOfficer2,135$107,0113 March 20262,135 shares from 3 March 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
22 January 2026Peters John SheldonOfficer9,000$810,00022 January 20269,000 shares from 22 January 2026Fidelity Brokerage Services LLCStock Option ExerciseForm 144
22 January 2026Daniel SchreiberDirector144,000$13.9 million22 January 2026135,733 shares from 22 January 2026Goldman Sachs & Co. LLCAcquired from issuer in private transactionForm 144
6 January 2026Peters John SheldonOfficer10,000$800,0006 January 202610,000 shares from 6 January 2026Fidelity Brokerage Services LLCStock Option ExerciseForm 144
11 December 2025Schwartz DebraDirector4,200$351,08211 December 20254,200 shares from 11 December 2025Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
11 December 2025Eckstein AdinaOfficer7,919$620,61211 December 202515,838 shares from 10 December 2025Oppenheimer & Co. Inc.RSUForm 144
10 December 2025Peters John SheldonOfficer3,554$287,87410 December 20253,554 shares from 10 December 2025Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
10 December 2025Eckstein AdinaOfficer7,919$626,94710 December 202529,237 shares from 9 December 2025Oppenheimer & Co. Inc.RSUForm 144
8 December 2025Eckstein AdinaOfficer70,794$5.6 million8 December 202541,557 shares from 8 December 2025Oppenheimer & Co. Inc.Employee Stock Option Plan; RSUForm 144
3 December 2025Peters John SheldonOfficer2,667$193,0113 December 20255,344 shares from 2 December 2025Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
2 December 2025Prosor MayaOfficer198$14,4012 December 2025198 shares from 2 December 2025Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
2 December 2025Peters John SheldonOfficer2,677$194,7112 December 2025No matching Form 4 saleFidelity Brokerage Services LLCRestricted Stock VestingForm 144
2 December 2025Bixby Timothy EOfficer2,862$208,1672 December 20252,862 shares from 2 December 2025Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
24 November 2025Peters John SheldonOfficer3,798$278,20524 November 20253,798 shares from 24 November 2025Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
20 November 2025Peters John SheldonOfficer18,930$1.4 million20 November 202518,930 shares from 20 November 2025Fidelity Brokerage Services LLCRestricted Stock Vesting; Stock Option ExerciseForm 144
12 November 2025Bixby Timothy EOfficer30,000$2.3 million11 November 202530,000 shares from 11 November 2025Charles Schwab CorporationOpen Market PurchaseForm 144
10 November 2025Eckstein AdinaOfficer5,988$467,06410 November 20255,988 shares from 10 November 2025Fidelity Brokerage Services LLCOption Granted - 04/05/2022Form 144
7 November 2025Eckstein AdinaOfficer20,000$1.4 million7 November 2025No matching Form 4 saleFidelity Brokerage Services LLCOption Granted - 04/05/2022Form 144
7 November 2025Eckstein AdinaOfficer20,000$1.5 million7 November 202540,000 shares from 7 November 2025Fidelity Brokerage Services LLCOption Granted - 04/05/2022Form 144
A Form 144 is the notice an insider files with the SEC before selling restricted or control shares over the Rule 144 thresholds; it says what may be sold, not what was.
Read moreValue is the filer's own aggregate market value. Sold, per Form 4: the same seller's open-market sales on Form 4 from the notice's date to 90 days after, added up, as they appear on the insiders page; a holder who files no Form 4, such as some large holders, never shows one. What is a Form 144?