LMND Lemonade, Inc.

NYSE
$49.40

Lemonade, Inc. (LMND) Insider Activity

What the officers, directors and large holders did with their own shares. Only open-market purchases and sales count toward the totals — grants, option exercises and shares withheld for tax are compensation mechanics, not decisions, and they're listed separately below.

30D 90D 6M 1Y
Insider signal In line Selling ran in line with LMND's own trailing one-year pace, with 77% of sale value under a prearranged plan.
Cluster activity 0 buyers in the last 30 days 0 buyers in the last 90 days 3 sellers in the last 90 days
Insiders buying
1
2 transactions
Insiders selling
6
37 transactions
Purchases
$485.5K
8,740 shares
Sales
$37.7M
466,216 shares
Net activity
-$37.2M
purchases less sales

How much of that selling was preplanned? 77% planned / 23% discretionary

10b5-1 plan sales $29.2M 16 transactions · 345,390 shares
Discretionary sales $8.5M 21 transactions · 120,826 shares

Largest single sale: $12.0M.

Where they traded

Buy Sell Dot area is proportional to transaction value.

Last open-market purchase: March 10, 2026 , by Angelidis-Smith Maria .

Recent open-market activity

Date Insider Role Action Shares Price Value Held after
Peters John Sheldon Chief Insurance Officer Sell 10b5-1 2,249 $54.45 $122.5K 73,834 −3% of holding
BIXBY TIMOTHY E Chief Financial Officer Sell 1,893 $54.63 $103.4K 172,370 −1.1% of holding
Prosor Maya Chief Business Officer Sell 1,040 $54.63 $56.8K 186,533 −0.6% of holding
Peters John Sheldon Chief Insurance Officer Sell 859 $54.63 $46.9K 76,083 −1.1% of holding
Peters John Sheldon Chief Insurance Officer Sell 11,000 $52.55 $578.1K 76,942 −12.5% of holding
BIXBY TIMOTHY E Chief Financial Officer Sell 10b5-1 73,000 $79.18 $5.8M 174,263 −29.5% of holding
Peters John Sheldon Chief Insurance Officer Sell 3,444 $79.00 $272.1K 77,942 −4.2% of holding
Peters John Sheldon Chief Insurance Officer Sell 10b5-1 3,608 $52.94 $191.0K 81,386 −4.2% of holding
BIXBY TIMOTHY E Chief Financial Officer Sell 2,227 $53.17 $118.4K 247,263 −0.9% of holding
Peters John Sheldon Chief Insurance Officer Sell 1,735 $53.17 $92.2K 84,994 −2% of holding
Prosor Maya Chief Business Officer Sell 1,220 $53.17 $64.9K 187,573 −0.6% of holding
Angelidis-Smith Maria 2 fills Director Buy 8,740 $55.55 $485.5K 38,944
Peters John Sheldon Chief Insurance Officer Sell 10b5-1 3,571 $52.50 $187.5K 76,729 −4.4% of holding
BIXBY TIMOTHY E Chief Financial Officer Sell 2,135 $50.12 $107.0K 249,490 −0.8% of holding
Peters John Sheldon Chief Insurance Officer Sell 1,773 $50.12 $88.9K 80,300 −2.2% of holding
Prosor Maya Chief Business Officer Sell 223 $50.12 $11.2K 7,404 −2.9% of holding
Schreiber Daniel A. Chief Executive Officer Sell 10b5-1 9,108 $99.04 $902.1K 1,514,426 −0.6% of holding
Schreiber Daniel A. Chief Executive Officer Sell 10b5-1 126,625 $94.74 $12.0M 1,523,534 −7.7% of holding
Peters John Sheldon Chief Insurance Officer Sell 10b5-1 9,000 $90.00 $810.0K 70,228 −11.4% of holding
Peters John Sheldon Chief Insurance Officer Sell 10b5-1 10,000 $80.00 $800.0K 60,771 −14.1% of holding
Eckstein Adina Chief Operating Officer Sell 10b5-1 7,919 $84.15 $666.4K 188,391 −4% of holding
Schwartz Debra Director Sell 4,200 $83.59 $351.1K 21,567 −16.3% of holding
Eckstein Adina Chief Operating Officer Sell 10b5-1 7,919 $81.15 $642.6K 196,310 −3.9% of holding
Peters John Sheldon Chief Insurance Officer Sell 3,554 $81.00 $287.9K 70,771 −4.8% of holding
Eckstein Adina Chief Operating Officer Sell 10b5-1 29,237 $77.17 $2.3M 204,229 −12.5% of holding
Eckstein Adina 3 fills Chief Operating Officer Sell 10b5-1 41,557 $78.95 $3.3M 227,987 −15.4% of holding
Peters John Sheldon Chief Insurance Officer Sell 10b5-1 2,667 $72.37 $193.0K 74,325 −3.5% of holding
BIXBY TIMOTHY E Chief Financial Officer Sell 2,862 $72.74 $208.2K 251,625 −1.1% of holding
Peters John Sheldon Chief Insurance Officer Sell 2,677 $72.74 $194.7K 76,992 −3.4% of holding
Prosor Maya Chief Business Officer Sell 198 $72.74 $14.4K 7,627 −2.5% of holding
Peters John Sheldon Chief Insurance Officer Sell 3,798 $73.25 $278.2K 79,669 −4.6% of holding
Peters John Sheldon Chief Insurance Officer Sell 10b5-1 18,930 $72.77 $1.4M 83,467 −18.5% of holding
BIXBY TIMOTHY E Chief Financial Officer Sell 30,000 $75.51 $2.3M None left
Eckstein Adina Chief Operating Officer Sell 5,988 $78.00 $467.1K 227,987 −2.6% of holding
Eckstein Adina 2 fills Chief Operating Officer Sell 40,000 $73.02 $2.9M 227,987 −14.9% of holding

Form 4s are due within two business days of a transaction, so this is close to real time — unlike the quarterly 13F data on the Institutional tab. A single large sale often reflects a prearranged 10b5-1 plan rather than a fresh view, so read a pattern of sales rather than any one of them.