TOST Toast, Inc. Insider Trading

General Counsel Elworthy sells 108,000 shares ($2.8M) via 10b5-1 plan at TOST; holds 125,755 option shares after

Brian R Elworthy, General Counsel at Toast, executed 2 separate sales totaling 108,000 shares for $2,796,029.88 on 2026-05-29, reducing his non-derivative holdings from 297.6K to 189.6K shares. This is a scheduled transaction under a 10b5-1 trading plan adopted on 2026-02-27, meaning it reflects a pre-arranged schedule rather than a discretionary decision. The 30-day return following his prior TOST sales has averaged between -0.8% and +33.6%, with mixed outcomes, while his cross-ticker track record shows prior sells followed by +10.2% average 30-day returns. The stock is currently -50.0% from its 52-week high of $49.66 and trading at $24.82, below the blended sale price of $25.89.

Fredette (TOST President) sold 19,627 shares at $28.00 on 2024-09-24; held 2.08M shares post-sale.

Fredette sold 19,627 shares at $28.00, reducing holdings by 0.9% to 2,078,682 shares. This sale occurs against a backdrop of recent frequent trades at TOST: five prior trades across Sept 12–23, all sales, with outcomes not yet measurable. His cross-ticker track record shows a 100% well-timed rate on prior sells (10 trades, avg 90d return -27.6%), though this metric reflects outcomes measured after those prior transactions and does not yet apply to this Sept 24 sale. The stock has risen 10.4% over 30 days and 6.0% over 90 days, currently trading at $27.33, near the 52-week high of $27.99. TOST fundamentals show strong revenue growth of 41.5% year-over-year to $1.2B quarterly revenue, offset by a full-year net loss despite the $14.0M net income in the latest quarter.

Toast President Fredette sold 152,295 shares for $4.2M at $27.38 avg (Sept 20–23) as stock hits 52-week high

Stephen Fredette, President of Toast, executed 2 separate sales totaling 152,295 shares for $4,169,336.07 on 2024-09-20 and 2024-09-23. The sales occurred as TOST reached its 52-week high of $27.99, coinciding with a +18.2% surge over the prior 30 days and +8.8% over 90 days. His post-transaction holdings remain substantial at 2,098,309 shares (2.10M shares), representing a -6.8% reduction versus his prior position of 2,250,604 shares. This transaction occurs against a backdrop of strong recent company performance (revenue growth of +41.5% annually, quarterly revenue of $1,242,000,000.00), though Toast remains unprofitable on a full-year basis with net income of $14,000,000.00 in the latest quarter against negative full-year net income.

TOST President sells 40,948 shares over 2 days at $27.00–$27.03; stock at 52-week high

Fredette Stephen, President of Toast, Inc., executed two separate sales totaling 40,948 shares for $1,106,921.68, reducing his post-transaction holdings to 2,304,737 shares (-1.7% vs pre-transaction). The sales occurred on 2024-09-18 and 2024-09-19 at prices ($27.00 and $27.03 blended to $27.03) that align with the stock's current price of $27.71 at the 52-week high (+0.0% from high). His cross-ticker track record shows 7 prior sells with a 90d well-timed rate of 100.00% (avg 90d return: -27.6%), indicating his sales historically preceded price declines; however, at TOST specifically, 5 prior trades remain too recent to assess 90d outcomes. The company reported revenue growth of +41.5% year-over-year and recent quarterly revenue of $1,242,000,000.00, but remains unprofitable on a full-year basis (full-year net income was negative). The timing of these sales at the stock's 52-week peak and the President's demonstrated ability to time sales historically at other tickers merit investor attention, though the modest 1.7% reduction in his TOST holdings suggests this is not a dramatic conviction shift.

Director Comparato sold 115,000 TOST shares (48.9% of holdings) for $3.1M at $26.65 on 2024-09-17

Director Christopher P Comparato executed a substantial sale of 115,000 shares at $26.65, reducing his stake from 235,107 to 120,107 shares—a 48.9% reduction in holdings. The sale occurred near the 52-week high of $27.71, with the stock currently at $26.31. At the same-ticker level, Comparato's prior TOST sales in June, July, and August have produced mixed 30-day returns (ranging from -8.7% to +9.6%), with only 0 of 1 measurable 90-day outcomes showing a decline after his sales. His cross-ticker track record shows 13 prior sells with a 44.44% well-timed rate and average negative 90-day returns of -1.7%, suggesting modest predictive value. Against broader context: Toast reported $1.2B in revenue with +41.5% annual growth, yet the company was unprofitable over its most recent full fiscal year. The combination of significant share reduction and timing near recent highs warrants attention to whether this represents a material shift in insider conviction at a growth-stage but unprofitable software company.

President Fredette Stephen sells 101,574 shares (101.6K) at $25.57–$26.09 for $2,613,261.16 ($2.6M)

Fredette Stephen, President of Toast, Inc., executed 2 separate sales totaling 101,574 shares for $2,613,261.16 on 2024-09-12, reducing his holdings to 2,345,685 shares (-4.2% vs pre-transaction holdings). The blended average price of $25.73 sits near the current price of $26.19 and within 5.5% of the 52-week high of $27.71, suggesting the sales occurred near recent resistance. Toast's fundamentals show strong growth—annual revenue growth of +41.5% and latest quarterly revenue of $1,242,000,000.00—yet the company remains unprofitable on a full-year basis, which adds complexity to valuation. His cross-ticker track record demonstrates strong prior timing (4 prior sells with a 100.00% well-timed rate at the 90-day mark; avg 90d return of -27.6%), and same-ticker history corroborates this pattern: 2 of 2 prior TOST sells at the 90-day mark were well-timed (2023-07-13 sales with -27.0% and -28.1% post-sale declines). The convergence of material transaction size, strong historical timing accuracy, and unprofitable revenue growth trajectory warrant attention.

Toast President sold 310,112 shares for $7.4M in two transactions; stock +5.4% in 30 days post-sale.

Fredette Stephen, President of Toast, Inc., filed two separate open-market sales on 2024-09-10 and 2024-09-11, totaling 310,112 shares for $7,449,552.39 at a blended average price of $24.02. Post-transaction, he holds 2,497,259 shares, representing an 11.0% reduction in his stake at the time of sale. The stock has since appreciated to $26.09 (current price), outpacing the blended sale price by approximately $2.07 per share. Across his cross-ticker track record, his prior 4 sales posted a 90-day well-timed rate of 100.00%, but his same-ticker history at TOST shows only 2 prior measurable sells (both from 2023) with negative 90-day returns of -27.0% and -28.1%—consistent with well-timed timing. However, the current 30-day price action (+5.4%) contradicts that historical pattern at this ticker, suggesting the recent sales may not have preceded a decline as his prior TOST sales did.

Director Comparato sells 100,000 shares at $24.35 avg; stock down -11.7% in 30d, -4.6% in 90d

Director Christopher P Comparato executed 2 separate sales totaling 100,000 shares (100.0K shares) for $2,434,744.00 ($2.4M) at a blended average price of $24.35, reducing his holdings by 45.4% from 220,107 shares (220.1K shares) to 120,107 shares (120.1K shares). The timing of this sale is notable given that TOST has fallen -11.7% in the 30 days since and -4.6% in the 90 days since the transaction, while the current price of $24.21 sits -12.6% from the 52-week high and within a 52-week range of $13.81–$27.71. Across his cross-ticker track record, Comparato has executed 11 prior sells with an average 90-day return of -4.6% and a well-timed rate of 57.14%, but at TOST specifically, his 1 measurable prior 90-day outcome (a sale on 2023-12-15) returned +42.8%—a poorly-timed sell in retrospect. The company reported $1.2B in latest quarterly revenue and +41.5% annual revenue growth, but remains unprofitable at the full-year level, which may be weighing on investor sentiment.

Director Comparato sells 90,000 TOST shares for $2,388,879.30; now holds 112,282 shares (-44.5%)

Christopher P Comparato, a director, executed 2 separate sales totaling 90,000 shares for $2,388,879.30 on 2024-07-17, reducing his holdings by 44.5% to 112,282 shares. The sales occurred at blended average price of $26.54, while the stock currently trades at $27.17 and is up 25.7% over 90 days. At this same ticker (TOST), Comparato's prior 5 trades show mixed timing outcomes: 3 measurable sales from 2023–2024 had 90-day returns of +42.8%, +44.7%, and +0.9%, meaning 0 of 3 were well-timed by the sell standard (negative 90-day return post-sale). This substantial reduction in holdings, combined with the stock's strong recent momentum and the company's unprofitable state despite 41.5% annual revenue growth, merits investor attention to confirm whether this sale reflects board-level strategic repositioning or other material factors not yet disclosed.

CRO Vassil Jonathan sold 100.0K TOST shares at $25.55 (-75.8% of holdings); stock now $27.30 (+20.2% in 30d)

Vassil Jonathan, Toast's Chief Revenue Officer, sold 100,000 shares (100.0K shares) at $25.55 on 2024-07-15, reducing his holdings by 75.8% to 31,919 shares (31.9K shares) and raising $2,555,400.00 ($2.6M). The sale occurred at a price that was 6.4% below the current price of $27.30, which itself has appreciated 20.2% over the prior 30 days. His cross-ticker track record shows a well-timed rate of 25.00%, indicating a mixed ability to time sales across other stocks. However, at Toast specifically, his prior five trades show a 1-of-3 (33%) well-timed rate at the 90-day mark, with two recent May 2024 sales posting modest negative 30-day returns (-0.7% and -3.2%). The sale occurs against a backdrop of strong revenue growth (41.5% annual expansion to $1.1B in the latest quarter) but continued unprofitability (company net income was negative over the most recent full fiscal year). The size and proportion of this position reduction warrants monitoring, particularly given timing against recent strength and the company's ongoing path to profitability.