Brian R Elworthy

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.

Toast General Counsel sold 339,368 shares for $14,456,050.19 on 2025-06-02; post-sale holdings 39.4K shares (-89.6%)

General Counsel Brian R Elworthy executed 4 separate sales totaling 339,368 shares for $14,456,050.19 at blended average $42.60, reducing his position from 378,736 to 39,368 shares (-89.6% of pre-transaction holdings). The transaction occurs as TOST trades at $41.63, within 8.0% of its 52-week high, and the stock has rallied +15.6% over 30 days and +14.2% over 90 days. Notably, Elworthy's prior two sales at TOST (October 2024 and February 2024) were followed by positive 90-day returns of +21.4% and +25.2% respectively, meaning the stock rose after both prior exits. The current fundamental backdrop shows $1.3B in quarterly revenue with +28.3% annual revenue growth, though P/E of 1387.67 reflects minimal net income relative to valuation. This large equity reduction by a senior executive warrants examination of whether the timing reflects confidence in current valuations or other considerations.

Toast General Counsel sold 300,000 shares ($9.1M) at $30.39, reducing stake by 62.8% to 177.8K shares held.

General Counsel Brian R Elworthy executed a substantial single sale of 300,000 shares at $30.39 on 2024-10-18, reducing his holdings from 477.8K to 177.8K shares—a 62.8% reduction in stake. The sale price of $30.39 is just 3.1% below the 52-week high of $30.32, near the stock's recent strength (up 18.4% over 90 days and 6.0% over 30 days). Notably, his prior TOST sale on 2024-02-01 occurred when the stock subsequently rose 25.2% over 90 days, indicating the previous sale was poorly timed as an exit signal. Toast remains unprofitable on a full-year basis despite strong revenue growth of 41.5% year-over-year, creating a backdrop where insider dispositions merit attention alongside the company's path to sustained profitability.