Chief Revenue Officer Vassil Jonathan sold $470K worth of newly exercised options at $32.89, just 1.1% below the 90-day high. This mechanical transaction follows his established pattern of 16 prior sales and carries no conviction signal about his view on the stock.

Where it could go — Our 1-4 conviction officer sells: 56% beat SPY at 30d; watch earnings reaction as key near-term catalyst.

CRO Vassil Jonathan sold 11,170 shares at $30.16 through an option exercise transaction, maintaining his existing stake percentage. This appears to be routine option monetization rather than a bearish signal, though it continues a pattern of consistent selling by TOST executives with no insider buying support.

Where it could go — Our 1-4 conviction officer sells: 59% beat SPY at 30d with avg +3.2% vs SPY; watch $30.53 as resistance, $23.91 as support.

TOST CFO Elena Gomez sold $335K worth of shares, reducing her directly held stake by 5.9% at a price 5.0% below the 90-day high. This sale is part of a consistent pattern for this insider, who has executed 13 prior sells and no buys, and lacks the corroboration of any other recent insider purchases.

Where it could go — Our 1-4 conviction officer sells: 58% beat SPY at 30d (n=2571, avg +3.1% vs SPY); watch $30.36 as the bull trigger, $22.26 as the bear break.

President Fredette Stephen sold $264K worth of TOST shares at $28.85, reducing his direct holdings by 1% while the stock traded just 5% below its 90-day high. This sale fits his established pattern of routine disposals rather than signaling new concern, especially given the stock's strong analyst consensus and recent positive performance after similar signals.

Where it could go — Our 1-4 conviction officer sells: 58% beat SPY at 30d (n=2571, avg +3.1% vs SPY); watch $30.36 as resistance, $22.26 as support.

General Counsel Brian Elworthy sold $183K worth of shares at $28.85, a price 29.6% above the 90-day low, reducing his directly held stake by -3.1%. This is his 15th recorded sale with zero prior buys, fitting a pattern of routine diversification rather than a new signal of concern.

Where it could go — Our 1-4 conviction officer sells: 58% beat SPY at 30d; watch $30.36 as the bull break, $22.26 as the bear floor.

CEO Narang Aman sold $414K worth of shares, reducing their direct stake by 16.9% at a price 5.0% below the 90-day high. This follows 12 prior sales with no buys, indicating routine diversification rather than a new concern.

Where it could go — Our 1-4 conviction officer sells: 58% beat SPY at 30d (n=2571, avg +3.1% vs SPY); watch $30.36 as resistance, $22.26 as support.

Chief Revenue Officer Vassil Jonathan sold $192K worth of TOST shares, reducing his direct holdings by 8.7% near the middle of the stock's 90-day range. This represents his 15th verified sale on record and follows his established pattern of regular disposals rather than signaling new concern.

Where it could go — Our 1-4 conviction officer sells: 58% beat SPY at 30d with +3.1% average outperformance; watch $30.36 as resistance, $22.26 as support.

Brian R. Elworthy sold 92,864 shares at ~$25.85 ($2.4M); 54,000 of them came from a same-day option exercise at $2.21. The remaining 38,864 shares came from existing holdings, leaving 204,778 directly held shares.

Where it could go — Significant reduction of existing holdings—about 42% of the sale trimmed direct shares, with the option exercise providing substantial liquidity.