Vassil Jonathan

TOST CRO Vassil Jonathan sold 66,390 shares at $35.86 on 2026-01-02; stock now at $34.50, down 30.0% from 52-week high.

Vassil Jonathan, Chief Revenue Officer of Toast, Inc., sold 66,390 shares (44.0% of pre-transaction holdings) at $35.86 on 2026-01-02, reducing his stake from 150,979 to 84,589 shares. The transaction occurred near a 52-week high (current price $34.50 is -30.0% from that peak), suggesting the CRO was divesting into relative strength. His prior five trades at TOST show mixed timing outcomes: while his cross-ticker track record averaged 90-day returns of 8.3%, none of his five prior TOST sales materialized as well-timed sells (defined as negative 90-day returns), with four of five generating positive 90-day returns averaging +7.8%. The large magnitude of this sale—reducing his holdings by nearly half and representing $2.4M in value—alongside the stock's subsequent 3.3% decline in the 30 days post-trade suggests the CRO's decision to divest a material position warrants monitoring against near-term business momentum and earnings trajectory.

Toast CRO Vassil Jonathan sells 100,000 shares (64.4% of holdings) in 2 transactions for $4.3M on 2025-06-02

Vassil Jonathan, Chief Revenue Officer of Toast, Inc., executed 2 separate sales on 2025-06-02, selling 38,788 shares at $42.14 and 61,212 shares at $42.90 for a combined $4,260,304.76. This represents a -64.4% reduction in his holdings, from 155,220 shares to 55,220 shares. The blended average transaction price of $42.60 is approximately $0.97 above the current price of $41.63. At the same-ticker level, his prior 2 measurable sales at TOST (on 2024-11-08) showed positive 30-day and 90-day returns of +9.0%/+17.9% and +4.2%/+12.7% respectively—both instances where the stock subsequently rose after his sales, indicating poorly-timed exits at that ticker. His cross-ticker track record shows a 90-day well-timed rate of 27.27%, well below the threshold for strong timing acumen. The magnitude of this stake reduction and the CRO's insider role warrant scrutiny into the company's trajectory.

Toast CRO Vassil Jonathan sold 100,000 shares (100.0K shares) for $4,113,825.18 on 2025-05-09 at blended $41.14, reducing holdings by 64.4%.

Vassil Jonathan, Chief Revenue Officer, executed three separate sales totaling 100,000 shares (100.0K shares) at prices ranging from $40.90 to $42.43, reducing his holdings from 155,220 shares to 55,220 shares. The sale occurred at blended average price $41.14, while the stock now trades at $43.96 and is up 29.0% over the past 30 days and +10.6% over 90 days. Across his same-ticker history at TOST (5 prior trades), none of the insider's previous sells were well-timed at the 90-day mark, with post-sale returns ranging from -3.0% to +33.6% at 30 days. The 64.4% reduction in holdings represents material disposition of a CRO's stake in a $1.3B-revenue growth company (+28.3% annual revenue growth), warranting scrutiny of the insider's forward-looking perspective on business momentum and valuation.

CRO Vassil Jonathan sold 100,000 shares of TOST for $3.7M on Nov 8, reducing holdings by 71.5%

Vassil Jonathan, Chief Revenue Officer of Toast Inc., executed 3 separate sales totaling 100,000 shares for $3,655,158.06 on 2024-11-08, at prices ranging from $35.61 to $37.25 (blended average $36.55). This represents a -71.5% reduction in his holdings, dropping from 139,834 shares to 39,834 shares post-transaction. The timing coincides with strong recent price momentum: the stock is at its 52-week high of $39.43, having risen +39.1% over the prior 30 days and +59.1% over 90 days. Looking at his same-ticker history at TOST, prior sells have been mixed: one prior sale on 2024-10-18 outcomes remain unmeasurable, but prior 90-day outcomes ranged from -8.2% to +21.6% (2 of 4 prior measurable 90-day outcomes were negative, indicating 50% well-timed rate at this ticker). Fundamentally, Toast reported $1.3B in latest-quarter revenue with +41.5% annual revenue growth, though the company remains unprofitable on a full-fiscal-year basis with negative net income.

Toast CRO Vassil Jonathan sells 50,000 shares (56.6% of holdings) for $1.5M at $30.38 on 2024-10-18.

Vassil Jonathan, Chief Revenue Officer of Toast, Inc., executed a substantial open-market sale of 50,000 shares on 2024-10-18 at $30.38, reducing his holdings from 88,266 to 38,266 shares and realizing $1,519,250.00. This represents a 56.6% reduction in his position—a significant portfolio action from a senior executive responsible for revenue generation. At his cross-ticker track record, his 7 prior sells show a 90-day well-timed rate of 42.86%, indicating below-median accuracy; his 5 prior sales at TOST itself have been mixed, with only 2 of 5 well-timed at the 90-day mark. The stock is currently priced at $29.37, down 3.1% from its 52-week high of $30.32 near the transaction price, and has gained 18.4% over 90 days post-transaction—a run-up the insider did not participate in. Toast remains operationally challenged, unprofitable on a full-year basis despite posting $1.2B in quarterly revenue and 41.5% annual growth, creating ambiguity about whether this sale reflects portfolio management or concern about near-term execution risk.

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.