Shah Dharmesh

HubSpot CTO Dharmesh Shah makes first open-market purchase in three years, buying amid stock decline from 52-week highs after record selling pattern.

Dharmesh Shah, HubSpot's Chief Technology Officer and board member, has reversed a three-year selling pattern with his first open-market purchase—a significant regime change. Over the past three years, Shah sold shares consistently, and that selling pattern proved well-timed: every one of his prior sales at HubSpot preceded stock declines over both the following month and quarter, indicating he had been exiting strength. This purchase happens as the stock trades substantially below its 52-week high, suggesting Shah is now buying into weakness rather than selling into strength. HubSpot remains a growing, profitable company, though the stock's recent volatility and multi-quarter decline provide context for why a long-time seller might now be rotating into accumulation. The shift from serial seller to buyer—combined with his historical accuracy in reading the stock's near-term direction—makes this entry point worth scrutiny, particularly for investors trying to gauge insider conviction at current valuations.

CTO Dharmesh Shah sells 22,000 HUBS shares for $11.0M; 5 of 5 prior HUBS sales posted negative 90-day returns.

Shah Dharmesh, Chief Technology Officer, executed 7 separate sales totaling 22,000 shares for $11,019,039.78 across September 8–9, 2025, at a blended average price of $500.87. Post-transaction holdings of 1,271,058 shares represent a -1.7% reduction. Notably, Shah's prior trades at HUBS show a consistent pattern: all 5 prior sells (executed on 2024-12-17) posted negative 90-day returns ranging from -16.7% to -17.8%, indicating a 100% well-timed sell rate at this specific ticker. His cross-ticker track record across 20 prior sells shows a 90-day well-timed rate of 100.00% with an average 90-day return of -18.3%. The current stock price of $489.18 is -40.3% from the 52-week high of $819.71 and has declined -14.2% over 90 days; Shah's transaction prices of $500.51–$503.25 occurred at levels now above current price. The market remains substantially elevated in valuation (P/E 5435.33) despite negative current-quarter net income of $-3,258,000.

HubSpot CTO Shah Dharmesh sold 25,000 shares for $18.5M on 2024-12-17 at blended avg $739.89, holding 1.27M shares post-sale

Shah Dharmesh executed 11 separate sales totaling 25,000 shares for $18,497,195.88 on 2024-12-17, reducing his holdings by 1.9% to 1.27M shares. The sale occurred near the 52-week high of $757.40, with the blended average price of $739.89 representing 2.1% below peak valuation. Dharmesh had recently completed five separate sells on 2024-12-10 (outcomes not yet measurable), indicating active liquidation activity in the past week. His cross-ticker track record shows 20 prior open-market sells across all tickers, though same-ticker historical timing outcomes remain unresolved. The current price of $702.45 sits 5.0% below the blended sale price and 7.3% below the 52-week high, though the 90-day return context (stock up 33.3%) means the sale did not precede a major decline. HubSpot remains substantially unprofitable on a full-year basis despite strong 25.4% revenue growth and a $36.3B market cap.

HubSpot CTO Shah Dharmesh sells 25,000 shares for $18.2M in 24 transactions on 2024-12-10

On December 10, 2024, Shah Dharmesh executed 24 separate sales totaling 25,000 shares for $18,192,999.09 at prices ranging from $711.91 to $738.89, representing 1.9% of his pre-transaction holdings of 1,322,077 shares. The sustained, multi-tranche execution across a narrow price band ($711.91–$738.89) and modest position reduction suggest a structured disposition rather than urgent liquidation. Across his cross-ticker track record, Dharmesh's prior 20 open-market sells have posted a 100.00% well-timed rate at the 90-day mark with an average 90d return of -7.3%, indicating historically strong sell-side timing; however, this pattern is not necessarily predictive of this specific transaction's outcome. The stock currently trades at $734.49, up 4.7% over 30 days and 49.5% over 90 days, placing it near its 52-week high of $757.40. No scheduled trading plan (10b5-1) is disclosed for this transaction.

CTO Shah Dharmesh sells 25,000 shares ($16.8M) across 19 transactions on 2024-11-19; prior HUBS sales all well-timed

Shah Dharmesh executed 19 separate sales totaling 25,000 shares for $16,815,415.01 on 2024-11-19 at a blended average price of $672.62, reducing his holdings by 1.9%. The current stock price of $694.48 stands 30.3% above the 30-day mark and 39.8% above the 90-day mark, suggesting this sale occurred at a relatively depressed valuation in the near term. His five prior sales at HUBS all exhibited negative 90-day returns (ranging from -9.6% to -9.8%), meaning he sold before subsequent price declines—a 100% hit rate on same-ticker execution. However, his cross-ticker track record shows an average 90-day return of -11.4% after sells with a well-timed rate of 100.00%, indicating consistency in selling ahead of downturns, though this current filing's post-trade price action (-1.0% from the 52-week high) has moved opposite to that historical pattern. The absence of any FLAG notation means this is an open-market trade rather than a preplanned 10b5-1 execution, and the company remains unprofitable on a full-year basis despite 25.4% annual revenue growth.

Shah Dharmesh (CTO) sells 25.0K shares of HUBS for $14.7M in 13 transactions on 2024-07-08; stock down 17.9% from 52-week high, down 6.1% in 30 days.

Shah Dharmesh executed 13 separate sales totaling 25,000 shares for $14,671,369.26 at prices ranging from $577.11 to $590.48, reducing his holdings by 1.8% to 1,348,929 shares. The transaction occurred on 2024-07-08 when the stock was trading near the blended average price of $586.85, yet the current price of $560.21 now sits 17.9% below the 52-week high and down 6.1% over the prior 30 days. His prior sales at HUBS on 2024-06-03 showed negative 30-day returns (ranging from -1.1% to -3.3%), and his cross-ticker track record shows a 0.00% well-timed rate at the 90-day mark, indicating his prior open-market sells have not historically preceded further declines. The company reported positive annual revenue growth of 25.4% and a market cap of $28,549,670,193.03, though it remains unprofitable on a full-year basis with net income of $5,934,000.00 in the latest quarter against revenue of $617,414,000.00.