Matthew Jacobson

Director Matthew Jacobson sold 38.6K shares of DDOG for $10.0M (May 29–Jun 1, 2026) while holding 584.1K shares post-sale.

Matthew Jacobson, Director at Datadog, executed 3 separate sales totaling 38,594 shares for $9,999,682.48 across two trading days (May 29–June 1, 2026), reducing his holdings by 6.2% to 584,132 shares. The blended average sale price of $259.10 sits modestly below the current price of $269.13, and notably below the 52-week high of $278.70. His prior sales at Datadog across 4 distinct trades in May 2026 all showed positive 90-day returns (ranging +45.8% to +48.0%), indicating those earlier sales were not well-timed (the stock rose after he sold). This filing shows continued selling despite the stock having gained 91.5% over the past 30 days and 127.4% over 90 days, a period of strong momentum that preceded the current trade's execution window. The transaction reflects a director reducing a meaningful but not dominant share position amid sustained upward price action.

Director Jacobson divests ~53k shares in four tranches totaling ~$10M; pattern repeats well-timed prior exits.

Jacobson Matthew, a director, executed four sales totaling approximately $10 million in shares on a single trading day when the stock reached its 52-week high. This disposition represents a continuation of his established pattern: he has conducted 116 prior open-market sales over the past three years and no open-market purchases, making this his 120th sale in the window. His three previous sales at Datadog, executed in November, all preceded significant stock declines—evidence of consistent sell-side timing accuracy. While the company remains profitable with strong revenue growth, the director's sustained selling activity combined with his historically well-timed prior exits at this ticker suggests he may be identifying weakness or valuation concerns that aren't yet reflected in current pricing. The concentrated timing of all four sales on the same day at the stock's peak price level indicates deliberate liquidation rather than routine rebalancing.

Director sells entire 1.16M share stake at $22.72 blended average; stock down 40.7% in 90 days.

Jacobson Matthew, a Director at GitLab (GTLB), executed 16 separate sales on 2026-03-19 and 2026-03-20 totaling 1,159,908 shares for $26,350,369.16, eliminating his entire post-transaction holding of 0 shares. The blended average price was $22.72. Over the same 90-day lookback period, GTLB declined 40.7%, and his prior 5 trades at this ticker were uniformly well-timed at the 90-day mark, with the most recent December 2025 sale followed by a -39.9% 90-day return. The company carries negative full-year net income ($-8,276,000.00 latest quarter) despite 25.8% annual revenue growth, and the stock trades 58.3% below its 52-week high of $53.43. A complete exit by a sitting Director in a high-volatility, unprofitable growth company during an extended decline is material.

Director Jacobson Matthew sold 334.8K GTLB shares at $38.08 (100% of holdings) for $12.7M; stock down 48.6% from 52-week high.

Director Matthew Jacobson liquidated his entire 334,827 share position in GitLab, representing a complete exit. The sale occurred at $38.08 per share, generating $12,749,843.85 in proceeds, while the stock now trades at $37.57, down 48.6% from its 52-week high of $73.14 and down 20.4% over the past 90 days. Jacobson's cross-ticker track record shows a 100.00% well-timed rate across 20 prior open-market sells, with an average 90-day return of -23.9% after his sales, and at GitLab specifically, all 5 of his prior trades were well-timed at the 90-day mark. The company remains unprofitable with a net loss of $8.3M in the latest quarter, despite 30.9% annual revenue growth to $244.4M, leaving investors to assess whether the full-position exit reflects broader concern about profitability trajectory or execution risk in a growth-stage SaaS company.

Director Matthew Jacobson sells entire 436.1K-share DDOG stake for $87.1M in 10 transactions on Nov 10-11

Matthew Jacobson, Director at Datadog, executed 10 separate sales totaling 436,116 shares for $87,067,465.68 at blended average price of $199.64, reducing his holdings to zero. This represents complete liquidation of a substantial position across two trading days. His cross-ticker track record shows an average 30-day return of -9.0% following prior sells, suggesting a pattern of liquidations that coincide with or precede market pullbacks, though this specific transaction warrants examination of whether it was discretionary or plan-based. The magnitude (436.1K shares, full position exit) combined with recent stock performance (currently trading at $185.97, down 6.9% from the $199.72 52-week high reached during these sales) and strong underlying fundamentals (26.1% annual revenue growth, $885.7M latest-quarter revenue) creates a notable divergence between the insider's liquidation and the company's operational trajectory.

Director Jacobson Matthew sold 63,587 shares of GTLB for $3,189,676.53 across 4 transactions on 2025-09-23, liquidating 97.9% of holdings to 1,370 shares.

Jacobson Matthew executed 4 separate sales totaling 63,587 shares for $3,189,676.53 at $50.16 per share on 2025-09-23, reducing his holdings from 64,957 shares to 1,370 shares—a 97.9% reduction in position. This follows five prior sells at GTLB completed just 4–5 days earlier on 2025-09-18 and 2025-09-19, establishing a pattern of accelerated liquidation. The company remains unprofitable with net income of $-9,208,000.00 on quarterly revenue of $235,960,000.00, though annual revenue growth is strong at 30.9%. The transaction price of $50.16 now sits 36.1% below the 52-week high of $73.14, placing it near the lower end of the annual range.

Director Jacobson sold 233,382 shares (90.8% of pre-transaction holdings) at $50.17 on 2025-09-19 for $11.7M

Jacobson Matthew, a Director at GitLab, executed 4 separate sales on 2025-09-19 totaling 233,382 shares (233.4K shares) for $11,707,701.38 ($11.7M) at a blended average price of $50.17, reducing his holdings from 257,138 shares to 23,756 shares (a 90.8% reduction). The sales occurred at $50.17 while the current price stands at $48.84, positioning the sales above current levels by approximately $1.33 per share. GitLab remains unprofitable with net income of $-9,208,000.00 ($-9.2M) over its most recent full fiscal year, though the company grew revenue 30.9% annually to $235,960,000.00 ($236.0M) in the latest quarter. The substantial concentration of the sale—four transactions liquidating the vast majority of Jacobson's position on a single day—combined with the company's ongoing losses despite strong growth, warrants investor attention to the underlying strategic positioning and capital allocation context.

Director Jacobson Matthew sold 443.4K shares of GTLB for $22.4M over Sept 17–18; reduced stake from 549.4K to 105.9K shares (-80.7%).

Director Jacobson Matthew executed 12 separate sales totaling 443,447 shares for $22,385,849.96 across two trading days (Sept 17–18), reducing his holdings by 80.7% from 549.4K to 105.9K shares. The blended average sale price was $50.48, versus the current price of $50.20 (a modest 0.6% difference), meaning the director sold near current market levels during a period when the stock has rebounded significantly from its 52-week low but remains 31.4% below the 52-week high. GitLab remains unprofitable on a full-year basis (net income of $-9.2M), though revenue grew 30.9% year-over-year to $236.0M. The scale and speed of this liquidation—removing over four-fifths of his stated position in two days—marks a material reduction in his direct equity stake in the company.

Director Jacobson Matthew sold 143,205 shares of GTLB for $6,701,492.78 at $46.80 on 2025-09-08; stock at $49.01 currently.

Director Jacobson Matthew executed two separate sales totaling 143,205 shares for $6,701,492.78 at a blended average price of $46.80 on 2025-09-08, reducing his holdings from 968,495 to 825,290 shares (-14.8%). The sales occurred while GitLab's stock trades at $49.01, 33.0% below its 52-week high of $73.14 and up 26.2% over the prior 30 days. GitLab remains unprofitable (net income of $-9,208,000.00 in the latest quarter) despite revenue growth of +30.9% year-over-year, indicating the company is in a high-growth, pre-profitability phase. His cross-ticker track record shows 20 prior sells with an average 30-day return of +13.2%, though timing metrics at the 90-day mark have not established a consistent pattern. This sale represents a material reduction in a meaningful position but maintains substantial retained ownership (825.3K shares post-transaction).

Director Jacobson Matthew sold 683,511 shares ($87.1M) over two days; holdings fell 72.5% to 259.8K shares

Jacobson Matthew executed 14 separate sales totaling 683,511 shares for $87,106,996.35 across August 26–27, 2025, reducing his holdings by 72.5% from 943,316 shares to 259,805 shares. The blended average sale price was $127.44, while the current price stands at $140.96—a gap suggesting these sales occurred before a subsequent price appreciation of approximately 10.7%. At DDOG specifically, his prior sell on 2025-05-08 showed a 90-day return of +26.6%, and more recent sells on 2025-08-22 and 2025-08-25 lack measurable outcomes yet. His cross-ticker track record shows 0.00% well-timed rate on sells (average 90-day return post-sell: +13.4%), indicating poor historical timing on the broader portfolio. The substantial scale and rapid two-day execution, combined with the historical pattern of underperformance on sell timing, warrant attention to whether a structural change in conviction occurred.