Jacobson Samantha, Chief Strategy Officer at The Trade Desk (TTD), has filed 40 Form 4 transactions over the past year, all concentrated in a single company. The pattern is overwhelmingly one-sided: zero open-market purchases and roughly $2.39 million in total sales, with the only recent sell occurring on May 28, 2026, when she disposed of shares worth approximately $1.13 million. That single transaction accounts for nearly half of her cumulative sell volume, marking a notable acceleration in her divestment activity.
The remaining filings are largely mechanical or compensatory in nature. A cluster of four "D" transactions on May 18, 2026, each valued at zero, represent sales back to the issuer without cash consideration, likely tied to equity plan administration. Similarly, the "A" grants on May 24 and March 3 carry no dollar value, reflecting standard compensation awards rather than discretionary buying. The bulk of her other activity consists of "F" transactions—shares withheld to cover tax obligations on vesting events—which recur on a predictable quarterly schedule: May 15, February 15, November 15, and August 15. These withholdings range from roughly $4,200 to $117,400 per event, with the largest single withholding of $117,426 occurring on August 15, 2025.
The data paints a clear picture of an executive who is not accumulating stock but rather monetizing her position through scheduled sales and tax-related liquidations. The absence of any "P" purchases—the only code indicating conviction buying—combined with the outsized May 2026 sale, suggests a net bearish bias in her recent activity. While the recurring "F" transactions are automatic and not discretionary, the $1.13 million open-market sale stands apart as a deliberate reduction, signaling that Jacobson is trimming her exposure to TTD at current valuation levels.
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