Darling Scott, Chief Legal Officer of Upstart Holdings (UPST), has filed 39 Form 4 transactions over the past year, all concentrated in a single company. The pattern is unambiguous: Scott has executed zero open-market purchases and zero acquisitions, while selling approximately $3.62 million worth of UPST stock. The recent activity, spanning September 2025 through May 2026, shows 13 open-market sales totaling roughly $1.5 million, with the largest single dispositions occurring on December 12, 2025 ($369,600), November 20, 2025 ($267,670), and September 3, 2025 ($277,654). The most recent sales came on May 20, 2026 ($190,912) and May 15, 2026 ($21,476 combined).
The transaction stream is heavily weighted toward routine compensation mechanics rather than discretionary trading. Each sale is paired with an option exercise (code M) or a tax-withholding event (code J), suggesting Scott is liquidating vested equity to cover obligations or generate liquidity. For instance, the December 12, 2025 sale of $369,600 followed a $26,440 option exercise, and the November 20, 2025 sale of $267,670 was accompanied by a zero-value code J transaction. The February 28, 2026 filings show two zero-value grants (code A), which are compensation awards, not purchases. Notably, there are no code P transactions—no open-market buys—anywhere in the record, and the selling has been persistent rather than episodic, with at least one sale in every month from September 2025 through May 2026.
The absence of any buying activity, combined with the steady cadence of sales tied to option exercises, paints a picture of an executive monetizing equity compensation rather than expressing a directional view. The dollar values vary widely—from $8,248 to $369,600—but the direction is consistent. Over the trailing twelve months, Scott has been a net seller of UPST stock in every reporting period, with total proceeds exceeding $3.6 million and no offsetting acquisitions.
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