Form 4: Upstart CLO Scott Darling Executes Stock Sale

Upstart Holdings Chief Legal Officer Scott Darling sold 6,634 shares of common stock to satisfy tax obligations related to RSU vesting.

Summary

• Chief Legal Officer Scott Darling sold 6,634 shares of Upstart Holdings (UPST) common stock on May 20, 2026.
• The shares were sold at a weighted average price of $28.7778 per share, with individual transaction prices ranging from $28.24 to $29.07.
• The sale was conducted to cover tax withholding obligations associated with the vesting of restricted stock units (RSUs).
• Following the transaction, the reporting person maintains direct ownership of 88,728 shares and indirect ownership of 39,698 shares held by the Darling Family Trust.

Sentiment

Score: 5

Explanation: StockSavvy.ai views this as a neutral event, as the sale is purely administrative and related to tax obligations rather than a strategic exit by management.

Positives

• The transaction was a routine administrative sale to satisfy tax obligations rather than a discretionary divestment of equity.

Negatives

• The sale reduces the direct equity stake held by a key member of the executive leadership team.

Risks

• Executive stock sales, even for tax purposes, can sometimes be perceived negatively by retail investors as a lack of confidence in future price appreciation.

Future Outlook

No forward-looking guidance or strategic outlook was provided in this regulatory filing.

Industry Context

StockSavvy.ai notes that routine 'sell-to-cover' transactions are standard practice for executives receiving equity-based compensation and generally do not signal a change in corporate strategy or internal sentiment.

Comparison to Industry Standards

• The transaction aligns with standard corporate governance practices where executives sell a portion of vested RSUs to satisfy mandatory tax withholding requirements.

Related Party Transactions

• The reporting person transferred 7,247 shares of Common Stock to the Darling Family Trust.

Stakeholder Impact

• Minimal impact on shareholders as the transaction was a pre-planned tax-related sale.

Next Steps

• No future actions or milestones were disclosed in this filing.

Key Dates

Keywords

Upstart Holdings, UPST, Insider Trading, Form 4, Executive Compensation, Equity Vesting