Form 4: Upstart Holdings Chief Legal Officer Executes Pre-Planned Stock Option Exercise and Share Sales

Upstart Holdings' Chief Legal Officer, Scott Darling, engaged in a pre-planned transaction on June 3, 2025, exercising stock options and subsequently selling a portion of his common stock holdings.

Summary

• Scott Darling, Chief Legal Officer of Upstart Holdings, Inc. (UPST), executed transactions on June 3, 2025, under a Rule 10b5-1 trading plan adopted on November 27, 2024.
• Darling acquired 1,000 shares of Upstart common stock by exercising employee stock options at a price of $13.22 per share.
• Following the option exercise, Darling sold 1,000 shares of common stock at a weighted average price of $50.0155 per share, with prices ranging from $50.00 to $50.025.
• Additionally, Darling sold another 6,383 shares of common stock at a price of $50.00 per share.
• After these transactions, Scott Darling beneficially owns 137,014 shares of non-derivative common stock, which includes restricted stock units (RSUs).
• Darling also holds 223,527 employee stock options, with 1/48 of the shares subject to the option vesting monthly starting January 20, 2023, and an expiration date of December 31, 2032.

Sentiment

Score: 4

Explanation: The sentiment is slightly negative due to the insider selling, even though it was pre-planned. While the 10b5-1 plan mitigates the negative signal, a reduction in executive holdings can still be viewed with caution by investors.

Positives

• The exercise of stock options at a strike price of $13.22 allowed the Chief Legal Officer to realize a significant gain, as the shares were subsequently sold at prices around $50.00.
• The transactions were conducted under a pre-established Rule 10b5-1 trading plan, indicating that the sales were scheduled in advance and not based on immediate, non-public information.

Negatives

• The sale of 7,383 shares by a key executive, even if pre-planned, could be interpreted by some investors as a signal of reduced confidence in the company's near-term stock performance.
• The total number of non-derivative shares beneficially owned by the Chief Legal Officer decreased from 144,397 to 137,014 following the transactions.

Future Outlook

The document does not contain any forward-looking statements or guidance regarding the company's future financial performance or strategic outlook.

Industry Context

This Form 4 filing reports an individual insider transaction and does not provide broader industry context or trends. It reflects a routine executive equity compensation event within the financial technology sector.

Corporate Governance

Stakeholder Impact

• Shareholders: May interpret the executive's share sales as a slight negative signal, potentially impacting investor sentiment, although the pre-planned nature of the sales lessens this impact.
• Employees: No direct impact mentioned, but executive transactions are often observed for broader company health indicators.

Next Steps

• Continued monthly vesting of remaining employee stock options for Scott Darling, subject to his continued service.

Key Dates

Recommendation

Keywords

Upstart Holdings, UPST, SEC Form 4, Insider Trading, Stock Option Exercise, Share Sale, Rule 10b5-1 Plan, Chief Legal Officer, Executive Compensation, Equity Compensation