Form 4: Upstart Holdings Chief Legal Officer Executes Pre-Planned Stock Sales

Upstart Holdings, Inc.'s Chief Legal Officer, Scott Darling, completed pre-scheduled sales of common stock totaling 7,000 shares, following the exercise of employee stock options.

Summary

• Scott Darling, Chief Legal Officer of Upstart Holdings, Inc. (UPST), engaged in pre-planned stock transactions on July 1, 2025, and July 2, 2025.
• On July 1, 2025, Darling exercised options to acquire 2,000 shares of common stock at an exercise price of $13.22 per share and subsequently sold 2,000 shares at $63.56 per share.
• On July 2, 2025, Darling exercised options to acquire an additional 5,000 shares of common stock at an exercise price of $13.22 per share and sold 5,000 shares at a weighted average price of $70.0352 per share.
• The sales on July 2, 2025, occurred in multiple transactions with prices ranging from $70.00 to $70.07.
• All reported option exercises and sales were conducted pursuant to a Rule 10b5-1 trading plan adopted by Darling on November 27, 2024.
• Following these transactions, Darling's direct beneficial ownership of common stock is 137,014 shares, which includes certain restricted stock units (RSUs).
• Darling's beneficial ownership of employee stock options (right to buy) decreased to 213,527 after the exercises.

Sentiment

Score: 6

Explanation: The sentiment is slightly positive to neutral. While insider selling can be a yellow flag, the execution under a pre-arranged 10b5-1 plan mitigates concerns about opportunistic selling. The significant profit realized from the option exercises also highlights the value creation for the insider.

Positives

• The transactions were executed under a Rule 10b5-1 trading plan, indicating pre-scheduled sales not based on new, non-public information, which can mitigate concerns about opportunistic insider selling.
• The significant difference between the option exercise price ($13.22) and the sale prices ($63.56 and $70.0352) demonstrates substantial gains for the insider, reflecting past stock appreciation.

Negatives

• Insider selling, even if pre-planned, can sometimes be perceived negatively by the market as it reduces management's direct equity exposure in the company.

Risks

• Potential for negative market sentiment or downward pressure on the stock price due to insider selling, despite the pre-arranged nature of the transactions.

Future Outlook

NA

Industry Context

NA

Stakeholder Impact

• Shareholders: May interpret the insider selling as a signal, though the pre-arranged 10b5-1 plan suggests it is not based on new negative information. The high sale price could also be viewed as management capitalizing on strong stock performance.

Key Dates

Keywords

Upstart Holdings, UPST, Scott Darling, Chief Legal Officer, Form 4, insider trading, stock options, Rule 10b5-1 plan, equity sales, beneficial ownership