Form 4: Upstart CLO Sells Shares for Tax Obligations

Upstart Holdings' Chief Legal Officer, Scott Darling, sold a total of 6,853 shares of common stock on August 20, 2025, primarily to cover tax withholding obligations related to RSU vesting.

Summary

• Scott Darling, Chief Legal Officer of Upstart Holdings, Inc., sold 6,853 shares of common stock on August 20, 2025.
• The sales were primarily conducted to cover tax withholding obligations associated with the vesting of restricted stock units (RSUs).
• The transactions were executed under a Rule 10b5-1 trading plan adopted on November 27, 2024.
• Sales included 6,713 shares at a weighted average price of $61.1197, 1 share at $61.8, and 139 shares at $63.31.
• Following these transactions, Darling's direct beneficial ownership stands at 130,300 shares of common stock.
• The reported beneficial ownership includes 139 shares acquired on August 15, 2025, under the Issuer's 2020 Employee Stock Purchase Plan.

Sentiment

Score: 5

Explanation: The transaction is a routine insider sale to cover tax obligations from RSU vesting, executed under a 10b5-1 plan. This is a neutral event and does not indicate a change in management's confidence or company fundamentals.

Positives

• The transactions were executed under a pre-arranged Rule 10b5-1 trading plan, indicating planned and transparent insider activity.
• The majority of sales were for tax withholding obligations, which is a routine and expected event for executives receiving equity compensation.
• The reporting person also acquired 139 shares under the Employee Stock Purchase Plan, indicating continued participation in company equity programs.

Negatives

• The sale of shares by a Chief Legal Officer, even for tax purposes, reduces their direct equity stake in the company.

Future Outlook

NA

Industry Context

This is a routine insider transaction for tax purposes, common across all industries for executives with equity compensation. It does not reflect broader industry trends.

Related Party Transactions

• The reported transactions involve the sale of company stock by a Chief Legal Officer, which is inherently a related party transaction as it involves an insider.

Stakeholder Impact

• Shareholders: The sale slightly reduces the Chief Legal Officer's direct ownership, but the reason (tax obligations) suggests it's not a reflection of negative sentiment. The pre-arranged 10b5-1 plan provides transparency.
• Employees: The acquisition of shares through the Employee Stock Purchase Plan indicates continued employee participation in equity programs.

Key Dates

Recommendation

The filing details a routine insider sale by the Chief Legal Officer to cover tax obligations associated with RSU vesting, executed under a pre-arranged 10b5-1 plan. Such transactions are common and generally do not signal a change in the company's fundamental outlook or management's confidence. Therefore, it does not warrant a change in investment recommendation based solely on this filing.

Keywords

Upstart Holdings, UPST, Scott Darling, Chief Legal Officer, Insider Trading, Form 4, Stock Sale, RSU Vesting, Tax Withholding, 10b5-1 Plan, Equity Compensation