Is Upstart Stock a Buy, Sell, or Hold After the Chief Legal Officer Sold Shares?
Key Points
Chief Legal Officer Darling Scott sold 1,000 shares of Upstart stock on Oct. 24, 2025.
Upstart is having a strong 2025 with 102% year-over-year revenue growth to $257 million.
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On October 24, 2025, Darling Scott, Chief Legal Officer of Upstart (NASDAQ:UPST), exercised 1,000 options and immediately sold the resulting shares, according to an SEC Form 4 filing.
Transaction summary
| Metric | Value |
|---|---|
| Shares sold | 1,000 |
| Transaction value | ~$55,000 |
| Post-transaction shares | 123,148 |
| Post-transaction value (direct ownership) | ~$6.77 million |
Transaction value based on SEC Form 4 weighted average purchase price ($55.01); after the transaction, Darling Scott held 123,148 shares with a post-transaction position value of $6.77 million.
Key questions
How does this transaction compare to prior sell trades by Darling Scott?
The current sale of 1,000 shares is materially smaller than Darling Scott’s historical median for sell trades, which stands at 3,938 shares per transaction. Recent sell periods saw median transaction sizes of 6,200 shares.
What impact does the exercise and sale have on direct ownership?
Following the exercise and immediate sale, Darling Scott's direct ownership of Upstart common stock fell to 123,148 shares.
Was the transaction price aligned with recent market levels?
Shares were sold at $55.01 per share. On the transaction date, Upstart closed at $52.69, and as of market close on Oct. 31, 2025, the current price was $47.52.
Company overview
| Metric | Value |
|---|---|
| Market capitalization | $4.57 billion |
| Revenue (TTM) | $844.07 million |
| Net income (TTM) | ($6.35 million) |
| 1-year price change | -1.98% |
Note: 1-year price change calculated as of October 24, 2025.
Company snapshot
Upstart operates in the financial technology sector, providing artificial intelligence-driven lending solutions to financial institutions and consumers. Its platform is designed to improve credit access and streamline loan origination for a broad range of U.S. banking partners and borrowers.
The company offers a cloud-based AI lending platform that aggregates consumer loan demand and connects it to a network of bank partners. It targets U.S. banks, credit unions, and individual borrowers seeking personal loans and other consumer credit solutions.
Foolish take
Upstart's Chief Legal Officer Darling Scott's sale of 1,000 shares doesn't raise any red flags, considering it represents a small portion of the 123,148 shares owned after the transaction. As a result, if you're a shareholder, hold onto your shares; the sale isn't a signal to sell Upstart stock.
But with shares down substantially from the 52-week high of $96.43 reached in February, is now a good time to buy? Upstart is having a strong 2025. In the second quarter, revenue rose 102% year over year to $257 million.
The company expects sales to continue growing this year, reaching $1.1 billion. That's a significant jump up from 2024's $637 million.
Considering this success, why is its stock down? Wall Street is concerned about a weakening credit market, which can impact loan performance and eventually hurt Upstart's revenue.
With its stock price down, Upstart's price-to-sales ratio of 5 is the lowest it's been since April, when new tariff policies caused the stock market to crash. This suggests Upstart shares are at an attractive valuation. Combined with its strong revenue growth, Upstart looks like a worthwhile investment.
Glossary
Options: Contracts giving the right to buy or sell shares at a set price before expiration.
Exercise (of options): The act of using an option to buy or sell the underlying shares.
Immediate sale: Selling shares as soon as they are acquired, often after exercising options.
Direct ownership: Shares held personally by an individual, not through trusts or indirect means.
Form 4: A required SEC filing disclosing insider trades by company officers, directors, or significant shareholders.
Weighted average purchase price: The average price paid per share, adjusted for the number of shares bought at each price.
Disposition: The act of selling or otherwise getting rid of an asset or security.
Plan-based activity: Transactions made under a prearranged trading plan, often for compliance with insider trading rules.
Cloud-based AI lending platform: An online system using artificial intelligence to match borrowers with lenders.
TTM: The 12-month period ending with the most recent quarterly report.
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Robert Izquierdo has positions in Upstart. The Motley Fool has positions in and recommends Upstart. The Motley Fool has a disclosure policy.
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