C3.ai Chairman Thomas Siebel Executes Bold Buy‑Sell Play, Selling Shares at $11.66 While Re‑Investing at $2.04 in Same Rule 10b5‑1 Plan to Lock Gains and Bet on Long‑Term AI Growth

Insider Activity Highlights a Strategic Re‑balance

The latest Rule 10b5‑1 transaction on February 10th shows Executive Chairman Thomas Siebel buying 511,732 shares of Class A stock at an average price of $2.04, while a matching sale of the same number of shares at $11.66 was executed under the same plan. The dual activity reflects a “buy‑sell” strategy that locks in gains on a sizeable block while re‑investing at a discounted price. For investors, the move signals that Siebel remains willing to lock in profits while still betting on a long‑term upside—an uncommon blend of short‑term liquidity and long‑term confidence.

Market Sentiment and Price Momentum

The deal came in a period of muted buzz (16 % below average) and a slight negative sentiment score (–6). The share price, which closed at $10.84, is still 2.27 % higher than the week’s average and sits comfortably above the 52‑week low of $9.99, though the year‑to‑date decline of 67 % and a negative P/E of –4.07 paint a cautious backdrop. Siebel’s purchase, coupled with his historical pattern of frequent, rule‑based trades, suggests he is not reacting to short‑term volatility but is aligning his personal portfolio with the company’s strategic trajectory—most notably the recent Vonage partnership that could unlock new revenue streams.

Implications for Investors and the Company’s Outlook

Siebel’s trading cadence—buying and selling in blocks of hundreds of thousands of shares—indicates a disciplined approach that balances liquidity needs with a commitment to the company’s AI platform. The recent sale at $11.66 represents a significant profit margin, which could be interpreted as confidence that the stock will continue to rebound. Simultaneously, the new purchase at $2.04 shows a willingness to reinvest at a lower valuation, potentially signaling a bullish view on the company’s long‑term growth prospects amid a partnership that broadens its field‑service AI offering.

For shareholders, the insider activity can be seen as a vote of confidence: the chairman is willing to buy large blocks when the price is low and sell when it is high, a pattern that historically aligns with the company’s broader strategic initiatives. This behavior can reduce the perception of insider risk and may encourage other investors to hold or add to their positions, especially as the Vonage deal could translate into tangible revenue upside in the coming quarters.

Profile of Thomas Siebel: A Consistent, Rule‑Based Investor

Thomas Siebel has a long history of Rule 10b5‑1 trading at C3.ai, with a mix of buys, sells, and option exercises that typically occur in large, evenly sized blocks. Over the past year, he has sold roughly 2.5 million shares at an average of $12–15, generating significant proceeds, while also buying a comparable amount at $2–3—prices well below the mid‑2025 peak. His transactions are almost exclusively through trust vehicles (e.g., The Siebel Living Trust) and managed funds, underscoring a structured approach to wealth management rather than opportunistic speculation. Siebel’s disciplined pattern aligns with his public statements about a long‑term vision for AI and a commitment to maintaining a sizable personal stake in the company’s success.