Cloudflare CFO Thomas Seifert Buys 10,000 Shares Amid Volatile Market, Signaling Confidence in Long‑Term Growth

Insider Activity Spotlight: Cloudflare’s CFO Buys Amid a Quiet Trading Plan

On January 20, 2026, Cloudflare’s Chief Financial Officer, Thomas Seifert, executed a Rule 10b‑5‑1 trading‑plan purchase of 10,000 shares of Class A common stock at roughly $169.97 per share, just 0.04 % below the market close of $169.97. The transaction is part of a broader, pre‑established plan that also includes a series of sales executed the same day at progressively higher prices, with the last sale completing at $181.78. The net effect of the day’s activity was a modest increase in the CFO’s holdings to 147,486 shares.

The timing of the trade is noteworthy. Cloudflare’s stock has recently been under pressure—its 52‑week low sits at $89.42, yet the share price closed at $177.42 on the day before the filing, a 15.88 % monthly decline but still 37.15 % above the year‑to‑date high. The CFO’s buy comes amid a dip in the stock’s short‑term sentiment score of –23 and a high communication intensity (buzz = 30.17 %) on social media platforms. In such a climate, a CFO’s purchase can signal confidence in the company’s longer‑term fundamentals.

What This Means for Investors

Insider buying in a high‑volatility environment often reassures shareholders that senior management believes the stock is undervalued relative to its intrinsic worth. Seifert’s purchase—together with the larger series of sales at higher prices—suggests a disciplined approach to liquidity management rather than a speculative play. For investors, this may reduce the perceived risk of a sudden liquidity event and reinforce the view that the CFO is positioning the company to weather continued market swings.

From a valuation perspective, Cloudflare’s price‑to‑earnings ratio of –625.81 reflects a negative earnings environment, typical of high‑growth tech firms that reinvest heavily. The CFO’s recent activity, coupled with the company’s recent acquisition of the Astro technology team and the resolution of a significant security vulnerability, points to an emphasis on product diversification and customer trust. Together, these factors could support a rebound in earnings as the company monetizes new services and retains its customer base.

Thomas Seifert: A Pattern of Structured Trades

Examining Seifert’s transaction history reveals a consistent use of Rule 10b‑5‑1 plans. Since December 2025, he has executed a mixture of buys and sells of both Class A and Class B shares. The most recent plan, adopted on November 26, 2024, has generated a series of incremental sales that gradually increase in price over time—a classic “step‑up” strategy. In December 2025, Seifert bought 10,000 Class A shares at $200.58, then sold 1,000 shares at $200.58 and 4,836 shares at $201.52, followed by a further 3,328 shares at $202.37. Similar patterns appear in earlier periods (e.g., a 1,000‑share sell at $198.64 in late December 2025, a 483‑share sell at $203.35). This disciplined approach indicates a long‑term view, with the CFO using the trading plan to manage liquidity while avoiding market impact.

Beyond the trading plan, Seifert’s activity includes occasional option sales and conversions of Class B to Class A shares. In January 2026, he sold 10,000 Employee Stock Options (right to buy) at $0.00 (i.e., exercised the option to purchase the underlying shares). He also bought 10,000 Class B shares on the same day, potentially to maintain a balanced equity exposure across the two classes. The CFO’s holdings in Class B stock, including large block holdings of 150,000 shares and multiple 46,100‑share blocks held through trusts, suggest an interest in maintaining a diversified ownership structure.

Outlook: Confidence Amid Volatility

The combination of a well‑structured trading plan, consistent insider buying, and recent product‑growth initiatives positions Cloudflare for a gradual recovery. While the stock’s short‑term sentiment remains negative and the market cap remains sizeable at $64.5 bn, the CFO’s disciplined activity can serve as a catalyst for investor confidence. As Cloudflare continues to invest in high‑performance web development and strengthens its security posture, the CFO’s incremental purchases may be read as a vote of confidence in the company’s long‑term strategic direction.