Cloudflare CEO Matthew Prince Sells $32.6M in NET Stock

Matthew Prince, the co-founder, CEO and Board Co-Chair of Cloudflare (NET), sold 157,152 Class A shares for about $32.6 million over three consecutive sessions on May 19, 20 and 21, 2026, according to Form 4 filings (accession 0001786925-26-000019 among them). He sold an identical 52,384 shares each day at prices between roughly $200.50 and $213.65 — the metronomic consistency that signals a prearranged plan rather than a discretionary decision.

The sales ran under a Rule 10b5-1 trading plan that Prince adopted on February 11, 2025, well over a year before execution. Each day's sale was funded by converting 52,384 Class B shares into an equal number of Class A — a mechanical step that lets a founder monetize the supervoting Class B stock that does not trade publicly. This is structured, calendar-driven liquidity, not a signal that Cloudflare's CEO is souring on the business.

Critically, Prince remains one of Cloudflare's largest owners. Beyond the directly-held Class A shares left after the sales, he controls large Class B positions through family trusts — each convertible into Class A — and a February 2026 Schedule 13G filing lists him as a 7.7% beneficial owner of the company, equivalent to roughly 26 million shares. Anyone reading the $32.6 million as an exit is misreading the filing: this trims a sliver of a stake worth billions.

Why the Class B conversion matters

Cloudflare, like many founder-led tech companies, uses a dual-class structure: Class B shares carry extra votes and are held by insiders, while Class A trades on the public market. Because Class B does not trade, a founder who wants to diversify must first convert to Class A, then sell — which is exactly the three-step pattern the May filings show. The conversions do not dilute Prince's voting control in any meaningful way at this scale; they simply unlock a small, scheduled amount of liquidity from an otherwise illiquid supervoting class. Prince's full Form 4 history shows this conversion-and-sell cadence is a recurring feature of his 10b5-1 plans, not a new development.

Selling into an internet-infrastructure rally

The ~$200-plus share price tells the rest of the story. Cloudflare provides the content-delivery, security and edge-computing layer that sits in front of a large share of the internet, and its stock has rallied as investors rewarded its expanding role in AI inference at the network edge. Selling into that strength through a pre-set plan is routine for a founder whose net worth is overwhelmingly tied to a single appreciating stock. Investors comparing Cloudflare to other infrastructure-software names often watch Datadog, Zscaler and legacy CDN peer Akamai alongside it.

Who else owns Cloudflare

Cloudflare's institutional register features genuine active conviction alongside the usual index funds. Capital World Investors has been among the largest active holders, reporting an 11.5% stake in an earlier Schedule 13G, and Baillie Gifford — the Edinburgh growth shop — has also held a 5%-plus position. In fact, Cloudflare ranked among Baillie Gifford's top-ten holdings; our Baillie Gifford Q1 2026 13F analysis shows the firm trimmed NET by about 5% of shares last quarter. That mix of founder ownership and high-conviction growth investors is part of the Cloudflare shareholder profile.

What to watch next

The February 11, 2025 plan remains active, so expect the conversion-and-sell pattern to recur on its schedule — each tranche will appear in new Form 4 filings within two business days. The substantive catalyst is Cloudflare's next quarterly report, expected in early August 2026, which will test whether edge and AI-inference momentum justifies the rally Prince is selling into. A real signal would require him adopting a markedly larger plan or selling outside the established cadence; until then, Prince's insider activity reads as scheduled diversification by a controlling founder. Track every filing and the full holder base on the Cloudflare stock page.

FAQ

How much Cloudflare stock did Matthew Prince sell in May 2026?

Matthew Prince sold 157,152 Class A shares of Cloudflare (NET) for about $32.6 million over three sessions on May 19-21, 2026, at prices ranging from roughly $200.50 to $213.65 per share.

Why did Matthew Prince convert Class B shares before selling?

Cloudflare's Class B supervoting shares do not trade publicly, so Prince converted 52,384 Class B shares into Class A each day before selling them — a routine step for diversifying a founder's stake under a 10b5-1 plan.

Does Matthew Prince still own Cloudflare stock?

Yes. Prince retains directly-held Class A shares plus large Class B positions through family trusts, and a February 2026 Schedule 13G lists him as a 7.7% beneficial owner, roughly 26 million shares.

Were the Cloudflare CEO's sales discretionary?

No. The May 2026 sales were executed under a Rule 10b5-1 trading plan adopted February 11, 2025, which pre-schedules trades so they cannot be timed on material non-public information.