Cloudflare (NET) CEO-linked trusts sell 52,384 shares after Class B to A conversion
Filing Impact
Filing Sentiment
Form Type
4
Rhea-AI Filing Summary
Cloudflare, Inc. insider activity centers on pre-planned sales and a matching share conversion. On June 24, 2026, trusts and entities associated with CEO and Board Co-Chair Matthew Prince sold a total of 52,384 shares of Class A Common Stock in open‑market transactions under a Rule 10b5-1 trading plan adopted on February 11, 2025, at weighted average prices in the low‑to‑mid $220 range per share. The sales were facilitated by the conversion of 52,384 shares of Class B Common Stock into Class A Common Stock, with each Class B share convertible into one Class A share and having no expiration date. Prince also reports 360,807 Class A shares held directly as of June 22, 2026, and multiple trusts holding Class B shares, including one block of 6,928,408 Class B shares that are convertible into an equal number of Class A shares.
Positive
- None.
Negative
- None.
Insights
Pre-planned CEO‑related sales offset by matching share conversion and large remaining holdings.
The filing shows trusts and entities associated with Cloudflare CEO Matthew Prince selling 52,384 Class A shares in open‑market trades on June 24, 2026. These sales were executed under a Rule 10b5-1 trading plan, indicating they were pre‑scheduled rather than timed opportunistically.
The disposition was paired with a conversion of 52,384 Class B shares into Class A, so the sales came from newly converted stock. Prince still reports 360,807 Class A shares held directly and multiple trusts holding sizable blocks of Class B that are convertible to Class A, including 6,928,408 Class B shares in one trust.
Because the transactions are plan‑based and Prince retains substantial direct and indirect exposure through Class A and convertible Class B holdings, this activity typically reads as routine portfolio management rather than a thesis‑changing signal.
Insider Trade Summary 10b5-1
Net Seller: 52,384 shares ($11,749,771)
Net Sell
18 txns
Insider
Prince Matthew
Role
CEO & Board Co-Chair
Sold
52,384 shs ($11.75M)
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Conversion | Class B Common Stock | 52,384 | $0.00 | -- |
| Conversion | Class A Common Stock | 52,384 | $0.00 | -- |
| Sale | Class A Common Stock | 2,883 | $221.4594 | $638K |
| Sale | Class A Common Stock | 9,740 | $222.5551 | $2.17M |
| Sale | Class A Common Stock | 11,001 | $223.4642 | $2.46M |
| Sale | Class A Common Stock | 8,153 | $224.4011 | $1.83M |
| Sale | Class A Common Stock | 11,304 | $225.4768 | $2.55M |
| Sale | Class A Common Stock | 7,731 | $226.3026 | $1.75M |
| Sale | Class A Common Stock | 1,475 | $227.3087 | $335K |
| Sale | Class A Common Stock | 97 | $228.1428 | $22K |
| holding | Class B Common Stock | -- | -- | -- |
| holding | Class B Common Stock | -- | -- | -- |
| holding | Class B Common Stock | -- | -- | -- |
| holding | Class B Common Stock | -- | -- | -- |
| holding | Class B Common Stock | -- | -- | -- |
| holding | Class B Common Stock | -- | -- | -- |
| holding | Class B Common Stock | -- | -- | -- |
| holding | Class A Common Stock | -- | -- | -- |
Holdings After Transaction:
Class B Common Stock — 4,296,167 shares (Indirect, See footnote);
Class A Common Stock — 52,384 shares (Indirect, See footnote);
Class A Common Stock — 360,807 shares (Direct, null)
Footnotes (1)
- Each share of Class B Common Stock is convertible at any time into Class A Common Stock on a one-to-one basis at the reporting person's election and has no expiration date. The shares are held of record by The Matthew Prince Revocable Trust dated October 29, 2015, for which the reporting person serves as trustee. The sale reported in this Form 4 was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on February 11, 2025. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $220.915 to $221.905, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in footnotes (4) through (11) to this Form 4. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $221.92 to $222.9175, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $222.92 to $223.91, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $223.92 to $224.9175, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $224.925 to $225.9225, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $225.925 to $226.9175, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $226.9275 to $227.8775, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $228.12 to $228.17, inclusive. The shares are held of record by The Prince Family Nonexempt Irrevocable Trust dated March 29, 2016, for which the reporting person serves as an investment advisor. The shares are held of record by The Prince Family Exempt Irrevocable Trust dated March 29, 2016, for which the reporting person serves as an investment advisor. The shares are held of record by 2021 Remainder Trust. The shares are held of record by The Matthew Prince 2024 Grantor Retained Annuity Trust dated 05/20/2024, for which the reporting person serves as co-trustee and investment advisor. The shares are held of record by The Matthew Prince 2024 Grantor Retained Annuity Trust 2 dated August 20, 2024, for which the reporting person serves as co-trustee and investment advisor. The shares are held of record by The Matthew Prince 2025 Grantor Retained Annuity Trust dated May 10, 2025, for which the reporting person serves as an investment advisor. The shares are held of record by The Matthew Prince 2025 Grantor Retained Annuity Trust 2 dated August 11, 2025, for which the reporting person serves as co-trustee and investment advisor.
Key Figures
Shares sold: 52,384 shares
Highest reported sale price: $228.17/share
Representative sale price: $228.1428/share
+3 more
6 metrics
Shares sold
52,384 shares
Total Class A shares sold in open-market transactions on June 24, 2026
Highest reported sale price
$228.17/share
Upper end of weighted price range in footnote F11
Representative sale price
$228.1428/share
Weighted average price for one June 24, 2026 Class A sale tranche
Shares converted
52,384 shares
Class B Common Stock converted into Class A Common Stock on June 24, 2026
Direct Class A holding
360,807 shares
Class A Common Stock held directly as of June 22, 2026
Large Class B block
6,928,408 shares
Class B Common Stock in one trust, convertible one-for-one into Class A
Key Terms
Rule 10b5-1 trading plan, Class B Common Stock, Revocable Trust, Grantor Retained Annuity Trust, +1 more
5 terms
Rule 10b5-1 trading plan regulatory
"The sale reported in this Form 4 was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on February 11, 2025."
A Rule 10b5-1 trading plan is a pre-arranged schedule that allows company insiders to buy or sell stock at specific times, even if they have inside information. It helps prevent accusations of unfair trading by making these transactions look planned and transparent, rather than sneaky or illegal.
Class B Common Stock financial
"Each share of Class B Common Stock is convertible at any time into Class A Common Stock on a one-to-one basis..."
A class B common stock is one of multiple types of a company’s ordinary shares that carries specific rights—often different voting power or dividend priority—compared with other classes. For investors it matters because those differences affect how much influence you have over company decisions, the income you might receive, and how freely the shares trade; think of it like owning a car with different keys: some keys let you start the engine and open the trunk, others only unlock the door.
Revocable Trust financial
"The shares are held of record by The Matthew Prince Revocable Trust dated October 29, 2015, for which the reporting person serves as trustee."
A revocable trust is a legal arrangement where the person who creates it keeps control and can change or cancel the trust at any time, while naming who will manage and receive the assets later. Think of it like a flexible folder for your investments and property that can be relabeled or reworked as circumstances change; it matters to investors because it determines how ownership is recorded, how easily assets transfer on incapacity or death, and whether holdings bypass public probate proceedings.
Grantor Retained Annuity Trust financial
"The shares are held of record by The Matthew Prince 2024 Grantor Retained Annuity Trust dated 05/20/2024..."
A grantor retained annuity trust (GRAT) is an estate-planning tool where the person who creates the trust transfers assets into it but receives fixed cash payments (an annuity) from the trust for a set number of years; whatever remains after that term passes to designated beneficiaries. It matters to investors because it can shift future appreciation of assets out of the creator’s taxable estate—like putting an asset into a timed vending machine that pays you fixed amounts while any extra value that grows inside the machine goes to heirs with reduced gift or estate tax consequences.
weighted average price financial
"The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions..."
Weighted average price is the average price of a security where each trade or component is counted according to its size, so bigger trades pull the average more than smaller ones. Think of it like calculating the average cost of a grocery haul where items you bought more of have greater influence on the final per-item cost. Investors use it to understand the true average price paid or received, judge execution quality, and compare trading performance against market movement.
FAQ
What did Cloudflare (NET) disclose about Matthew Prince’s recent stock transactions?
Cloudflare reported that entities associated with CEO Matthew Prince sold 52,384 shares of Class A Common Stock on June 24, 2026. These open‑market sales occurred under a pre‑arranged Rule 10b5‑1 trading plan adopted on February 11, 2025, and were paired with a matching Class B to Class A conversion.
What is the significance of Cloudflare’s Class B Common Stock in this Form 4?
Each share of Cloudflare Class B Common Stock is convertible at any time into one share of Class A Common Stock and has no expiration date. In this filing, 52,384 Class B shares were converted into Class A shares, which were then sold, and several trusts retain large Class B blocks convertible into Class A.