Cloudflare (NET) CEO trades 86K shares while keeping sizable Class B stake
Filing Impact
Filing Sentiment
Form Type
4
Rhea-AI Filing Summary
Cloudflare, Inc. CEO Matthew Prince reported a series of indirect transactions in Class A and Class B Common Stock. Trusts associated with him converted Class B Common Stock into 86,014 shares of Class A Common Stock at a conversion price of $0.00 per share, then sold the resulting Class A shares in multiple open-market trades at weighted average prices in the mid-$240s per share. The filing notes these sales were made under a Rule 10b5-1 trading plan adopted by the reporting person on February 26, 2026. As of July 1, 2026, he also held 360,807 shares of Class A Common Stock directly, and several indirect Class B positions that are each convertible into large blocks of Class A shares.
Positive
- None.
Negative
- None.
Insider Trade Summary 10b5-1
Net Seller: 86,014 shares ($21,099,988)
Net Sell
36 txns
Insider
Prince Matthew
Role
CEO & Board Co-Chair
Sold
86,014 shs ($21.10M)
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Conversion | Class B Common Stock | 18,752 | $0.00 | -- |
| Conversion | Class B Common Stock | 33,631 | $0.00 | -- |
| Conversion | Class A Common Stock | 18,752 | $0.00 | -- |
| Sale | Class A Common Stock | 106 | $244.8702 | $26K |
| Sale | Class A Common Stock | 4,182 | $245.9338 | $1.03M |
| Sale | Class A Common Stock | 4,686 | $246.6262 | $1.16M |
| Sale | Class A Common Stock | 5,170 | $247.646 | $1.28M |
| Sale | Class A Common Stock | 3,624 | $248.6202 | $901K |
| Sale | Class A Common Stock | 965 | $249.5209 | $241K |
| Sale | Class A Common Stock | 19 | $250.3897 | $5K |
| Conversion | Class A Common Stock | 33,631 | $0.00 | -- |
| Sale | Class A Common Stock | 288 | $243.8195 | $70K |
| Sale | Class A Common Stock | 1,883 | $245.6074 | $462K |
| Sale | Class A Common Stock | 11,370 | $246.2398 | $2.80M |
| Sale | Class A Common Stock | 8,804 | $247.3796 | $2.18M |
| Sale | Class A Common Stock | 7,678 | $248.3155 | $1.91M |
| Sale | Class A Common Stock | 3,288 | $249.2007 | $819K |
| Sale | Class A Common Stock | 320 | $249.993 | $80K |
| Conversion | Class B Common Stock | 33,631 | $0.00 | -- |
| Conversion | Class A Common Stock | 33,631 | $0.00 | -- |
| Sale | Class A Common Stock | 4,709 | $239.6359 | $1.13M |
| Sale | Class A Common Stock | 5,738 | $240.4814 | $1.38M |
| Sale | Class A Common Stock | 8,724 | $241.6077 | $2.11M |
| Sale | Class A Common Stock | 6,481 | $242.3757 | $1.57M |
| Sale | Class A Common Stock | 762 | $243.4556 | $186K |
| Sale | Class A Common Stock | 1,738 | $244.6423 | $425K |
| Sale | Class A Common Stock | 2,510 | $245.4885 | $616K |
| Sale | Class A Common Stock | 2,405 | $246.7104 | $593K |
| Sale | Class A Common Stock | 564 | $247.3302 | $139K |
| 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 — 4,239,876 shares (Indirect, See footnote);
Class A Common Stock — 18,752 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 Prince 2021 Remainder Trust dated September 23, 2021, for which the reporting person serves as an investment advisor. The sale reported in this Form 4 was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on February 26, 2026. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $239.035 to $240.0325, inclusive. The reporting person undertakes to provide 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 (12) and (14) through (27) 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 $240.0375 to $241.035, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $241.04 to $242.035, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $242.04 to $243.03, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $243.04 to $243.93, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $244.0675 to $245.05, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $245.07 to $246.02, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $246.23 to $247.215, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $247.23 to $247.485, inclusive. 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 price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $244.18 to $245.05, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $245.1825 to $246.18, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $246.185 to $247.18, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $247.185 to $248.175, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $248.185 to $249.175, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $249.225 to $250.1075, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $250.345 to $250.43, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $243.5125 to $244.18, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $244.825 to $245.8225, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $245.825 to $246.81, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $246.83 to $247.8275, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $247.8375 to $248.83, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $248.85 to $249.81, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $249.85 to $250.43, 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 The Matthew Prince 2024 Grantor Retained Annuity Trust dated May 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: 86,014 shares
Sale price range: $239.035–$250.43 per share
Conversion price: $0.00 per share
+3 more
6 metrics
Shares sold
86,014 shares
Net open-market sales of Class A Common Stock
Sale price range
$239.035–$250.43 per share
Weighted average price ranges from multiple transaction footnotes
Conversion price
$0.00 per share
Class B to Class A conversion exercise price
Direct Class A holdings
360,807 shares
Class A Common Stock held directly as of July 1, 2026
Derivative block example
2,000,000 underlying shares
One indirect Class B position convertible into Class A
Rule 10b5-1 plan date
February 26, 2026
Adoption date of pre-arranged trading plan
Key Terms
Rule 10b5-1 trading plan, Class B Common Stock, weighted average price, Grantor Retained Annuity Trust, +2 more
6 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 26, 2026."
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.
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.
Grantor Retained Annuity Trust financial
"The shares are held of record by The Matthew Prince 2024 Grantor Retained Annuity Trust dated May 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.
investment advisor financial
"for which the reporting person serves as an investment advisor."
An investment advisor is a person or firm that provides personalized guidance on buying, selling and managing investments and often oversees client portfolios for a fee. For investors this matters because the advisor shapes risk, costs and long-term returns, and is typically required by law to act in the client’s best interests — think of them as a financial coach or GPS that helps navigate choices and avoid costly detours.
Revocable Trust financial
"The shares are held of record by The Matthew Prince Revocable Trust dated October 29, 2015..."
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.
FAQ
What insider transactions did Cloudflare (NET) report for CEO Matthew Prince?
Cloudflare reported that CEO Matthew Prince’s associated trusts converted derivative Class B shares into 86,014 Class A shares and sold them in open-market trades. These were indirect transactions, not direct personal sales of his individual holdings.
Were the Cloudflare (NET) insider sales made under a Rule 10b5-1 plan?
Yes. A footnote states the sale reported in this Form 4 was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on February 26, 2026, indicating the trades were pre-arranged.