Automattic's 33-hour coup should change how you sign software contracts

On 9 September, Automattic's board voted to put Matt Mullenweg on paid leave. Thirty-three hours and twenty minutes later he was back. The directors who had moved against him were gone, and so were the chief financial officer and the chief legal officer. If you run a WooCommerce store, hold a WordPress.com enterprise account or buy ads on Tumblr, the company on the other side of your contract spent a day and a half without an agreed answer to who was in charge.

My first reaction was the one I expect most operators had. I filed it as boardroom soap opera, fun to read and irrelevant to procurement. I changed my mind when I read what the two outgoing executives did with those hours. Mark Davies, who was to be interim CEO, and Andy Missan, the legal chief, each signed the other's severance agreement, effective 10 September, worth a year of salary plus extra equity vesting if their exits qualify. When the people responsible for the money and the contracts are countersigning each other's payouts, I do not assume anyone was handling customer escalations on contract terms that week.

Then look at how it ended. Mullenweg controls 84% of the vote, a figure he gave on stage at TechCrunch Disrupt 2024. He used it to remove General Ann Dunwoody from the board, while Sue Decker and Toni Schneider resigned. Their replacements include Hugh Howey, author of the Silo novels, the relationship author Amy Chan, and two co-founders of IRL, a social app that shut down after investigations found nearly all its users were bots. He told staff that for purposes of Delaware law he is CEO, president, treasurer and secretary. The board has still not said why it tried to remove him. Automattic's spokesperson says he has "full support of the board", which is easy to believe of a board he appointed a fortnight ago.

I think buyers should treat this as a single point of failure on the vendor side, and price it the way they would price a vendor running on one data centre.

You could argue that founder control is exactly the stability buyers want. The board moved against Mullenweg and lost within a day and a half. At a company with a scattered shareholder base, that fight could have run for months and frozen the roadmap. A founder with a controlling stake thinks in decades, and nobody can sell your vendor to a private equity firm without his signature. I take that seriously. I also have to admit I found no data on how enterprise customers reacted to the ouster, so I cannot tell you that anyone walked.

The risk I care about is what a controlling founder can do to customers when nobody can stop him, and Automattic has form. In October 2024, in the middle of its fight with WP Engine, WordPress.org forked the Advanced Custom Fields plugin into Secure Custom Fields, and users who relied on WordPress.org for automatic updates were moved to the fork. The security consultant Tim Nash said the new version was no more secure than the original. In December 2024 Judge Araceli Martínez-Olguín granted WP Engine a preliminary injunction, finding it likely to win on intentional interference with contractual relations, and accepted the loss of a $40,000 client contract as evidence of irreparable harm. A ruling in September 2025 let most of WP Engine's claims proceed, including defamation and unfair competition. Automattic calls the suit baseless and says the injunction was made before discovery. Fair enough, no court has ruled on the merits. For a buyer, the relevant fact is that a hosting customer lost business because of a fight between two vendors, and a federal judge found that loss credible.

Since his return, Mullenweg has replaced his litigation counsel with Susman Godfrey and removed the finance and legal chiefs who might have argued for caution. WP Engine's lawyers accused him in July of destroying evidence. In his own statement after the reshuffle, he said what happens over the coming half-year will set the company's course for two decades. I believe him, and I would not want my checkout or my content system riding on that bet without a way out.

Standard contract protections do nothing here. A change-of-control clause never triggers, because the same man held the vote throughout. If you buy from Automattic or any vendor where one person holds the vote, add a termination right triggered by the departure of the CFO or general counsel, or by replacement of most of the board inside a single quarter. Insist on data export in a format you can run on another host, and tie any multi-year discount to your right to leave.

Mullenweg's own six-month clock runs out next March. Until then I would sign nothing with Automattic that renews past that point without a governance exit clause. This week, send every founder-controlled vendor on your list one written question: who can overrule the CEO. If the answer is nobody, cap the term at a year.

Prompted by Automattic has a new board after failed attempt to put CEO on leave | TechCrunch, TechCrunch.