Automattic Shakeup: Interim CEO and Legal Chief Signed Reciprocal Severance Deals During Mullenweg Leave

TL;DR

• During CEO Matt Mullenweg's brief leave in late August, interim CEO Mark Davies and General Counsel Andy Missan signed each other's severance agreements, granting one year of salary plus accelerated equity vesting.
• The reciprocal arrangement was approved without Mullenweg or a fully independent board vote, raising serious questions about oversight at the privately held WordPress parent company.
• The episode highlights deepening internal power struggles at Automattic following a year of lawsuits, executive turnover, and clashes over WordPress governance.

A Leave At The Top

Automattic, the $7.5 billion parent company behind WordPress.com, WooCommerce, and Tumblr, is facing a fresh governance crisis.

Founder and longtime CEO Matt Mullenweg took a brief personal leave in late August 2026, handing day-to-day control to Chief Financial Officer Mark Davies as interim CEO. What was supposed to be a routine, short-term handoff has now turned into one of the most scrutinized moments in the company's 21-year history.

According to internal documents and sources familiar with the matter, during that window Davies and the company's top lawyer, General Counsel and Chief Legal Officer Andy Missan, executed new severance agreements for each other.

In effect, the two men in charge of the company while Mullenweg was out approved each other's golden parachutes.

The Paper Trail: Who Signed What

Corporate filings and insider accounts paint a remarkably circular picture.

As interim CEO, Davies signed off on an enhanced severance package for Missan. Days later, in his capacity as the senior legal officer overseeing corporate governance, Missan signed off on a mirror-image package for Davies.

Neither agreement was in place in that form before the leave, sources say. Both were finalized while Mullenweg was away and before the full board could conduct a formal review.

An Automattic spokesperson has not disputed that the signatures occurred, but characterized them as standard retention agreements consistent with market practice for executives at this level. Mullenweg himself has not publicly commented on the validity of the deals since returning in early September.

One Year Pay Plus Equity: Inside The Payouts

The terms are generous even by Silicon Valley standards.

Each agreement reportedly guarantees 12 months of base salary in the event of termination without cause, plus continued health benefits and accelerated vesting of additional equity.

For Davies, who joined Automattic in 2023 after stints at Vivendi, AOL and Skype, and for Missan, a veteran legal chief who has steered the company through its bruising legal battle with WP Engine, the equity component is the real prize. Automattic is privately held but offers liquidity via secondary sales and buybacks, meaning accelerated vesting could translate into a seven-figure payout.

Employment experts say single-trigger or double-trigger acceleration of that size is typically reserved for founders or C-suite hires at public companies, and almost always requires independent compensation committee approval - not a reciprocal sign-off between the two beneficiaries.

A Textbook Governance Failure?

Governance experts are calling the arrangement a red flag.

The core issue is not the size of the severance, but the process. Allowing two acting executives to approve each other's compensation creates a clear conflict of interest, bypassing the checks that boards, investors, and employees expect.

Automattic has long operated with an unusual structure. Mullenweg controls the company and the WordPress Foundation, and the board has historically included close allies and insiders rather than a majority of independent directors. Critics argue that vacuum made this kind of deal possible.

If the CEO is out, who watches the interim CEO? In a public company, that would be the independent board. At Automattic, sources say, there was no meaningful check during those two weeks.

Power Struggle Or Self-Preservation?

Inside Automattic, interpretations diverge sharply.

One camp views the deals as self-preservation. The past 18 months have been tumultuous, with mass buyouts in late 2024, the resignations of several senior leaders, and the ongoing WP Engine litigation that has drained resources and morale. Davies and Missan, thrust into the top jobs during a volatile period, wanted protection before making hard calls.

Another camp sees a quiet power play. By locking in one year of pay and equity vesting, the two executives significantly raised the cost of removing them, effectively entrenching themselves just as Mullenweg was preparing a broader leadership reshuffle upon his return.

Several former employees described the move on social media as symptomatic of a trust breakdown between Mullenweg and his executive bench - a founder who centralized power for two decades now facing lieutenants who are lawyering up.

What Happens Next

Mullenweg is now back as CEO, and Davies has returned to the CFO role. But the severance agreements remain in effect, unless the board moves to rescind or amend them.

That puts Automattic's board in a difficult spot. Voiding deals signed by an authorized interim CEO could trigger immediate legal claims from two of its most powerful executives. Leaving them in place risks further backlash from staff and the broader WordPress open-source community, which has grown increasingly vocal about Automattic's corporate governance.

Legal scholars say the incident could also surface in the company's ongoing litigation with WP Engine, where questions about control, fiduciary duty, and use of WordPress resources are already central.

For now, Automattic has declined to say whether an independent review is underway. But for a company that powers more than 40% of the web, a two-week leave just exposed how fragile its succession plan really is.

AndroGuider Team

Articles written by the AndroGuider team. We try to make them thorough and informational while being easy to read.