April 4, 2023 faces exec team exodus and makes layoffs ‘by stealth’

The European rival to Stripe has lost six executives in the last nine months, and sources say it’s carrying out dozens of behind-the-scenes layoffs each week

Amy O'Brien

5 min read

Guillaume Pousaz, CEO of

Just over a year after raising $1bn in a Series D funding round, Europe’s gilded payments startup is facing an exodus from its executive team and making a series of unannounced layoffs.

In the last nine months, six executives that reported directly to CEO Guillaume Pousaz have left the company, according to people familiar with the moves. 

After publicly cutting staff by 5% in September last year, sources also tell Sifted that Checkout has made further cuts in a series of “layoffs by stealth” over the last three months. 


Exec exodus

In the past nine months, six executives that reported directly to Pousaz, including two members of the C-suite, have quit or been fired, according to three people familiar with the matter. That means the C-suite has dropped from eight to six members.

Head of crypto strategy Jess Houlgrave resigned from the company in March, after joining three years ago as chief of staff. She has updated her LinkedIn to show that she's now left the company. 

Her departure follows that of Checkout’s chief marketing officer Leela Srinivasan last month. Pousaz announced that she was leaving in a company all-hands meeting on February 1. She had been at the company for a year and a half, and sat in the C-suite.

This coincided with the public announcement of chief financial officer Celine Dufetel’s promotion to "president and chief operating officer" (having previously been CFO and COO), with an increased remit including marketing.

Dufetel and chief people officer Kerry Van Voris are the only female members of Checkout's C-suite remaining.

Mike Benchimol, the company’s former chief operating officer — who sat on the company board — also resigned in summer last year and left at the end of 2022. He’d transitioned to a role as head of strategic financial partnerships in April 2022, according to his LinkedIn. A Checkout spokesperson said that Benchimol left on mutually agreed-upon terms in January 2023. 

Olivia Broderick, who was Checkout’s general counsel and head of regulatory for almost two and a half years, left the company in September last year.

Riaz Bordie, the company’s ex-CTO and then SVP of engineering, resigned in November last year. He had been at the company for nine years. Chief revenue officer Nick Worswick, formerly chief sales officer at WeWork, was fired in July 2022, the same people tell Sifted. He had been at the company for a year and a half, and was a member of the C-suite. A Checkout spokesperson said that Worswick had left mutually agreed-upon terms. 

Dozens of other senior employees, including multiple legal, risk and compliance directors, have left the company in the last 12 months, according to documents seen by Sifted. Their departures have been a combination of layoffs and resignations over company culture or changing business strategy, the three people say.  

When Sifted contacted about these departures, a spokesperson said: “Departures from our executive team are by mutual agreement and we are grateful for their contributions and leadership in establishing the foundations of our business and in getting to where it is today.”


Layoffs by stealth

Checkout has also been reducing its overall headcount gradually over the last three months, three former employees tell Sifted. 

Checkout’s entire customer services operations team in London, bar one, was laid off at the end of February, according to two employees who recently left the company. Two members of the five-strong French underwriting team were laid off mid-March, according to the two former employees, as were half the talent acquisition team.  

People are just waiting around to see if they get laid off. It's death by 1,000 cuts

Last week, about 20 Checkout employees from marketing and commercial teams were laid off, the former employees tell Sifted. Individuals from several other teams, including HR and learning and development, have taken to LinkedIn to announce they’ve been laid off over the last few weeks. 

“We are seeing about 20 to 30 deactivations on Slack a week right now from Checkout,” one of the former employees says.

This is “layoffs by stealth”, says one of the former employees.

“Every team apart from sales has been losing at least a few people,” another former employee tells Sifted. 

Since the September layoffs, Checkout’s LinkedIn page shows the company has lost another 100 employees overall. A spokesperson said the company’s current headcount stands at 1,840. Before the September 2022 layoffs, headcount was 2,034.

“It has been awful for employees, one fell swoop would have been much better,” one of the former employees tells Sifted. 

“Every week, they don't know who is going to disappear and people are just waiting around to see if they get laid off. It's death by 1,000 cuts.”

The company’s Glassdoor page also contains several reviews citing layoffs in the last three months, as does the more tech-focused forum Blind.

“Pressure from late stage investors is real, and this translates into people being pushed to quit, instead of doing a formal layoff,” says one former employee’s Glassdoor review. 

“Feb '23 — Another massive round of redundancies impacting talented people. Mar '23 — More layoffs and redundancies impacted more people,” another Glassdoor review reads. 

Meanwhile over on a Blind thread, several people advise a Checkout job candidate to avoid the company.

“There are rolling layoffs that are happening weekly. Long-time employees are pushed out with little/no explanation and treated horribly,” says one comment. 

“There have been several rounds of stealth layoffs and generally pushing people to leave through highly unpopular policy decisions,” another comment says.

A spokesperson for Checkout said the headcount reductions are “a combination of natural attrition and resource planning”.

Amy O’Brien is Sifted’s fintech reporter. She tweets from @Amy_EOBrien and writes our fintech newsletter — you can sign up here.

Update: April 24, 2023. This article has been updated to clarify the size of the French underwriting team.

Update: April 26, 2023. The article has been updated to include comments from a Checkout spokesperson saying that Benchimol and Worswick left on mutually agreed-upon terms. 

Amy O'Brien

Amy O'Brien was a reporter at Sifted, covering fintech