“House of cards is beginning to crumble”: Deel targets Rippling over alleged witness payments
Deel spotlights sworn testimony and demands unredacted agreements.
The bitter legal feud between global HR tech rivals Deel and Rippling has entered a new phase, one that raises serious questions about witness payments, redacted evidence, and the aggressive tactics fueling one of the industry’s most acrimonious battles. In a newly released affidavit and a blog post published over the weekend, Deel is publicly challenging the credibility and conduct of its competitor, as a transatlantic courtroom war stretches from California to Delaware to Ireland.
At the heart of the controversy is Keith O’Brien, a former Rippling employee who admitted to leaking company documents to Deel while on Rippling’s payroll. In an affidavit recently made public, Rippling’s former general counsel, Vanessa Wu, details that Rippling terminated O’Brien and then paid him a severance in exchange for signing an agreement not to sue. According to the same affidavit, Rippling later entered a second agreement with O’Brien, this time to pay for his out-of-pocket legal and other expenses as part of his cooperation in ongoing litigation.
Deel is now demanding to compel Rippling to hand over unredacted versions of both agreements, arguing that these documents could shed light on the extent of coordination between Rippling and its former employee. Deel has seized on what it describes as an extraordinary situation: a fired employee who admitted to misconduct, later being financially supported by his former employer as a cooperating witness.
"Rippling's alleged case all centers on Keith O'Brien - a paid witness," a Deel company spokesperson told CTech. "Rippling has withheld the agreements it entered into with Mr. O'Brien and the materials provided have been heavily redacted. Today we had to ask the Irish court to order production of the unredacted and full agreements detailing what exactly Rippling has paid for Mr. O'Brien's testimony.
"And on Friday in the US case, Rippling asked the court to amend its lawsuit - days after its General Counsel quit and we filed a countersuit. It's clear that the legal house of cards that Rippling has built is beginning to crumble."
The new revelations come just days after Deel published a blog post that doubled down on its accusations against Rippling. The post describes Deel’s recent countersuit in Delaware as a necessary response to what it calls a "years-long smear" campaign waged by Rippling, a campaign it claims was orchestrated to slow down a more successful competitor. “Rippling’s strategy of lawyering its way to victory isn’t working,” Deel wrote. “We decided we couldn’t let Rippling’s attacks on our company stand any longer. That’s why we sued Rippling - because at some point, enough is enough.”
The Delaware countersuit alleges that Rippling hired PR consultants to spread negative stories and used marketing language that referred to Deel’s services as “snake oil.” Deel also claims Rippling worked to infiltrate the company and manipulate public perception through disinformation.
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Rippling initially filed suit in California, accusing Deel of corporate espionage and recruiting O’Brien to serve as a mole inside its Dublin office. Deel strongly denies those allegations, calling them defamatory and retaliatory. With both companies now valued at more than $12 billion and operating in over 150 countries, the litigation is more than a public spectacle - it’s a proxy battle for global dominance in a compliance-heavy, high-stakes market.
According to Deel’s blog post, Rippling recently amended its California lawsuit rather than risk dismissal. “The legal house of cards that Rippling has built is beginning to crumble,” Deel wrote. It also previewed upcoming developments in the Irish proceedings, stating: “How Rippling’s Russia whistleblower became a paid ‘witness’ against Deel is one of the many questions Rippling eventually will have to answer.”
As both companies bring in heavyweight legal talent to lead their efforts - Deel with Broadcom veteran DeAnn Work, and Rippling with Snap’s former top lawyer Chris Handman - what began as a commercial rivalry now resembles a geopolitical legal thriller. The next chapter will unfold in Dublin, where Deel is betting that the facts behind sealed witness agreements could turn the tide in a case that has already upended the HR tech world.
