The ongoing Rippling-Deel spy scandal just took another bizarre twist. Keith O’Brien, the self-confessed corporate spy at the center of the case, has now been granted a restraining order by an Irish judge after alleging that he and his family have been followed, watched, and harassed for weeks by unidentified men.
According to court filings reviewed by TechCrunch, O’Brien described multiple surveillance incidents, including being tailed by men in a gray Skoda Superb and, more frequently, a short-haired man driving a black SUV—sometimes with a large dog. O’Brien claims these individuals have been lurking outside his home and following his car, creating what he described as a state of “emotional and psychological damage” for him and his family.
He even hired a security consultancy after growing suspicious that tracking devices might have been planted on his vehicle. “We’ve been experiencing anxiety at home and in public,” O’Brien said in his affidavit. “It has affected our sleep and concentration. We are scared for our children’s safety.”
From Slack Honeypot to Star Witness
O’Brien first made headlines in April when he confessed to being a spy for Deel, a direct competitor to Rippling. He admitted to receiving €5,000 a month to steal confidential Rippling data—including internal communications, customer info, and product updates. The operation unraveled when Rippling planted a honeypot Slack channel, catching O’Brien red-handed.
In a dramatic sequence of events, O’Brien allegedly tried to destroy the evidence by pretending to flush his phone at the office and later smashing it to pieces at his mother-in-law’s home, scattering fragments down the drain.
Now, O’Brien has flipped sides and is testifying for Rippling, which is covering his legal costs. The HR tech rivals have been locked in a legal showdown, with Deel also filing a countersuit alleging that Rippling spied on them, using an employee who posed as a customer.
O’Brien’s claims of surveillance have added a thriller-like layer to the legal war. Though his legal team suggested the harassment might be linked to his whistleblower role, they acknowledged in court that there is no direct evidence tying the mysterious men to Deel. Deel has also publicly denied any connection to the black SUV or any surveillance activity.
Legal Battles and Startup Rivalries Turn Personal
The judge who approved the restraining order couldn’t help but remark on the surreal nature of the events, comparing it to something out of a “1970s cops and robbers TV show,” according to Business Post.
Regardless of how the lawsuits between Rippling and Deel unfold, O’Brien has become the very human centerpiece in a tug-of-war between two billion-dollar HR tech startups. What started as a cold corporate rivalry has now spilled into people’s homes and families—with real-world consequences far beyond the courtroom.
His testimony paints a bleak picture of a life caught between loyalty, fear, and legal fallout. If the tech world once saw O’Brien’s confession as juicy drama, this latest development serves as a cautionary tale: being a startup spy isn’t nearly as glamorous as fiction makes it seem.
