If the idea of living the secret agent life sounds thrilling, think again—Keith O’Brien’s latest affidavit paints a very different picture. His story serves as a stark reminder of the risks and realities behind the spy game.
Recently, an Irish judge granted O’Brien a restraining order against several unidentified men, according to court documents. O’Brien testified that he’s been followed multiple times—once by two men in a gray Skoda Superb and more frequently by a heavy-set, short-haired man in a black SUV, sometimes with a large dog in tow. These men reportedly watched his car and kept tabs on his home, fueling his fears of being targeted.
O’Brien’s tale has captivated the tech industry since his dramatic confession in April. He claimed to be a spy for Deel, earning €5,000 a month to steal inside information from Rippling—covering everything from product details to customer data. Rippling uncovered his activities by setting up a honeypot Slack channel, and on the day he was caught, O’Brien allegedly tried to destroy evidence by flushing his phone down the toilet and later smashing it, dropping pieces into a drain at his mother-in-law’s house.
Now, O’Brien is a key witness in Rippling’s lawsuit against Deel. Interestingly, Rippling is covering his legal and related expenses, according to its lawyers. The rivalry between the two HR tech giants runs deep—Deel, once a Rippling customer, now offers competing products and is countersuing Rippling, claiming it was also spied on by a Rippling employee impersonating a customer.
In recent court testimony, O’Brien described attempting to lose the black SUV by taking unpredictable routes, only to see it reappear behind him. He hired a security firm, fearing someone might be placing tracking devices on his vehicle. His experiences have taken an emotional toll, he said, causing anxiety for himself and his wife, affecting their sleep and concentration, and raising concerns about their four children’s safety.
Both O’Brien and his lawyer suggest these incidents might be related to harassment linked to his role as a star witness. However, they also admitted there’s no concrete evidence connecting the men to Deel. Deel has denied any knowledge of the man in the black SUV.
When the judge granted the restraining order, he reportedly quipped, “As if they are in a 1970s cops and robbers TV show.”
As this legal battle unfolds between these two well-funded HR startups, O’Brien finds himself caught in a tense and painful tug of war. His testimony reveals a story filled with intrigue, danger, and personal upheaval—reminding us all that the spy life is far from glamorous.
