The real-life saga of confessed corporate spy Keith O’Brien — now at the center of a fierce legal battle between HR tech rivals Rippling and Deel — has taken another dramatic twist. On Friday, an Irish judge granted O’Brien a restraining order after he testified about repeated incidents of being followed and surveilled by unknown individuals, escalating the intrigue in one of tech’s most talked-about courtroom dramas.
O’Brien, who admitted earlier this year to being paid €5,000 a month by Deel to steal sensitive data from Rippling, is now the star witness in Rippling’s lawsuit against its former client and current competitor. In his latest affidavit, O’Brien described being followed by two unidentified men in a gray Skoda Superb and, on multiple occasions, by a short-haired, heavyset man driving a black SUV — sometimes accompanied by a large dog. O’Brien also testified that these events caused “emotional and psychological” distress to him and his family.
“We have been experiencing anxiety at home and in public. It has affected our sleep and our concentration,” he wrote. He also expressed fears for the safety of his four children.
The judge, in granting the restraining order, reportedly quipped that the situation sounded like something out of a 1970s cops-and-robbers television show, according to Business Post.
This new chapter in the ongoing Rippling vs. Deel courtroom saga has only heightened the stakes. O’Brien previously made headlines in April after Rippling exposed him via a honeypot Slack channel. His subsequent attempts to destroy evidence — including allegedly flushing his phone and later smashing it — added colorful detail to what was already a sensational case of tech espionage.
Rippling’s lawyers testified that the company is covering O’Brien’s legal costs as he serves as their key witness. Meanwhile, Deel has countersued Rippling, alleging that the rival HR platform also engaged in corporate spying — this time by having an employee impersonate a customer to extract sensitive information.
Though O’Brien’s lawyer suggested the surveillance incidents were likely harassment linked to his testimony, they admitted in court that they had no evidence tying the alleged stalkers to Deel. For its part, Deel has denied any involvement, asserting that it knows nothing about the man in the black SUV or the surveillance activities described.
For now, the restraining order may offer O’Brien and his family some measure of relief — but it also underscores the human cost of what has become a bitter, high-stakes legal fight between two rapidly growing, well-funded startups.
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As this legal tug-of-war unfolds, the tech industry watches closely. The implications could stretch far beyond HR software, touching on the broader ethics of competitive intelligence in Silicon Valley’s high-speed, high-stakes race for market dominance.
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