Rippling Spy Claims Surveillance, Wife Fears for Family Safety

The real-life drama involving a confessed Rippling spy has taken another turn, resembling something out of a spy thriller. Keith O’Brien, who previously admitted to spying for Deel, has been granted a restraining order against unidentified men he claims have been following him and watching his home. According to court documents reviewed by TechCrunch, O’Brien testified that he was followed on multiple occasions, once by two men in a gray Skoda Superb and more frequently by a short-haired, heavy-set man in a black SUV, sometimes accompanied by a large dog.

O’Brien’s story initially gained traction after his confession in April, where he admitted to being paid €5,000 a month by Deel to pilfer Rippling’s confidential data, including product and customer information. Rippling reportedly caught him after setting up a honeypot Slack channel. In a dramatic turn of events, O’Brien allegedly attempted to destroy his phone by flushing it down a toilet and later smashing it, disposing of the pieces at his mother-in-law’s residence.

Now, O’Brien is a key witness in Rippling’s lawsuit against Deel, with Rippling covering his legal expenses, as testified by their lawyers. Deel has countersued Rippling, alleging they were also spied on by a Rippling employee who impersonated a customer. The rivalry between these two HR tech companies has been intense since Deel began offering competing products after once being a Rippling customer.

O’Brien testified that he attempted to evade the black SUV by making sudden turns and taking circuitous routes home, but the vehicle consistently reappeared. He has since hired a security consulting company and suspects tracking devices were being placed on his car.

According to O’Brien, these incidents have caused significant “emotional and psychological” distress for him and his wife, leading to anxiety, sleep disturbances, and impaired concentration. The couple fears for the safety of their four children. While O’Brien and his lawyer suspect the surveillance is related to his role as a star witness, they admitted in court that they lack concrete evidence linking the men to Deel. Deel has also denied any knowledge of the man in the black SUV.

The judge in the case remarked, according to the Irish publication Business Post, “As if they are in a 1970s cops and robbers” TV show when granting the injunction.

Regardless of the outcome of the legal battles, O’Brien finds himself at the center of a contentious dispute between these well-funded HR startups, a position that, according to his testimony, is far from comfortable.