Rippling spy says men have been following him, and his wife is afraid

If becoming a spy sounds like an exciting way to live like a le Carré character, let this newest affidavit from confessed Rippling spy Keith O’Brien serve as a warning.

On Friday, an Irish judge granted O’Brien a restraining order against several men who have not yet been identified, according to the court order seen by TechCrunch. O’Brien testified that multiple men — two in a gray Skoda Superb on one occasion, and more often, a short-haired, heavy-set man in a black SUV, sometimes accompanied by a large dog — had repeatedly followed his car and watched his home.

O’Brien’s story has captured the imagination of the tech industry after his colorful confession in April, in which he alleged that he was a spy for Deel. He said he was paid €5,000 a month to steal Rippling’s internal data on everything from products to customers. Rippling caught him by setting up a honeypot Slack channel. On the day he was caught, O’Brien pretended to flush his phone down the corporate toilet and later smashed it, dropping pieces down the drain at his mother-in-law’s house, according to his affidavit. 

Now he’s the star witness for Rippling in its lawsuit against Deel. Rippling is even picking up the tab for his legal and related expenses, its lawyers testified. Deel is also countersuing Rippling, claiming it was spied on too, by a Rippling employee impersonating a customer. The two HR tech companies have been bitter rivals for years after Deel — once a Rippling customer — began offering competing products. 

In the latest part of the saga, O’Brien testified that he tried to lose the black SUV following his car by making sudden turns and taking roundabout ways to get home, only to see it reappear in his rearview mirror. He hired a security consulting company and feared that someone was placing tracking devices on his car.

O’Brien claims all of these incidents have created “emotional and psychological” damage for himself and his wife. “We have been experiencing anxiety at home and in public. It has affected our sleep and our concentration,” O’Brien said in his latest affidavit. They are fearful for the safety of their four children.

He and his lawyer speculated that this was intended as harassment related to his role as star witness. However, O’Brien’s lawyer also admitted in court that they had no evidence tying the men to Deel. Deel also denied knowing anything about the man in the black SUV.

According to the Irish publication Business Post, when granting the injunction, the judge apparently said, “As if they are in a 1970s cops and robbers” TV show. 

Whatever happens in the dueling court cases, O’Brien has made himself the rope in a bitter tug of war between these two well-funded HR startups. And from what he says in his testimony, it sounds painful.