Rippling Spy Says Men Have Been Following Him, and His Wife Is Afraid

TL;DR

• Keith O’Brien, the self-confessed spy in Rippling’s lawsuit against Deel, has been granted a restraining order after reporting ongoing harassment and surveillance.
  
• O’Brien claims he and his family are being followed and intimidated by unidentified individuals amid his role as a key witness.
  
• Both Rippling and Deel are locked in a bitter legal battle over allegations of corporate espionage in the HR tech industry.
  
• The harassment may be linked to the ongoing trial, although no direct evidence has tied the behavior to Deel.
  

The Ongoing Espionage Drama in HR Tech

The saga involving two major HR technology rivals — Rippling and Deel — has taken a dramatic turn. Keith O’Brien, a confessed spy for Deel who is now a central witness in Rippling’s lawsuit, testified in Irish court that he and his family are being harassed and surveilled by unknown individuals.

O’Brien, who admitted in April to leaking internal Rippling data in exchange for €5,000 per month from Deel, recently secured a restraining order in Ireland. The court documents, seen by TechCrunch, reveal that he reported multiple incidents of stalking — including being followed by a man in a black SUV, often accompanied by a large dog, and being trailed by a gray Skoda Superb on another occasion.

The legal dispute underscores how corporate espionage in high-stakes tech sectors is no longer confined to fictional thrillers. It also raises questions about witness protection in complex international litigation.

The Confession That Sparked a Legal Firestorm

Earlier this year, O’Brien admitted that Deel paid him to infiltrate Rippling’s internal systems. He accessed sensitive information on product strategies, customer lists, and business development efforts, a move that Rippling claims caused material harm.

Rippling eventually caught O’Brien using a honeypot Slack channel, designed to bait the mole. According to his affidavit, when confronted, he pretended to flush his phone down the company toilet, only to later destroy the device and dispose of its parts at his mother-in-law’s home.

His confession has now made him the star witness in Rippling’s legal crusade against Deel — one that has garnered substantial media attention.

Deel’s Counterlawsuit and Denials

In response, Deel has countersued, claiming Rippling also spied on them using one of its own employees who allegedly impersonated a customer. Deel has categorically denied any knowledge or involvement with the individuals allegedly stalking O’Brien.

Despite O’Brien and his attorney’s speculation that the surveillance is tied to his whistleblowing, no direct evidence has emerged linking the harassment to Deel. Even the Irish court acknowledged the speculative nature of the accusations but granted the injunction based on O’Brien’s testimony and concerns for family safety.

Surveillance, Safety, and Legal Protection

The details shared by O’Brien are chilling: evasive driving to lose tails, suspected GPS tracking, and hiring private security consultants. These allegations paint a picture of a witness caught in the crossfire between two powerful, well-funded startups.

O’Brien stated in his latest court filing that both he and his wife are experiencing “emotional and psychological distress” and live in fear for the safety of their four children. The court injunction now legally prevents further physical or digital surveillance of the family.

A High-Stakes Rivalry: Deel vs. Rippling

Rippling and Deel have been on a collision course since Deel transitioned from being a Rippling customer to a direct competitor. Both companies offer HR and payroll software globally and are valued in the multi-billion-dollar range. Their rivalry is one of the most high-profile disputes in the fast-evolving HR technology landscape.

With Rippling footing O’Brien’s legal and related expenses, the optics suggest the company is heavily invested in both the litigation and narrative control surrounding the case.

Courtroom Drama or Corporate Intimidation?

The presiding judge in Ireland reportedly quipped that the case resembled a “1970s cops and robbers” show, highlighting the theatrical and murky nature of events. While no criminal charges have been filed, the civil proceedings are painting a dark picture of modern tech industry tactics, including infiltration, surveillance, and public spectacle.

Whether or not the harassment O’Brien reports is directly tied to Deel, the situation underscores the personal toll of corporate legal warfare. Witnesses in high-profile cases can become lightning rods, drawing attention and risk in equal measure.

Timeline of the Rippling vs. Deel Espionage Dispute

Conclusion: Spy Games with Real-World Consequences

The unfolding legal battle between Rippling and Deel offers a rare, dramatic look into the competitive intensity and ethical grey zones of the modern HR tech world. While Keith O’Brien’s testimony has become central to Rippling’s case, it has also seemingly made him — and his family — targets of troubling harassment.

Regardless of who is behind the intimidation, the message is clear: the stakes in startup rivalries are no longer limited to valuation battles or feature wars — they now include reputation, personal safety, and legal high drama. As the courtroom drama continues, all eyes will be on whether this case leads to greater accountability or simply another chapter in Silicon Valley’s playbook of extremes.