Deel and Rippling lawyer up in cross-border legal showdown
Veteran GCs step into a dispute that spans three continents and billions in market value.
In one of the most acrimonious rivalries in global tech, the legal arms race between HR software giants Deel and Rippling is escalating—this time with major moves inside their legal departments. As high-stakes litigation unfolds across Ireland and the United States, both companies are bringing in seasoned legal generals to lead the next phase of what has become a courtroom war of attrition.
DeAnn Work, who has previously held senior legal roles at Broadcom and Altaba and a veteran of high-profile legal disputes, has joined Deel as General Counsel. In a LinkedIn post, Work described Deel as one of the fastest-growing companies in the global HR technology space, and said she was “looking forward to supporting Deel’s continued growth” as it operates in over 150 countries.
Across the aisle, Rippling CEO Conrad Parker said that Chris Handman—former General Counsel of Snap Inc. and a respected figure in Silicon Valley legal circles—will join as GC in June. Handman replaces Vanessa Wu, who will stay on as Senior Counsel, focusing on litigation and overseeing Rippling’s global payments entities.
The timing is no accident.
What began as a business rivalry has erupted into a multi-jurisdictional legal brawl that now includes allegations of corporate espionage, reputational sabotage, and international cat-and-mouse games over legal service.
Last week, Deel formally accepted legal service in Ireland after weeks of procedural wrangling that saw Rippling accuse its rival of “actively evading” attempts to serve documents—claims that were widely covered after failed efforts by bailiffs in multiple countries. Deel’s legal team in Dublin ultimately agreed to accept service on behalf of CEO Alex Bouaziz, fintech attorney Asif Malik, and executive Andrea David Mieli.
The underlying lawsuit, filed in Ireland’s High Court, accuses Deel of recruiting a Rippling employee, Keith O’Brien, to act as a corporate spy inside Rippling’s Dublin office. O’Brien has admitted under oath that he passed confidential Rippling materials to Deel for a monthly payment of $6,000. Deel has vigorously denied the allegations, calling them defamatory and retaliatory.
The legal conflict, however, is not limited to Europe. Deel has filed a countersuit in Delaware, alleging that Rippling orchestrated a campaign of sabotage involving bribery, disinformation, and infiltration. Deel claims Rippling hired PR consultants and lobbyists to plant negative stories and even referred to Deel’s own services as “snake oil” in its marketing materials.
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With both firms now valued above $12 billion and jockeying for control of a high-growth, compliance-heavy market, the legal stakes are about more than just reputation. They’re about strategic dominance in a field where trust, confidentiality, and operational integrity are essential.
For Deel, the appointment of Work marks a professionalization of its legal function after a period in which Philippe Bouaziz—father of CEO Alex Bouaziz—had reportedly served as the company’s interim general counsel. The move comes at a moment when Deel must navigate simultaneous legal battles, regulatory scrutiny, and complex jurisdictional dynamics, especially as its CEO continues to reside in Israel.
Rippling, for its part, has opted for continuity paired with litigation expertise. By transitioning Wu into a senior role focused on legal offensives and bringing in Handman as GC, the company is preparing for a prolonged battle that could define not only the contours of the HR tech market but also how global startups wield legal tools as competitive weapons.
