Startups Weekly: Stay Tuned for the Rippling Espionage Movie
San Francisco, CA – April 4, 2025
This week’s startup scene delivered a plot twist straight out of a Hollywood thriller, with HR tech giant Rippling dropping a bombshell that’s got everyone buzzing: a corporate espionage saga involving rival Deel that’s so wild, it’s begging for a big-screen adaptation. In the latest edition of Startups Weekly from TechCrunch, writer Anna Heim teases, “Stay tuned for the Rippling espionage movie,” as the feud between these two unicorns escalates from boardroom rivalry to a legal showdown packed with cloak-and-dagger drama.
The saga kicked into high gear on April 2 when Rippling released an affidavit from Keith O’Brien, a former employee who confessed to spying for Deel while on Rippling’s payroll. O’Brien’s sworn statement, filed in Dublin’s High Court, reads like a script: secret payments in cryptocurrency, coded Slack searches, and a frantic phone-smashing escape at his mother-in-law’s house after a court order cornered him. Rippling’s lawsuit, launched March 17 in San Francisco federal court, accuses Deel of orchestrating a months-long scheme to steal trade secrets—everything from sales pipelines to customer demos—allegedly directed by Deel’s CEO Alex Bouaziz and CFO Philippe Bouaziz. “Pass the popcorn,” Heim quips, noting how Rippling’s CEO Parker Conrad has turned the affidavit into a public spectacle, complete with a tweetstorm and a PR blitz.
The stakes are sky-high. Rippling, valued at $13.5 billion, and Deel, pegged at $12 billion, are titans in the HR tech space, battling for dominance in a market fueled by remote work’s boom. Rippling claims O’Brien’s espionage—over 6,000 Slack searches, including 23 daily hits for “Deel”—gave Deel an edge in poaching clients and staff. Deel fires back, calling it a “sensationalized” distraction from Rippling’s own woes, like alleged sanctions violations in Russia (which Rippling denies). “This is more entertaining than when they decline to disclose any details,” Heim writes, capturing the startup world’s glee at the unfolding chaos.
Posts on X reflect the hype, with users dubbing it “Silicon Valley’s spy flick” and speculating on casting—Conrad as the relentless avenger, Bouaziz as the cunning mastermind. Yet, beneath the drama, there’s substance: Rippling’s seeking a $16 billion valuation in a new funding round, per Bloomberg, even as it flexes legal muscle. Deel, meanwhile, shrugs off the suit, with investors reportedly unfazed, per The Information. “Founders aren’t always reliable when they hint at something suspicious,” Heim cautions, but the affidavit’s details—crypto payoffs, a staged Slack trap—lend Rippling’s case a gritty edge.
As the lawsuit churns toward a jury trial, the startup ecosystem’s glued to the screen. Will Rippling’s sting operation hold up in court? Can Deel counterpunch with its own narrative? One thing’s certain: this HR tech rivalry’s got more twists than a summer blockbuster—and we’re all waiting for the next reel.
By Staff Writer, TechCrunch Startups Desk