The Deel CEO and The Spy Who Slacked It Up

Happy Friday and welcome to April, Job Board Doctor friends.

Yes, I promised a compelling newsletter on tariffs this week, but with the Rippling v Deel corporate espionage scandal continuing to provide endless content opportunities I just couldn’t say no. This week, the Deel CEO and his alleged role in the scandal comes into clear focus.

What follows isn’t fiction. It’s not satire. It’s an affidavit filed in Irish High Court by Keith O’Brien — a former compliance manager at Rippling who admitted to spying on his employer for a competitor, Deel. I uploaded the entirety of the affidavit, originally published by Tech Crunch, for your Friday afternoon amusement. Trust me, there are times it is laugh out loud funny and 100% forehead slapping.

But make no mistake: this isn’t a story of a rogue employee. It’s a spy story gone way off the rails where the alleged handlers are not shadowy (or slick) operatives but Deel CEO, Alex Bouaziz, his father, CFO, Philipe Bouaziz, other members of Deel’s C-Suite, and a significant other.

What follows are highlights and quotes from the affidavit filed in the Irish High Court on April Fool’s Day 2025.

July 2023: Calm Before the Storm

Keith O’Brien starts work at Rippling’s Dublin office, focused on payroll and compliance across Europe. No headlines. No drama. Just a normal guy punching in at his 9-5.

March 2024: The JOB OFFER THAT NEVER CAME

O’Brien applies for a role at Deel but doesn’t get the job. He reaches out to CEO Alex Bouaziz via LinkedIn for feedback.

“You were an excellent candidate, but the presentation… was not good enough.”
📄 Page 1

The simple LinkedIn conversation opened the backchannel to espionage.

Mid-2024: Side Hustles & Startup Espionage

O’Brien launches a payroll consulting company called Global Payroll Geeks. He reconnects with Bouaziz and mentions he might leave Rippling to go full time on his new venture.

Instead of encouragement, he gets a very different kind of offer.

“He suggested that I remain at Rippling and become a ‘spy’ for Deel… specifically mentioning James Bond.”
📄 Page 2

Yes, you read that right.

About 30 minutes after the call, O’Brien agrees. Within hours, he’s on a WhatsApp call with Alex and his dad. Communications are immediately moved to Telegram and those messages are set to auto-delete in 24 hours.

Payment discussions begin. So not only does it take less than an hour for Mr. O’Brien to agree to begin spying on his current employer, Rippling, for the company who rejected him, Deel. He agreed to do it for 5,000 GBP a month. 

October 6, 2024: The First Payoff

O’Brien receives approximately 6,000 USD from an account tied to the COO’s wife to his Revolut account. Future payments shift to  the cryptocurrency, Ethereum, “to leave no trace.” The payment correspondence used code phrases to confirm if Alex was satisfied with the intel received or if payment would be delayed.

“Send that watch to London.”
“The buyer is happy.”
📄 Page 3

Even payments had code names. A third person in the payment chats is referred to only as “The Watchman.”

Late 2024 – Early 2025: The Flow of Stolen Data

For this brief window, and for very little money, Mr. O’Brien shared internal Rippling info regarding:

• Customer lists
• Sales pipeline and Salesforce data
• Internal Slack messages
• Product roadmaps
• Google Drive files
• Engineering details
• Strategic weaknesses
• Employee profiles for poaching

During this time, the Deel CEO, Alex becomes a near-constant presence in Keith’s workday, asking for internal intel from Slack, Salesforce, and Google Drive. His messages were a mix of paranoia and power.

“Hey boss, good weekend??”
“This channel is beast.”
“Send me the ‘superstars.’”
📄 Pages 4–5

O’Brien says he sometimes sent up to 6 screen recordings a day — and would get messages from Bouaziz if he hadn’t checked in in a few hours.

To be clear, this wasn’t passive receipt of tips. Allegedly, it was coordinated, continuous intelligence gathering, managed personally by Deel’s CEO.

February 2025: The Trap

Rippling sets a honey pot — a fake Slack channel named #d-defectors. O’Brien searches it. Moments later, Bouaziz panics:

“Oh shit.”
📄 Page 6

O’Brien later admits he was frightened. He suspected they’d been caught.

March 14, 2025: The Court Order

A court-appointed solicitor serves O’Brien with a High Court order at the office. He lies about the location of his phone, then flees to the bathroom.

“I flushed the toilet a couple of times.”
📄 Page 6

He resets his phone to factory settings in a panic. He then flees the Rippling office.

March 15, 2025: Axe, Burn, Delete

On advice from Deel’s in-house legal counsel, O’Brien destroys the phone completely:

“I smashed my old phone with an axe and put it down the drain at my mother-in-law’s house.”
📄 Page 8

He deletes LinkedIn. He’s directed to buy a burner phone. Communications continue on Telegram with Deel lawyers.

Mid-March 2025: Operation Cover-Up

O’Brien is allegedly offered relocation to Dubai, legal support, and even a consulting contract with Deel.

He’s instructed to lie to the Central Bank of Ireland:

“There’s going to be a shift in the narrative.”
📄 Page 9

The lie? That Rippling facilitated sanctioned Russian payments — a claim O’Brien later admits was completely fabricated.

March 25, 2025: The Breaking Point

Keith O’Brien receives a message from a friend:

“The truth will set you free.”
📄 Page 11

And from a family member:

“Just tell the truth.”
📄 Page 11

He decides to cooperate. Turns over the burner phone. Surrenders devices to Rippling’s team. Begins cooperating with an investigation that names Deel executives directly.

“I was fearful for my safety, given the power and wealth of the individuals involved.”
📄 Page 10

April 1, 2025: The Affidavit

Keith O’Brien’s sworn affidavit is filed in High Court. It reads like a really, really stupid and incompetent spy thriller: crypto payoffs, burner phones, Telegram ops, and executive-level coordination of corporate espionage.

But this isn’t just salacious drama. It raises urgent questions:

• Why was Deel’s CEO personally involved in espionage operations?
• Why did the CFO — his father — participate in payoff arrangements?
• Why did Deel’s in-house legal team advise destruction of evidence and relocation offers? 

Honestly, I am not even sure I have done the affidavit justice. Not just for the sheer absurdity of it all… but because it demonstrates that when leadership loses its ethical compass, it can warp an entire operation. To me this is sheer greed with a good mix of incompetence and ego.

🚨I think this entire tale will serve as this week’s reality check.

What is your favorite quote from the affadavit? Let me know.

🎲 And the Winner Is… Maybe YOU?

Just because I love you guys, Kennedy has agreed to extend this Job Board Doctor free stuff for one more week.

If you’re a Director-level or above in HR or Talent Acquisition and thinking about heading to Unleash America in Vegas this May — you might be eligible for a complimentary pass.

Want in? For this week only (maybe more, if you act right) you can message my brilliant, beautiful, and very much like me (but WAY cooler) eldest child, Kennedy Cook, via DM on LinkedIn.

If you land a pass, let me know — we’ll get a Job Board Doctor x Unleash America “ussie” in May. Cheers!

Coming Up Next Week

We’ll get back to the state of tariffs and their projected impact — both on the global economy and the talent acquisition world we live in. Unless, Deel (allegedly) decides to try to steal the nuclear codes. Fingers crossed.

Until then,

The Doc

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