Oshri Cohen is a battle-tested Fractional CTO who’s led global dev teams, built multi-million-dollar payment systems, and rescued more than 30 companies from the brink of technical collapse. With a career that began in teenage hacking and evolved into executive leadership across industries like health tech, fintech, and e-commerce, Oshri brings a rare blend of hands-on engineering expertise and strategic business acumen. Known for his blunt honesty, chameleon-like adaptability, and mission to “get fired” by making tech teams self-sufficient, he’s the guy founders call when everything’s on fire—and he thrives in the heat.

Episode Description:

What happens when a hacker-turned-CTO ditches convention and builds a career out of saving struggling tech teams across industries? In this episode of Software Without Borders, I sit down with Oshri Cohen, a fearless, no-nonsense fractional CTO who thrives at the intersection of chaos and clarity. From coding viruses as a teenager to leading global teams, Oshri brings unmatched energy and insight into what it really means to guide a company through technical transformation. We cover everything—from the absurdity of inflated CTO titles to why his goal is to work himself out of a job. It’s candid. It’s unfiltered. It’s a deep dive into the mindset of a CTO who sees through the noise and fixes what’s broken—fast. Whether you’re a founder wondering if you need a CTO, or a technologist eyeing the fractional path, this one is packed with perspective. Don’t miss this bold, raw conversation about the future of tech leadership.

Key Takeaways:

Not All CTO Roles Are Created Equal

The title "CTO" means wildly different things depending on a company’s stage. Oshri breaks it down into four phases—from hands-on dev to visionary leader—and argues most companies confuse the role entirely.

Fractional CTOs Are the Fixers

Oshri often steps into companies already on life support. His approach is simple: stabilize, train, and work himself out of the job. His real value lies in preventing problems before code is even touched.

The CTO as a Chameleon

A fractional CTO must wear many hats—therapist, strategist, tech lead, even babysitter. Oshri thrives in this fluidity, adapting based on what's most broken today.

You’re Not Building for Average—You’re Building for the Spike

One of Oshri’s clients had peak traffic needs that their infrastructure wasn’t ready for. He reframed the problem: design systems around time as a resource—not just users or throughput.

AI is Not the Savior—It’s the Distraction

Despite the buzz, Oshri warns that AI is promoting keyboard-driven busywork over deep, strategic thinking. The industry is undervaluing senior talent in favor of junior devs who can prompt a bot.

Chapter Markers:

00:00 – Costa Rica Life & Connectivity Woes

04:00 – From Teenage Hacker to Dev Prodigy

08:00 – Hustling Through the Dot-Com Bust

13:00 – Building a Consulting Empire

16:00 – Creating Twilio Before Twilio

20:00 – Why Most Startups Don’t Need a CTO

25:00 – The 4 CTO Archetypes

35:00 – Why Oshri Wants to Get Fired

43:00 – Contracts, Pricing, and Perceived Value

50:00 – The Future of Tech Talent in the AI Era

Keywords:

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