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 i...
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.
Guest Details:
Oshri Cohen – Fractional CTO, RedCorner.io
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.
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.
Saving Money Isn’t Always the Win
Oshri shares how he saved a client $10K/month by proposing an open-source Mailchimp alternative. But fractional leaders often struggle to prove their value because great work becomes invisible when things run smoothly.
The Ultimate Goal Is to Get Fired
Ironically, Oshri’s metric for success is simple: the company runs so well, they no longer need him. That means training teams to be independent, not reliant on heroics.
Chapter Markers:
00:00 – Costa Rica Life & Connectivity Woes
Oshri shares life off-the-grid and how it reflects his flexible work style.
04:00 – From Teenage Hacker to Dev Prodigy
A wild origin story involving C++, viruses, and early coding ethics.
08:00 – Hustling Through the Dot-Com Bust
How Oshri landed developer roles during an economic drought.
13:00 – Building a Consulting Empire
Selling Microsoft CRM and implementing early automation before it was trendy.
16:00 – Creating Twilio Before Twilio
How a campus shooting in Montreal sparked an SMS idea a decade early.
20:00 – Why Most Startups Don’t Need a CTO
Oshri’s breakdown of fractional work and why strategy trumps headcount.
25:00 – The 4 CTO Archetypes
Developer → Manager → Leader → Visionary. Most people can’t do all four.
35:00 – Why Oshri Wants to Get Fired
Fractional success = team independence. But it comes with a visibility cost.
43:00 – Contracts, Pricing, and Perceived Value
How Oshri structures engagements and educates clients on invisible ROI.
50:00 – The Future of Tech Talent in the AI Era
Harsh truths about AI, developer value, and the mentorship vacuum.
Keywords:
fractional CTO, software leadership, startup technology strategy, CTO evolution, Oshri Cohen, CTO phases, fractional tech executive, technology consulting, software architecture, developer career path, managing dev teams, AI in tech, software without borders, Andy Hilliard podcast, CTO value, dev agency problems, startup CTO roles, scaling tech teams, open source email marketing, Mailchimp alternative, CTO business impact, getting fired as a CTO, peak infrastructure planning, event-based systems, tech leadership insights, remote tech consulting, Costa Rica digital nomad
