CPTO Coaching for the CTO-to-CPTO Transition

Many CPTOs are former CTOs. You got promoted because you’re the senior technical leader the company trusts. The company wants to move to a simpler setup with clear responsibilities and someone who owns AI. Now you’re drowning in product decisions you’ve never made before. Your engineering instincts (“build it right”) clash with product reality (“ship and learn”). PMs speak a different language - and you manage them now. The CEO expects opinions on user research, pricing, and roadmap prioritization.

And AI is transforming everything. Product Engineers are rising, roles are merging, and you own this transition across BOTH product and engineering. You’re supposed to have the vision for all of it.

If you feel like you’re faking half the job - you’re not alone.

I’m Stephan Schmidt - 40+ years of software development (I still code every day, or Claude does now), 25+ years of engineering management, and crucially: I was a CPTO myself at eventsofa before our exit - before people talked about the role and held a combined CTO/Interim Head of Product role at brands4friends/eBay Inc. This isn’t theory. I’ve lived the identity shift, the context-switching between product and tech, and the pressure of managing two demanding domains at once.

Now I help CPTOs across Europe and worldwide navigate this transition, build the right VP structure underneath, and lead AI transformation across both functions. Whether you’re a recently promoted CTO struggling with product decisions, or a CPO who inherited tech responsibilities, I specialize in helping CPTOs organize the transition to AI - strategy that spans discovery AND delivery.

Looking for pure CTO coaching instead? Check out my CTO coaching services - the foundation of what I do.

The Amazing CTO Program - My Coaching Model

My coaching model is based on four pillars for getting you unstuck and making you grow and successful - whether you’re a CTO, CPTO, or VP of Engineering.

• Consulting: I help you fix all current problems that are blocking you - in both product and tech
• Mentoring: Focusing on knowledge transfer to enable you to grow and scale for what is coming
• Coaching: Changing your behavior to make you successful in this expanded role
• Branding: Be seen the way you want to be seen - as the strategic leader, not just “the techie”

The CPTO role demands you shift your identity from technical expert to outcomes-focused executive. That’s a behavior change, not just knowledge transfer.

Schedule a Welcome Call

Book your free 30-minute discovery call below. Let's talk honestly about your challenges and whether coaching is the right next step for you.

Current availability: Booking 2-3 weeks out for new coaching engagements

Common CPTO Challenges I Help Solve

The CPTO role is brutal. You’re supposed to be two executives in one, except you only have experience being one of them. Here’s what I see in my coaching work.

This is the most common pattern. You were the CTO. The company grew. Someone said “let’s combine product and tech under one leader” - and you were the obvious choice. Congratulations. Now you’re in trouble.

• Identity Crisis - For years, you were “the techie”. That’s how people saw you. That’s how you saw yourself. Now you’re supposed to have opinions on user research and pricing strategy. You’re not sure who you are anymore.

• Engineering Instincts That Don’t Apply - You want to “build it right”. But product reality is “ship and learn”. Both are valid - in their domain. Knowing when to apply which instinct is the hard part. And it’s not obvious.

• Managing People Who Think Differently - Engineers think in systems, constraints, and correctness. PMs think in user needs, business impact, and speed. You’ve spent years managing the first group. Now you manage both. The conversations are different. The feedback is different. The motivation is different.

• Learning a New Vocabulary - Product has its own frameworks. Jobs-to-be-done, user story mapping, opportunity scoring, outcome-based roadmaps. Some of it is useful. Some of it is buzzwords. You need to learn enough to know the difference.

This is where the CPTO role becomes strategically critical. And where most CPTOs are struggling.

AI is transforming both product and engineering simultaneously. The old division of labor - “product decides what, engineering decides how” - is breaking down. AI tools don’t respect that boundary. AI features require tight integration of discovery AND delivery. Who owns this transition?

The CPTO.

• The Rise of Product Engineers - Job postings for “Product Engineer” are growing fast. These are developers who do more product work, or PMs who can code. The role sits between your two organizations. In the AI era, this becomes the norm, not the exception. Who leads this transition? You do.

• AI Strategy Across Both Functions - AI isn’t just a product feature. It’s also a development tool. Your engineers need different skills. Your PMs need to understand AI capabilities and limitations. The strategy must span both. One leader, one vision.

• Upskilling Two Different Groups - Engineers need to learn prompt engineering, AI integration, responsible AI practices. PMs need to learn what AI can and can’t do, how to write for AI features, AI product ethics. Same goal, different training. You’re responsible for both.

• Don’t Let AI Go The Way of Product - Twenty years ago, engineers owned product ideas. Then Product Managers arrived. Engineering lost that ownership. AI is a similar inflection point. Someone will own AI strategy at your company. Make sure it’s you.

In the AI era, the CPTO becomes the most important executive role in a company. That’s not hyperbole - it’s where the future of work is headed.

Here’s the mistake most new CPTOs make: trying to do everything themselves. That’s impossible. You need strong VPs underneath.

• You Need Real VPs - VP of Engineering for engineering execution. VP of Product for product strategy. They do the craft work. You do the outcomes and alignment. If you don’t have good VPs, you’ll fail - not because you’re bad, but because the job is impossible without them.

• CPTO Is More Expensive, Not Less - Companies sometimes create the CPTO role to “save money” by replacing CTO and CPO with one person. That’s backwards. A CPTO plus two strong VPs costs more than just a CTO and CPO. But you get better alignment and clearer accountability.

• Managing By Outcomes, Not Craft - As a CTO, you could evaluate code quality directly. You could spot bad architecture. As a CPTO, you can’t be the expert in both product and engineering. You manage by results: delivery velocity, customer satisfaction, churn, NPS. Learn to trust your VPs on the craft details.

• Delegation Across Two Disciplines - You already knew how to delegate engineering work. Now you need to delegate product work too - and you don’t have the same intuition for what “good” looks like. That’s uncomfortable. It’s also necessary.

The irony of the CPTO role: the tension between product and engineering doesn’t disappear. It just moves inside your head.

• “Ship Fast” vs “Build It Right” - As a CTO, you could argue for quality. As a CPO, you could argue for speed. As a CPTO, you own both arguments. You have to make the tradeoff yourself. Every time.

• No More Finger-Pointing - When product and engineering are separate, they can blame each other. “Product gave us bad specs.” “Engineering is too slow.” As CPTO, there’s no one else to blame. The buck stops with you for everything.

• Unified Roadmap Ownership - One roadmap. One prioritization. No more “product roadmap” vs “tech roadmap” vs “reliability roadmap”. You own the whole thing. That’s power - but also pressure.

The CPTO role is two full-time jobs in one. Time management isn’t just helpful - it’s survival.

• Context-Switching All Day - Morning: architecture review. Afternoon: user research readout. Evening: board deck prep. Your brain has to switch between completely different modes of thinking. It’s exhausting.

• Which Meetings to Attend - You can’t be in all the engineering meetings AND all the product meetings. You have to choose. The wrong choice means you miss critical context. The right choice isn’t obvious.

• Protecting Strategic Time - With two organizations pulling at you, it’s easy to spend all day in operational fires. But your job is strategy. If you don’t protect time for thinking, you’re just a very expensive meeting attendee.

• CEO Expects All The Answers - You’re the one executive who owns the entire product development lifecycle. The CEO expects you to know why features are delayed, why customers churn, why the architecture won’t scale. No hiding behind “that’s product’s responsibility” or “ask engineering”.

• Board Storytelling Gets Harder - As CTO, you talked about technical metrics: uptime, velocity, tech debt. As CPTO, you need to connect product outcomes to business results. That’s a different skill. Many technical leaders struggle with it.

• Metrics Across Both Domains - Your board deck needs to show product success (NPS, retention, feature adoption) AND technical health (reliability, velocity, security). Telling a coherent story that spans both is an art.

Why Choose My CPTO Coaching?

I’ve Actually Been a CPTO

This isn’t theory. I was CPTO at eventsofa before our exit. I managed both product and engineering. I navigated the identity shift from “techie” to “outcomes leader”. I made the mistakes and learned from them.

Deep Technical Credibility - I still code every day (or Claude does now). I’m a nerd who learned to be an executive. When you talk about microservices or technical debt, I get it at a deep level because I’m still in the trenches.

Real Product Experience - Not just “I worked with product teams”. I owned product decisions. I learned the frameworks. I struggled with the same vocabulary issues you’re facing.

AI Transformation Specialist - I specialize in helping CTOs and CPTOs organize the transition to AI. Strategy across both product and engineering. This is the biggest challenge CPTOs face right now - and where most generic coaches can’t help.

European Expertise + Global Reach - Based in Germany, I’ve coached 80+ tech leaders across Europe and worldwide. I understand European culture, regulatory challenges (GDPR, etc.), and the unique European tech ecosystem.

Problem-First Approach - We start with what’s blocking you RIGHT NOW. Not theory, not abstract goals - we fix the urgent problems first, then build long-term capacity.

Real 1:1 Personalized Sessions - No groups. No generic advice. Just you and me for real 60 minutes every week or every two weeks. We talk about YOUR unique situation across both product and tech.

What makes me unique as a coach

• 40+ years of software development experience
• 25+ years of engineering management experience
• 80+ CTOs, and founders mentored and coached
• 3x startups founder

Schedule a Welcome Call

Book your free 30-minute discovery call below. Let's talk honestly about your challenges and whether coaching is the right next step for you.

Current availability: Booking 2-3 weeks out for new coaching engagements

What Makes My CPTO Coaching Different

• Unlike generic executive coaches: I’ve actually been a CPTO. I understand both product and engineering challenges because I’ve managed both. My coaching combines leadership development with deep understanding of both domains.
• Unlike pure CTO coaches: I understand the product side - the frameworks, the vocabulary, the metrics. I can help you navigate that unfamiliar territory.
• Unlike consultants: We don’t just fix problems - we change your behavior so you can handle future challenges yourself.
• Unlike theory-focused advisors: I’ve actually done this - managed both organizations, made the tradeoffs, navigated the politics, made the hard calls.

The CPTO Role and AI

Want to understand more about the CPTO role, when it makes sense, and how to succeed in it? Read my guide on What is a CPTO - covering CPTO vs CTO vs CPO, when the role works (and when it doesn’t), and career paths into the CPTO position.

Articles from Stephan