Thought Leader Interview: Isaac Sacolick
On scaling through process, letting go of control, and why founders must become teachers to grow.
In this Thought Leader Interview, we feature Isaac Sacolick, President of StarCIO, a leadership and advisory firm helping companies develop competitive advantages in innovation, AI, data, and digital transformation. With a career that spans startup CTO roles, enterprise CIO positions at global companies, bestselling books, and one of the most-read technology leadership blogs on the internet, Isaac has spent decades guiding leaders through the messy, non-linear realities of transformational change.
What makes Isaac’s perspective invaluable to founders is how deeply he understands both worlds: the scrappy, 80-hour-week chaos of early startups, and the complexity of scaling teams, systems, and product disciplines inside large organizations. His message is clear: growth depends less on adding people and more on maturing how you operate, collaborate, and teach.
From Startup CTO to Transformation Leader
You’ve worked as a CTO in multiple startups and later as a CIO in large enterprises. What first drew you into the technology and innovation world?
I always say I accidentally fell into startups. Coming out of grad school, I joined a small biotech company, and when the internet explosion hit, I realized, “This is where the future is going.” Within two years, I propelled myself into a Director of Software Development role, then into a CTO role shortly after.
I spent 10 years loving the energy, the risks, and the unknowns. Every day we were solving questions like, What if our next funding round is half what we expect? What if it comes from a strategic instead of a VC? What if it doesn’t come at all? That kind of problem-solving hooked me.
After a decade in startups, including some exits that went well and some that didn’t, I realized if I wanted to stay in the game but couldn’t move to the Valley for family reasons, I needed enterprise experience. Companies were just beginning to hire leaders out of startups to help them figure out this “internet thing” and bring startup agile, CX, and data capabilities into the enterprise. That led me to CIO roles at BusinessWeek, Dodge Data & Analytics, and later a financial services research company. Ironically, all of them were doing startup-like work inside a big company: customer-facing tech, analytics, AI, digital product development.
Along the way, I started a blog, originally by accident, and it turned into a 700+ article leadership resource. That led to speaking, then to my first book, Driving Digital, and eventually to starting StarCIO.
When Growth Hits: Why Process Must Come Before People
Founders often feel the pressure to hire as soon as revenue starts climbing. What’s your advice for the moment when they think, “Okay, we need more people”?
My advice is simple: think process before people.
Startups run on smart, dedicated founders putting in 60–70 hour weeks and solving today’s fire with brute force. But the moment you start adding people, everything changes. Now you’re not doing the work, you’re teaching someone else how to do the work. If the business has no repeatable processes, no tooling, and no operational rhythm, it becomes impossible to onboard effectively.
A 10-person business might be able to run sales out of spreadsheets. But once you start scaling? You need real systems, real structure, and clarity around what’s productized and what’s not. Otherwise, every new person increases chaos instead of reducing it.
Hiring without process is not scaling; it’s gambling.
Some founders might push back and say, “I don’t have time to build processes. I need help today.” What do you say to them?
There’s nothing wrong with experimenting. Sometimes hiring a pair of hands works beautifully. Other times, it just puts more work on your shoulders.
But here’s the truth: scaling is fundamentally about teaching. You’re passing on customer knowledge, tribal knowledge, operational knowledge, half of which you couldn’t explain cleanly on the first try even if you wanted to.
Founders underestimate how much thinking it takes to describe why and how they do what they do. Teaching is a skill. Listening is a skill. Iterating is a skill.
You’re going to bring people in who know things you don’t: new tools, new technologies, AI techniques. And you’re also going to bring in people who know far less than you do about the product, the customers, and the history. Scaling means embracing both realities and creating space for learning on both sides.
Founder Expectations That Come With Growth
You mention a big mistake you see CTOs and founders make during scale. What is it?
They assume the next hire will work the way they work.
Founders have lived through the last 18 months of intensity, late nights, broken systems, production fires, sales calls, and customer escalations. Then someone new joins, and the founder thinks, They should be able to figure this out in two weeks.
But the new person is entering an undocumented, evolving, messy system. No amount of talent replaces tribal knowledge overnight.
If you want to scale, you have to shed responsibilities deliberately. You have to let other people make mistakes. You have to test whether something that lived in your head can live in the organization.
Letting go isn’t optional; it’s the job.
You’ve talked about the importance of Agile as a mindset, not just a development tool. Why is this so crucial during scale?
Agile is essential because growth is iterative. It requires:
setting goals,
giving people room to experiment,
reviewing what worked,
capturing customer and stakeholder feedback ,
and adjusting priorities quickly.
Agile is the antidote to the illusion that “I told them once, so they should get it.” You’re not trying to be perfect; you’re trying to learn fast without breaking the company.
Agile forces the founder to move from doing to coaching to evaluating—and that’s the evolution that makes growthpossible.
The Hidden Cost of Customizing for Every Customer
You mentioned the tension between CROs wanting to customize everything to close deals and CTOs fighting the operational cost of that approach. How should founders think about this?
This is one of the oldest battles in tech. If you customize everything for everyone, you’re not a product company, you’re a services company. And that’s okay, as long as you realize that’s what you’re doing.
A true product organization requires discipline:
What’s fixed?
What’s variable?
What’s allowed customization, and at what price?
And what breaks if we say yes to this deal?
Product management is the hardest discipline in the company. They must balance sales demands, customer needs, market trends, tech debt, security, legal, and sprint capacity, then make prioritization decisions that everyone agrees to follow.
Founders must understand this: You cannot scale if the CEO is still acting as the product officer. At some point, you must hand over the reins and let someone own the roadmap.
Getting Real Alignment Among Leaders
With product, sales, engineering, and operations all having different pressures, how do you get true alignment?
Alignment comes from clarity around two things:
What kind of company you really are, product vs. services.
How prioritization is debated and decided, and ensures that the organization respects the product management and technology leaders responsibilities.
Without those, every team creates its own fiefdom, fights for its own comfort, and optimizes for its own metrics. Alignment collapses.
The CEO’s role evolves from “the person who decides everything” to “the person who intervenes only when the stakes justify breaking the rules.”
That maturity, knowing when to stick to the playbook and when to blow it up, is what allows startups to scale without losing their mind.
Isaac’s journey reveals a truth that many founders learn only the hard way:
Growth requires letting go of control.
Scaling requires process, teaching, and alignment.
And leadership requires evolving your identity as the company grows.
His work at StarCIO continues to equip founders and executives with the skills, systems, and mindsets needed to build organizations that don’t just grow, but transform.