Why Hiring Big Tech Execs Fails in Startups

One of the most common scaling mistakes CEOs make is hiring a Big Tech exec only to fire them six months later.

They say everything right in the interview. Their past performance was stellar, and faithfully backed up by quality referrals. This person really was an A-player in their previous role.

Yet at your company, it’s not working. They delegate, give you great reports, and reassure you that results will come. But after six months, the results aren’t there.

Why does this happen?

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A Quick Announcement

Just before we jump in, I’m taking on a small number of CEOs who want to scale their businesses with me this year.

Some frequently asked questions:

Will I get results? Yes. Last year, my clients collectively raised nearly $1Bn in venture capital. 4 were acquired (on great terms), and 6 surpassed $100M in revenue.

How much time does it require? Some invest an hour a month. Others invest more. But part of the value of working with me is what you'll subtract, not what you add.

Will I work with you directly? Yes. I’m the only coach in my program. 

Who is it for? VC-backed tech CEOs ($5–250M annual revenue) who are serious about working with the best, learning from the best, and being the best.

When is the deadline? I onboard new CEOs once a quarter. The deadline for this intake is February 18. The CEOs already signed up are genuinely outstanding, and I have two spots left.

Apply here. It takes under 30 seconds.

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Now let’s get back to that Big Tech hire.

Last month, I gave a live CEO Masterclass on organising your leadership team.

One of the concepts that resonated with my CEOs was the idea of builders and operators.

The recipe for success in a company of thousands of people isn’t the same as in a company of tens or hundreds. The rules are different.

And this is where builders and operators come in.

Builder versus Operators

Operators are people who learn the rules of the existing system, and operate within those rules.

However, if your company doesn’t have a good system to operate, they end up failing.

Great systems create great operators. Great builders create great systems.

Unlike operators, builders don’t like following rules. They tend to throw existing things away and build something from scratch, outside of existing structures.

Sound familiar? It should if you're a founder, because the majority of founders are builders.

Builders can be challenging to work with. They aren’t always the most collaborative people. But when going from zero to one and creating something from nothing, they often outperform operators—especially in GTM, product, and tech.

High-performing execs at Big Tech companies are often operators who understand how the systems worked there, but not at your company, especially when there isn't a proven system already in place.

I found a charming YouTube video (10 mins) on the difference between operators and builders here that uses Obama and Trump as examples.

Do you need a builder or an operator? It depends on whether they are inheriting a system that works, or whether they need to build one from scratch.

If you don’t have a proven system in a particular function, you probably need a builder type.

Since many founders are builders, they are the ones who often have to work out the right system before hiring an operator to run it.

How to Identify Builders and Operators

In practice, it's hard to figure out if someone is a builder or an operator.

Operators often present themselves as builders.

This is partly down to interview best practice: it sounds better to say you built the system rather than ran it.

Builders often call themselves operators too, often because they don’t differentiate the two profiles.

So the only way to figure out if someone is a builder or an operator is to ask probing questions. 

Ask about a time they built something, and then ask probing questions to understand how they went about it.

• What problem existed before you built this?
• What did you personally design from scratch?
• What was the messiest or most uncomfortable part of building it?
• What assumptions did you get wrong early on?
• Which parts of what you built would you not reuse at a smaller company?

You can also ask about what they do in their spare time.

Builders gotta build. They often build things in their spare time (a new shed, toys for their children, side projects, etc.).

Operators gotta operate. They often operate things in their spare time (they like coffee machines, coaching their kid’s football teams, running a professional network, etc.).

These will give you signals as to whether you’re dealing with a builder or an operator.

The Right Profile at the Right Time

As you scale, you outgrow systems. This means it helps to identify whether you need a new system or whether the existing system just needs to be operated and scaled.

If you put an operator where you need a builder, things won’t happen. And if you put a builder where you need an operator, you’ll get chaos.

Decide the profile you need right now, and hire accordingly.

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Related Reading: 

• Is your hiring process missing what really matters?
  Use this recruiting approach to properly assess candidates before you make a costly mistake.
• Are referrals giving you false confidence?
  Learn why recommendations can mislead, and how to evaluate talent for yourself.
• Are you trying to scale without leverage?
  Discover why every startup CEO needs a Chief of Staff, and what the right one unlocks.

Originally published on February 11th, 2026