Technical Leadership Hiring

You've never done this job You're about to hire for it

The Problem

Hiring for a job you've never done

Your product needs real technical leadership. Maybe you've been leaning on contractors, a scrappy team, or sheer willpower — but you've hit the point where you need someone senior to own the technology. So you set out to hire a CTO, or a VP of Engineering, or a Head of Engineering.

And immediately you're in unfamiliar territory. You can't fully assess whether a candidate is genuinely excellent or just interviews well. You're not sure whether you need a CTO or a strong senior engineer. Titles are inflated, résumés blur together, and every candidate sounds credible. The stakes are enormous — this person will shape your architecture, your team, and your pace for years — and it's the one hire your own experience can't help you judge.

Get it right and everything gets easier. Get it wrong and you lose a year, a lot of money, and often the team they build around them.

It's the highest-leverage hire a non-technical founder makes, and the only one they can't evaluate on their own judgment alone.

Different Situations, Same Gap

First-Time Founders Hiring Technical Leadership

You've built the company on product and customer insight, not engineering. Now you need a technical leader and you're staring at a slate of candidates with no real way to tell the strong ones from the ones who just present well.

Founders Recovering From a Bad Hire

Your last technical leader didn't work out — the wrong level, the wrong fit, or the wrong role entirely. You can't afford to repeat it, and you want a process this time instead of another gamble.

Founders Unsure What Role They Need

You assume you need a CTO, but you're not certain. Maybe it's a hands-on lead, maybe it's a VP later and a senior engineer now. You need someone to help you separate what the company needs today from what it'll need in two years.

The Usual Approaches

All feel reasonable, none of them work

"Hire someone I already know"

Reaching for a friend or former colleague feels safe, but familiarity isn't fit. It narrows the field to who you happen to know and skips the evaluation entirely — trading a real assessment for comfort.

"Let a recruiter handle it"

A generic recruiter can fill a pipeline, but they can't assess technical depth or tell you whether a candidate can actually lead. You end up back where you started: unable to judge the shortlist they hand you.

"Just hire the most senior title"

Chasing the biggest title or the FAANG résumé often means over-hiring for the wrong stage — someone who thrives with scale and process, not the ambiguity of an early team. Impressive on paper, wrong for the moment.

"Go with my gut in the interview"

Gut instinct is exactly the tool that fails here, because the signal you're reading — confidence, polish, rapport — isn't the signal that predicts technical leadership. Comfortable, and consistently wrong.

The process

From Unclear to Decided

  1. 1

    Get real about the role (week 1)

    Define What's Needed Now — and What's "Later"

    We start by separating the role the company actually needs today from the one you're imagining. CTO or senior lead? Hands-on builder or team-builder? We write a clear, honest description of the role, the level, and the outcomes it owns — so you're hiring for reality, not aspiration.

  2. 2

    Build the hiring process (week 1–2)

    Put a Real Process in Place

    I build the hiring process around that definition: where to source, screening stages, what to test for at each stage, and how to compare candidates consistently. You get a repeatable structure instead of a series of one-off gut calls.

  3. 3

    Run the interviews (ongoing)

    Who Runs What

    I run the technical interviews — probing depth, judgment, architecture thinking, and how they lead. You run the parts only you can: founder fit, motivation, how they'd work with you. I give you the read on what you're seeing, and you make the call.

  4. 4

    Recommendation (at decision)

    A Clear, Honest Recommendation

    When it's time to decide, you get a straight recommendation on each finalist — strengths, risks, the level they truly are, and how they'd fit what you're building. Not a rubber stamp — the honest read you need to make the call with confidence.

I've Been on Both Sides of This Interview

So I know what real depth looks like under questioning, and what just interviews well. That judgment is the whole hire.

We get honest about the role you actually need now versus the one you're imagining. I build the hiring process around that. I run the technical interviews you can't run alone. Then you get a straight read on each finalist — strengths, risks, and the level they actually are.

You stay the decision-maker. You just make the call with evidence instead of hope.

"I thought I needed a CTO. Ian helped me see I needed a strong hands-on lead now and a CTO later — and then ran the technical interviews I had no way to run myself. We hired the right person at the right level, and it changed the trajectory of the company."

Rose Huang

Founder & CEO

Make this hire the one that works

A short call to talk through the role you need and how the process would run. Fee is 5% of the accepted offer.

Let's talk