Fractional CTO · Executive coaching

Technical leadership for the messy stretch between traction and scale

You don't need a full-time CTO to get through this stretch.
You need someone who's already been through it.

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  • Faster, predictable delivery
  • Stronger technical foundations
  • Less Chaos

Inflection points

I help at the moments that define your company's trajectory

  • Architecture or technical debt is blocking velocity

    Early on, startups build to survive, which often leads to cutting corners. This is expected and needed. But when you can't onboard customers, or features are progressively taking longer to produce, there are a number of things that can improve the situation.

    • Review the architecture, and set a target shape for the next 12-18 months
    • Triage the debt - what to fix, what to carry, what to isolate
    • Sequence a refactor that ships alongside the roadmap, not instead of it
    • Size for where you are now, not 10 yrs from now

  • Adding capacity isn't adding output

    You've hired fast, have all the latest AI tools, but the teams output hasn't changed. Adding more people slowed delivery down, not sped it up.

    • Build an AI-first development process, not as a tack-on
    • Draw ownership boundaries, so teams ship without waiting on each other
    • Push decision rights down, so work stops queueing behind three people
    • Rebuild onboarding, so a new hire is productive in weeks, not quarters

  • Delivery can't be predicted

    The funding is in and the market is real, but you can't tell anyone with confidence when something will land. Some quarters the team flies, others it stalls, and nobody can point to what actually changed.

    • Map the value stream - how the work actually moves, end to end
    • Switch status from pull to push, so it is visible instead of chased
    • Limit work-in-progress, trading thrash for throughput
    • Automate deployment and testing, so releases are repeatable

  • Your customers are the QA

    Nothing catches a regression before a customer does. Testing happens when someone remembers, your first alert is a support ticket, and quality has never been written down as something the product owes anyone.

    • Run regression and end-user testing on every change
    • Add observability and pro-active alerting, so you know before the customer does
    • Make quality a product requirement, not a cleanup task
    • Instrument usage, to answer who actually uses what

  • Your leadership playbook has stopped scaling

    You're a founder or first engineering leader now leading through managers. Fixing things yourself is what made you effective; at this size it's what stops your managers from ever getting good. And there's no one inside the company you can think that through with.

    • Coach what to delegate, and how to let it go wrong safely
    • Develop your managers, so escalations stop a level below you
    • Set an operating rhythm that replaces you being in the room
    • Work through the calls only you can make, with someone outside the company

  • Your AI features aren't defensible

    Your AI feature is a prompt away from being your competitor's — you're both calling the same API. What can't be copied is the data you own, the workflow you sit inside, and an evaluation loop that makes your answers better every month.

    • Define a data strategy - what you can own that a competitor can't buy
    • Build evaluation sets and scoring, so “better” stops being an opinion
    • Embed into the customer's workflow, rather than sitting alongside it
    • Close feedback loops that compound with every customer you add

Two ways to work together

Fractional CTO

Embedded technology leadership

The judgment of a CTO who's done this before — architecture, hiring, and execution — working with your team week to week, without the full-time hire.

Explore Fractional CTO Executive Coaching

A trusted partner with no agenda

Coaching for founders and technical leaders — think through the calls that keep you up at night with an operator who's carried the risk.

Explore Executive Coaching

"Ian has been an invaluable technical advisor and steadying force for me as a founder. He combines strong engineering judgment with rare emotional intelligence - helping me make better technical and product decisions while staying focused, grounded, and clear through the uncertainty of building an early-stage company."

Rose Huang
Founder / CEO Accelidea

"Ian helped TrueNorth (Series B startup) level-up its engineering power. Within the first months, Ian was able to take this young team from being months behind on the roadmap to a team that consistently delivered work on time."

Getter Hiss
(Former) Mobile Team Lead at TrueNorth

"Our outsourced team was months behind schedule and continuously delivering buggy code. Ian helped us identify different team structure options, and facilitating a clear plan of action that got us back on track and improved the quality of our deliveries."

T.J. Cooley
CEO at Namara

"After shipping a new data product, Shareaholic faced rising monthly infrastructure costs. By migrating development languages and re-architecting our data serving systems, Ian helped us achieved an 80% cost reduction and a 5X capacity increase."

Christopher Gillett
(Former) CTO at Shareaholic

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Let's talk about where you're headed

A short discovery call — no pitch, just a conversation about the calls you're facing and where a hand would help

Let's talk