Jeremy Lightsmith
Let's talk

Your team is building.
But is it building the right things?

I help founders who've outgrown their technical leadership get visibility, get aligned, and get their team moving again.

Book a free intro call

You've built something real. But something's off.

Things are taking longer and longer. Systems break occasionally. You can't tell what's possible, what isn't, or how long anything will take. Your engineers are trying to do everything — and achieving nothing cohesive.

You feel out of control. At the mercy of someone you suspect is unqualified. Scared it might all come crashing down. And nagged by the feeling that there has to be a better way — you just can't see it from where you're standing.

What changes when you bring in the right technical leader

Visibility

You know what's going on in engineering — without needing to become an engineer.

Alignment

Your team stops spinning. Everyone is rowing in the same direction, toward the same goal.

Momentum

Velocity returns. You stop wondering why things take so long — and start seeing them ship.

Control

You know how to affect what gets built and when — without taking over how engineers do their work.

Jeremy Lightsmith

I've been on both sides of this.

As CEO of an early-stage startup, I've lived the founder's fear — the team going sideways, the sense that things are slipping, the suspicion that something is deeply wrong and you can't quite see what. I know what that feels like, and I know it doesn't fix itself.

As a CTO and technical lead across startups and enterprises, I've spent my career making the work visible and creating the feedback loops that let founders drive what gets built — without taking away the craft from the engineers who know how.

  • Transparent Classroom — Founded and led as CEO and CTO. Built the engineering org from zero: chose the stack, designed the architecture, grew to a 14-person self-managed team with $3M ARR, consistently outperforming 100-person competitors.
  • Mechanical Orchard — Used value stream mapping with actual data to make the waste visible to everyone, collaboratively designed a better process, and built a pull-based management system. Things got exponentially faster. Also led LLM adoption into the team's workflow.
  • TalentWall — Assessed an unstable codebase and led a full rewrite — while simultaneously hardening the existing system to support a growing business. On time, no disruption.
  • Nordstrom Innovation Lab — Built the lab's process from scratch (Lean Startup, Design Thinking, Liberating Structures), validated products at speed, then left teams able to run the process themselves.
  • ThoughtWorks + Pivotal Labs — 9 years at two of the most respected technical consulting firms in the industry, leading teams and client engagements at early-stage startups and enterprise orgs.

I bring the technical depth to work directly with your engineers, the leadership experience to set and hold a coherent direction, and the process fluency to build a team that can execute. I'm as comfortable writing code as I am in a board conversation. And I build toward a team that can run without me.

What fractional means

You get a seasoned CTO — someone who can work directly with your engineers, lead architecture decisions, and translate between the technical and the business — without the cost or commitment of a full-time executive hire.

Most early-stage companies don't need a full-time CTO. They need experienced technical leadership at the right moments: when the team is stuck, when a key decision needs to be made, when something is slowing everything else down. That's what I provide.

What my clients share: they're capable builders who've hit a wall they can't navigate from inside. The team is good. The problem is leadership — not talent.

Here's how it works

Starting with a two-week assessment — then ongoing or project-based from there

01

Meet the team

We start with you, then the team. I listen more than I talk. I want to understand the people, the product, the pressure, and where the friction is coming from — before I form any opinions.

02

The assessment

I look at the codebase, the process, the way work flows, and the way decisions get made. I come back with a clear picture: what's working, what isn't, and what I'd recommend. No jargon, no finger-pointing — just an honest map.

03

Build what you need

From there, we figure out together what the right engagement looks like — ongoing fractional CTO work, a focused project, or something in between. Either way: you know what's going on, you know how to affect it, and your team is rowing together.

Ready to see what's going on?

We start with a free intro call. No commitment — just an honest conversation about where you are.

Book a free intro call