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Your Fractional
Head of AI

I help companies build an AI operating system. Your teams share context instead of hoarding it, and AI picks up the repetitive work so your people can focus on the stuff that actually matters.

See How It Works

15+

Years in Tech

12+

AI Products Shipped

3

Fortune 500 Brands

HubSpot logoMapbox logoTesla logo
Colin Gillingham

You have AI tools. You don't have a system.

Half your team is using ChatGPT. Nobody knows what the other half is doing with it. Sales insights sit in call recordings that product never sees. Support answers the same questions your docs already cover. Your people are still doing work that a well-configured agent could handle in seconds.

WithoutWith You
Everyone using different AI toolsOne connected system
Tribal knowledge trapped in peopleContext that flows between teams
Reps manually researching every leadAI does the prep, humans close
No way to measure what's workingClear before/after on time saved

Your AI Operating System

Make Your Team AI-Native

Your team has access to Claude Code, Glean, NotebookLM, Codex — but nobody's shown them how to actually use any of it. I get each department proficient on the tools that matter for their role, write the playbooks, and sit with leadership to figure out what to build, what to buy, and what to skip.

Team Training

Engineers get Claude Code and Codex, researchers get NotebookLM, everyone gets Glean — matched to how they actually work

2-5x output per person

Playbooks

Step-by-step docs so your team can run and maintain everything after I leave

Ongoing reference

Strategic Advisory

Honest answers for leadership on where AI will actually move the needle for your business

Avoid costly mistakes

How It Works

  1. 1

    Discovery Call

    30 minutes. We walk through your current AI usage, where your team is losing time, and what a system could look like.

  2. 2

    AI Game Plan

    I audit your current setup, find the quick wins, and hand you a 90-day roadmap.

  3. 3

    Embedded Partnership

    I work alongside your team. Quick wins by day 30, measurable results by day 90.

Background

I've spent 15+ years scaling growth and operations at Tesla (one of the first hundred employees), Mapbox, and HubSpot, where I'm a Group PM leading the automations platform. The work has always been the same: find what's slowing teams down and build the system that fixes it. AI is the most powerful tool I've had for that, and I've been going deep on it for the last three and a half years — building products like UXLoops and PhoneScreen AI.

Read more on my blog

Pricing

Flat rates. No surprises. Cancel anytime.

AI Workshop
$5,000

One-day intensive

  • Full audit of your current AI usage and gaps
  • You leave with a concrete AI Game Plan
  • Quick wins you can act on immediately
  • 90-day roadmap with recommended tools and stack
Limited Availability
Ongoing Advisory
$8,000/month

3-month minimum, then month-to-month

  • AI strategy and tool recommendations
  • Hands-on team coaching
  • I prototype and build workflows with your team
  • Async Slack/email support between sessions

Most people start with a Workshop, then move to a retainer if it's a good fit.