Colton Hess

Let's get you activated!

For ambitious leaders and their teams who know AI could help them scale their impact but don't have time to figure it out alone. I'll sit beside you, build something real with you in tools like Claude Code, and leave you feeling empowered and able to keep going on your own.

Book an Activation Consultation Or write me →

What this unlocks

This isn't about doing the same work faster, or hiring fewer people. It's about thinking bigger about the impact you can make.

Bigger about what you can build now that you couldn't a year ago... the tool your team keeps asking for, or a personal command center that keeps up with your life, made real in an afternoon instead of a budget cycle. Bigger about the work you can finally take off your own plate, so your attention goes where only you can put it.

And bigger about what your whole team could do, not just the few who've already found their footing. The work gives everyone a running start into the future.

Three shapes the work takes

Same practice. Different shapes, depending on what you need.

Activation Sessions

A single working session built around a real project you bring. Just you, or a small group of two to four leaders. Most people start here.

A deeply personalized experience that takes something overwhelming and makes it fun. (Why "activation"? Every reaction has an activation energy... the spark it takes to get going. A session is that spark, and then the reaction is yours.) You walk out more confident, more grounded, and ready to put these tools to work where they matter.

1:1 Executive AI Coaching

Deeply personalized coaching from someone who understands startups and agentic AI tools. We work through your real projects together, deepen your AI fluency, and grow what's possible in your role over time. Plus a sounding board for the bigger AI questions in your org.

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Applied AI in Residence

The deepest shape. I start by sitting with the leaders to understand the team, the challenges, and the culture. From there I work with the broader org through activation sessions and workshops. Then I stay involved over weeks or months, supporting everyone through the transition as AI becomes part of how the org actually thinks and works.

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Why I do this

I love working with ambitious leaders. There's a moment in almost every session where someone who came in a little unsure, a little overwhelmed, a little behind, crosses the threshold... where the wall becomes a door, and what they believe is theirs to build expands. You can see the weight lift off their shoulders. The smile that breaks when overwhelm turns to empowerment.

They stop seeing AI as something they're failing to keep up with and start seeing it as an opportunity in front of them. They start thinking bigger about the impact they could make.

I love watching people get a running start into the new world we're moving into. And then watching them turn around and inspire and activate the people around them.

That's why I do this. The threshold-crossing. The shift from anxious to empowered. The world needs the impact you've been holding back on, and the tools to make it real are sitting right here. I'd love to help you get there!

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What people say

From people who walked in unsure and walked out building.

“
I had no idea what was possible with Claude Code until working with Colton. I'm now overwhelmed with possible ways to create and build tools that can upgrade my personal and professional life.
Catherine
“
Colton made something intimidating into an exciting learning opportunity. I now feel more comfortable trying things with AI that previously I always tried to steer away from.
Bean
“
I went from feeling intimidated and scared about AI taking my job away to inspired and empowered about everything I can build.
Kat
“
Colton has enabled me to feel like I am on the cutting edge of technology for the first time in my life.
Effie
“
I'm still shocked by how my ability and confidence using Claude Code did a complete 180 after a 20-minute session with Colton.
Tricia

Questions people ask

What does Activation Playbook mean by AI activation?
Activation is the act of getting started, which is the hard part. Think of it like activation energy in chemistry: every reaction needs a spark to get going, and once it does, it carries itself. A session is that spark. Agentic AI like Claude Code goes to work on your real project in the room, the reaction gets going, and it becomes yours to carry. And here's the deeper part: what changes isn't just a skill, it's your self-concept. The wall becomes a door, and what you believe is yours to build expands. The bottleneck was never your imagination... it was believing the bigger thing was actually yours to build.
What is Activation Playbook?
Activation Playbook is a practice offering hands-on AI coaching and training for leaders and teams. It activates ambitious, impact-focused leaders on agentic AI, in three shapes: Activation Sessions, 1:1 Executive AI Coaching, and Applied AI in Residence. The mode is the same across all three... hands-on, in the room with you, building real things with tools like Claude Code. Think of it less as training and more as a peer you borrow.
Who is Activation Playbook for?
Activation Playbook is for ambitious, impact-focused leaders: founders, startup CEOs, executive teams, and nonprofit and mission-driven leaders who already sense AI matters but don't have time to figure it out alone. Most have played with Claude or ChatGPT and want to move past the chat window into AI doing real work alongside them. They want a peer they can borrow... not another deck, not another keynote. If you want to think bigger about what you can build, you're the fit.
How is Activation Playbook different from AI consulting?
Activation Playbook is different from AI consulting because nothing gets handed off. AI consulting leaves you a deck of recommendations and a project someone else built. Activation Playbook skips the handoff entirely... the work starts on your real project with Claude Code from the first hour, so you walk out with something that runs and the muscle memory to keep building. It's done-with-you, not done-for-you. The session is the work, not a rehearsal for it.
Do you need to know how to code to use Claude Code?
No, you don't need to know how to code to use Claude Code, and that's exactly the work I do at Activation Playbook. All kinds of non-technical founders are running real startups and shipping their own software now, just by describing what they want to AI in plain English... and that's how I work too. English has become the most important coding language: if you can articulate the vision and the problem, Claude Code handles the rest. That's the skill. You bring the judgment and the taste.
Do I need a fractional Chief AI Officer, or is there a simpler option?
A fractional Chief AI Officer is a part-time executive who fills an interim AI leadership seat on your org chart and owns decisions, usually for a steep monthly retainer. Activation Playbook isn't a fractional Chief AI Officer. Here's what it is instead, and why it fits most founders and teams better: it's the lighter, more accessible alternative. Most founders and small teams don't need a seat filled... they need to become more capable themselves. I work alongside you, building real things with Claude Code, so you grow your own sense of agency and don't outsource it.

Try it on your own first.

Want a softer way in? Get a free, personalized playbook plus a set of modules to walk you through Claude Code at your own pace. No call, no follow-up push. The lighter doorway in.

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Or, if you'd rather talk: book an Activation Consultation →