AI coaching for executives, on the work already on your calendar.
You signed off on the AI spend. Now spend the hour in the tool with someone who uses it every day. Private, hands-on coaching for owners and leadership teams, until you can run AI agents yourself instead of just approving them. When a session uncovers something worth building, we build it.
Get on Eli's calendar.
Drop your number and we will text you to set up a first conversation about your team and your work.
Rather talk now? Book a 30 minute call with Eli.
- 1:1 coaching for owners, CEOs, and executives
- AI workshops for your leadership team
- Hands-on in Claude and ChatGPT, not slides
- We build what the sessions uncover
we have led engineering at
01the problem
You are not behind. You are unpracticed.
Most executive AI training stops at awareness. Awareness is not capability, and nobody gave you the reps.
- The team did the AI training. Everyone nodded. Nothing about the work changed.
- Your VPs are already using it, quietly and unevenly, and nobody knows what is working or what is safe.
- You approve AI budgets without having used the tools on a real decision of your own.
- Every vendor demo looks great, then stalls somewhere between the pilot and production.
02what the coaching covers
From approving AI to managing it.
The goal is to turn executives into agent managers: people who can brief AI the way they brief a team, check the work, and know when it is wrong.
1:1 executive coaching
Private sessions for the owner, the CEO, or one executive. No audience and no dumb questions. We work inside your own reports, documents, inbox, and decisions.
Leadership team workshops
A working session with your leadership team on a shared workflow, like board prep, pipeline review, or reporting, so the team builds one common way of working with AI.
Becoming an agent manager
Delegating to AI the way you delegate to people: a clear brief, the right context, a review step, and the judgment to catch output that is confidently wrong.
Claude and ChatGPT, hands-on
You drive, on your work, with a coach who uses these tools daily. Research, analysis, drafting, and multi-step agent work on the problems already on your desk.
Guardrails for company data
What goes into an AI tool, what stays out, and how to set up accounts so your team uses AI without leaking what matters.
Then we build it
When a session finds a workflow worth automating, Insomnia Club scopes it with a fixed budget and builds it: agents, integrations, or custom software your team owns.
03who it is for
Built for the people who own the P&L.
A fit if you are
- An owner or executive at a company doing $10M or more a year
- The person who approves AI spend but has not run it on your own work
- A leadership team whose people use AI unevenly, with no shared playbook
- An operator who wants ROI, not a certificate
Not a fit if you want
- A course, a certification, or a recorded webinar
- A slide deck about AI trends
- Someone to use the tools for you while you watch
04how it works
Four steps, starting with your calendar.
Talk to Eli
A 30 minute call about what you run, where your week goes, and what you have already tried with AI.
Pick the real work
We choose workflows from your actual calendar and inbox, not exercises. That is what makes it stick.
Hour by hour, in the tool
You drive, the coach sits beside you. One hour at a time on your own work, until it is second nature.
Build what earns it
Anything worth automating gets a scoped plan and a fixed number before work starts, then working software every two weeks.
05proof
We use this every day.
Insomnia Club is an AI-augmented software agency, founded in 2022 and led by founder and CEO Eli Skenandore. We use AI agents to run our own operations every day, from ad campaigns to lead follow-up, and we build them for clients.
Pinned Golf
AI automation threaded through the engineering process reduced the engineering need from five engineers to one.
Nestwell
Fractional CTO from zero to one on a $30K budget. The company raised $1.2M+ after shipping.
Supreme Dental
An AI smile preview built on generative imaging plus an LLM assistant, inside two native apps live in the app stores.
Our own operations
Our ad campaigns, lead alerts, and follow-up run through AI agents we built and manage ourselves. We coach what we use.
06faq
Executive AI coaching, answered straight.
What is AI coaching for executives?
Hands-on sessions, one-on-one or with your leadership team, where executives use AI tools like Claude and ChatGPT on their own real work with a coach who uses them every day. The goal is capability, not awareness: you leave able to brief, manage, and check AI agents yourself.
How is this different from AI training for executives?
Most executive AI training teaches features on sample tasks to a room. Coaching happens on the work already on your calendar, at your pace, in private. Nothing is hypothetical, so what you learn is what you use the next morning.
Do I need to be technical?
No. You will not write code. If you can delegate to a person, you can learn to delegate to an AI agent. That is the skill we coach.
Can you run an AI workshop for our leadership team?
Yes. Leadership team sessions work on one shared workflow, such as board prep, pipeline review, or reporting, so the whole team builds a common way of working with AI instead of each person improvising alone.
Which AI tools do you coach on?
Mainly Claude and ChatGPT. We also cover where AI fits into the tools your team already uses, and when a custom build makes more sense than another subscription.
What happens after the coaching?
If the sessions uncover a workflow worth automating, Insomnia Club can build it: scoped against a business case, priced as a fixed number before work starts, with working software every two weeks. There is no obligation to build anything.
Is AI coaching for business owners different from coaching for a CEO?
The method is the same and the work is different. Owners usually start with their own time: email, reporting, hiring, and decisions. CEOs of larger teams usually start with the leadership team and how AI work gets delegated and reviewed.
What does it cost?
It depends on the format: one executive, or a full leadership team. You get a clear number on the first call, before anything starts.
07start here
Book the first hour.
Drop your number and we will set up a first conversation, or pick a time on Eli's calendar directly.
Get on Eli's calendar.
Drop your number and we will text you to set up a first conversation about your team and your work.
Rather talk now? Book a 30 minute call with Eli.