Quick Read
Six questions. About two minutes. You get an instant profile, compared with the target for your function.
Start Quick ReadStop Reading About AI.Start Leading With It.
Executive AI Coaching for senior leaders who want real skills, not another webinar. Five sessions over up to 8 weeks, built around the work already on your desk.
What participants say
I'm the execution guy. Without getting hands-on and seeing what's possible, I feel like I'm sitting on the sidelines. This program gave me the direction I needed to actually start building.
Kim G.
VP Product, Cirium
In vendor calls, in strategy conversations — I can hold my own because I've actually built things, not just read about them.
McCall B-S.
Director of Product Management, CHG
Why I built this
Hear from Jen on why LevelUp exists, and how leaders actually build with AI here.
Does This Sound Familiar?
Tools Are Too Complicated
You've signed up for AI platforms, watched the tutorials, and tried to implement them. The tools still sit unused while you keep doing things the old way.
No Time to Learn
Between strategy meetings, board prep, and daily leadership, who has time to master new tools? The ones meant to save time take time you don't have.
Don't Know Where to Start
ChatGPT, Claude, Copilot, coding agents. Which ones matter? Without someone who uses these tools, the first step stays stuck.
These challenges are exactly why I built LevelUp. You don't need another webinar or a YouTube playlist. You need a guide who's done this before, working with you one-on-one to build the skills that actually matter for your role.
Want a read on where you stand first?
The AI Fluency for Leaders assessment is free. It is a diagnostic, not the program. Six dimensions. You pick how deep to go.
General Fluency
How often do you use AI tools for work or personal tasks?
Analysis & Judgment
When AI produces analysis, how do you evaluate it?
Integration
How connected is AI to the other tools, data sources, and services you rely on?
Building
How much have you used AI to build, change, or deploy software or tools?
Agentic
How much work do autonomous or scheduled AI agents handle for you?
Operating Model
How central is AI to your day-to-day way of working?
Full assessment
Every dimension, in depth, plus a focused plan for where to go next.
Take the full assessmentCoaching built around the work already on your desk
Five one-on-one sessions over up to 8 weeks, plus Slack and course materials. The curriculum is custom. The examples are yours. You build the tools. I coach.
We pick a track together: Agentic Assistant if you want AI workflows you actually use, Prototyper/Builder if you want to ship something you can demo, or Strategic Champion if your job is leading adoption.
Leadership teams can train together. That is Executive Team Training, with its own package below.
From curious to confident
Four phases, in order. Five coaching sessions over up to 8 weeks, plus about 4 to 6 hours of practice each week, designed for a calendar that is already full.
Discovery Session
It starts with a conversation about where you are today: your role, your goals, your comfort with the tools, and where AI could actually change your work. This is not a sales pitch. It is a genuine check on whether coaching is right for you, before you enroll.
Custom Curriculum
From that conversation, I build a curriculum around your objectives. Every exercise uses your real work. Every deliverable is something you will actually use. No generic demos, no toy examples.
Build and Learn
Between sessions you work through projects that become tools you keep: an assistant, a working prototype, something deployed. Five coaching sessions over up to 8 weeks keep you moving through the 'why isn't this working' moments.
Launch and Lead
You leave with a portfolio of AI work, a personal development roadmap, and the fluency to champion adoption. You will not just know about AI. You will have built with it, shipped it, and be ready to teach others.
Hear from past participants
What helped me a lot is the direct interaction with Jen, getting into the details. [These are] things that you really don't get in a self-paced course.
Joe W.
VP Product Strategy, Flexera
Is this right for you?
This is one-on-one coaching for a senior leader who will do the work. If the left column sounds like you, the packages are next.
A good match if
- You're a senior leader (VP, Director, C-suite) who will do the work yourself
- You want to build with AI, not collect a certificate
- You can protect about 4 to 6 hours a week, plus 5 coaching sessions over up to 8 weeks
Probably not if
- You want someone else to build the tools for you
- You're looking for a credential or a packaged course
- You can't protect weekly practice time
Packages
Executive AI Coaching
One-on-one coaching for a single leader.
$4,500
Monthly plans available.
- 45-minute orientation and goal-setting session
- Custom curriculum built around your role and objectives
- 5 coaching sessions over up to 8 weeks, plus Slack and course materials
- Portfolio of work and personal development roadmap
Pick a track together: Agentic Assistant for daily AI workflows, Prototyper/Builder to ship a working prototype, or Strategic Champion to lead adoption.
Book a Discovery CallExecutive Team Training
For leadership teams building AI capability together. Group workshop sessions plus individual coaching.
Call for pricing
- Team discovery session to identify shared goals and individual needs
- Customized group curriculum with role-specific exercises
- Group workshop sessions with hands-on implementation
- Individual coaching for each participant
- Leadership briefing on AI strategy and organizational readiness
- 90-day follow-up support
Book a discovery call
30 minutes. We'll talk about your goals, your current experience, and whether coaching is the right next step.
- A conversation about your goals and current AI experience
- A read on whether this program fits
- How the sessions run, and what you can expect to build
Common Questions
What Executive AI Coaching is, what it takes, and whether it fits your calendar. Team training has its own question below.
Senior leaders, directors, VPs, and C-suite executives who want to develop practical AI skills. You don't need a technical background. You do need to be willing to roll up your sleeves and build things.
That's completely fine. Most of our participants start with little to no hands-on experience with AI tools. Coaching is designed to meet you where you are and build skills progressively. By the end, you'll have built real tools and deployed real applications.
Online courses give you generic information. Executive AI Coaching gives you a personal coach, a custom curriculum built around your specific goals, and accountability to actually follow through. You're not watching someone else build things. You're building them yourself, with expert guidance when you get stuck.
About 4-6 hours per week of practice, plus 5 coaching sessions over up to 8 weeks. Designed for a busy executive calendar.
A portfolio of real AI work: a personal AI assistant you'll use daily, at least one deployed prototype, and the fluency to lead AI conversations in your organization. You'll also receive a personal development roadmap for continued learning.
Yes. Our Executive Team Training program combines group workshops with individual coaching for leadership teams. It's ideal for executive teams, department heads, or cross-functional leadership groups who want to build shared AI capability. Book a discovery call to learn more.
Agentic Assistant is for building AI workflows you'll use every week. Prototyper/Builder is for shipping a working prototype. Strategic Champion is for leading adoption in your organization. We choose together on the discovery call, based on the work already on your desk.
That depends on your track and goals. We work with industry-leading tools including Claude, ChatGPT, Cursor, and various prototyping platforms. We're tool-agnostic and focused on teaching you how to evaluate and use whatever tools best fit your needs.
Still deciding? The assessment is free, and it is still just a diagnostic.