Executive AI Setup
Build your AI stack, upskill as you go
A focused 1:1 where we build your AI stack together, so you upskill as you go and walk out ready to run it. Two to three hours hands-on, plus a 30-minute follow-up within 30 days. Starts at $2,500.
Upskill by co-creating
You do the work, while I sit with you
This isn’t a done-for-you setup. You run the mouse.
I sit beside you and guide.
Every prompt, every configuration, every workflow gets built with your hands on the keyboard. That’s the point: you leave with a working setup and the confidence to actually use it, extend it, and troubleshoot it on your own.
Sound familiar?
Two ways executives usually land here
“I know I should be using AI more, but I don’t trust myself not to leak something I shouldn’t. I want someone to just help me set this up properly.”
“I’ve been poking at AI tools for months and I’m frustrated. I want to actually automate things, not just chat with a bot.”
Either way, you’re in the right place.
What you get
One engagement, four moving parts
- Custom prework that kicks off your AI Readiness. A tailored set of questions about your role, your work, and how you think. It gets me up to speed before our session, and it produces a context document your AI can use from day one.
- A 2 to 3 hour working session. Hands-on setup. Live configuration. Walkthrough. You leave with it working.
- Written follow-up. A summary of what was built, how to use it, and what to try next.
- A 30-minute follow-up call. Scheduled within 30 days of your session, to work through any “wait, how do I do this again?” questions and figure out what’s next.
Two example outcomes
What a finished setup actually looks like
Every setup is built around how you work, so no two look the same. These are two realistic shapes it can take. Most executives land somewhere in between.
A safety-focused setup
Might include:
- A private, privacy-respecting AI workspace configured for your organization’s constraints
- Clear guardrails on what to share and what not to share
- Templates for common use cases (drafting, summarizing, thinking out loud)
- A written “how I use AI” reference you can share with your team
An agent-focused setup
Might include:
- One or two custom agents or workflows tailored to your work
- Integration with the tools you already use (calendar, email, docs)
- A system for handing off recurring tasks to AI
- A short playbook for expanding into new workflows over time
Pricing
Starts at $2,500
Final scope and price are confirmed after the fit call, based on what you actually want to build. No retainer required. A 90-day check-in and annual calibration are available if you want an ongoing relationship afterward, but most executives are set up to run on their own after the initial session.
About Amanda
Who you’re working with
I’m an AI strategy consultant based in San Francisco. I work with executives and family offices on thoughtful, human-centered AI adoption. I hold a Stanford Human-Centered AI certificate and have a background with Fortune 500 companies. Most of my 1:1 work comes through speaking engagements at Chief and The Upside, and through referrals from people I’ve worked with before.
Let’s talk
We’ll talk through what you’re working on, what you want the setup to do, and whether this is a fit. No pressure.
Book a 20-minute Fit Check