Executive AI Coaching
Executive AI coaching: the operating system I built for myself, taught to you.
I automated my own executive work. I can help you do the same. One-on-one coaching for executives anywhere. In person in San Diego, virtual everywhere else.
Book a 20-minute intro call →The Willard OS
Two years ago my calendar and inbox owned me. Today they do not. I built a personal operating system, the Willard OS, on top of Obsidian and Claude. It runs my client work, my ventures, my reading, and most of the writing I used to do by hand.
I spend about $1,500 a month on AI tools and automation. It is the best line item in my budget. The hours it returns and the decisions it sharpens are worth several times the cost.
Concretely: every morning Gmail opens with drafts queued for me to review and send. That is 90 minutes of daily inbox time, gone. Deals, regulatory news, and competitor moves are pre-screened to my own criteria and analyzed before I sit down. That is 10 hours a week of manual research, gone, with the first pass written to my brief rather than someone else’s algorithm.
I am a physician and biopharma strategist (MD, MPH) who needed his own work to scale. The system I built for myself is the system I now teach.
Who I coach
C-suite leaders, founder-CEOs, and senior operators who have run out of personal bandwidth and want a system that compounds. Location does not matter. San Diego clients can meet in person; everyone else works with me over Zoom.
What executive AI coaching delivers
- A calendar and inbox you actually trust
- A personal knowledge base in Obsidian, tuned to your work
- A working stack of AI tools (Claude, Granola, and others) wired into your day
- Decision frameworks for the demands that recur every week
- An operating rhythm that protects deep work and senior judgment
How it works
We start with a 20-minute call. If it is a fit, we agree on a cadence, usually weekly or every two weeks, and a duration. San Diego clients can meet in person; everyone else meets on Zoom. Rates depend on cadence and scope, and we set them on the intro call.
Frequently asked
- What is executive AI coaching?
- One-on-one work to build a personal operating system for senior leaders, using Obsidian, Claude, and a small stack of complementary tools. The goal is a calendar, inbox, knowledge base, and decision rhythm you actually trust, with AI doing the parts that should not be on your desk.
- Do you coach executives outside San Diego?
- Yes. San Diego is the in-person option; everyone else works with me over Zoom. The methodology is identical and the result is the same.
- What tools do you teach?
- Obsidian for the knowledge base, Claude as the daily AI partner, Granola for meeting capture, and a handful of utilities for calendar and inbox hygiene. You leave with the stack wired into your day, not a reading list.