Step 1 - AI Era Career Strategy

I work with senior and staff engineers who are feeling unmoored by what AI is doing to software engineering.

This is for you if:
• The tools work on a greenfield project but fall apart on your real, legacy codebase
• You've tried AI coding seriously and can't figure out why everyone else seems to be getting results you're not
• You're expected to lead your team on AI-native coding and you're not sure you believe in it yourself
• You're hoping this blows over. You know that's not a strategy.
• The tools work. The code ships. You're just not sure you're proud of any of it anymore.

If this sounds familiar, reach out.

Who I am
I use Claude Code as my daily driver on an a mature, 18-year-old production Ruby on Rails codebase. I am fully bought in on AI-native development. Not as a trend to observe from a distance, but as the most interesting thing happening in software engineering right now.

I have been at Academia.edu for almost 12 years and have done every job in engineering there is - full-stack product, SRE, infra lead, director, VP of Engineering. Being a mentor to engineers has been a constant throughout. I restructured my VP role to become mostly IC because I didn't want to manage this transition to AI-native, I wanted to live it. Now I am back to shipping code daily using Claude Code, and I love it.

Before Academia.edu: I was an independent software vendor in the late 90s, worked at Goldman Sachs, co-founded a startup that got into YCombinator, and ran a consultancy for six years. It took me 15 years to stop pinballing around.

How this works
Three steps. Each is a prerequisite for the next.

Step 1 - AI Era Career Strategy (start here)
A single 60-minute session. We talk about your codebase, your role, what you're worried about. You leave knowing what your actual problem is and what to do about it.
Sometimes the answer is Step 2. Sometimes it's something you can fix on your own and I'll tell you that too.
$150 / 60 minutes

Step 2 - AI-Native on Legacy Code (the core work)
Three sessions, two hours each. $1,800, sold as a package.
You bring a real ticket from your real codebase. We work it together.

Session 1: you watch. I drive.
Session 2: you drive. I correct in real time.
Session 3: you drive. I am mostly quiet.

I designed these sessions to make myself obsolete and you independent - after three sessions you won't need me. A real ticket on a real legacy codebase is very much preferred. I will happily sign an NDA. If these are not an option, we will figure out how to make it work for your specific case.

Step 3 - Continued Guidance (for graduates only)
For engineers who have finished the package and want an ongoing thought partner. We meet twice a month. You bring whatever you're stuck on. Use it to stay current as the tools keep changing, or just to have someone to gut-check decisions with.
This plan works best if you have completed the AI-Native on Legacy Code package. Exceptions possible - let's discuss.