Max Sheahan

It started at a speakeasy. The No Name Bar in Boulder, a 50-capacity room where I booked live music six nights a week and grew nightly revenue from $200 to $3,000. The venue ran on relationships. Gregory Alan Isakov played secret shows to work on new material several times a year. Nate Cook and The Yawpers held a monthly residency. The Samples would play a show, then individual members would come back to headline on their own. Nathaniel Rateliff sent me a demo. I booked him for $50 and free food. He is selling out Madison Square Garden now.

Seeking earlier nights and a push past my comfort zone, I went to Kampala, Uganda, and taught six subjects across K–12 at a small international school. I wrote a social studies curriculum from scratch because there wasn't one. Every student passed the IGCSE Writing Exam.

I came back and spent seven years teaching ELA in Eugene, Oregon. At Cascade Middle School, every time the district adopted new curriculum, teachers tied themselves in knots trying to adapt. I led development of district-wide ELA power standards: identified the standards that matter most, rewrote them in student-facing language, and built common formative assessments and rubrics. Adopted across all grade levels. It gave our district a solid base from which to be proactive instead of reactive.

A few months ago I started building an AI tool to help me write lesson plans, and I could not stop. Eight shipped products in six weeks. The biggest is Chalk, a K–12 AI platform with 14 tools across 9 subjects and all grade levels. Teachers upload content and get differentiated versions for multiple readiness levels. A Voice Profile system analyzes their writing so output sounds like them, not a chatbot. Runs on Google Apps Script and the Claude API. Deployed and used by real teachers.

I built these because I got tired of tools that treated teachers like they did not understand their own students. The gap between what teachers actually need and what product teams imagine they need is one of the most expensive problems in edtech.

I now sit on my district's AI committee and am advising Superintendent Kraig Sproles on district-wide AI tool adoption. I understand the buy side: how districts evaluate tools, what makes administrators nervous, what makes them excited, and why the gap between a product demo and actual classroom implementation is where most edtech value gets lost.

I hold an M.A. in English and an M.Ed. I am looking for the role where my passion for education and building are integrated and indispensable to your organization.