Journey
I've spent 25 years building software products, growing engineering teams, and figuring out what to do when nobody has the answer yet. The thread through all of it: I like being close to the work and close to the business at the same time.
The Long Build
Applied Educational Systems · 1998 – 2021
Built an EdTech platform from six employees and $0 to 100K daily users, $5M ARR, and a PE acquisition.
I joined Applied Educational Systems as a developer in 1998 and stayed for twenty-three years. That sounds like one long chapter, but it was really several different companies inside the same name.
The most important one started in 2011, when the company restarted as a subscription service with six employees and zero revenue. I built the platform, hired the team, and helped shape everything from the product roadmap to the customer support process. At various points I was managing engineers, curriculum writers, and support staff simultaneously — up to thirteen direct reports across three teams.
Over that stretch I led three complete platform rebuilds: Java client-server to Ruby on Rails, then Rails to a React front-end with a Rails API backend. Each migration was a bet on where the market was going, and each one had to interoperate with the system it was replacing — we didn't have the luxury of stopping everything for a multi-year rewrite.
By 2020, the platform was serving 100,000 daily users and 1.5 million total learners with less than fifteen minutes of annual downtime. We grew from zero to $5 million in annual recurring revenue, hit 120% net revenue retention, and improved our NPS from 39 to 80. I built the integrations that got us into some of the largest school districts in the country — connecting with Canvas, Clever, Classlink, and the alphabet of education interoperability standards.
I left in 2021 because I'd done what I came to do and wanted to keep growing. The company was acquired by private equity the following year. The platform, team, and processes I'd built were key factors in positioning it for that exit.
The Startup Sprint
Assemble Stream / Zuckerberg Media · 2021 – 2024
First employee. Broadway live-streaming, a full platform pivot, and two greenfield builds in three years.
After twenty-three years at one company, I did the opposite: I joined Randi Zuckerberg's startup as the first full-time employee. There was no team, no infrastructure, no playbook. I built all three.
The original idea was live-streaming Broadway shows to remote audiences during the pandemic. We went from concept to thousands of concurrent viewers in months, streaming Clyde'sat Second Stage Theater with Stripe ticketing, DRM, and the operational tooling to make it all work. It was the fastest thing I'd ever shipped.
Then the business pivoted — away from streaming, toward an artist engagement and portfolio platform called The Hug. That meant another greenfield build: a Shopify headless storefront, an NFT marketplace across multiple blockchains, virtual galleries, social features, and paid educational content. I hired a team of four engineers, set the technical standards, and managed the architecture through the shift.
The company eventually shut down under investor pressure. But I learned something important about myself — I can build something from nothing, pivot hard, and build something from nothing again. The ability to do that more than once is the skill, not the outcome.
The AI Chapter
Okaya · 2024 – Present
Head of Engineering at an AI startup building mental readiness tools for pilots, firefighters, and healthcare workers.
Okaya is building AI-powered tools to help high-stakes professionals — pilots, firefighters, healthcare workers — monitor and improve their mental readiness. I joined as Head of Engineering to turn a research prototype into a real product.
This is where I went deep on AI. I'm building LLM-powered assessment tools that integrate OpenAI's APIs, real-time voice interaction, custom heuristic models, and semantic search. The work forces hard questions about when AI adds genuine value and when simpler approaches are the right call — especially when the people using your product are making life-or-death decisions.
I built testing and validation frameworks for LLM outputs, designed for explainability and transparency in non-deterministic systems, and kept compliance (HIPAA, GDPR) front of mind from day one. The whole thing runs on AWS — CDK, Lambda, ECS, DynamoDB, OpenSearch — with infrastructure as code and automated deployments.
It's early-stage, messy, and exactly the kind of problem I like: ambiguous, high-stakes, and requiring someone who can translate research into something that ships.
Before All That
1995 – 1998
Factory automation, pharmacy systems, and mainframe protocols — legacy modernization from the start.
I started in the mid-90s — factory automation software at Wonderware, order processing systems at a mail-order pharmacy called Novacom, and an internship at Unisys building OSI network protocols for mainframe communication. All of it involved taking over legacy Unix systems and modernizing them for Windows NT, which in retrospect was good training for a career spent migrating platforms.
Education
BS in Computer Science from Millersville University, 1995. Graduated with honors.
Outside the Day Job
I'm on the board of CPOSC (Central PA Open Source Conference), where I handle fundraising and sponsor outreach. I give talks at Tech Lancaster meetups on AI, LLM frameworks, and technology strategy. And I'm a guest lecturer at Harrisburg University, teaching agile and product development to state employees in their innovation program — two years running.
On the side, I advise startups navigating technical decisions — bridging the gap between investors, leadership, and engineering teams. More about that on my consulting page.