About
That has been the work for nearly twenty years, in classrooms, startups, and executive teams. The job titles changed along the way. The thread never did.
TeachBuildLeadAdvise
I didn't start in software. I started in a classroom.
My undergraduate degree is in education, and I spent time working with students in public school classrooms before software became my career. That might sound like a detour. It turned out to be the foundation. Teaching forces you to understand how people actually learn, how to break a complicated idea into pieces someone can use, and how to tell the difference between a person who is stuck and a person who is about to break through. I have used those skills every day since, just with different students.
I had been writing code since the late nineties, and after college I started my first company building websites and web applications for local businesses. One company turned into several. I co-founded a web consultancy, an enterprise software company, and, more recently, a marketplace for small businesses and a small game studio. Running your own company teaches you things no job can: how to make decisions with incomplete information, how to sell, and how much of "technical" success is really about people and priorities.
I also spent years inside growing software companies, including AdvancedMD, Jane, and Route. At Route I managed multiple teams of more than fifty engineers and QA while the company grew from a startup into a $1B company in three years. At AdvancedMD, as VP of Engineering and Partnerships, I owned the partnerships and integrations department, leading engineering, product, and support for the company's API and partner integrations and working with the executive team on build, partner, or buy decisions. As SVP of Technology at Clicklease, I led the full technology organization: engineering, IT, DevOps, information security, and the service desk.
Somewhere in there I picked up an MBA, because I kept finding that the hardest engineering decisions were actually business decisions wearing a technical costume.
Today I work as an advisor, fractional technology leader, and educator. I help companies use AI where it actually creates value, strengthen engineering organizations that have outgrown their habits, and develop the technical leaders who make everything else possible. I still build, too. I co-founded Gatherly Lane, a marketplace that connects small businesses with customers who will love them, and D4rk Rebel Games, where I get to mix my engineering background with a favorite pastime.
The common thread has never been a technology or a title. It's been building systems, teaching people, developing leaders, and helping organizations solve problems that matter.
Where I've been
Included for context, not as a pitch. The roles below are where the judgment I bring to advisory work came from.
Advise companies on where AI creates real value, how to strengthen their engineering organizations, and how to develop the technical leaders who carry the work forward. Engagements range from focused strategy sprints and ongoing advisory to fractional CTO roles and workshops.
Building a marketplace that empowers small businesses, and a game studio.
Led the technology organization: engineering, IT, DevOps, information security, and the tech service desk. The focus was a platform that's fast to ship on, reliable to run, and secure by design, in a regulated financial services space.
Owned the partnerships and integrations department: engineering, product, and support for the company's API and partner integrations. Led partner discussions as part of the build, partner, or buy strategy and worked closely with the executive team to deliver on it.
Managed multiple teams, more than fifty engineers and QA, delivering the consumer experience. Built AI and ML strategies to automate processes and recommend products to customers. Helped the company grow from a startup to a $1B company in three years.
Multiple startups, in roles from senior engineer to director of engineering to co-founder. Started three companies spanning web development and consulting to software for enterprise customers. Nearly six years of senior engineering in medical software. Led engineering, QA, and product teams across several companies.
How I work
When trust and respect are central to a team's culture, people build each other up, skills deepen, and business goals can be aligned with individual interests. That culture is built deliberately or not at all.
People deserve to know what success looks like and how they're doing against it. Expectations should be written down, measurable, agreed on, and revisited. Nobody should be left wondering.
The most useful feedback is direct and kind at the same time. And when someone on the team goes quiet, that silence is usually a signal that something doesn't feel safe to say.
People grow most when they're challenged just past their current ability and supported while they're there. That's true for engineers, managers, and executives alike. I wrote about this.
When I'm not building or teaching, you'll usually find me running, somewhere outdoors, or with my family.
Let's talk
If you're working through an AI, engineering, technology, or leadership challenge, I'd be happy to hear what's going on and see whether I can help. No pitch. Just a conversation.