What It's Like to Work at Headway

What is your role, and what attracted you to Headway? Describe the moment when you knew you’d found the right fit.

As chief technology officer at Headway, I lead our engineering organization and shape our technology strategy. What drew me to Headway was personal; my own experience with therapy showed me how life-changing mental health care can be but also how difficult it can be to access.

I knew this was the right fit during my conversations with the team about their vision. Mental health care runs on outdated, disconnected tech stacks that make life harder for both therapists and patients. At Headway, we’re fixing that. We’re building the infrastructure to connect these broken systems and using AI — especially large language models — to save therapists time and help people find the right provider faster. The team’s mix of technical excellence and real compassion for this problem made it clear to me that this is where I wanted to be.

What's your favorite part about working at Headway?

My favorite part about Headway is the direct impact our work has on people’s lives. When we improve our platform, we’re not just increasing metrics; we’re helping someone find a therapist who might change their life, or helping a provider spend less time on paperwork and more time with patients.

I also love the technical challenges we’re solving. Building infrastructure that connects patients, providers and insurance companies has us work on both extremes of technical complexity. We build optical character recognition for faxes coming from doctors, but we also work on LLMs for patient to therapist matching. It’s interesting technical work that also happens to serve a meaningful purpose.

The team culture is something special, too. Everyone here truly believes in the mission of expanding access to mental health care. That shared purpose creates a lovely environment where people are motivated to solve hard problems together rather than just advance their careers.

What advice would you give to job seekers looking to join your growing team?

Headway is aggressively growing the engineering team by investing in a substantial number of new software engineers. We are solving a generational problem and need the best talent to help us achieve it. If you’re interested in joining us, show us how you think about solving problems, not just your technical skills. We’re building systems that haven’t existed before, so we need people who can navigate ambiguity and find creative solutions.

Also, connect with the mission. Mental health care access is a problem that affects virtually everyone, either directly or through someone they care about. The most successful people on our team are those who understand why this work matters. Finally, be ready to grow. We’re scaling rapidly, which means there are constantly new challenges to tackle and opportunities to expand your impact. The best engineers on our team are those who see problems as opportunities to learn something new.