Headway Career Growth & Development

Why did you join Headway’s cybersecurity team? What does a typical day look like for you?

I’ve been interested in cybersecurity since college, and my interest was so strong that I decided to pursue a PhD. I joined Headway because I was excited about the mission of building a mental health care platform that everyone can access. Trust, primarily focusing on security and privacy to start with, is particularly important for both the therapist and the patient to feel comfortable on our platform. I was the first security hire and enjoy being that because I can build from zero to one and see how the organization has grown.

My day-to-day work varies a lot. Some days, I’m writing code. Some days, I’m working on organizational strategy. On some other days, I’m reviewing docs and providing security guidance. I really like the variety and being able to flex into different areas.

What makes Headway’s approach to cybersecurity unique? What gets you most excited to get out of bed each day?

We are much more focused on trust rather than just risk mitigation. This means we work closely with engineering and product counterparts across the company to ensure that we deliver a secure product. We also look to help fix issues rather than just surfacing risks.

I’m excited to get out of bed and work on securing a product with an important mission and work with a world-class team. There’s always something new to learn!

How can someone accelerate their cybersecurity career at Headway?

Trust is a growing team within Headway, offering experienced security engineers the opportunity to work with leadership in co-defining their areas of ownership and impact as we move out of early startup mode and into operating as a later-stage upstart. There’s a tremendous amount of room for continued growth given the diversity of problems to potentially solve, and the diversity of users we’re building for — patients, providers, therapists, insurance customers and employees.

Engineers on the team have the opportunity to influence and build for multiple domains within security, advancing in both their breadth of security knowledge as well as depth of expertise in important functions within emerging industries like security and privacy. There’s no upper limit to learning opportunities as we flex into different areas and increase the scope of learning new things, all while being supported by a world-class team.

How do you structure mentorship and technical learning for engineers?

Every project is a growth opportunity and chance to learn something new. At a high-growth company, there’s always an interesting problem looking for an owner, so we match scope to where someone wants to stretch. We’ve also been leveraging Eddy, our AI assistant, as a new way to speed up learning new parts of the code base, new software development techniques and more! 

An engineer on our team spotted a machine learning opportunity in our billing flow, and without formal ML experience, dove in. We connected him with an experienced machine learning engineer, but he pushed the problem forward and learned a lot while delivering real outcomes. The team wrote about it here. 

To support continuous learning, I run dedicated career conversations with every report where performance cycles are part of that ongoing dialogue and never the beginning or end of it. At the org level, we run a formal engineering mentorship program that purposefully pairs ICs across teams so people get a voice and perspective outside their immediate bubble. It’s co-run by engineering managers and ICs and refreshed quarterly.

What internal mobility or upskilling programs have you launched recently?

Across my year here, I’ve seen explosive growth on my team, with team members taking on a tech lead role, growing into a management position, and taking on the challenging senior to staff promotion. We also are big believers that you need variety and novelty in problems to grow and support moves across the org for team members chasing new domains and to cross-pollinate expertise. 

With all these changes also comes a lot of hiring. We’re super intentional about the mix of levels so existing engineers have room to grow into bigger scope. This gives everyone a chance to have peers they can mentor and be mentored by, no matter their level of experience.

To help support that next level of leadership growth, we run a program for apprentice engineering managers, which is a six-month rotation leading a team and getting structured coaching, a peer group and full manager training. This opportunity is a two-way door: If at the end it isn’t aligned with your career goals, you can return to an IC role. This has been pivotal for team members to take the risk and try it out without having to fully commit. This track has grown a lot of important leaders in our company and is a core growth engine!

How do you identify and support future technical leaders?

I look for people who find problems, not just solve them — the natural curiosity and comfort with ambiguity that shows up when someone leans into cross-functional terrain, whether that’s product, infrastructure or operations. Engineers who naturally grow their peers often turn out to be the ones ready for a formal leadership role, people management or otherwise. I’m a big believer every senior-plus role requires leadership; it doesn’t always look like managing people. That’s a core part of our career ladder and why we have a fully parallel IC and EM track.

We are also intentional in building a culture where EMs are mentors and talent scouts across the whole group. My EM group meets regularly to do a talent review; an opportunity to support the team’s development goals and spot cross-group opportunities. This helps find real concrete opportunities for team members to step up and take on more ownership or drive a real outcome for the business, but with support from a sponsor. It’s one of the most rewarding parts of my job — finding the growth opportunity right at the edge of comfort and seeing team members step up, knock it out of the park, and really step into a leadership role.