Pros: Great mission, great people, strong performance, and roadmap.

Cons: A bit intense, but hey, we want to actually make an impact. When people care, things usually get a bit intense :)

Pros: The culture at Headway is phenomenal — people are genuinely kind, motivated, and mission-driven. The energy across the company is contagious, and you can feel how much everyone cares about what we’re building. The growth trajectory is incredible, and it’s exciting to be part of a team scaling this fast. The onboarding process was one of the best I’ve experienced in tech — thoughtful, well-organized, and designed to set you up for success from day one.

Cons: Not many so far. The pace is fast and the company is evolving quickly, so there’s some ambiguity at times—but that’s also part of what makes it exciting.

Pros: The people are the single biggest reason I'm here. High empathy, high EQ, high grit, low ego. It's a combination that I haven't seen anywhere else, and it shows up in how people work together: candor without politics, ambition without elbows. Feedback flows in both directions, and disagreements get worked out on the merits. The culture is genuinely anti-political. Decisions get made on substance rather than territory, and the bar for being a good colleague is high. If you've worked at places where the hardest part of the job was navigating internal dynamics, Headway will feel different. We've made real, meaningful progress on becoming an AI-native company. Not the surface-level "we use Claude Code" version, but actual investment in how AI changes how we build, operate, and serve patients and providers. Leadership is putting weight behind it, ICs are getting tools and runway, and the work is changing in concrete ways. The mission is real. We're moving access to mental healthcare in a market where most players talk a good game and don't deliver. The work matters, the numbers are big, and the impact compounds.

Cons: We're growing fast, and the organization is moving fast to match. That comes with real growing pains: norms and processes are still forming in places, priorities shift as the business scales, and cross-team coordination gets harder as we add surface area. If you need a fully built operating system on day one, the rate of change will feel uncomfortable. If you're energized by helping build the system as you go, it's an asset.