Engineering Manager (Growth)

Headway's Mission

One in four people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway's mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

Engineering at Headway

Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide. The engineering team at Headway is a small but mighty team using technology to build that future (and have a fun time while doing it!).

Principles that guide us:

• Focus on the mission: We view software as a means of effecting change in the world, not as an end unto itself. We write software to empower our patients and therapist to better solve the problems they're facing.
• Ship small, learn fast: We are building new and novel products and believe that we learn what our users need by quickly shipping and iteration
• Everything is a product: Whether it's our patient search experience or a developer productivity improvement, we treat everything we build at Headway as a product with end-users in mind.
• Optimize for trust: We believe that engineers should be continually learning. To learn effectively and to be productive, engineers must feel safe asking questions and discussing mistakes.

Tools we use:

• Languages: Python 3, TypeScript
• Libraries & Frameworks: FastAPI, SQLAlchemy, React, Remix, Next.js
• Datastores: Postgres, Redis
• Infrastructure: AWS (Fargate, ECS, S3, and more), Spark and Kafka
• Monitoring: Datadog, PagerDuty, Sentry
• Version Control: Github
• Vulnerability Management: Snyk, Semgrep
• Cloud Security: Lacework
• AI Tools: Cursor, Claude, Gemini, Eddy (our in-house cloud agent harness)

About This Role

This role sits at the intersection of growth, product development, and marketing. You'll have the freedom to innovate and experiment while collaborating with a diverse group of cross-functional partners from across the company. This is an opportunity to tackle complex, rewarding problems in a highly collaborative, supportive environment that values technical excellence and operational rigor. You'll build systems that help patients discover and access mental health care, directly improving lives and transforming the healthcare landscape. Your work in this role will shape how thousands of patients connect with care, making a lasting impact on Headway's mission to reimagine mental healthcare access for all.

As an engineering leader at Headway, you will be responsible for leading and growing the team behind these core growth initiatives through people development, strategic planning, and hands-on technical support. You'll play a leading role in defining what and how these systems are built, setting up how the team operates, and ultimately driving best-in-class experiences that convert interest into action.

This is a critical leadership role for Headway and our mission to make mental healthcare more accessible.

Provider Growth Pod: Supporting providers isn't just about connecting them with patients it starts much earlier, with helping them discover Headway and understand the value we provide. Our providers are at the heart of Headway's mission and enabling more of them to join our platform is critical to expanding access to care. This role is focused on building the tools, systems, and experiences that help providers learn about Headway, express interest, and begin their journey. From our referral engine and AI-assisted marketing experiences to intelligent lead capture, scoring, and routing infrastructure, you'll be responsible for the end-to-end technical foundation that drives provider acquisition. That includes building systems where AI helps personalize how providers discover and evaluate Headway not just pushing traffic, but converting the right providers at the right moment. By helping more providers discover, trust, and join Headway, you'll directly impact both provider supply and patient access.

Who You Are

We're looking for experienced engineering team leaders and people managers who are product-minded, data-informed, and energized by growth. As an Engineering Manager at Headway, you will work closely with Engineering Leadership, Product, Marketing, Design, Data, and RevOps to shape the future of our growth strategy. This is an exciting opportunity for a passionate, mission-aligned engineering leader to make an immediate impact at a high-growth company.

Responsibilities

• Lead and manage an engineering team focused on growth
• Partner closely with cross-functional stakeholders to build systems that enable rapid experimentation and long-term scale
• Partner closely with Product, Design, Marketing, Data to rapidly iterate through A/B testing
• Collaborate with activation and onboarding teams to ensure a seamless end-to-end user experience from first touch to first appointment
• Drive alignment across your team on process, prioritization, and product outcomes
• Develop and grow your team through weekly 1-1s, mentorship, and feedback
• Work with and help develop aspiring engineering leaders within the engineering team
• Contribute to the broader company strategy and product roadmap
• Help build out our engineering team as our headcount grows from 120 to 175+ through the remainder of the year
• Leads Teams into the AI Era: You don't just tolerate AI tools you actively shape how your team uses them. You've thought carefully about where AI accelerates engineering work and where it doesn't, and you help your engineers develop genuine fluency rather than surface-level familiarity. Whether it's AI-assisted code review, LLM-powered features, or rethinking which workflows to automate, you bring a builder's mindset: what should we automate, what should stay human, and how do we ship it responsibly in a healthcare context?
• We expect our engineering managers to remain active technical contributors pairing with engineers, driving key design decisions, and personally owning select deliverables. You'll lead through doing, not just directing.

Additional Experiences

• You have 3+ years of experience as an Engineering Manager at a high-growth startup or scale-up, building and leading high performing teams that have effectively delivered business outcomes through technical investments
• You have 5+ years of experience as a Software Engineer
• You're energized by experimentation and growth and can balance short-term learning with long-term scale
• You have a strong product mindset and have built strong cross-functional relationships that drive optimal user experiences and build trust with users
• You have a strong technical foundation that allows you to ensure your team is making appropriate technical decisions
• You are flexible and adaptable; you understand that the best growth teams must learn and iterate quickly, and that growth roadmaps are dynamic as a result
• Nice to have: Prior experience with SEO and paid advertising
• Nice to have: Prior experience with Python and React and working with AWS infrastructure
• Nice to have: Experience in health tech, building user-facing products
• Nice to have: Experience applying AI/ML to growth contexts personalization, intelligent routing, LLM-powered content, or experimentation at scale
• BS, MS in Computer Science or related field

Our Interview Process

After you apply to Headway, here are some details of what to expect during the interview process.

• Initial screen: You'