Head of Engineering - Remote

Head of Engineering - Remote About Thriveworks Thriveworks is one of the leading mental healthcare companies in the USA, with over 2,800 employees, founded by and still led by clinicians. We have recently launched a new vision to become America's most valued mental healthcare company—where our teams can fulfill their purpose and do their best work, where clients are treated with warmth and respect, and where communities benefit from access to high-quality care that helps them heal and thrive in life. Thriveworks is committed to providing accessible, top-tier mental health services through a network of licensed therapists and mental health professionals. As we enter this exciting new chapter, our mission remains focused on helping people live happier, healthier lives through both in-person and online counseling services. About the Job We're looking for a Senior Director of Engineering to lead our product engineering team. This is a high-ownership, high-visibility role that sits at the center of how Thriveworks delivers on its mission: building and operating the technology platform that connects people with the mental health care that can change their lives. You'll be the head of engineering for our product engineering team—leading a distributed group of talented engineers, owning the technical roadmap, and setting the standard for what great engineering looks like at Thriveworks. You'll partner closely with Product and Design leadership to shape how we build, not just what we build. And you'll be a key voice in how we evolve our platform—modernizing our architecture, deepening our reliability practices, and thoughtfully bringing agentic AI into our engineering workflow. This is a role for someone who leads from the front. You'll be close enough to the work to make good decisions and earn trust, and experienced enough to know when to delegate and when to get involved. You understand that in healthcare technology, quality and reliability aren't trade-offs—they're the job. Your Background You've led engineering teams through meaningful technical evolution—not just feature delivery, but the work of making a platform more reliable, more maintainable, and more capable over time. You've managed distributed teams and know how to build culture and alignment across time zones and chat threads. You've navigated the complexity of healthcare technology, or something close to it—where compliance, data sensitivity, and patient impact make quality non-negotiable. You've owned architectural decisions alongside experienced tech leads and know the difference between driving alignment and making unilateral calls. You've built or evolved platform reliability practices—incident response, observability, on-call culture—and you understand what it takes to sustain them. Past colleagues would describe you as sharp, direct, collaborative, and deeply invested in the people around you. Bonus points if you've led teams through an agentic AI adoption curve and have real opinions about how to do it well. Key Responsibilities Lead and grow a distributed product engineering team, fostering a culture of craft, psychological safety, and continuous improvement. Own engineering quality standards—code review practices, testing philosophy, documentation expectations, and how the team thinks about technical debt. Drive architectural evolution in partnership with tech leads, including ongoing modernization of our platform and our integrations with AdvanceMD EHR, Salesforce, and third-party insurance and credentialing systems. Own site reliability: incident response, on-call structure, observability tooling (Datadog), and the broader SRE function as it matures. Shape how our engineering team adopts agentic coding tools—setting the tone, building guardrails, and developing the internal practices that make AI-assisted development a genuine accelerant. Partner with Product and Design leadership to influence how work is scoped, sequenced, and executed—ensuring engineering perspective is part of the planning process, not just the delivery. Own the engineering hiring process end-to-end: defining roles, calibrating candidates, and building a team that raises the collective bar. Represent engineering in cross-functional leadership conversations, translating technical context into business impact and vice versa. Build and maintain a healthy, high-trust relationship with your team—creating the conditions for engineers to do the best work of their careers. Requirements 8+ years of software engineering experience, with at least 4 years in engineering leadership roles. Demonstrated success leading distributed engineering teams, including hiring, development, and culture-building. Hands-on experience with modern web application architectures and the judgment to make sound architectural decisions. Experience owning or significantly contributing to site reliability, observability, and incident management practices. Strong cross-functional communication skills—comfortable partnering with Product, Design, Operations, and executive stakeholders. Preferred Healthcare technology experience, or experience in another regulated industry where compliance, data privacy, and system reliability are foundational. Familiarity with our core stack: TypeScript, Node.js, NestJS, Next.js/React, PostgreSQL. Experience leading teams through meaningful AI tooling adoption, particularly agentic or LLM-assisted development workflows. Background in multi-system integration environments (EHR, CRM, payment processing, insurance verification, or similar). Experience scaling engineering practices in a high-growth company. Benefits An amazing team culture Healthcare, Dental, Vision, and life insurance benefits 401K with 3% employer match Paid time off and paid holidays Additional coverage options are available, such as Short Term Disability, Long Term Disability, and Group Accident Insurance Professional development & advancement opportunities Successful Thriveworks employees believe in our mission; they embody our core values, which focus on Community, Purpose, Integrity, Access, Quality, and the ability to achieve our goals and work well together. If you fit the bill and belong on our team, apply today! Thriveworks is an Equal Opportunity Employer. Our people are our most valuable assets. We embrace and encourage differences in age, color, disability, ethnicity, gender identity or expression, national origin, physical and mental ability, race, religion, sexual orientation, veteran status, and other characteristics that make our employees unique. We encourage and welcome diverse candidates to apply for any position you are qualified for to bring your unique perspective to our team. Interested in joining Team Thriveworks? We're thrilled to meet you! With Job scams becoming more and more frequent, here's how to know you're speaking with a real member of our team: Our recruiters and other team members will only email you from [email protected] or an @thriveworks.com email address. Our recruiters and other team members may also contact you via text or phone to schedule an interview. A google meets interview invitation will be sent via email and will only come from an @thriveworks.com email address. Our interviews will take place over Google Meet (not Microsoft Teams, Zoom, or any other platform). We will never ask you to purchase or send us equipment. If you see a scam related to Thriveworks, please report it to [email protected]. You can contact [email protected] with any questions or concerns. Thriveworks is an Equal Opportunity Employer. Our people are our most valuable assets. We embrace and encourage differences in age, color, disability, ethnicity, gender identity or expression, national origin, physical and mental ability, race, religion, sexual orientation, veteran status, and other characteristics that make our employees unique. We encourage and welcome diverse candidates to apply for any position you are qualified for to bring your unique perspective to our team. By clicking Apply, you acknowledge that Thriveworks may contact you regarding your application.