Director

Two Chairs is transforming the mental health system, believing the current status quo is inadequate. We are committed to raising industry standards through exceptional clinician experiences, improved client outcomes, groundbreaking innovation, and access to high-quality care. Recognized as a 2025 Great Place to Work and Fortune's Best Workplaces in Healthcare, we value diversity, equity, inclusion, and belonging, encouraging applications from all backgrounds.

About the Role:

Technology is pivotal in our mission to fix U.S. mental healthcare. As the Head of Engineering & Data, you will lead the two core technical functions at Two Chairs, overseeing a team of approximately 30 engineers, engineering managers, data scientists, and data engineers. Reporting to the VP of Product & Engineering, you will bridge the gap between our technical teams and the broader organization. We pride ourselves on efficiently delivering impactful technology that enhances behavioral healthcare and seek a leader with similar ambition.

We are looking for a highly empathetic, collaborative leader who builds trust across engineering and data. You should possess excellent communication skills and a structured approach to execution, enabling talented teams to perform at their best. Your direct reports are experienced and technically proficient; your role is to unite them, champion their needs, and support their growth as we continue to evolve and refine our processes.

If you have a proven history of building healthy technical teams in environments that prioritize both speed and quality, we encourage you to apply.

Core Responsibilities:

• People Leadership: Coach and develop engineering managers and data leads. Maintain high performance standards with empathetic leadership, advocating for team well-being and capacity. Foster talent retention and a culture of psychological safety, inclusion, and continuous growth.
• Communication & Alignment: Act as a clear, trusted voice for Engineering and Data across the company. Translate technical complexities for non-technical stakeholders and champion technical roadmap investments. Establish clarity on priorities, decisions, and ownership to enable team autonomy and accountability.
• Collaboration & Execution: Refine execution rhythms suitable for our company stage, including sprint rituals, tech support workflows, cross-squad coordination, and collaboration interfaces with partner teams (Ops, Clinical, Finance, People). Own technical trade-off decisions and track initiative completion. Partner closely with product and design leaders to shape the roadmap and deliver high-quality software impacting hundreds of therapists and tens of thousands of clients. Continue nurturing our collaborative model where engineers, data teammates, product managers, and designers work cohesively to solve problems.
• Technical Strategy: Collaborate with executive and leadership teams to develop a credible multi-year technical vision aligned with product and business priorities, informed by team expertise. Synthesize team perspectives into a shared direction without overriding those closest to the work. Translate our AI strategy into practical product investments and drive adoption of AI coding and analysis tools within engineering and data teams.

Impact and Success Indicators:

• First 90 Days: Build genuine trust with direct reports and the leadership team. Develop a clear understanding of current status and areas needing attention. Establish initial execution rhythms and cross-functional relationships.
• First Year: Engineering and Data teams will exhibit strong execution cadences, clear future visions, and feel engaged and productive. Cross-functional partners will view you as a valuable thought partner. We will see improved technical foundations and significant productivity/efficiency gains through enhanced AI adoption.

Qualifications:

• Proven track record of leading technical teams and managing managers, with a genuine focus on people development.
• Strong business acumen and a drive to build technology that advances key company priorities.
• Experience managing both engineering and data teams. Prior leadership in only one area is acceptable if accompanied by familiarity and respect for the other.
• Experience in high-urgency environments such as startups, high-growth companies, or operationally complex settings requiring discipline and focus.
• A communication style that fosters trust across technical and non-technical audiences.
• Experience incrementally maturing lean teams, rather than solely relying on large-company playbooks.
• Strong follow-through and a bias towards completion.
• Experience with AI-powered tooling and its application in engineering and data workflows.
• Curiosity about healthcare or mission-driven organizations; experience in behavioral health or service-based companies is a plus.

Compensation & Benefits:

Salary range: $233,900 - $275,200, dependent on qualifications and experience. Additional benefits include equity, generous paid time off (including nine paid holidays and a Winter Office Closure), comprehensive medical, dental, and vision coverage, 401(k) retirement savings, a $200 Work from Home reimbursement, an annual $1,000 Productivity & Wellness Stipend, an annual $500 subsidized company contribution to FSA/HSA, and paid parental leave.

Outreach Notice to Applicants:

We appreciate your interest in joining Two Chairs. To ensure a fair and consistent hiring process, please refrain from contacting current employees about the role, your application, or the interview process. Our talent acquisition team will review all applications and reach out directly to qualified candidates. Applicants must be authorized to work for any employer in the U.S. Sponsorship for employment visas is not available at this time.