Director, Engineering and Data

Two Chairs is building a new kind of mental health system based on the idea that the status quo isn't good enough. Industry-best clinician experiences, better client outcomes, groundbreaking innovation, and access to the highest quality care are how we'll raise the bar for the entire industry. We're honored to have been recognized as a 2025 Great Place to Work and 2025 Fortune's Best Workplaces in Healthcare.

One of our company values is "Embrace Differences" and diversity, equity, inclusion, and belonging are the principles guiding how we build our business and teams. We encourage interested candidates from all backgrounds to apply even if they don't think they meet every expectation of the role.

About the role

Mental health care in the U.S. is broken, and technology is central to how we're fixing it. As Head of Engineering & Data, you'll lead the two technical functions at the heart of Two Chairs: roughly 30 engineers, engineering managers, data scientists, and data engineers. You'll report to our VP of Product & Engineering and serve as the connective tissue between our technical teams and the rest of the organization. We’re proud of shipping powerful technology that improves behavioral healthcare in an efficient way, and are looking for a leader who matches that ambition.

We're looking for a high-EQ, deeply collaborative leader who earns trust across both engineering and data, communicates with clarity and care, and brings the kind of structured follow-through that helps talented teams do their best work. Your direct reports are experienced and technically strong. Your job is to bring them together, advocate for their needs, and help them thrive in a moment where we’re continuing to evolve and iterate on how we work.

If you've built healthy technical teams at companies where bias to action and quality both matter, we'd love to talk.

Core Areas of Responsibility

• People Leadership
  • Coach and develop your direct reports: engineering managers and data leads
  • Hold a high bar for performance while leading with empathy; advocate for team health and capacity
  • Retain strong talent and foster a culture of psychological safety, inclusion, and continuous growth
• Communication & Alignment
  • Serve as a clear, trusted voice for Engineering and Data across the organization
  • Translate technical complexity for non-technical partners and make space for technical investments on the roadmap
  • Create clarity around priorities, decisions, and ownership so teams can execute with autonomy and accountability
• Collaboration & Execution
  • Iterate on execution rhythms that fit our company stage: sprint rituals, tech support workflows, cross-squad coordination, and collaboration interfaces with partner teams (Ops, Clinical, Finance, People)
  • Own how technical tradeoffs get made and how initiatives get tracked to completion
  • Partner closely with product and design leaders to shape our roadmap and deliver high-quality software to hundreds of therapists and tens of thousands of clients who benefit from their care
  • Continue to foster the close-knit collaboration model that enables us to do our best work: where engineers, data teammates, product managers, and designers move together to solve each problem we're up against
• Technical Strategy
  • Work with our executive and leadership teams to develop a credible multi-year technical vision grounded in our product and business priorities and rooted in the perspectives and expertise of the team
  • Synthesize perspectives from across the team into a shared direction without overriding the people closest to the work
  • Help translate our AI strategy into incremental practical investments in the product while driving engineering and data team adoption of AI coding and analysis tools.

Impact and Success Indicators 

Where you’ll make an impact in the first 90 days:

• Build genuine trust with your direct reports and the leadership team
• Develop a clear point of view on where we are and what needs attention
• Begin establishing the execution rhythms and cross-functional relationships that will define your impact

 Where you’ll make an impact in the first year:

• Engineering and Data will have strong execution cadences, clear visions for the future, and feel engaged & productive
• Cross-functional partners will describe you as a true thought partner
• We’ll have leveled-up our technical foundations and found real productivity and efficiency gains thanks to stronger & wiser AI adoption