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

We’re looking for someone with:

• A track record of leading technical teams and managing managers, with genuine care for the people they lead

• Strong business orientation and a desire to build technology that moves the most important priorities at the company

• Experience managing both engineering teams and data teams. Primary leadership experience with just data or eng is acceptable as long as it comes with familiarity and respect for the craft of the other

• Experience at a company where urgency was real: a startup, high-growth company, or operationally complex environment where discipline and focus were required

• A communication style that builds trust across technical and non-technical audiences

• Experience maturing scrappy teams incrementally, not by importing big-company playbooks

• Strong follow-through and a bias toward finishing things

• Experience in AI-powered tooling and how it applies to engineering and data workflows

• Curiosity about healthcare or other mission-driven environments; behavioral health domain or experience in services companies is a plus

Compensation & Benefits

The offer range is dependent on qualifications and experience. New hires can reasonably expect an offer between $233,900 and $275,200.

Additional perks and benefits:

• Equity in a high-growth start-up

• Paid time off, including nine paid holidays and a Winter Office Closure from Christmas Day (Observed) through New Year's Day

• Comprehensive medical, dental, and vision coverage

• 401(k) Retirement savings options

• One-time $200 Work from Home reimbursement

• Annual $1,000 Productivity & Wellness Stipend

• Annual $500 subsidized company contribution to your healthcare FSA or HSA

• Paid parental leave

Outreach Notice to Applicants

We are thrilled that you’re interested in joining our team! To ensure a consistent and equitable hiring process for all candidates, we kindly ask that you refrain from reaching out to current employees regarding the role, your application, or the interview process. Our talent acquisition team is committed to carefully reviewing all applications and will reach out directly if they decide to move forward.

All applicants must be authorized to work for ANY employer in the U.S. We are unable to sponsor or take over sponsorship of an employment Visa at this time.