Senior Director, Product

Two Chairs; Chicago (IL); On-site; USD 250,000 - 280,000; Full time

Benefits offered by this job

Equity

Paid time off

Medical coverage

401(k)

Work from home stipend

Productivity & Wellness stipend

Healthcare FSA/HSA contribution

Parental leave

Job summary

Two Chairs is seeking a Senior Director of Product to lead a four‑PM team serving therapists and clients. You will partner with Engineering, Design, and Data to set priorities, shape a multi-year product strategy, and drive initiatives with clinical and commercial impact.

You will coach senior PMs, manage planning cycles, and communicate roadmap value to executives, with a focus on inclusion and psychological safety in a fast‑paced healthcare environment.

Qualifications

• Track record of leading product teams and managing senior PMs
• Experience growing senior PMs into principal PMs
• Strong prioritization judgment and ability to say no with rationale
• Close working relationship with Engineering, Design, and Data leaders
• Ability to build trust with founders or CEOs
• Experience setting multi-year product strategy and communicating it to leadership
• Startup or high-growth experience with urgency and limited resources
• Empathy and commitment to inclusion and psychological safety
• Healthcare experience is a plus, especially on the commercial side
• Curiosity about healthcare and clinicians who use products

Responsibilities

• Manage, coach, and develop a team of PMs with high autonomy and clear expectations
• Grow senior PMs and their craft, with a POV on PM evolution and AI impact
• Maintain a high performance bar while leading with empathy and focusing on team health
• Build a culture of psychological safety, inclusion, and continuous learning
• Develop and communicate a multi-year product strategy aligned to vision and priorities
• Own annual and quarterly planning, roadmap alignment, and technical foundations
• Tell the roadmap story to the product team and across the company
• Establish lean, incremental ways of working in product
• Build strong cross-functional partnerships withEngineering, Design, and Data leaders
• Help connect product and technology to commercial value across clinical, operations, and finance sections

Skills

Leadership

Product management

Strategic thinking

Prioritization

Cross-functional collaboration

Coaching

Empathy

Inclusion & psychological safety

Healthcare industry exposure

Tools

AI product craft

Job description

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 Senior Director of Product, you'll lead Product Management at Two Chairs: a small team of four senior product managers who build for hundreds of therapists and tens of thousands of clients. You'll report to our SVP of Product & Engineering and work as a peer to our Head of Engineering & Data and our Senior Director of Design.

We're looking for a strategic leader who can set a clear product direction, tell the story behind the roadmap, and make hard prioritization calls with the people who are affected by them. You'll build trust with our clinical, operations, and commercial leaders as well as with our executive team. Your PMs are experienced and self-directed. Your job is to coach them, grow them, back them up, and give them the clarity and focus to do their best work.

If you've led product at a startup or high-growth company where urgency was real and the stakes for the people using the product were high, we'd love to talk.

Core Areas of Responsibility

• Manage, coach, and develop a team of PMs, with high autonomy and clear expectations
• Grow senior PMs and their craft, with a clear point of view on what that growth looks like and a POV on how the PM craft should evolve with AI
• Hold a high bar for performance while leading with empathy; advocate for team health, capacity, and growth
• Build a culture of psychological safety, inclusion, and continuous learning
• Develop and communicate a multi-year product strategy tied to the company's vision and business priorities
• Own annual and quarterly planning, including how roadmap, estimation, launch windows, and technical foundations fit together
• Tell the story of the roadmap and its impact to the product team and across the company
• Establish product ways of working that fit a lean team, introduced incrementally and followed through
• Cross-Functional Partnership
  • Build a close, same-team relationship with Engineering, Design, and Data leaders
  • Build trust with leaders in Clinical, Operations, Finance, and commercial teams, and with the CEO and executive team
  • Help the company connect product and technology to commercial value, including in market-facing conversations
  • Absorbing and coalesce diverse inputs in a complex business, forming a coherent roadmap across clinical, client, and commercial users
  • Bring empathy for the therapists and clients who use our products and who are central to our care

Impact and Success Indicators

In your first 90 days, you'll build trust with your PMs and with your peers in Engineering, Design, and Data. You'll learn our business, including how clinical and operational work actually happens, and form a clear point of view on where product is strong and where it needs attention.

In your first year, the Product team will have a clear strategy, a planning process that feels dependable, and a working relationship with Engineering, Design, and Data that people describe as one team. Clinical, operations, and executive partners will see you as a trusted partner, and your PMs will feel supported and growing. You’ll be key to shipping software that drives therapist, client, and commercial impact and own core company OKRs.

We're looking for someone with:

• A track record of leading product teams and managing senior PMs, with a coaching style that gives experienced people room to run
• Clear opinions on PM craft, and experience growing senior PMs into principal PMs
• Strong prioritization judgment, and the willingness to say no and explain why
• A close working relationship with Engineering, Design, and Data leaders, and a record of avoiding the "us versus them" dynamic between product and engineering
• The ability to build trust with function heads outside product, and with founders or CEOs
• Experience setting multi-year product strategy and communicating it clearly to leadership
• Startup or high-growth experience, where urgency was real and resources were limited
• Empathy and a commitment to inclusion and psychological safety
• Healthcare experience is a plus, especially on the commercial side (health plans, payers, or market-facing work); experience in complex B2B or services businesses also counts
• Curiosity about healthcare or other mission-driven work, and about the clinicians who use our products

The offer range is dependent on qualifications and experience. New hires can reasonably expect an offer between $250,000 and $280,000.

Additional perks and benefits:

• Equity in a high-growth start-up
• Paid time off, including nine paid holidays and an additional 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 to support your personal and professional goals
• 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.

If you need a reasonable accommodation, please let your recruiter know so our People Team can assist you.

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.