About the Role

Headway seeks a Chief of Staff to support two organizations: a Payer partnerships team that is reshaping how mental healthcare is funded and delivered at scale, and a Clinical organization that sets the quality and operational standards for care across tens of thousands of providers. Together, they are the fast-moving bridge between Headway's marketplace and the health system. This role is at the critical junction of mental health delivery, quality and reimbursement, as Headway is scaling from a growth-stage company into a durable institution.

As Chief of Staff to the Payer and Clinical teams, you will be the operating layer that makes this possible. Your primary job is cross-functional: you sit at the intersection of product, clinical, commercial, and strategy - translating the CCO's strategic intent into clear, shared goals across functions and making sure execution follows. You'll also run the rhythm of the Clinical org, driving the process that turns strategy into plans with named owners and real dates, and be the person who sees misalignment forming before it becomes a missed quarter. This is not a coordinator role and it is not a shadow CCO. You won't own a revenue target or a clinical program. This is a unique opportunity to work alongside a seasoned CCO and exceptional people leader, owning how work moves in a high-functioning and complex organization.

You Will

• Drive cross-functional initiative execution. This is your highest-leverage work. Act as the bridge between the CCO and Product, R&D, Finance, and other functions to prevent misalignment before it compounds. Translate strategic intent into clear, shared goals across teams. Track execution, surface blockers proactively, and close the gap between what was decided and what actually happens.
• Act as connective tissue across the CCO org and with key cross-functional partners, spotting misalignment early and helping leaders converge on direction before it costs a quarter.
• Own the Clinical team's operating cadences. Design and facilitate leadership meetings, planning cycles, and forums that consistently drive clear decisions and accountability.
• Surface trade-offs rather than resolve them quietly. Bring our CCO and leadership team options, costs, and a recommendation so that prioritization calls are explicit and visible.
• Write for the leadership team. Decision memos, and first-pass CCO-wide communications.
• Design and implement processes that improve org-wide efficiency.
• Lead internal initiatives without a natural home. You'll be involved in new operating models, cross-functional programs that span Commercial, Clinical, R&D, and Finance. You'll be handed problems, not projects.
• Handle ad hoc asks without losing momentum. When urgent, unplanned requests land (a last-minute comms prep, a one-off deliverable, a problem that doesn't fit anyone's job description) you show up as a reliable partner to the business ready to lean in.

You'd Be a Great Fit If...

• 5+ years in operations, program management, strategy, or a prior Chief of Staff role in tech. Experience supporting a C-suite executive directly is strongly preferred. A strong project management or ops background is what this role calls for vs commercial experience.
• You've operated inside a high-growth company at scale, ideally 1,000+ employees, where the informal operating model has already broken and the formal one is still being built.
• You're a genuinely excellent writer. You can take a complex, multi-stakeholder situation and produce the brief, memo, or deck that moves a decision. You're comfortable writing in someone else's voice when the situation calls for it.
• You're an exceptional project manager and can hold many workstreams in your head simultaneously, know which one is at risk before anyone tells you, and drive all of them to completion.
• You operate through influence rather than authority. You've built standing with peers who didn't report to you and have influenced executives. You're comfortable with friction - nudging teams toward alignment is part of the job, not a sign something's wrong.
• You bring structure to ambiguity without smothering speed - and you have the judgment to know which of those two matters more in a given week.
• Nice to have: consulting or strategy background, an MBA, prior healthcare or payer experience, or time inside a company scaling through a major organizational inflection point. AI-native in how you work.

Compensation and Benefits:

The expected base pay range for this position is $180,000-$225,000 based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
  
  • Equity compensation
  • Medical, Dental, and Vision coverage
  • HSA / FSA
  • 401K
  • Work-from-Home Stipend
  • Therapy Reimbursement
  • 16-week parental leave for eligible employees
  • Carrot Fertility annual reimbursement and membership
  • 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
  • Flexible PTO
  • Employee Assistance Program (EAP)
  • Training and professional development