Chief of Staff, Payer

Headway; Northern (KY); Hybrid; USD 180,000 - 225,000; Full time

Benefits offered by this job

Equity compensation

Medical, Dental, and Vision coverage

HSA / FSA

401K

Work-from-Home Stipend

Therapy Reimbursement

16-week parental leave

Carrot Fertility annual reimbursement

13 paid holidays

Flexible PTO

Employee Assistance Program (EAP)

Training and professional development

Job summary

Headway is building a transformative mental healthcare platform in the United States. We are seeking a Chief of Staff to support the Payer partnerships and Clinical teams, acting as the operating layer to translate the CCO's strategy into actionable plans and to drive alignment across functions.

You will own cross-functional execution, design and facilitate leadership cadences, and surface trade-offs to enable transparent prioritization.

Qualifications

• 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.
• Excellent writing and ability to produce briefs, memos, or decks that move decisions.

Responsibilities

• Drive cross-functional initiative execution and translate strategy into clear goals across teams.
• Coordinate the Clinical team operating cadences, leadership meetings and planning cycles.
• Surface trade-offs with cost and benefits, enabling explicit prioritization decisions.

Job description

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

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

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

Headway participates in E-Verify. To learn more, click here.