Director, Business Operations

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.

The patient experience is at the crux of our mission here at Headway to increase affordable access. As the Director, Business Operations for the Patient Group, you will be the "operational spine" for the patient charter responsible for connecting patients to the right care and partnering with them throughout their mental health journey.

You will:

• Drive Strategy through Operational Excellence: You will architect the "operational spine" for the Patient Group, not just running the rhythm, but actively partnering with Product, Engineering, Data, Design and GTM leads to shape group strategy and translate vision into the roadmaps and execution plans that deliver results.

• Navigate Tradeoffs & Accelerate Growth: You’ll build the frameworks that guide our most critical decisions, from sizing new opportunities to facilitating the high-stakes tradeoff discussions that ensure we are betting on the right strategic levers.

• Partner Deeply with Product & Engineering: You will work shoulder-to-shoulder with Product and Engineering leaders to define priorities, shape roadmaps, and drive execution against the highest-impact opportunities.

• Serve as the Connective Tissue: You’ll be the vital link between the group and cross-functional stakeholders. Beyond just reporting progress, you know how to bring the right people together to solve complex problems, ensuring work is tied to measurable impact and that all dependencies are aligned across the organization.

• Build a High-Impact Team: You will lead and mentor a lean Business Operations team dedicated to scaling our patient acquisition, overseeing the operational strategy for our core experience, growth initiatives, and strategic partnerships.

You’d be a great fit if:

• Have 10+ years of experience in Business Operations or Strategy & Operations in growth-focused roles

• Have 5+ years of experience managing high-performing teams.

• Are a strategic operator, moving effortlessly between architecting long-term strategies and diving into the granular models and metrics required to hit today’s goals.

• Have deep product and data intuition, with the ability to define product strategy and performance metrics that drive innovation.

• Have led high-stakes, cross-functional processes, aligning senior stakeholders around priorities, tradeoffs, and timelines, especially in ambiguous or rapidly changing environments.

• Excel at synthesizing messy inputs into clear, compelling narratives that inform high-level decisions around resourcing, strategy, and organizational design.

• Act as a strategic orchestrator, identifying cross-functional dependencies and proactively bringing the right people together to unblock projects and ensure progress results in company-wide success.

• Care deeply about delivering meaningful impact — for providers, patients, and Headway’s mission.

Compensation and Benefits:

The expected base pay range for this position is $169,000-$265,000 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.

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A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.