Director, Business Operations- Payer & Outcomes

Headway’s mission is to rewire the mental healthcare system so it works for everyone. To do that, we must not only help patients and providers, we must also innovate for the payers who finance care. Payers sit at the center of how mental health benefits are designed and paid for, but today, their tools and structures often limit access instead of expanding it. Our Payer team will lead the charge on rethinking how Headway works with insurance companies via benefits design, care navigation and more to help them deliver better care while managing costs.

As Director of Business Operations for the Payer Group, you will work in close partnership with Product to drive innovation in how Headway collaborates with payers and, in doing so, influence how mental healthcare in America is financed. You will both lead the group’s operations and build the teams, systems, and processes needed to ensure the organization operates at a high bar as it grows.

You will:

• Drive Strategy through Operational Excellence: You will architect the "operational spine" for the Payer Group, not just running the rhythm, but actively partnering with Product, Engineering, Data, Design and Commercial team leads to shape group strategy and translate vision into the roadmaps and execution plans that deliver results. You will lead the end-to-end planning and performance management for the group, defining the metrics that actually move the needle, and setting the targets that hold the group accountable for top-tier execution.
• Build a High-Impact Team: You will lead and mentor a Business Operations and Operations team dedicated to scaling our network monitoring efforts and overseeing the operational strategy for our Payer-facing initiatives.
• 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.

You’d be a great fit if:

• Have 10+ years of experience in Business Operations or Strategy & Operations, ideally with experience in building healthcare or AI products
• Have 5+ years of experience managing and growing 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 $169,600-$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