Director, Business Operations- Payer & Outcomes at Headway

This role is designed for a seasoned operator with over 10 years of experience, specifically at the intersection of healthcare and high-growth technology. The i

Work type: remote

Location: Remote

Salary: $169,600 – $265,000/yr

Type: Full-time

Summary

This role is designed for a seasoned operator with over 10 years of experience, specifically at the intersection of healthcare and high-growth technology. The ideal candidate has spent at least 5 years leading teams and possesses a strong "product intuition," meaning they can translate complex data and insurance dynamics into actionable roadmaps. You’ll be the bridge between clinical outcomes and financial sustainability, making this perfect for someone who thrives in strategic, high-stakes environments. The compensation is highly competitive, reaching up to $265k plus equity, and the company is well-backed by tier-one investors like a16z and GV. As a fully remote Series D company, you get the stability of a proven business model with the autonomy and mission-driven culture of a startup. Unique perks like therapy reimbursement and a "holiday break" week in December underscore their commitment to mental health. **You might be a good fit if you...** * Have successfully scaled operations within the healthcare or AI sectors. * Fluently speak the language of both "Product" (metrics/roadmaps) and "Payer" (insurance/benefits). * Enjoy building organizational "spines"—the systems and frameworks that make growth sustainable. * Are comfortable navigating the ambiguity of a rapidly evolving mental health landscape.

Job Description

Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance.

1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice.

Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.

We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

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 & Outcomes 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 & Outcomes Group, you will work in close partnership with Product and Clinical to drive innovation in how Headway drives value for patients and 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 & Outcomes Group, not just running the rhythm, but actively partnering with Product, Data, Clinical 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

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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