Revenue Strategy and Operations Lead (Insights & AI)

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 Team & Role

Headway's Provider Growth team is one of the largest and highest-performing sales organizations in mental health. We drive new provider activation across the country, supported by an established playbook, performance infrastructure, and a growing AI-enabled stack.

We're hiring an Insights & AI Lead to own and push that foundation further. You'll generate insights that drive decisions, build tools reps and managers rely on, and see strategic work through from analysis to execution.

This role reports directly to the Senior Manager of RevOps Insights and has a direct line to Revenue leadership.

• You Will
  • Identify and build AI-powered tools that help PGAs prioritize providers, optimize outreach, and convert effectively
  • Deliver proactive strategic analysis on funnel trends, pipeline health, and cohort performance; own the initiatives that action these insights
  • Support the WBR and executive operating cadence with analytical inputs and data-driven recommendations
  • Build tools that let Sales leaders self-serve performance questions
• You’d be a great fit if…
  • You're AI-fluent, having applied AI tools to tackle real operational problems
  • You're a strategic initiative driver: you can scope ambiguous problems, build structured analyses, and bring stakeholders to a decision
  • You have strong analytical depth: data modeling, trend diagnosis, and forecasting (SQL knowledge a plus)
  • You have 3-6 years in strategy, sales operations, or analytics at a growth-stage company; experience supporting a high-velocity sales team is a strong plus

The expected base pay range for this position is 105,400 - 155,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for performance-based variable compensation and an equity grant, depending on the position and level.

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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