Insights & AI Lead
Job Description
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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
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Headway
View Company ProfileHeadway is a massive, highly disruptive HealthTech platform fundamentally rewiring the broken mental healthcare system in the United States. Headquartered in New York City, the company tackles the critical access problem where over 70% of therapists do not accept insurance due to overwhelming administrative burdens. Under the hood, Headway operates as a powerful, software-driven national network that seamlessly connects patients, mental health providers, and top-tier insurance companies (like Aetna, Cigna, and UnitedHealthcare). They handle all the heavy lifting for providers—including credentialing, billing, and revenue cycle management—allowing therapists to easily build private practices while accepting insurance. Their primary target audience spans millions of Americans seeking affordable, in-network mental health care, as well as thousands of licensed psychiatrists and therapists looking to eliminate administrative friction. What sets Headway apart in the rapidly scaling digital health landscape is its asset-free network model; by removing the billing nightmare, they empower patients to find highly personalized, covered therapy sessions (often for $0) while scaling to over 65,000 providers and 30 million completed sessions nationwide.
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