Applied AI Lead, Rev Ops

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

The Rev Ops team at Headway powers our revenue engine by generating insights, building workflows, and running AI-native operations that drive our commercial teams to deliver provider and patient growth at scale

This role exists to make our revenue motions deeply automated and continuously optimized. You'll build and ship AI-powered workflows, evaluate and deploy AI-native tools, and partner across our GTM and R&D teams to replace manual effort with intelligent systems that drive growth.

Rev Ops at Headway is AI-first. Operators are expected to use AI tools like Claude, Clay, Glean, and Attention to build, ship, and iterate workflows directly, staying involved through deployment and ongoing optimization. We're looking for people who already work this way and see AI as the primary way in which they operate.

• You Will

  • Build, ship, and iterate AI-powered workflows that take real work off reps' plates, using prompt engineering, agentic workflows, and orchestration to cut manual effort and surface faster, more reliable insights, partnering with R&D to productize what works.

  • Own and evolve core revenue workflows across the provider and health systems GTM teams, making rep motions scalable and AI first as Headway scales

  • Lead major Rev Ops initiatives end to end, from problem definition and data analysis through implementation and rollout, including evaluating and deploying AI-native tools like Attention, Clay, Glean, and Claude

  • Design from the front line by shadowing rep, then partner cross-functionally for business and frontline rep priorities

  • Lead with data, using quantitative analysis to evaluate process performance, surface bottlenecks, set clear measures of success, and recommend ROI-driven improvements you can defend to senior stakeholders.

• You’d be a great fit if…

  • You have 5+ years of experience in Revenue Operations, Business Operations, Strategy, or similar roles within high-growth, operationally complex environments.

  • You are AI fluent: you can build, ship, and iterate revenue workflows using AI tools, partnering with R&D where it makes sense. You're comfortable with prompt engineering, agentic workflows, and AI orchestration, and you understand APIs and how data moves between tools well enough to wire them together yourself. Bonus if you're comfortable in Python for the cases no-code can't handle

  • You can pull and interrogate data independently (SQL fluency, or the ability to get there fast with AI), partner effectively with the Data team when needed, and don’t need to wait for others when you need an answer

  • You have a strong track record of leading large, cross-functional projects that involve engineering, systems, data, and process change

  • You can build workflows based on touching grass and shadowing reps. You prioritize the highest-leverage problems, set clear measures of success, and improve continuously based on adoption and feedback

  • You are an excellent communicator who can simplify complexity, create alignment, and move teams toward action.

  • You thrive in ambiguity, take ownership, and are energized by building and scaling new capabilities

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 https://headway.co/careers. 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.