About the Team & RoleThe 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 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 5-7 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
