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. Headway participates in E-Verify. To learn more, click here. 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.

• Own the end-to-end renewal forecasting process • Establish and maintain Lytx's Retain & Grow performance metrics • Partner with Finance to align on metric definitions, target-setting methodology, and reporting cadences • Proactively identify forecast gaps and surface revenue risk early • Monitor and analyze the renewal and expansion pipeline • Build frameworks and dashboards for pipeline visibility • Develop scalable frameworks to identify at-risk renewals and expansion opportunities • Define and operationalize escalation paths • Lead annual and in-year territory planning • Identify expansion whitespace within the existing customer base • Collaborate with Sales leadership, Enablement, and HR to implement territory changes • Serve as a strategic operations partner to KAM and CS leaders

• Sales & Marketing Alignment: Serve as the operational liaison between Sales and Marketing, ensuring consistent lead management, handoff processes, and pipeline hygiene • Partner with Marketing to optimize lead scoring, campaign attribution, and MQL-to-SQL conversion workflows • Support Sales leadership with territory planning, quota setting, and bookings tracking • Cross-Functional Collaboration: Work closely with Finance, Deal Desk, and Customer Experience teams to ensure accurate marketing deliverables and smooth customer lifecycle handoffs • Support onboarding of new sales and marketing team members with process documentation and tool training • Manage special projects and strategic initiatives as directed by VP of Revenue Operations and SVP of Marketing • Process Optimization: Design, document, and continuously improve end-to-end GTM processes, from demand generation through closed-won • Identify and resolve bottlenecks across the sales and marketing funnel to improve efficiency and throughput • Develop and maintain standard operating procedures (SOPs) for key revenue-generating workflows • Forecasting & Planning Support: Assist in managing the sales forecast process and pipeline review cadences • Support annual and quarterly planning for Sales and Marketing, including headcount modeling, capacity planning, and budget alignment • Develop TAM/whitespace analyses and prospect playbooks to support pipeline generation efforts • Territory Planning & Ownership Support: Support annual territory planning efforts by preparing data, validating assignments, and executing approved changes • Maintain territory and ownership updates throughout the year related to new hires, terminations, and role changes • Perform day-to-day territory and ownership maintenance across Salesforce, Chili Piper, and other revenue systems • Ensure accurate ownership and routing for accounts, contacts, leads, and related activities to support sales execution • Assist with data hygiene efforts by identifying inconsistencies and escalating issues to the Rev Ops Team Lead as needed • Reporting & Analytics: Liaison with key stakeholder driving requirements for dashboards and reports across Sales and Marketing KPIs using tools such as Salesforce and Power BI • Own and drive Marketing rhythm of business meetings • Support weekly pipeline review meetings, monthly and quarterly marketing business reviews with intelligence-driven insights • Technology Stack Management: Serve as a key Product Owner and power user for the Marketing GTM tech stack, including Salesforce, Gong, and Clay • Evaluate, implement, and drive adoption of new tools that improve Sales and Marketing effectiveness • Partner with Systems Team to ensure integrations are functioning correctly and data flows seamlessly across platforms

• Support lead & pipeline reporting, performance dashboards, forecasting metrics and executive reporting. • Own day-to-day administration and optimization of HubSpot, including workflows, properties, lifecycle stages, permissions, automation, and data management. • Manage and optimize integrations across the GTM tech stack, ensuring accurate data flow and alignment between systems. • Partner with sales and marketing to define, operationalize, and evolve KPIs for campaign attribution, conversion, and forecasting. • Support annual planning initiatives and ongoing business performance analysis & partner with leadership on territory planning, capacity planning, quota administration, and operational decision-making. • Analyze business performance to identify bottlenecks, process gaps, and growth opportunities. • Develop dashboards and reporting that provide actionable insights across the funnel • Evaluate and implement automation and AI-driven solutions that improve productivity and scalability • Partner with business stakeholders to translate operational requirements into scalable CRM processes, automation, and system enhancements. • Establish and maintain CRM governance, including data quality standards, field management, documentation, and change control processes. • Ensure HubSpot effectively supports our go-to-market motions and business objectives • Leverage deep HubSpot knowledge to improve reporting, automation, lead management, forecasting, and operational workflows • Support integrations across the GTM tech stack • Conduct regular audits for data integrity and drive continuous improvements to process and tooling. • Help define scalable processes across the customer lifecycle, from lead management through renewal and expansion • Drive adoption of operational best practices, data governance standards, and process consistency across teams