Revenue Operations Senior Manager, Systems

Summary

Join Headway's Revenue Operations team and lead the charge in shaping and running the revenue engine. As the Revenue Systems leader, you will own Headway's revenue tech stack and system strategy, leading a high-performing team. Collaborate with GTM leaders to identify high-impact opportunities for system innovation, designing and implementing solutions to help teams reach their goals. You will define and own Headway's revenue systems strategy and roadmap, pushing GTM teams towards an AI-first mindset. This role requires a revenue systems expert with 8+ years of experience and a passion for leading and coaching systems teams. The position offers a competitive salary and a comprehensive benefits package.

Requirements

• You are a revenue systems expert, with 8+ years of experience implementing and optimizing systems first hand and at least 4+ years of experience owning systems strategy/roadmap
• You are energized by the current pace of innovation and believe that building AI-powered systems is the best way to scale a revenue organization
• You are a Salesforce expert, you are well versed in other revenue applications (like Chili Piper, Outreach, Marketo and Gong), and you have a strong data architecture understanding
• You have a vision on how all revenue systems work together, and you shape it by collaborating x-functionally with other leaders
• You thrive at operating in a hyper growth startup, remaining flexible and willing to adjust course when needed
• You are willing to get your hands dirty to build the systems function from scratch, you get energized about building and consider no task is beneath you
• You have a passion for and experience leading systems teams and coaching more junior team members

Responsibilities

• Collaborate cross-functionally to translate business needs and problems into systems strategy with a focus on hitting revenue targets
• Define and own Headway’s revenue systems strategy and roadmap to meet Headway’s ambitious short-term and medium/long-term revenue goals while minimizing tech debt
• Push GTM teams into an “AI-first” mindset—solving issues via automation & AI-led improvements
• Wire existing tech stack together to maximize efficiency
• Define and operationalize a real-time approach to optimize system performance
• Collaborate with EPD leadership to optimize data architecture for both coverage and hygiene
• Manage and develop a high-performing team

Benefits

• Equity Compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development