Our Revenue Operations team shapes and runs the machine that powers Headway growth by (1) unifying GTM teams, (2) driving insight-based execution, and (3) building the infrastructure to scale Headway’s revenue engine. As our Revenue Systems leader, you will own Headway’s revenue tech stack and system strategy and lead a team of high performing system experts as we scale our growth.
You will partner with GTM leaders (marketing, sales, customer success) to identify high-impact opportunities where system innovation can transform revenue generation. Your role will be crucial in designing and implementing solutions that help our GTM teams reach their goals. You will report to Headway’s revenue operations leader.
If you're driven to build impactful solutions, thrive in the fast-paced ambiguity of hyper-growth, and excel at leading high-performing teams, this role is for you.
- You will...
- 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
- You’d be a great fit if…
- 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
Compensation and Benefits:
The expected base pay range for this position is $146,200 - $215,000, based on a variety of factors including qualifications, experience, and geographic location.
We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.
Benefits offered include:
- 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
