Revenue Operations Senior Manager, Systems

Headway; New York, San Francisco, Seattle (NY, CA, WA); Remote; USD 146,000 - 215,000; Full time

Job summary

A leading company focused on transforming mental healthcare is seeking a Revenue Operations Senior Manager. The successful candidate will manage the revenue system strategy, collaborate cross-functionally, and ensure the efficient operation of their technology stack. This role is key to facilitating growth in a dynamic, high-impact sector with competitive compensation.

Benefits

Equity Compensation

Medical, Dental, and Vision coverage

HSA / FSA

401K

Work-from-Home Stipend

Therapy Reimbursement

16-week parental leave

Flexible PTO

Employee Assistance Program

Training and professional development

Qualifications

• 8+ years of experience implementing and optimizing revenue systems.
• 4+ years of experience owning systems strategy.
• Proven track record in building AI-powered systems.

Responsibilities

• Own Headway’s revenue tech stack and system strategy.
• Collaborate with GTM leaders to improve revenue generation.
• Manage and develop a team of systems experts.

Skills

Revenue systems

AI-led improvements

Salesforce

Cross-functional collaboration

Tools

Chili Piper

Outreach

Marketo

Gong

Job description

Revenue Operations Senior Manager, Systems

Remote

Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance.

1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice.

Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 45,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.

We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

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 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

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 employees work remotely across the US, with the option to work from offices in New York City, San Francisco and Seattle. Headway participates in E-Verify. To learn more, clickhere.

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