Revenue Systems Leader

Position Overview

Headway is seeking a Revenue Systems Leader to own the company's revenue tech stack and system strategy. This role is crucial for shaping and running the machine that powers Headway's growth by unifying go-to-market (GTM) teams, driving insight-based execution, and building the infrastructure to scale the revenue engine. You will lead a team of high-performing system experts and partner with GTM leaders (marketing, sales, customer success) to identify opportunities for system innovation that transforms revenue generation. This position reports to Headway’s revenue operations leader.

About Headway

Headway's mission is to build a new mental health care system that everyone can access. We have developed software that connects people with therapists who accept insurance, addressing the significant barrier of cost in mental healthcare. Founded in 2019, Headway has grown into a national network of over 45,000 mental healthcare providers across all 50 states, serving over 1 million patients. We are a Series D company with over $325 million in funding from prominent investors including a16z, Accel, GV, Spark Capital, Thrive Capital, Forerunner Ventures, and Health Care Service Corporation. We aim to make your time here the most meaningful experience of your career.

Responsibilities

• Collaborate cross-functionally to translate business needs and problems into a systems strategy focused on achieving revenue targets.
• Define and own Headway’s revenue systems strategy and roadmap to meet ambitious short-term and medium/long-term revenue goals while minimizing tech debt.
• Foster an "AI-first" mindset within GTM teams, emphasizing automation and AI-led improvements.
• Integrate the existing tech stack 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 of systems experts.

Requirements

• 8+ years of experience in implementing and optimizing revenue systems firsthand.
• At least 4+ years of experience owning systems strategy and roadmaps.
• Expertise in Salesforce and a strong understanding of other revenue applications such as Chili Piper, Outreach, Marketo, and Gong.
• A solid understanding of data architecture.
• A clear vision for how all revenue systems should work together and the ability to shape this vision through cross-functional collaboration.
• Proven ability to thrive in a hyper-growth startup environment, remaining flexible and adaptable.
• Willingness to be hands-on and build systems functions from the ground up; a proactive and diligent approach to all tasks.
• Passion for and experience in leading systems teams and coaching junior members.
• Energized by innovation and a belief in AI-powered systems for scaling revenue organizations.

Compensation and Benefits

• Salary Range: $146,200 - $215,000 (based on qualifications, experience, and geographic location).

Employment Type

• [Employment Type Not Specified]

Location Type

• [Location Type Not Specified]

Application Instructions

• [Application Instructions Not Specified]