About the Team & Role

At Headway, our Total Rewards team plays a critical role in shaping how we attract, retain, and reward top talent. As a Compensation Lead, you’ll be at the forefront of driving Headway’s evolving compensation philosophy, ensuring that our programs are competitive, equitable, and aligned with our business goals.

You’ll partner closely with People, Finance, and Leadership teams to design, implement, and continuously improve compensation frameworks that support Headway’s growth. This role offers a unique opportunity to not just execute on compensation practices, but to influence strategy, improve processes, and make a lasting impact on how we reward our people.

You Will:

Develop, implement, and continuously refine Headway’s compensation philosophy, ensuring alignment with business goals and industry best practices. Lead market benchmarking efforts using compensation survey data (e.g., Radford) to maintain competitive and equitable pay structures. Manage compensation programs end-to-end, including new hire offers, promotions, annual compensation cycles, bonus programs, and equity refreshes. Serve as the subject matter expert (SME) for compensation tools (e.g., Workday Comp, Carta), driving system improvements and data accuracy. Partner with cross-functional stakeholders (HRBPs, Finance, Talent Acquisition, and business leaders) to advise on compensation decisions and strategies. Identify and implement process improvements to enhance efficiency, reduce turnaround times, and support Headway’s growth at scale. Ensure compliance with compensation-related laws and regulations, including pay transparency requirements, through audits and data governance initiatives.

You’d Be a Great Fit If:

You have strong analytical and problem-solving skills, with the ability to translate data into actionable insights and strategic recommendations. You’re a process builder who thrives in environments where you can create, optimize, and scale compensation frameworks from the ground up. You’re an effective collaborator and influencer, comfortable working cross-functionally with stakeholders at all levels of the organization. You’re adaptable and thrive in fast-paced, high-growth environments, balancing shifting priorities with a bias for action. You have a keen eye for detail and are passionate about ensuring data accuracy, compliance, and operational excellence in all aspects of compensation. You’re committed to continuous improvement, always looking for ways to enhance processes, tools, and stakeholder experiences.

Compensation and Benefits:

Salary information is based on a single salary target per role and is differentiated based on geographic location (Group A, B, or C) Group A: $149,000 Group B: $134,100 Group C: $119,200 Examples of cities located in each Compensation grouping: Group A = NYC, SF/Bay Area, LA Area, Seattle, Boston, Austin, and San Diego Group B = Chicago, Miami, Denver, Washington DC, Philadelphia, Atlanta, Minneapolis, Nashville, Sacramento, Phoenix, and Portland Group C = All remaining cities  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

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