Compensation Lead

Summary

Join Headway's Total Rewards team as a Compensation Lead and play a critical role in attracting, retaining, and rewarding top talent. You will be at the forefront of driving Headway's compensation philosophy, ensuring competitive and equitable pay structures. Partner with various teams to design, implement, and improve compensation frameworks. This role offers the opportunity to influence strategy, improve processes, and make a lasting impact on how Headway rewards its employees. You will manage compensation programs end-to-end and serve as a subject matter expert for compensation tools. This position requires strong analytical and problem-solving skills, collaboration, and adaptability in a fast-paced environment.

Requirements

• 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

Responsibilities

• 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

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