Head of Total Rewards & People Operations

About the role:

Headway is seeking a strategic, execution-oriented leader to serve as our Head of Total Rewards & People Operations. This role will lead our Total Rewards, People Operations, and People Analytics teams — ensuring we operate with rigor, scale, and discipline as we continue to grow.

Reporting to the Chief People Officer, this leader will define and execute the strategies that enable Headway to deliver best-in-class compensation and benefits programs, seamless employee experiences, and data-driven people insights. This role is pivotal in building the infrastructure required to operate like a public company — strengthening our incentive architecture, benefits strategy, and operational systems to attract and retain exceptional talent.

This is a senior leadership role that will partner closely with our executive team on all compensation and rewards topics, from executive compensation strategy through enterprise-wide adjustments. The ideal candidate brings deep experience designing and operating complex compensation programs at scale, paired with the operational acumen to build durable systems that support long-term growth.

• You Will
• Manage and mentor the Total Rewards, People Operations, and People Analytics teams, fostering a high-performing, feedback-rich culture that consistently delivers for the business.
• Lead the People Team’s AI strategy, identifying where AI can drive meaningful efficiency and quality gains across Total Rewards, Operations, Analytics, and HRBP workflows, and building the capabilities within the team to leverage these tools responsibly and effectively.
• Architect and scale the People Team tools and systems infrastructure, leveraging AI and best-in-class technology to ensure we are using the most innovative, efficient solutions as we grow. This includes owning our People tech stack strategy — evaluating, rationalizing, and implementing systems that support scale, data integrity, automation, and an exceptional employee experience.
• Build systems and programs that drive Total Rewards excellence, including shepherding critical strategic initiatives such as exploring a transition to a self-funded benefits model in 2026 and strengthening our overall compensation and benefits infrastructure.
• Support the continued evolution of our compensation architecture including scalable leveling frameworks, incentive design, and governance that enable us to hire and retain top-tier talent.
• Partner closely with the executive team on compensation strategy, advising on executive compensation, broad-based adjustments, equity philosophy, and performance-linked reward structures.
• Build and scale a robust People Analytics function, defining the metrics that matter most, strengthening reporting capabilities, and equipping leaders with actionable insights to drive talent decisions.
• Create a best-in-class People Operations engine that sets our HRBPs and business leaders up for success — delivering seamless execution across critical employee moments, from onboarding through promotion, compensation, and lifecycle transitions.
• Define and monitor key People metrics, using data to diagnose gaps, anticipate risk, and design solutions that drive measurable business impact.
• You’d be a great fit if…
• You have 12+ years of experience leading TR and People Ops teams, with a deep focus on Business Partnership and Strategy.
• Track record of successfully leading & operating within high-growth, talent-dense organizations.
• You’re a first principles thinker, a clear communicator with deep HR strategy experience
• You’re an innovator who likes to design programs that meet the unique needs of the organizations they support.
• You have a strong command of people analytics and Total Rewards and take an analytical approach to problem solving.

Compensation and Benefits:

The expected base pay range for this position is $251,200 - $314,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

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

[To be included if role is bonus eligible][Other compensation includes: discretionary bonuses and/or commission. Commission payments are monthly.]