Headway

People Operations

• 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.

Head of Total Rewards, People Ops

Recruitment

• Lead and mentor a team of Business recruiters (GTM + G&A); fostering a culture of excellence
• Partner closely with C-suite and senior leaders across GTM and G&A to design hiring strategies aligned to business priorities, headcount plans, and market realities
• Translate complex hiring goals into milestone-driven execution plans
• Use data to proactively diagnose hiring challenges in close partnership with recruiters
• Elevate sourcing and closing capability across the team, especially in competitive GTM markets with candidates managing multiple offers
• Serve as a trusted advisor to executives, communicating tradeoffs clearly, delivering difficult feedback when needed, and influencing decisions with structured recommendations
• Continuously improve the candidate and hiring manager experience, ensuring Headway’s business hiring process is efficient and aligned with our values

Senior Manager, Business Recruiting

Business Operations

• Drive Strategy through Operational Excellence: You will architect the "operational spine" for the Payer Group, not just running the rhythm, but actively partnering with Product, Engineering, Data, Design and Commercial team leads to shape group strategy and translate vision into the roadmaps and execution plans that deliver results. You will lead the end-to-end planning and performance management for the group, defining the metrics that actually move the needle, and setting the targets that hold the group accountable for top-tier execution.
• Build a High-Impact Team: You will lead and mentor a Business Operations and Operations team dedicated to scaling our network monitoring efforts and overseeing the operational strategy for our Payer-facing initiatives.
• Navigate Tradeoffs & Accelerate Growth: You’ll build the frameworks that guide our most critical decisions, from sizing new opportunities to facilitating the high-stakes tradeoff discussions that ensure we are betting on the right strategic levers.
• Partner Deeply with Product & Engineering: You will work shoulder-to-shoulder with Product and Engineering leaders to define priorities, shape roadmaps, and drive execution against the highest-impact opportunities.
• Serve as the Connective Tissue: You’ll be the vital link between the group and cross-functional stakeholders. Beyond just reporting progress, you know how to bring the right people together to solve complex problems, ensuring work is tied to measurable impact and that all dependencies are aligned across the organization.

Director, Business Operations – Payer & Outcomes

• Drive Strategy through Operational Excellence: You will architect the "operational spine" for the Patient Group, not just running the rhythm, but actively partnering with Product, Engineering, Data, Design and GTM leads to shape group strategy and translate vision into the roadmaps and execution plans that deliver results.
• Navigate Tradeoffs & Accelerate Growth: You’ll build the frameworks that guide our most critical decisions, from sizing new opportunities to facilitating the high-stakes tradeoff discussions that ensure we are betting on the right strategic levers.
• Partner Deeply with Product & Engineering: You will work shoulder-to-shoulder with Product and Engineering leaders to define priorities, shape roadmaps, and drive execution against the highest-impact opportunities.
• Serve as the Connective Tissue: You’ll be the vital link between the group and cross-functional stakeholders. Beyond just reporting progress, you know how to bring the right people together to solve complex problems, ensuring work is tied to measurable impact and that all dependencies are aligned across the organization.
• Build a High-Impact Team: You will lead and mentor a lean Business Operations team dedicated to scaling our patient acquisition, overseeing the operational strategy for our core experience, growth initiatives, and strategic partnerships.

Director, Business Operations – Patient

Account Manager

• Be responsible pitching to and understanding needs of new care partners
• Manage sales funnel from initial prospect through launch
• Build and grow relationships with care partners’ (health systems, medical clinics, and other strategic partners) teams and leadership
• Collaborate with cross functional, internal stakeholders to deliver insights to inform product and operations strategy

Head of Total Rewards, People Ops

Senior Manager, Business Recruiting

Director, Business Operations – Payer & Outcomes

Director, Business Operations – Patient

Senior Business Development Associate, Care Partnerships