Director, HR Business Partner

About the Role

This role is based out of either our New York City office or San Francisco office, and is in person 2 days a week.

As Director, HR Business Partner at Headway, you will lead a team of HR Business Partners while serving as a strategic thought partner to our CRO, CCO, CPO, COO, and other business-side executives and their leadership teams. You'll shape and execute people strategies that enable scale, strengthen leadership, and drive Olympic-level performance across the business organization. Partnering closely with senior leaders and coaching your team to do the same, you'll provide counsel on organizational design, performance management, talent planning, and leadership development, balancing near-term priorities with long-term organizational health and cultural integrity. You'll use data-driven insights and sound judgment to identify trends, influence decisions, and lead high-impact initiatives that elevate the employee experience, strengthen manager capability, and ensure our teams are empowered to perform at their best.

What You’ll Do

• Strategic Business Partnership: Act as a trusted advisor to executives across the business organization (CRO, CCO, CPO, COO, and their leadership teams). Anticipate organizational needs, connect people strategy to business outcomes, and challenge assumptions through evidence and insight.

• Team Leadership & Development: Manage and develop a team of HR Business Partners. Set clear priorities, coach them on their own executive partnerships, and build their capability to operate as strategic advisors in their own right.

• Talent Strategy & Performance: Lead performance management and talent review processes with rigor and fairness across the business organization. Coach leaders and your own team to recognize and reward top performance, address underperformance, and build high-performing, inclusive teams.

• Organizational Design & Effectiveness: Partner with leaders to design scalable org structures, strengthen alignment, and enable growth. Use workforce analytics and org design principles to optimize spans, layers, and team health.

• Leadership Coaching & Influence: Build trusted relationships with executives and managers, providing candid, actionable feedback that sharpens leadership effectiveness. Reinforce Headway's cultural principles and managerial excellence through coaching and systems, both directly and through your team.

• Analytical & Data-Driven Decision Making: Leverage people data to identify trends, diagnose root causes, and drive measurable improvements in organizational health. Set the analytical bar for your team's work product.

• Project Management & Operational Excellence: Lead complex, cross-functional people initiatives end-to-end, from scoping and planning to flawless execution and follow-through. Balance strategic impact with hands-on execution, and delegate effectively across your team, to ensure scalability and continuous improvement.

• Cultural Stewardship & Employee Experience: Model and amplify Headway's values and performance standards. Ensure fairness, inclusion, and consistency in decision-making across the business organization. Surface patterns in sentiment and proactively strengthen engagement and trust.

You’d Be a Great Fit If You...

• Have 12+ years of progressive experience in HR or HR-adjacent roles (e.g., Chief of Staff, Strategy, Consulting), with a track record of supporting senior executives in high-growth or scaling environments.

• Are a strategic operator who can anticipate organizational needs, shape people strategies, and influence through credibility and insight.

• Are data-driven, using qualitative and quantitative insights to inform decision-making, program design, and measurement of impact.

• Are a trusted coach and advisor, capable of balancing candor and empathy while influencing at all levels.

• Have deep expertise in org design, performance management, and leadership development.

• Thrive in fast-paced, high-growth settings where agility, sound judgment, and ownership are essential.

• Model Headway’s cultural principles and uphold our Olympic-level performance standard, driving clarity, accountability, and continuous improvement.