Director, HR Business Partner

About the Role

This role is located in either our New York City office or San Francisco office, and is in person 2-day a week. 

As an HR Business Partner, Director at Headway, you will serve as a strategic thought partner to our executives. You’ll shape and execute people strategies that enable scale, strengthen leadership, and drive Olympic-level performance. Partnering closely with senior leaders, 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. Anticipate organizational needs, connect people strategy to business outcomes, and challenge assumptions through evidence and insight.
• Talent Strategy & Performance: Lead performance management and talent review processes with rigor and fairness. Coach leaders 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.
• Analytical & Data-Driven Decision Making: Leverage people data to identify trends, diagnose root causes, and drive measurable improvements in organizational health.
• 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 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. 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), 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.

Compensation and Benefits:

• The expected base pay range for this position is $195,000-$250,000, based on a variety of factors including qualifications, experience, and geographic location. 

  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