Headway-posted 1 day ago
$195,000 - $250,000/Yr
Full-time • Director
Hybrid • San Francisco, NY
501-1,000 employees

Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance. 1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice. Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better. 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 our Revenue 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.

  • 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.
  • 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.
  • 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
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