Leadership Partner

About the Role

As a Leadership Partner, People Strategy at Headway, you will play a critical role in shaping the people strategy for our Engineering, Data, Product, Design, and Product Marketing teams. Partnering closely with the CTO and VP of Product, you will provide strategic counsel on performance management, leadership coaching, talent development, employee relations, and org design. You'll use data-driven insights to identify trends, influence decision-making, and drive scalable, high-impact people initiatives. Your work will uphold Headway’s values and Olympic-level performance culture, ensuring our teams are engaged, empowered, and performing at their best.

You Will

• Serve as a trusted advisor to Engineering, Data, Product, and Design leaders, providing strategic guidance on talent planning, leadership effectiveness, and org design.
• Lead key people processes, including performance calibrations, promotion reviews, compensation planning, and workforce planning, ensuring alignment with business objectives.
• Drive talent programs that enhance employee experience, manager capability, and leadership development.
• Leverage qualitative and quantitative data (e.g., engagement surveys, attrition trends, performance data) to identify trends, shape programs, and influence decision-making.
• Act as a culture amplifier, reinforcing Headway’s principles and fostering an inclusive, high-performance environment.

You’d be a great fit if…

• You have 10+ years of experience as a strategic HR Business Partner, with deep expertise in supporting Engineering, Product, and Design functions.
• You have exceptional judgment and problem-solving skills, with the ability to advise senior executives and influence at all levels.
• You are intellectually curious and solutions-oriented, able to translate challenges into high-impact talent strategies.
• You are data-driven, using qualitative and quantitative insights to inform decision-making, root cause analysis, and program design.
• You have experience owning and driving talent programs at scale, including performance cycles, compensation planning, leadership coaching, and org design.
• You can build trust and rapport with both executives and ICs, adapting your approach to meet the needs of diverse stakeholders.
• You are agile, fearless, and thrive in fast-paced, high-growth environments.

Compensation and Benefits:

• The expected base pay range for this position is $146,200-$215,000, 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