[Hiring] Compensation Lead @Headway

Role Description

At Headway, our Total Rewards team helps shape how we attract, retain, and reward the olympic-level building the future of healthcare. We own the pay ranges, equity programs, and compensation cycles behind thousands of pay decisions each year.

We're hiring a Compensation Lead to help build the next stage of our compensation function. This is a high-impact individual contributor role reporting to the Compensation Manager. You'll own the analysis, programs, and the systems and processes behind how Headway pays people, from market pricing and pay positioning, to offers, annual compensation cycles, and equity.

You’ll excel in the “gray area”: when questions arrive without a clear method or owner, you will be able to work out what's actually being decided, build the analysis that answers it, and explain it clearly to the people who have to act on it.

We're building a more modern, tech-enabled way of doing compensation work, and while you'll use AI and automation every day, your strategic thinking and judgment will make the final call.

You don't need to have spent your whole career in compensation, or have compensation experience at all, but you do need to be analytical, comfortable with ambiguity, and able to build partnership across People, Talent, and Finance. You’ll be strategic and business-facing, and should enjoy the hands-on, detail-heavy side of compensation work.

Qualifications

• 4+ years of experience in compensation or total rewards, consulting, finance, or a similar analytical role.
• Strong analytical and problem-solving skills, with advanced Excel or Google Sheets skills.
• Hands-on experience using AI tools to build, test, automate, and improve workflows.
• Clear, confident communicator who can explain complex or sensitive compensation topics to non-experts.
• High bar for accuracy and quality, particularly with sensitive compensation, equity, and performance data.
• Self-directed problem solver with a builder mindset who is comfortable with ambiguity.

Requirements

• Lead the analysis behind our annual compensation cycles: pricing roles against the market, updating our ranges, modeling budget scenarios, and preparing materials for leaders.
• Build recommendations behind new hire offers, promotions, and equity actions.
• Build models, frameworks, and tools that keep compensation decisions consistent as we scale.
• Help run and improve company-wide compensation processes.
• Simplify and scale team workflows to reduce manual effort.
• Use AI and automation in day-to-day work to pull context, flag exceptions, and automate recurring analysis.
• Serve as a trusted compensation partner to HRBPs, Talent Acquisition, managers, and other stakeholders.
• Bring rigor to compensation data and systems, partnering across tools to improve data quality.

Benefits

• Medical, dental, vision, HSA/FSA, 401(k) including match for 2027!
• Carrot Fertility reimbursement.
• Paid parental, medical, and caregiver leave.