Compensation Lead

About the Team & Role

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 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.

You Will:

• Lead the analysis behind our annual compensation cycles: pricing roles against the market, updating our ranges, modeling budget scenarios, and preparing the materials leaders need to make informed decisions

• Build the recommendations behind new hire offers, promotions, and equity actions, and dig into the cases that fall outside our guidelines with recruiters and HRBPs.

• Build the models, frameworks, and tools that keep compensation decisions consistent as we scale.

• Help run and improve our company-wide compensation processes and tighten the steps that create rework every time they come around.

• Simplify and scale how the team works, improving processes, documentation, reporting, and workflows to reduce manual effort for employees and partners.

• Use AI and automation in your day-to-day work to pull context, flag exceptions, draft decision materials, prototype solutions, and automate recurring analysis.

• Serve as a trusted compensation partner to HRBPs, Talent Acquisition, managers, and other stakeholders, bringing analytical rigor and sound judgment to their questions.

• Bring rigor to compensation data and systems, partnering across Workday, Pave, Carta, and other tools to improve data quality and catch issues before they reach a decision.

You’d Be a Great Fit If:

• You have 4+ years of experience in compensation or total rewards, consulting, finance, or a similar analytical role.

• You have strong analytical and problem-solving skills, with advanced Excel or Google Sheets skills and a track record of turning complex questions into clear recommendations.

• You have hands-on experience using AI tools to build, test, automate, and improve your own workflows, with good judgment about where AI helps and where human analysis matters most.

• You're a clear, confident communicator who can explain complex or sensitive compensation topics to non-experts, handle pushback, and build trust across functions.

• You have a high bar for accuracy and quality, particularly with sensitive compensation, equity, and performance data, and you handle it with discretion.

• You’re a self-directed problem solver with a builder mindset who is comfortable with ambiguity, enjoys creating structure, and looks for ways to improve how we work.