Compensation Lead

Headway

1d•$131,750 - $155,000

About The Position

Headway is hiring a Compensation Lead to help build the next stage of its compensation function. This high-impact individual contributor role reports to the Compensation Manager and owns analysis, programs, systems, and processes behind compensation decisions, including market pricing, pay positioning, offers, annual compensation cycles, and equity. The role calls for sound judgment in ambiguous situations: identifying the decision that needs to be made, developing the analysis to inform it, and communicating the conclusions clearly to stakeholders. The Compensation Lead will work across People, Talent, and Finance in a strategic, business-facing capacity while also handling detailed compensation work. The team is developing a modern, technology-enabled approach and uses AI and automation in everyday work, with human judgment guiding final decisions. Compensation experience is not essential if the candidate brings strong analytical ability, comfort with ambiguity, and effective cross-functional partnership skills. Headway is a mental healthcare company building software and services to make care more accessible. More than 90,000 providers across all 50 states use its software, serving over 2.6 million patients. The company is Series D and has raised more than $325 million.

Requirements

At least 4 years of experience in compensation, total rewards, consulting, finance, or a similar analytical role.
Strong analytical and problem-solving skills.
Advanced Excel or Google Sheets skills and a track record of turning complex questions into clear recommendations.
Hands-on experience using AI tools to build, test, automate, and improve personal workflows, with good judgment about the appropriate roles of AI and human analysis.
Clear, confident communication skills, including explaining complex or sensitive compensation topics to non-experts, handling pushback, and building cross-functional trust.
High standards for accuracy and quality, particularly with sensitive compensation, equity, and performance data, and the discretion to handle such data appropriately.
Self-directed problem-solving ability and a builder mindset; comfort with ambiguity, creating structure, and improving how work is done.

Responsibilities

Lead analysis for annual compensation cycles, including market-pricing roles, updating pay ranges, modeling budget scenarios, and preparing decision materials for leaders.
Develop recommendations for new-hire offers, promotions, and equity actions, and investigate cases outside established guidelines with recruiters and HR business partners.
Build models, frameworks, and tools that support consistent compensation decisions as the company scales.
Run and improve company-wide compensation processes, reducing recurring rework.
Improve processes, documentation, reporting, and workflows to reduce manual effort for employees and partners.
Use AI and automation to gather context, flag exceptions, draft decision materials, prototype solutions, and automate recurring analysis.
Partner with HR business partners, Talent Acquisition, managers, and other stakeholders, applying analytical rigor and sound judgment to compensation questions.
Improve compensation data quality and systems, partnering across Workday, Pave, Carta, and other tools to identify issues before they affect decisions.