Staff Recruiter, Executive Search

Headway•San Francisco, NY

7d•$182,750 - $215,000

About The Position

Headway is hiring an experienced Staff Recruiter to lead complex, executive and senior-level searches that will shape the next stage of our company’s growth. In this role, you’ll own and drive high-impact searches across Product, Engineering, Design, Data, Security, Operations, and G&A, partnering directly with senior leaders and executives to design the right hiring strategy, shape talent bar, and deliver exceptional outcomes. As a senior member of the recruiting team, you’ll operate as a true talent advisor and search leader. You’ll diagnose ambiguous hiring problems, architect structured search processes, influence executive stakeholders, and build world-class pipelines for some of the most critical roles at Headway. Your work will directly impact our ability to scale sustainably and serve providers and patients nationwide.

Requirements

You bring 6+ years of full-cycle recruiting in high-growth, tech-enabled environments, with meaningful experience hiring senior, director, and VP-level talent
You have deep experience in executive or senior technical recruiting, ideally across Product, Engineering, Design, Data, Security, or G&A
You operate as a trusted advisor to executives, influencing decisions through data, market insight, and structured thinking
You know how to untangle ambiguous or complex searches, build clarity, and drive a repeatable plan that produces predictable outcomes
You bring high agency and operational excellence—you run clean, structured searches that remove friction for both candidates and stakeholders
You think creatively about multi-channel sourcing, building senior pipelines through research, relationship-building, and market mapping
You communicate with clarity, presence, and executive polish, regardless of audience
You care deeply about raising the bar, running inclusive and consistent processes, and strengthening the hiring muscle across the organization

Responsibilities

Run end-to-end executive and senior-level searches, driving everything from role scoping to close and owning the narrative around candidate quality, funnel health, and search strategy
Partner closely with senior leaders and executives, advising on role definition, search design, talent bar, market dynamics, and how to run a predictable, inclusive hiring process
Architect structured search plans that diagnose bottlenecks early, set expectations, and provide clear visibility to stakeholders throughout the process
Design and execute targeted sourcing strategies that consistently deliver high-quality, senior-caliber talent
Use data to drive alignment and decisions, from setting funnel expectations to refining search approach based on real-time signal
Uplevel hiring quality and consistency, helping teams clarify what “great” looks like and reinforcing structured decision-making across the exec pipeline
Ensure best-in-class candidate experience, especially for senior talent, where thoughtful communication, coaching, and white-glove touchpoints are essential
Collaborate with sourcers and coordination partners to ensure a seamless, high-quality search experience end-to-end

Benefits

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