Staff Recruiter, Executive Search

Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance. 1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice. Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better. About the Role: 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 GA, 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. You will: 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 You’d be a great fit if… 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 GA 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 pip ... (truncated, view full listing at source)