Staff Technical Recruiter, Design

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

Headway is hiring an experienced Staff Recruiter to own our most complex and senior design searches — the hires that shape what we build and how fast we build it. In this role, you’ll run end-to-end searches across Product Design and Product Analytics/Research, partnering directly with the CPO, VPs of Product and Design, and their leadership teams to design the right hiring strategy, shape the 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 of design/creative talent 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 design/creative searches, from senior ICs to Director+ leaders, driving everything from role scoping to close and owning the narrative around candidate quality, funnel health, and search strategy

• Partner closely with the CPO, VPs of Product and Design, and their leadership teams, advising on role definition, leveling, 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 give stakeholders clear visibility throughout the process

• Design and execute targeted sourcing strategies that consistently deliver high-quality design & creative talent

• Use data to drive alignment and decisions, from setting funnel expectations to refining search approach based on real-time signal

• Uplevel design hiring quality and consistency, helping teams clarify what “great” looks like, sharpening competencies and portfolio modules, and reinforcing structured decision-making

• Build market intelligence on the talent landscape — compensation, org design, talent pools, and how peer companies structure and hire their teams

• Ensure best-in-class candidate experience, with executive-grade care for senior leaders, 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 design & creative talent

• You have deep experience recruiting talent — Product Design or Creative — and are comfortable running senior and executive-level searches

• You operate as a trusted advisor to executives, influencing decisions through data, market insight, and structured thinking

• You know how to untangle ambi