Staff Technical Recruiter, Design

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 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 can assess talent with credibility — you understand craft well enough to calibrate a designer’s scope, judgment, and impact

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