Staff Technical Recruiter

October 2, 2026
Remote, US
$144,000 – $225,000/yr

Who you are

  • 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

What the job involves

  • 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
  • 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