[Hiring] Staff Technical Recruiter @Headway

Role Description

Headway is hiring an experienced Staff Technical Recruiter to own our most complex and senior product 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 Management, Product Design, and Product Analytics/Research, partnering directly with the CPO, VPs of Product and Design, and their leadership teams to design the 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 product 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 product 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 product talent.
• Use data to drive alignment and decisions, from setting funnel expectations to refining search approach based on real-time signal.
• Uplevel product hiring quality and consistency, helping teams clarify what “great” looks like, sharpening product competencies and case exercises, and reinforcing structured decision-making.
• Build market intelligence on the product talent landscape — compensation, org design, talent pools, and how peer companies structure and hire their product teams.
• Ensure best-in-class candidate experience, with executive-grade care for senior product 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.

Qualifications

• You bring 6+ years of full-cycle recruiting in high-growth, tech-enabled environments, with meaningful experience hiring senior, director, and VP-level product talent.
• You have deep experience recruiting product talent — Product Management and/or Product Design — 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 product pipelines through research, relationship-building, and market mapping.
• You can assess product talent with credibility — you understand product craft well enough to calibrate a PM’s or 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.

Requirements

• The expected base pay range for this position is $144,000 - $225,000, based on a variety of factors including qualifications, experience, and geographic location.

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