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 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.

You will:

• 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

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 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

Compensation and Benefits:

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 offered include:

• 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

• Flexible PTO

• Employee Assistance Program (EAP)

• Training and professional development