Staff Recruiter, Executive Search

Headway is hiring an experienced Staff Recruiter to lead complex, executive and senior-level searches that will shape the next stage of our company’s growth. In this role, you’ll own and drive high-impact searches across Product, Engineering, Design, Data, Security, Operations, and G&A, partnering directly with senior leaders and executives to design the right hiring strategy, shape 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 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 executive and senior-level searches, driving everything from role scoping to close and owning the narrative around candidate quality, funnel health, and search strategy
• Partner closely with senior leaders and executives, advising on role definition, 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 provide clear visibility to stakeholders throughout the process
• Design and execute targeted sourcing strategies that consistently deliver high-quality, senior-caliber talent
• Use data to drive alignment and decisions, from setting funnel expectations to refining search approach based on real-time signal
• Uplevel hiring quality and consistency, helping teams clarify what “great” looks like and reinforcing structured decision-making across the exec pipeline
• Ensure best-in-class candidate experience, especially for senior talent, 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 bring 6+ years of full-cycle recruiting in high-growth, tech-enabled environments, with meaningful experience hiring senior, director, and VP-level talent
• You have deep experience in executive or senior technical recruiting, ideally across Product, Engineering, Design, Data, Security, or G&A
• 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 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. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• 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
• 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