Director, Technical Recruiting

Headway is hiring a Director of Technical Recruiting to lead and scale R&D hiring across Engineering, Data, Product, Design, Security, and IT. As the most senior leader overseeing technical recruiting, you will set the strategy, design the operating model, and deliver on a mission-critical hiring engine that fuels Headway’s growth.

You will lead and develop a high-performing team of senior recruiters and managers while partnering closely with leaders across R&D. The systems you build and the talent you bring in will directly impact Headway’s ability to serve providers and patients at scale.

In this role, you’ll blend people leadership, operational excellence, and strategic influence to build an Olympic-level recruiting team.

• Partner with leaders across technical teams to scale their departments, advising on search strategies and providing tailored, scalable solutions
• Leverage metrics to diagnose gaps and proactively provide solutions, keeping a strong pulse on tech hiring trends and the impact it has on your funnels
• Manage a team of senior recruiters and managers with a focus on performance and career growth, embracing Headway’s F.U.E.L. culture (Feedback Uplifts Every Level)
• Serve as a trusted advisor to senior executives, building strong relationships
• Deliver exceptional hiring outcomes by focusing teams on the highest-impact priorities, removing obstacles early, and aligning with cross functional teams
• Drive operational excellence by setting the standards and rhythms that enable a high-performing, high-velocity recruiting team
• Shape long-range R&D talent strategy and partner with executives on headcount planning and capacity modeling
• Influence the systems and tooling that underpin all tech hiring that will allow the TA team to work efficiently and effectively
• Strengthen Headway’s tech talent brand by ensuring an exceptional, consistent candidate experience across every touchpoint

• Bring 7+ years of recruiting leadership experience, including managing managers and senior recruiters in high-growth, tech-enabled environments
• Have a track record of scaling technical organizations, building diverse and inclusive teams, and maintaining a high talent bar
• Operate as a business partner to senior leaders, grounding strategies and recommendations in data and market insights
• Operate as a first-principles thinker, grounding your decisions in data, disentangling root issues in the funnel, and crafting scalable TA solutions that accelerate hiring
• Navigate ambiguity with structure and speed
• Communicate with clarity and executive presence, tailoring your message to different audiences and influencing decisions through structured, compelling storytelling
• Demonstrate a bias for operational excellence, continually improving how the team works and removing friction for candidates, recruiters, and stakeholders

The expected base pay range for this position is $212,000 - $265,000, based on a variety of factors including qualifications, experience, and geographic location.

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

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