Director, Technical Recruiting

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

About the role:

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.

You will:

• 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

You’d be a great fit if…

• 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

#LI-hybrid

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

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A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.