Director, Technical Recruiting

🕒 November 25, 2025

🏄 California, New York – Remote

🏄 California – Remote 🗽 New York – Remote

💵 $218.4k - $257k / year

⏰ Full Time

🔴 Lead

🎯 Recruiter

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Headway

WebsiteLinkedInAll Job Openings

201 - 500 employees

Founded 2019

⚕️ Healthcare Insurance

🧘 Wellness

Healthcare Insurance • Wellness

Headway is a platform that connects individuals with mental health providers, helping them find the right fit according to their needs and insurance coverage. By partnering with numerous insurance providers, Headway ensures that users can access mental health care affordably. It offers both in-person and virtual care options, and manages the payment and billing processes for a hassle-free experience. The platform's aim is to simplify the search and access to therapy and psychiatric support for users, allowing them to focus on their mental health without the administrative burdens.

📋 Description

• 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

🎯 Requirements

• 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.

🏖️ 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