Director, Technical Recruiting at Headway

This role is designed for a seasoned recruiting leader with at least 7 years of experience who has successfully managed other managers in high-growth, venture-b

Work type: hybrid

Location: Remote - New York; San Francisco, California, United States

Salary: $212,000 – $265,000/yr

Type: Full-time

Summary

This role is designed for a seasoned recruiting leader with at least 7 years of experience who has successfully managed other managers in high-growth, venture-backed tech environments. You should be a "first-principles" thinker who relies on data and capacity modeling to scale R&D departments including Engineering, Product, and Design. The compensation is highly competitive ($169k – $265k) and includes equity in a Series D startup backed by top-tier investors like a16z and Accel. The position is fully remote, though it emphasizes a "New York/San Francisco" executive presence. Standout perks include a dedicated holiday break in late December, therapy reimbursement, 16 weeks of parental leave, and a work-from-home stipend. **You might be a good fit if you...** * Have a proven track record of scaling technical teams at a high-velocity startup. * Enjoy "building the engine" by designing recruiting operating models and talent branding. * Are comfortable acting as a strategic advisor to senior executives and headcount planning. * Value a culture of radical feedback (F.U.E.L.) and professional development.

Job Description

Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance.

1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice.

Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.

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

• 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

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

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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