Staff Recruiter, Executive Search at Headway

This role is designed for a seasoned recruitment professional with at least 6 years of full-cycle experience, specifically within high-growth tech environments.

Work type: onsite

Location: New York, New York, United States; San Francisco, California, United States; Seattle, Washington, United States

Salary: $144,000 – $225,000/yr

Type: Full-time

Summary

This role is designed for a seasoned recruitment professional with at least 6 years of full-cycle experience, specifically within high-growth tech environments. The ideal candidate has a proven track record of managing "white-glove" executive searches for Director and VP-level roles across technical and operational functions. If you are a talent advisor who uses data to influence stakeholders and enjoys building structured hiring processes from scratch, you will thrive here. The compensation is highly competitive ($144,000 - $225,000) and includes equity in a well-funded Series D company backed by top-tier VCs like a16z and Accel. Beyond the salary, Headway offers standout perks like 16-week parental leave, fertility benefits through Carrot, therapy reimbursement, and a mandated holiday break between Christmas and New Year’s. While the role is listed as on-site in NYC, SF, or Seattle, the culture emphasizes flexibility and professional development. **You might be a good fit if you...** * Have led complex, senior-level searches for Product, Engineering, or Data leadership. * Can diagnose hiring bottlenecks using data and market mapping. * Thrive in high-agency environments where you act as a strategic partner to executives rather than just an order-taker. * Are passionate about the mental health tech space and building inclusive hiring standards.

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 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.

## You will:

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’d be a great fit if…

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

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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