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 90,000 providers across all 50 states run their practice on our software, serving over 2.6 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, and building much of it with AI. 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.
Headway is hiring an experienced Staff Recruiter to own our most complex and senior design searches — the hires that shape what we build and how fast we build it. In this role, you’ll run end-to-end searches across Product Design and Product Analytics/Research, partnering directly with the CPO, VPs of Product and Design, and their leadership teams to design the right hiring strategy, shape the 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 of design/creative talent 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.
Run end-to-end design/creative searches, from senior ICs to Director+ leaders, driving everything from role scoping to close and owning the narrative around candidate quality, funnel health, and search strategy
Partner closely with the CPO, VPs of Product and Design, and their leadership teams, advising on role definition, leveling, 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 give stakeholders clear visibility throughout the process
Design and execute targeted sourcing strategies that consistently deliver high-quality design & creative talent
Use data to drive alignment and decisions, from setting funnel expectations to refining search approach based on real-time signal
Uplevel design hiring quality and consistency, helping teams clarify what “great” looks like, sharpening competencies and portfolio modules, and reinforcing structured decision-making
Build market intelligence on the talent landscape — compensation, org design, talent pools, and how peer companies structure and hire their teams
Ensure best-in-class candidate experience, with executive-grade care for senior leaders, 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 bring 6+ years of full-cycle recruiting in high-growth, tech-enabled environments, with meaningful experience hiring senior, director, and VP-level design & creative talent
You have deep experience recruiting talent — Product Design or Creative — and are comfortable running senior and executive-level searches
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 can assess talent with credibility — you understand craft well enough to calibrate a designer’s scope, judgment, and impact
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
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.
Medical, dental, vision, HSA/FSA, 401(k) including match for 2027!, Carrot Fertility reimbursement, and paid parental, medical and caregiver leave.
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.