Clinical Evaluator, AI Products (Contract)

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 85,000 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 building AI powered tools for both patients and providers, and we are dedicated to ensuring that clinical experts are included throughout the process. As a Clinical Evaluator, you'll work with our Clinical and Product teams to refine evaluation rubrics that set the standards for what safe, clinically sound, high quality output looks like. You'll test our AI products against those standards to help decide when one is ready to launch. While the ultimate goal is a set of standards, building those standards is challenging – you'll frequently be asked to apply your clinical judgment flexibly and work through hard calls with your peer evaluators.

You will be great for this role if:

• You are a current licensed therapist or professional counselor with an independent, unrestricted license and 3+ years of direct therapy experience.

• You have a strong grasp of risk assessment, safety planning, documentation standards, and you notice quickly when an output could put a patient at risk.

• You are comfortable working alongside AI-assisted review tools: critically evaluating a model's output and giving structured feedback that improves both the rubric and the model over time.

• You can explain your clinical reasoning clearly in writing. You hold your view with conviction and change it quickly when a peer or the data makes a better case.

• You like working through ambiguous edge cases with peers until the group reaches a consistent, well-reasoned call.

• You are comfortable adapting to various healthcare technology platforms, and to workflows that continue to evolve as our programs scale.

• Experience with AI chart reviews, quality audits, or clinical documentation standards is a plus.

Role responsibilities:

• Review output from AI tools across Headway's patient and provider products for clinical accuracy, safety, and appropriateness.

• Apply evaluation rubrics and help improve them. Use your clinical judgment where a rubric falls short, and document your reasoning.

• Take part in calibration sessions and inter-rater reliability rounds, working through ambiguous cases with peers so our standards stay consistent and defensible.

• Work with the Clinical Product team to turn your clinical feedback into specific rubric or output changes.

• Take on other evaluation work as our AI programs grow, such as labeling datasets and reviewing new product use cases before launch.

• Complete all review and feedback work within Headway's designated systems, adhering to HIPAA and Headway's privacy and confidentiality requirements. Patient information is never stored or maintained outside those systems.

Compensation

We have two openings for contracted Clinical Evaluators. Each role requires a minimum commitment of 10 hours per week. Evaluators are paid an hourly rate of $125 and must set up or already have an LLC or S-Corp.

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.