Conversational AI Designer at Headway - New York, New York, United States; San Francisco, California, United States; Seattle, Washington, United States | $125,000 - $150,000

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

We are seeking a Conversational AI Designer to drive the execution and success of our self-resolution support strategy through our LLM-powered chatbot. This high-impact role is embedded within our Support Products engineering/product team. The ideal candidate possesses a combination of technical depth, familiarity with LLMs/industry trends in AI, and strong UX thinking to optimize how customers interact with the bot to resolve their support needs.

Your responsibilities will include building out LLM-powered automations within our support chatbot, coaching other teams on LLM conversation design, and identifying areas to improve/expand applications of automations. You will work closely with PM, eng, and CX partners; a successful candidate can take ownership of the roadmap and drive execution within their working group. As the foundational hire for this role at Headway, you will need to navigate ambiguity in defining responsibilities and success criteria.

What You'll Do at Headway:

Design and Optimize AI Support Flows: Design and optimize conversational flows and automations across chatbot, email, and voice assistants using complex LLM-powered interfaces.
Be Our Internal Expert: Be the company’s expert in conversation design for generative AI in the support space, partnering closely with other internal product teams and support verticals as they build and maintain their own AI automations.
Drive Delivery: Lead execution of a support automation roadmap defined in partnership with Support Products PM to increase self-serve resolution of customer questions and increase user satisfaction (CSAT).
Define Standards: Develop and maintain design guidelines and best practices for conversational and generative interfaces across the organization.

You’ll be great for this role if you:

Expertise in process automation: Bring 5+ years of experience working in the support or operation spaces with a focus on scaling human processes (ideally through the use of AI/ML, workflow building, and internal tooling improvements).
Data oriented: Can work with data partners to define key success metrics and drive analyses to understand how our automations are impacting our customers and workforce.
Generative AI Fluency: Possess deep expertise in Generative AI, prompt engineering, and designing for LLM-based systems.
Strategic Communicator: Demonstrate effective communication skills, using data to articulate the business and customer impact and an ability to navigate technical concepts.
Execution and Adaptability: Can scope inbound feature requests, estimate effort accurately, and adapt quickly to changing priorities in a fast-paced, high-impact team environment.

The expected base pay range for this position is $183,000 - $216,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for performance-based variable compensation and 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

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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.

Headway participates in E-Verify. To learn more, click here.

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