Staff Product Designer - AI-Driven Onboarding

Headway

New York (NY)

On-site

USD 212,000 - 265,000

Full time

14 days+

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Benefits offered by this job

Equity compensation

Medical, Dental, and Vision coverage

HSA / FSA

401K

Work-from-Home Stipend

Therapy Reimbursement

16-week parental leave for eligible

Carrot Fertility annual reimbursement

13 paid holidays + Holiday Break

Flexible PTO

EAP

Training and professional development

Job summary

Headway is redesigning provider onboarding with AI-powered, conversational experiences to replace multi-page credentialing forms. The design lead will own the onboarding funnel from interest to credentialing, partnering with PM and Eng to maximize conversions and speed to first appointment.

You'll prototype with Claude Code, Cursor, and MagicPatterns, shaping interaction patterns and trust signals. The role emphasizes AI-native practice and measurable impact on provider activation and patient

Qualifications

8+ years of product design experience with onboarding/activation focus
Experience shipping measurable conversion improvements
Systems thinking across form redesign and downstream workflows
Experience designing agentic/AI-powered workflows (beyond chatbots)
Strong visual and interaction design craft and rapid delivery
Prototype with AI tools and stay involved through launch

Responsibilities

Own the end-to-end provider onboarding experience from lead form submission through credentialing to first appointment.
Design AI-agent-powered intake flows replacing manual, multi-page credentialing forms.
Scale self-serve onboarding beyond v2 and enable automation with minimal human intervention.
Plan with AI tools to clarify problem space, test assumptions, and prototype flows.
Conduct provider research to validate solutions and identify where automation helps.
Contribute to the design system and share AI practices with the team.