Senior Designer, AI-Driven Provider Calendar & Messaging

Headway; United States; Remote; USD 110,000 - 150,000; Full time

Job summary

Headway is seeking a Senior Designer to lead our new Client Management pod, owning the design of calendar, scheduling, and messaging experiences used by thousands of providers daily. You’ll bring systems-minded craft to complex, state-heavy problems including availability, booking and reschedule, time zones, and notifications, keeping it all coherent with provider workflows.

Join Headway as we build an AI-first design team, using Claude, Cursor, and MagicPatterns to prototype and stay involved

Responsibilities

• Calendar scheduling and availability management, including booking and reschedule flows with timezone handling.
• Provider–patient messaging and the notification/reminder system.
• EHR-craft papercuts: identify and fix high-value usability issues across client management surfaces.
• Ensure coherence between scheduling, messaging, and provider/client profiles in collaboration with Product.

Skills

Design systems

UX design

User research

Tools

Claude

Cursor

MagicPatterns

Job description

Headway is seeking a Senior Designer to lead our new Client Management pod, owning the design of calendar, scheduling, and messaging experiences used by thousands of providers daily. You’ll bring systems-minded craft to complex, state-heavy problems including availability, booking and reschedule, time zones, and notifications, keeping it all coherent with provider workflows.

Join Headway as we build an AI-first design team, using Claude, Cursor, and MagicPatterns to prototype and stay involved