Senior Product Designer — Client Scheduling & Messaging

Headway; United States; Remote; USD 180,000 - 225,000; Full time

Benefits offered by this job

Equity compensation

Medical, Dental, and Vision coverage

Work-from-Home Stipend

Therapy Reimbursement

16-week parental leave

Job summary

Headway is seeking a Senior Designer to lead the Client Management pod, owning calendar, scheduling, and messaging experiences used by thousands of providers.

You will apply systems-minded craft to multi-state problems like timezones, availability, and notifications, ensuring coherence with provider lists and profiles. The team embraces AI-first design, using Claude Code and Cursor to prototype and ship improvements.

Qualifications

• 5+ years of product design experience on complex, workflow-heavy surfaces.
• Strong systems thinking and attention to edge cases in design.
• Experience partnering with PM, Eng, and Data across squads.

Responsibilities

• Own the design of calendar, scheduling, and messaging experiences across provider-facing surfaces.
• Maintain coherence with client management and provider workflows in collaboration with Product.
• Prototype and test ideas quickly using Claude Code, Cursor, or AI tooling to shape pixels and patterns.

Skills

Product design

Systems thinking

Cross-functional collaboration

Data-informed design

AI-assisted prototyping

Tools

Claude Code

Cursor

Job description

Headway is seeking a Senior Designer to lead the Client Management pod, owning calendar, scheduling, and messaging experiences used by thousands of providers.

You will apply systems-minded craft to multi-state problems like timezones, availability, and notifications, ensuring coherence with provider lists and profiles. The team embraces AI-first design, using Claude Code and Cursor to prototype and ship improvements.