Senior Product Designer: AI-Driven Scheduling & Messaging

Headway; New York (NY); On-site; USD 180,000 - 225,000; Full time

Benefits offered by this job

Equity compensation

Medical, Dental, Vision coverage

HSA / FSA

401K

Work-from-Home Stipend

Therapy Reimbursement

16 weeks parental leave

Carrot Fertility annual reimbursement

13 paid holidays + Holiday Break

Flexible PTO

Employee Assistance Program (EAP)

Training and professional development

Job summary

Headway is seeking a Senior Designer to lead the Client Management pod, shaping the calendar, scheduling, and provider messaging experience used daily by thousands of therapists.

You will apply systems thinking to multi-state scheduling challenges, ensure coherence with provider lists, and partner with product and data teams. This role is part of an AI-first design team that leverages Claude, Cursor, and MagicPatterns to prototype and deliver in code.

Qualifications

• 5+ years of product design experience on complex workflow surfaces.
• Strong visual and interaction craft with attention to edge cases.
• Systems thinker who turns multi-state problems into coherent experiences.
• Data-informed decision making using qualitative and quantitative insights.
• Proven cross-functional collaboration with PM, Eng and Data.
• Familiar with AI prototyping tools and workflows.

Responsibilities

• Own calendar, scheduling, and messaging design across provider-facing surfaces.
• Ensure coherence with client management and provider profiles.
• Address usability issues across scheduling flows and notifications.
• Collaborate with Product to align design with Helix system patterns.
• Engage in research and apply insights to design patterns.

Skills

Product design

Systems thinking

Data-informed

Cross-functional partner

AI prototyping

Tools

Claude

Cursor

MagicPatterns

Job description

Headway is seeking a Senior Designer to lead the Client Management pod, shaping the calendar, scheduling, and provider messaging experience used daily by thousands of therapists.

You will apply systems thinking to multi-state scheduling challenges, ensure coherence with provider lists, and partner with product and data teams. This role is part of an AI-first design team that leverages Claude, Cursor, and MagicPatterns to prototype and deliver in code.