Director, Design

Plenful • San Francisco, CA

6h • Hybrid

About The Position

Plenful is hiring a Director of Design to lead and grow its design team and set design direction across its products. The role partners with Product and Engineering leadership to shape product strategy, determine how products work, and measure their impact on customers. It is a player-coach position that combines team leadership and product direction with hands-on work on important customer problems.

The Director will define how design operates in an AI-native organization, using AI tools, code, and agents to move from customer insight to working software more quickly while maintaining quality and trust. The role also involves developing designers and future design leaders, evolving the design system, and showing how design contributes to customer outcomes, adoption, and trust.

Plenful builds an AI automation platform for healthcare operations, serving hospital and health systems, pharmacies, payors, and other healthcare organizations. Its products aim to reduce manual work and administrative burden, improve compliance, and help healthcare organizations unlock revenue for patient programs.

Requirements

• Experience leading and growing product design teams at hyper-growth companies while maintaining quality as the business and product surface area expand.
• A portfolio demonstrating strong product judgment and craft across complex B2B software, multi-step workflows, and systems serving users with different needs.
• Ability to connect design choices to customer and business outcomes and explain tradeoffs clearly.
• Ability to use research and testing to simplify complex products and choose an appropriate level of design depth for each decision.
• Hands-on experience using AI, code, or agents in design and product development, with good judgment about where AI is appropriate in the experience.
• Experience building design systems or practices that help teams move quickly without making design a bottleneck.

Nice To Haves

• Experience in healthcare, workflow automation, or another complex and regulated domain.

Responsibilities

• Set design strategy across Plenful’s products, partnering with Product and Engineering to prioritize work by customer impact, business value, and risk.
• Lead customer discovery and testing, translating complex healthcare workflows into clear, dependable experiences with thoughtful handoffs between people, automation, and AI.
• Establish an AI-native design practice using AI tools, code, and agents to explore ideas, build working prototypes, and move validated solutions toward production.
• Use faster design and development cycles to learn more quickly and improve product decisions.
• Coach and grow designers, develop future design leaders, and create an operating model that keeps design focused, collaborative, and responsive as the company scales.
• Evolve the design system and reusable patterns to support consistent, high-quality experiences across products.
• Demonstrate how design affects customer outcomes, adoption, and trust, and use that evidence to guide future work.

Benefits

• Full medical, dental, and vision insurance, with family participation.
• 401(k) with a company match of 50% of the first 3% contributed.
• Equity for every full-time employee.
• Unlimited PTO.
• Daily lunch stipend of $100 per week.
• Wellness stipend of $100 per month.
• Commuter benefits of $100 per month for San Francisco- and New York-based employees.
• Paid parental leave.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed