Director, Design

Plenful • San Francisco, CA

2d • 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 what the company builds, how products work, and how their impact on customers is measured.

This is a player-coach position combining team leadership and hands-on work on important customer problems. The Director will grow the design team, shape product direction, and define design practices for an AI-native organization that can move from customer insight to working software quickly while maintaining quality and trust. The role also focuses on translating complex healthcare workflows into clear, dependable product experiences and ensuring design contributes to customer outcomes, adoption, and trust.

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 clearly explain tradeoffs.
• Experience using research and testing to simplify complex products and choose an appropriate level of design depth for decisions.
• Hands-on experience using AI, code, or agents in design and product development, with sound judgment about where AI is useful or should not be part of 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 based on 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.
• 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 the team’s priorities.

Benefits

• Full medical, dental, and vision insurance for the employee, with family participation.
• 401(k) with company match of 50% of the first 3% contributed.
• Equity for every full-time employee.
• Unlimited paid time off.
• 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 City-based employees.
• Paid parental leave.
• Flexible hybrid work environment; R&D roles follow a hybrid model with two days per week in the San Francisco office.

What This Job Offers

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