Director, Design

About Plenful

Plenful is on a mission to transform healthcare operations from the inside out. Fresh off our $50M Series B and backed by Notable Capital, Bessemer Venture Partners, TQ Ventures, Susa/Kivu Ventures, and other leading investors, we’re building the category-defining AI automation platform that healthcare teams rely on to operate smarter, faster, and more efficiently. Our technology empowers healthcare operators across hospital and health systems, pharmacies and payors to eliminate manual work, reduce administrative burden, and improve compliance, all while unlocking critical revenue to fund programs for their in-need patient populations.

Built by healthcare operators for healthcare operators, Plenful is driven by a deep understanding of the challenges facing today’s care teams. We’re passionate about equipping healthcare workers with world-class tools that deliver real, measurable impact, and we’re proud to serve 100+ leading health systems, pharmacies, and healthcare organizations across the country. If you’re excited to help shape the future of healthcare, we’d love to meet you. Apply now to join our growing team.

About the Role

We’re looking for a Director of Design to lead and grow Plenful’s design team. You’ll set design direction across our products and partner with Product and Engineering leadership to shape what we build, how it works, and how we know it is helping customers.

This is a player-coach role. You’ll grow the design team, shape product direction, and stay hands-on with the most important customer problems. You’ll also define how design works in an AI-native organization, moving from insight to working software faster while protecting quality and trust.

What You’ll Do

• Set design strategy across Plenful’s products, partnering with Product and Engineering to choose work by customer impact, business value, and risk.

• Lead customer discovery and testing. Turn complex healthcare workflows into clear, dependable experiences, including thoughtful handoffs between people, automation, and AI.

• Establish an AI-native design practice: use AI tools, code, and agents to explore ideas, build working prototypes, and move validated solutions toward production. Use the speed to learn faster and make better product decisions.

• Coach and grow designers, build future design leaders, and create an operating model that keeps design focused, collaborative, and responsive as Plenful scales.

• Evolve the design system and reusable patterns so teams can deliver consistent, high-quality experiences across products.

• Show how design affects customer outcomes, adoption, and trust, and use that evidence to guide what the team does next.

You May Be a Fit If

• You have led and grown product design teams at hyper-growth companies, and know how to keep quality high as the business and product surface area expand.

• Your portfolio shows strong product judgment and craft across complex B2B software, multi-step workflows, and systems with different user needs.

• You connect design choices to customer and business outcomes, and can explain the tradeoffs clearly.

• You use research and testing to simplify complex products and choose the right level of design depth for the decision.

• You have hands-on experience using AI, code, or agents in design and product development, and good judgment about where AI helps or should stay out of the experience.

• You have built design systems or practices that help teams move quickly without making design a bottleneck.

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

Why You'll Love Working Here

• 🚀 Mission-Driven, World-Class Team — Join an exceptional group of professionals aligned around a meaningful mission and committed to making an impact

• 📈 Opportunities for Growth — Strengthen your expertise through collaboration with experienced, high-performing leaders across the organization

• 🏢 Flexible Hybrid Work Environment — We're remote-first, with meaningful office presence in San Francisco and New York. R&D roles follow a hybrid model, with two days per week in our San Francisco office

Benefits & Perks

• 🏥 Healthcare Coverage — Full medical, dental, and vision insurance for you and participation for your family

• 💰 401(k) with Company Match — Plenful matches 50% of your first 3% contributed

• 📊 Equity — Every full-time employee shares in our success

• 🌴 Unlimited PTO — Take the time you need, when you need it

• 🍽️ Daily Lunch Stipend — $100/week to cover your midday meals

• 💪 Wellness Stipend — $100/month to support your health and well-being

• 🚇 Commuter Benefits — $100/month for SF and NYC-based employees

• 👶 Parental Leave — Paid leave to support growing families