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

Plenful

New Jobs

Director, Design