5-7 years of experience leading product design teams in fast-paced environments
Strong portfolio showcasing product judgment in complex B2B software
Ability to connect design decisions to customer and business outcomes
Experience in simplifying complex products through research and testing
Hands-on experience with AI tools in design and product development
Proven track record of building effective design systems
Familiarity with healthcare or regulated domains is a plus
Responsibilities
Set design strategy in collaboration with Product and Engineering teams
Lead customer discovery and testing to enhance user experiences
Establish an AI-native design practice for rapid prototyping
Coach and develop designers to build future design leaders
Evolve design systems for consistent, high-quality product experiences
Demonstrate the impact of design on customer outcomes and guide team priorities
Benefits
Full medical, dental, and vision insurance for employees and families
401(k) plan with company match
Equity options for all full-time employees
Unlimited paid time off (PTO)
Weekly lunch stipend of $100
Monthly wellness stipend of $100
Commuter benefits for SF and NYC employees
Paid parental leave for growing families
Full Job Description
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
