Lead Product Designer I

CURRENT ROOT EMPLOYEES - Please apply using the career page in Workday. This career site is for external applicants only.

As part of Root's interview process, we kindly ask that all candidates be on camera for virtual interviews. This helps us create a more personal and engaging experience for both you and our interviewers. Being on camera is a standard requirement for our process and part of how we assess fit and communication style, so we do require it to move forward with any applicant's candidacy. If you have any concerns, feel free to let us know once you are contacted. We’re happy to talk it through.

The Opportunity

The UX team at Root Insurance is a collaborative, high-impact group on a mission to redefine insurance by designing products and experiences our customers love. Root’s broader mission is to unbreak insurance through data and technology to improve the lives of our customers. We believe in that mission deeply—and we take it seriously.

Root is a “work where it works best” company. We’ll support you working from wherever you thrive across the U.S.

Salary Range: $131,000 - $157,000 (Eligible for competitive bonus and equity offerings)

Here are three things we think you should know about this role and our team:

Culture

We’re a small, tight-knit team working to build something better than what exists today. We take pride in our craft, enjoy what we do, and strive to create a workplace where people can be themselves, feel challenged, and do work that matters. If you’re kind, humble, curious, and driven—we’d love to meet you.

How We View Product Design

At Root, design is not a service function—it’s a strategic partner. We believe great product designers think like product managers, psychologists, and systems thinkers all at once. We expect our designers to co-own the product roadmap, deeply understand customer problems, and drive solutions that create meaningful business and user impact. We care about clarity, execution, and follow-through just as much as creativity and ideas.

What You Should Expect in This Role

We’re building the future of our internal Claims tooling—and you’ll be joining from the ground up. Root’s claims adjusters are your primary users: fast-moving experts who rely on our tools to triage, investigate, and resolve complex claims. This is a high-complexity, zero-to-one product space that demands systems thinking, design rigor, and a relentless focus on operational efficiency and clarity.

You’ll work side-by-side with a dedicated UX researcher, product manager, engineers, and analytics partners to understand user needs, lead discovery efforts, and deliver design solutions that improve adjuster workflows and ultimately, customer outcomes. You’ll also contribute to adjacent domains like Independent Agents, but Claims will be your core area of ownership.

This is the right role for someone who:

• Thrives on deep collaboration and cross-functional ownership
   

• Loves taking messy problems and turning them into structured, scalable systems
   

• Communicates clearly, directly, honestly, and with purpose
   

• Understands how to drive real impact by simplifying complexity
   

• Is energized by leading in the face of ambiguity
   

If any or all of this excites you, we’d love to meet you.

What We’re Looking For

Must-have skills

• 5-10+ years of experience in product design, including complex system or B2B tooling
   

• Proven ability to lead projects independently from 0 > 1 and deliver on time
   

• Strong systems thinking and information architecture skills
   

• Excellent communication and storytelling, both written and verbal
   

• Ownership mindset with a high degree of comfort with ambiguity and a bias toward action
   

• Ability to synthesize discovery and research into concrete product design
   

• High attention to detail without losing the forest for the trees
   

• Ability to confidently communicate and defend your design decisions with rationale grounded in user needs and business goals
   

• Comfort giving and receiving constructive, professional, honest critique
   

We are also looking for

• Background in B2B SaaS, enterprise, and/or internal tooling design
   

• Experience designing expert-facing workflows and administrative tools
   

• Experience working in claims, logistics, operations, insurance, or similar domains
   

• Familiarity with AI-powered design tools and workflows

Please provide a portfolio PDF or link demonstrating system thinking, complex problem-solving, and communication. Applications without portfolios will not be considered.

Studies have shown that women and people of color are less likely to apply to jobs unless they meet every single qualification. At Root, Inc., we are dedicated to building a diverse and inclusive workplace, so if you’re excited about this role but your past experience doesn’t align perfectly with every qualification in the job description, we encourage you to apply anyway!

At Root, we judge people based on the merit of their work, not who they are. If you are passionate about what this role entails and solving real problems, we encourage you to apply. We want to learn about you and what you can add to our team.

We’re harnessing the power of technology to revolutionize insurance. Using machine learning and mobile telematic platforms, we’ve built one of the most innovative FinTech companies in the world. And we’re just getting started.

Our success is in large part due to our unwavering standards in hiring. We recognize that our products are only as good as the people building and promoting them. We want individuals who find solutions by going through the cycle of ideation to implementation with curiosity, rigor, and an analytical lens. Ask anyone who works here and you’ll hear similar reasons for why they joined:

Autonomy—for assertive self-starters, the opportunities to contribute are limitless.

Impact—by challenging the way it’s always been done, we solve problems that have a big impact on our business.

Collaboration—we encourage rich discussion and civil debate at every turn.

People—we are inspired by the collection of crazy-smart people around us.