Principal Designer & Product Manager

 

 

About The Company

They have quietly built the 14th largest, fastest-growing, and most profitable book of business in the $80B nonstandard auto insurance industry — with just 40 people. We did it by serving a customer the industry overlooked, with a product people love, powered by a passionate Individual Contributor culture. We also have a 4.8/5 rating on Trustpilot.

Almost none of that shows up yet in how the brand looks, feels, and communicates. That's the opportunity.

 

Principal Product Designer & PM 

You'll decide what we build, design it yourself, and own the design system behind it.

The job 

Reporting to the Head of Product, you’ll own how we find and keeps members across 16 states (and growing) - deciding what designs we use to help members make complex decisions, what we build or retire, and how it all shows up in our P&L and Trustpilot rating. Uniquely, while tackling particularly nuanced product designs yourself, you’ll also own the design system and tooling that Product uses. This means that you’ll own not just the product development, design, deployment and iteration cycle for a specific feature… you’ll also own the design infrastructure behind it. 

Most companies split this role in two, but we know firsthand that the highest capability, highest-ownership designers function as Product Managers in their own right, and that design infrastructure needs to live with its primary users in Product, not isolated from them. You'll make calls like these in your first 90 days: 

1. The core payment flow is leaking. Drop-off spikes at one step. You've got quant, not much qual. Do you run a research cycle, design & ship a fast A/B, or push back that it isn't a product problem at all? You pick, you design it, and you own the iterations. 

2. We need to create an entirely new pattern for our quote screen. The problem set is complicated, balancing space for our own product interactions with transparency into our partner/competitors’ pricing. Because each state has its own product nuances, each state requires design customization. Do you create a one-off first design or go straight to updating the design system to expedite state rollouts? 

3. A regulatory shift in a state changes the economics of the product for the existing business and future members. Do you design a new product approach, renegotiate carrier economics, wind-down the business, or wait? Economics could go negative quickly. Your pick, but we may be losing money in the time it takes for you to decide.

You'll have thought partners across engineering, growth, risk, and insurance, but you won't be managed. You'll form views on our members and the economics of the business by pulling on domain experts and reviewing it yourself. You'll have opinions, bring data, bring prototypes, and be wrong sometimes, in public. 

You will love this if: 

• You want a domain that compounds – insurance gets more interesting the longer you dig in – and you want to own problems, solutions, and the actual screens ● You've been the designer frustrated by a PM’s missing quant skills, indecisiveness, or overly-narrow brief 

• You believe that AI allows for new advances in tooling so that your taste and craft can help your peers draft designs more efficiently 

• You want decisions, not alignment 

• You're comfortable being the most junior person in the room on insurance and the most senior on product and craft 

• You want to be 1 of 40, not 1 of 400 

You will hate this if: 

• You’re only really interested in a pure Product or pure Design role 

• You want a PM/Design ladder or a PM/Design manager 

• You’re motivated by working on a product you personally use 

• You prefer tidy quarterly OKRs to dynamic prioritization 

• You judge your craft on “delight” rather than impact on business metrics

• You'd rather build for the mass affluent / early adopters than for the 80M Americans the financial system walked past 

About You: 

• 8+ years as a product designer that pulls data, works with engineering, and manages roll-out, testing, and iteration

• A portfolio that proves it - went 0-1, shipping flows you designed and owned the metrics for 

• Data-driven, with hands-on A/B testing, funnel analysis, and experimentation skills ● Figma-native; fluent in wireframing, prototyping, information architecture; real visual chops 

• Strong project management, working closely with senior engineers 

• Built or maintained a design system (and know when to bend it) 

• Relentless customer advocate, performing user research and finding data to address unique needs 

• Excited to apply the latest AI tools to make us work faster and more efficiently

• Seek simple, elegant solutions to complex problems 

• Value over-communication, rapid collaboration, and candid feedback 

• Nice to haves: experience in fintech or a highly regulated industry, experience running hands-on or field user research 

Compensation: $200-240k + equity

• Benefits

• They pay 100% of health, dental, and vision for you and your dependents.

• 401k (no match)

• Unlimited vacation,

• Remote work stipend

• 2-month parental leave