Jerry is building the first AI-powered advisor to manage all your physical assets.

Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.

Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.

We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and have been profitable since 2024. We're now expanding into home, motorcycle, RV, and beyond.

Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.

We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.

We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.

Why We’re Hiring

Our Business Operations & Analytics team has been a force multiplier and accelerant to our business that has helped us reach these pivotal milestones in spite of headwinds and within a highly competitive market. They are a team of former McKinsey, BCG and Bain consultants who drive data & insights, and inform decision-making across every corner of our business. They are analytical powerhouses and first principles problem solvers who push forward our most important initiatives across product, growth, tech, and operations.

Every business unit has a Business Operations & Analytics team member embedded within it — someone who doesn't just run analyses and build dashboards, but shapes what questions we should ask, what data to pull, what conclusions to draw, what decisions to make, and then drives our teams towards our next goal: go from 5M to 50M customers and become a $10B business in the next 4 years.

As our business continues to expand, there is growing demand for more Business Operations & Analytics team members. We are hiring 2-3 people to drive impact in these areas:

Growth Marketing

Product Development

AI & Automation

Strategic Partnerships

On leveling: You may see job ads for this role at different job levels. Our priority is finding the right people, we can be flexible with job title/leveling.

Why You Will (Or Won't) Like Working Here

No slides: If you've worked in consulting, you know what it feels like to be up at 3am reformatting a deck. That doesn't exist here. The only work that gets done at Jerry is work that will materially change the trajectory of our business — an important product, a new growth channel, a key metric, a critical partner relationship, etc.

No corporate fluff: The Business Operations & Analytics team is 14 insatiable learners who care deeply about solving difficult problems and making a tangible impact. Every person owns a critical domain. There is no bloat, unnecessary meetings, or waiting for approvals.

Hands-on: This is not a pure strategy role, you will also own execution. Your day-to-day will be surfacing analytical insights, driving decisions, and seeing them through end-to-end.

What You'll Own

You'll sit on our central Business Operations & Analytics team but you’ll be embedded in one of Jerry's core business areas — growth, product, AI and automation, strategic partnerships — and own the analytical function for that business unit end-to-end.

Define the right problems: Before any analysis, understand what business question it's answering and what decision it will inform. Push back if the question is flawed.

Data and insights: Define metrics, build reports, run analyses, design experiments, and surface data insights that move your team's key metrics.

Drive outcomes: Bring recommendations to your counterparts in product, growth, finance or operations, tell them what's happening and why, and what next steps should be.

Who You Are

First principles thinker: You break ambiguous problems into clear hypotheses before touching data. You're analytically strong (comfortable with SQL or Python) but your instinct is to ask "what are we trying to solve here?" before jumping to "what should I build?"

Direct communicator: You can walk a skeptical stakeholder through a complex finding and get buy-in quickly. You write clearly, speak precisely, and don't bury the lede.

Owner: You act like your name is on the door. If something is broken, you feel responsible for fixing it, even if it’s outside of your swim lane.

What You'll Bring

2+ years of experience at a consulting firm, investment bank, or high-growth technology company.

Strong analytical skills; ability to pull, structure, and interpret data independently.

Track record of owning ambiguous problems and delivering impact.

Clear, persuasive communicator who can influence decisions at the leadership level.

Our Tools

SQL (Clickhouse), Metabase, Python, Jupyter Hub, GitHub.