Head of Finance - Planning and Analysis

Your car and your home are your most important assets, yet the experience of owning them is stuck in the 90s. ai is building the first app to manage it all. We started with car insurance in 2019, became one of the top 3 brokers in the U.We’ve reached 5M+ customers, raised $240M+, and scaled revenue 70X. We’re now expanding into adjacent verticals (e.g. home, motorcycle, RV, etc) to become the one-stop-shop for all your physical assets.

We are hiring a Strategic Finance Manager, reporting to our VP of Finance, to build the analysis those decisions rest on. You will own the operating model and the planning cycle, partner with functional leaders across the company, and work closely with the CFO and the founders.

Alongside it, you are the analytical partner on new opportunities — the products, verticals, channels and partnerships we are deciding whether to back. And over your first year or two, as our newer products scale and the audience for our numbers widens beyond the people who already know the business, the reporting itself has to reach a standard that holds up to outside diligence.

Own Jerry’s driver-based operating model for the base business and expand it as we launch new insurance products and business lines.

Once Accounting closes the books, explain what moved against plan and prior period, why it moved, and what it means for the forecast.

Translate the financial results into clear business insights for the CFO, the founders, the board, and our investors, at a standard that survives external diligence.

Lead monthly business reviews: Work with functional leaders and turn what the numbers show into the business decisions that need to be made.

Build the financial case for new opportunities

Build the financial model for new product, vertical, channel or partnership: Monitor product and channel economics including CAC and payback, policy retention and lifetime value, contribution margin etc.

Frame build, buy or partner decisions: help refine the frameworks we use to compare the options and the return profile of each.

Build the business case before a commitment is made, support negotiation on terms, and give budget owners the visibility to manage their own numbers.

You decide which analysis will actually change a decision, and leave the rest alone.

You take ownership of outcomes and are comfortable building process where none exists yet.

4+ years of relevant experience, ideally combining 2+ years at a reputable investment bank, corporate development group, or private equity firm with 2+ years in strategic finance or FP&A at a high-growth company.

A bachelor’s degree in finance, accounting, economics, or a similarly quantitative field.

Strong financial modeling skills: driver-based operating models, three-statement mechanics, scenario and sensitivity analysis, and a working command of accounting concepts and GAAP.

Experience with unit economics in a consumer or marketplace business, including CAC, LTV, payback, cohort retention, and contribution margin.

A track record of translating complex analysis into a clear narrative for an executive or investor audience.

Startup or high-growth experience strongly preferred, including building financial processes from scratch.

Hands-on fluency with AI tools for analysis, research, and workflow automation.

Insurance, insurtech, fintech, or marketplace experience;

finance tech stack experience (NetSuite, Ramp, planning tools).

While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.

is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.

We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.

ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at

In addition to base salary, the compensation may include opportunities for equity grants.

We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.

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. 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. We started with car insurance in 2019, became one of the top 3 brokers in the U.We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.

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.