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Salary: USD 160,000 - 200,000 / annual
Jerry.ai is a Series C, YC-backed fintech startup with 5M+ customers and $240M in funding. Founded in 2017, the company launched its product in 2019 and achieved profitability in 2024. Jerry is building the first AI-powered advisor to manage all your physical assets—starting with car insurance and now expanding into home, motorcycle, RV, and boat insurance, along with complementary services like property tax, car repair shop bids, and roadside assistance.
The company's mission is to transform the fragmented and outdated experience of owning physical assets. Every step of the journey—buying, insuring, maintaining, repairing, selling—is currently complicated and expensive. Jerry aims to be the trusted friend in your pocket who handles everything seamlessly.
This is a GM-in-Training program designed to accelerate growth from 5M to 50M customers by 2030. The company launched 5 new products this year alone, each with distinct operational complexity, user personas, and scaling challenges. As the business expands, there is a growing list of high-leverage ideas but insufficient people to execute them.
You will report directly to the Cofounder/CEO and work on some of the highest-leverage problems in the business. You will have a unique opportunity to view and understand the company's day-to-day challenges during rapid growth, gaining exposure to every function at Jerry: product, growth, operations, finance, engineering, and data. You will learn how to execute big-picture strategies and navigate the intricacies of a complex, multi-vertical business.
A successful graduate from this program will go on to run and own a P&L for a business line at Jerry or elsewhere. This is designed for someone looking to greatly accelerate their career trajectory.
The company values owners who act like their name is on the door, first-principles thinkers who break ambiguous problems into clear hypotheses, tenacious individuals who are highly resilient, and people with a strong bias for action and sense of urgency.
The role requires being in the Palo Alto office five days a week, at least until you are capable of operating independently. Jerry is otherwise remote-first with offices in Palo Alto, New York City, Chicago, and Toronto.
QUALIFICATIONS:
- 4+ years of experience in management consulting, venture capital, private equity, or a startup environment
- Bachelor's degree in a quantitative discipline such as STEM, economics, or similar
- Able to work in-person in Palo Alto office alongside CEO and executive team
