GM-in-Training (YC cofounder/CEO-led)

About us: Jerry .ai is a Series C, YC-backed tech startup with 5M+ customers and $240M in funding. Founded in 2017, product launched in 2019, and achieved profitability in 2024. Our purpose: 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 are building the first AI-powered advisor to manage all your physical assets. We started with your car in 2019, now we’re expanding into new verticals (e.g. home, motorcycle, RV, boat). About this program: Our next chapter is about accelerating growth – going from 5M to 50M customers by 2030. This year alone, we launched 5 new products – home insurance, property tax, motorcycle insurance, car repair shop bids, and roadside assistance. Each of these new businesses comes with its own operational complexity, distinct user personas and pain points, and its own path to scale. As our business expands, we have a growing list of ideas but not enough people to execute them. This program exists to close that gap. We are looking for 2-3 GMs-in-Training to work directly with, and be mentored by, our Cofounder/CEO, and work on some of the highest-leverage problems in our business. Reporting directly to our CEO, you will have a unique opportunity to view and understand a company’s day-to-day challenges as it goes through a rapid growth phase. You will be exposed to every function at Jerry (i.e., product, growth, operations, finance, engineering, data), learn how to execute big-picture strategies and navigate the intricacies of a complex business. A successful graduate will go on to own P&L for a business line here or elsewhere. If you’re looking for an opportunity to greatly accelerate your career trajectory, we’d love to hear from you. Who we get excited about: Insatiable learner: You are constantly seeking to deepen your knowledge, sharpen your skills, and master whatever craft or goal you’ve set your mind to. Owner: You act like...

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