Product Manager-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. Why we exist: 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). Why we’re hiring: Our next chapter is about accelerating growth – 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 customer 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 Product Managers-in-Training to work directly with, and be mentored by, our Cofounder/CEO (2x YC founder), and work on building or scaling one of our new product verticals. Reporting directly to our CEO, you will have a unique opportunity to develop the craft of product building, learn how a serial founder/CEO thinks and makes decisions, and see/understand a late stage tech startup’s day-to-day challenges as it goes through a rapid growth phase. You will be exposed to nearly every function at the company (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 likely go on to become a product leader or commercial leader (e.g. owning P&L) 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...

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