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

Jerry - Palo Alto, CA, United States - In-office - posted 2026-10-23

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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 insurance, motorcycle insurance, property tax, car repair shop bids, roadside assistance, and beyond. This is a General Manager in Training program designed to accelerate high-potential professionals into P&L ownership roles. You will report directly to the Cofounder/CEO and work on some of the highest-leverage problems in the business. The company is scaling from 5M to 50M customers by 2030, and this year alone launched 5 new products, each with distinct operational complexity, user personas, and scaling challenges. In this role, you will: - Work directly with and be mentored by the Cofounder/CEO - Gain exposure to every function at Jerry: product, growth, operations, finance, engineering, and data - Learn how to execute big-picture strategies and navigate the intricacies of a complex, rapidly growing business - Own high-leverage projects and business initiatives - Develop the skills and experience needed to eventually own a P&L for a business line at Jerry or elsewhere The program requires in-person presence in the Palo Alto office five days a week for the first 6-12 months as you work alongside the CEO and executive team. A successful graduate will be positioned to lead a business line or vertical within Jerry's expanding portfolio. Jerry's culture emphasizes ownership, learning, and mastery. The team comprises leaders from Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. The company has been recognized as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and has received accolades in fintech and insurtech innovation. REQUIREMENTS: - 4+ years of experience in management consulting, venture capital, private equity, or a startup environment - Bachelor's degree in any discipline - Ability to work in-person in Palo Alto office five days a week for the first 6-12 months - Currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada (hiring eligibility requirement)

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