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

Jerry.ai•Palo Alto, CA

4d•$160,000 - $200,000•Onsite

About The Position

Jerry.ai is seeking 2–3 GMs-in-Training to work directly with and be mentored by its Cofounder/CEO as the company accelerates growth from 5 million to 50 million customers by 2030. The role addresses the execution needs created by Jerry’s expanding portfolio of businesses, including home insurance, property tax, motorcycle insurance, car repair shop bids, and roadside assistance. Each business has its own operational complexity, customer needs, and path to scale. Reporting directly to the CEO, you will gain exposure to the company’s day-to-day challenges during a rapid growth phase and work across product, growth, operations, finance, engineering, and data. You will learn to execute broader strategies and navigate a complex business. Successful program graduates may go on to own P&L for a business line at Jerry or elsewhere. The position requires working in person at the Palo Alto office five days a week, at least until you can operate independently, and alongside the CEO and executive team for the first 6–12 months. Jerry.ai is a YC-backed, Series C technology startup building an AI-powered advisor for managing physical assets. Founded in 2017, it launched its product in 2019, serves more than 5 million customers, has raised $240 million, and achieved profitability in 2024. Its business includes services related to cars and is expanding into home, motorcycle, RV, and boat verticals.

Requirements

At least 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 at the Palo Alto office alongside the CEO and executive team for the first 6–12 months.
Reside in an eligible location for full-time salaried employment: Arizona, California, Colorado, Florida, Georgia, Illinois, Massachusetts, North Carolina, New Jersey, Nevada, New York, Oregon, Tennessee, Texas, Utah, Virginia, or Ontario, Canada.
Demonstrate a strong desire to learn and develop expertise.
Take ownership and feel responsible for fixing problems, including those outside one’s immediate area of responsibility.
Show resilience when facing difficult or unresolved challenges.
Have a strong bias for action and urgency when progress is stalled.

Responsibilities

Work directly with and receive mentorship from the Cofounder/CEO on high-leverage business problems.
Help execute strategies as Jerry scales its existing and newly launched businesses.
Work across product, growth, operations, finance, engineering, and data.
Learn and contribute to addressing the operational complexity and distinct customer needs of expanding business lines.
Work toward the ability to own P&L for a business line after completing the program.