Product Manager-in-Training (YC cofounder/CEO-led)
About the role
This Product Manager-in-Training program is designed to accelerate your career by working directly with and being mentored by our Cofounder/CEO (2x YC founder). You will build or scale one of our new product verticals (home insurance, property tax, motorcycle insurance, car repair shop bids, roadside assistance, and more). Reporting directly to the CEO, you will develop the craft of product building, learn how a serial founder/CEO thinks and makes decisions, and gain exposure to nearly every function at the company (product, growth, operations, finance, engineering, data). You will execute big-picture strategies and navigate the intricacies of a complex business during a rapid growth phase. A successful graduate will likely go on to become a product leader or commercial leader (e.g., owning P&L) here or elsewhere.
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 your name is on the door. If something is broken, you feel responsible for fixing it, even if it’s outside of your swim lane.
- Tenacious: You are highly resilient. No challenge is too difficult, no issue unsolvable.
- Sense of urgency: You have a strong bias for action and are impatient when progress is stalled.
What you bring
- Ideally 1+ years of experience in a demanding environment such as management consulting, investment banking, venture capital, private equity, an early startup environment, or similar
- Bachelor's degree in any discipline
- Ability to work in-person in our Palo Alto office alongside our CEO and executive team at least for the first 6–12 months
Compensation
Base salary: $130,000–$160,000 USD (San Francisco Bay Area), flexible based on prior experience and appropriate job levelling. This position also includes stock options.
Benefits
- Health, dental, and vision coverage
- Paid time off
- Paid parental leave
- 401(k) plan with 4% employer matching
- Wellness benefits
Location & schedule
This role requires being in our Palo Alto office five days a week, at least until you are capable of operating independently (minimum 6–12 months). Remote work is not available for this position during the initial period.
Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
About Jerry.ai
Jerry is building the first AI-powered advisor to manage all your physical assets — cars, homes, motorcycles, RVs, boats, and more. Founded in 2017, product launched in 2019, and achieved profitability in 2024. We have 5M+ customers and $240M+ in funding (Series C, YC-backed). We started with car insurance, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. Now expanding into home, motorcycle, RV, and beyond. Our team comprises leaders from Nvidia, Meta, Amazon, BCG, McKinsey, Bain, GEICO, and other top organizations. We are consistently ranked as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and recognized for fintech/insurtech innovation, workplace culture, and leadership. Offices in Palo Alto, New York City, Chicago, and Toronto (remote work supported for most roles).