Product Manager-in-Training (YC cofounder/CEO-led)
About the Role
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. We are building the first AI-powered advisor to manage all your physical assets — starting with your car in 2019, now expanding into home, motorcycle, RV, and boat.
Our next chapter is 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 new business brings operational complexity, distinct customer pain points, and its own path to scale. We have a growing list of ideas but not enough people to execute them.
We are hiring 2–3 Product Managers-in-Training to work directly with, and be mentored by, our Cofounder/CEO (2x YC founder). Reporting directly to the CEO, you will build or scale one of our new product verticals, develop the craft of product building, learn how a serial founder/CEO thinks and makes decisions, and see a late-stage tech startup’s day-to-day challenges during rapid growth. You will be exposed to nearly every function (product, growth, operations, finance, engineering, data), learn to execute big-picture strategies, and navigate the intricacies of a complex business. A successful graduate will likely become a product leader or commercial leader (e.g., owning P&L) here or elsewhere.
Who We Get Excited About
- Insatiable learner: You constantly seek 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 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.
Requirements
- 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 & Benefits
Base salary: $130,000–$160,000 USD (San Francisco Bay Area), flexible based on prior experience and appropriate job levelling. Stock options included.
- Health, dental, and vision coverage
- Paid time off
- Paid parental leave
- 401(k) plan with 4% employer matching
- Wellness benefits
Location & Work Arrangement
This role requires being in our Palo Alto office five days a week, at least until you are capable of operating independently.
Jerry.ai can only 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. Full-time hourly employees must reside in: AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. We cannot accept applications from candidates residing elsewhere at this time.