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 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 new business comes with its own operational complexity, distinct customer pain points, and path to scale. We have a growing list of ideas but not enough people to execute them.
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 the CEO, you will 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 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 for this position within the San Francisco Bay Area is $130,000–$160,000 USD, with flexibility based on prior experience and appropriate job levelling. This position also offers stock options.
- Health, dental, and vision coverage
- Paid time off
- Paid parental leave
- 401(k) plan with 4% employer matching
- Wellness benefits
Location
This role requires being in our Palo Alto office five days a week, at least until you are capable of operating independently. 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. We cannot accept applications from candidates residing elsewhere at this time.