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 — car, home, motorcycle, RV, boat — transforming an ownership experience that is fragmented, complicated, and expensive into a seamless, trusted service.
We are hiring 2–3 Product Managers-in-Training to work directly with and be mentored by our Cofounder/CEO (2x YC founder). Reporting to the CEO, 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). You will be exposed to nearly every function — product, growth, operations, finance, engineering, data — and learn to execute big-picture strategies while navigating the intricacies of a rapidly growing late-stage startup. A successful graduate will likely become a product leader or commercial leader (e.g., owning P&L) here or elsewhere.
Qualifications
- Ideally 1+ years of experience in a demanding environment such as management consulting, investment banking, venture capital, private equity, an early startup, or similar
- Bachelor's degree in any discipline
- Ability to work in-person in our Palo Alto office alongside the CEO and executive team at least for the first 6–12 months
Qualities we value
- Insatiable learner: Constantly seeking to deepen knowledge, sharpen skills, and master your craft
- Owner: Acts like your name is on the door; feels responsible for fixing what’s broken, even outside your swim lane
- Tenacious: Highly resilient; no challenge too difficult, no issue unsolvable
- Sense of urgency: Strong bias for action; impatient when progress stalls
Pay
Base salary: $130,000–$160,000 USD (San Francisco Bay Area), plus stock options. We can be flexible based on prior experience and appropriate job leveling.
Benefits
- Health, dental, and vision coverage
- Paid time off
- Paid parental leave
- 401(K) plan with 4% employer matching
- Wellness benefits
Schedule & location
This role requires working in-person at our Palo Alto office five days a week, at least until you are capable of operating independently (expected first 6–12 months).
Jerry.ai hires 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. Candidates residing elsewhere cannot be considered at this time.