GM-in-Training (YC cofounderCEO-led)

About us:

Our purpose:

Your car home and motorcycle arent just purchases theyre the physical embodiment of the life youve worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey buying insuring maintaining repairing selling is fragmented complicated and expensive.

Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price lock in the best insurance rate without you lifting a finger remind you before that service appointment turns into an expensive repair and help you sell at the best price when the time is right. That friend is Jerry.

We are building the first AI-powered advisor to manage all your physical assets. We started with your car in 2019 now were expanding into new verticals (e.g. home motorcycle RV boat).

About this program:

Our next chapter is about accelerating growth going 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 of these new businesses comes with its own operational complexity distinct user personas and pain points and its own path to scale.

As our business expands we have a growing list of ideas but not enough people to execute them. This program exists to close that gap. We are looking for 2-3 GMs-in-Training to work directly with and be mentored by our Cofounder/CEO and work on some of the highest-leverage problems in our business.

Reporting directly to our CEO you will have a unique opportunity to view and understand a companys day-to-day challenges as it goes through a rapid growth phase. You will be exposed to every function at Jerry (i.e. product growth operations finance engineering data) learn how to execute big-picture strategies and navigate the intricacies of a complex business.

A successful graduate will go on to own P&L for a business line here or elsewhere. If youre looking for an opportunity to greatly accelerate your career trajectory wed love to hear from you.

Who we get excited about:

• Insatiable learner: You are constantly seeking to deepen your knowledge sharpen your skills and master whatever craft or goal youve 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 its 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:

• 4 years of experience in management consulting venture capital private equity or a startup environment

• Bachelors degree in any discipline

• Ability to work in-person in our Palo Alto office alongside our CEO and executive team for the first 6-12 months

Compensation:

This position offers base salary and stock options. The base salary for this position within the San Francisco Bay Area is $160000$200000 USD but we can be flexible based on your prior experience and appropriate job levelling. We also offer comprehensive benefits including health dental and vision coverage paid time off paid parental leave 401(K) plan with 4% employer matching and wellness benefits among others.

Location:

This role requires being in our Palo Alto office five days a week at least until you are capable of operating independently.

While we appreciate your interest and application due to the volume of applications we receive only applicants under consideration will be contacted.

Please note: 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.

is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race religion color national origin sex pregnancy reproductive health decisions or related medical conditions sexual orientation gender identity gender expression age veteran status disability genetic information or other characteristics protected by applicable local state or federal laws.

is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability please contact us at

The successful candidates starting pay will fall within the pay range listed on this job posting determined based on job-related factors including but not limited to skills experience qualifications work location and market conditions. Ranges are market-dependent and may be modified in the addition to base salary the compensation may include opportunities for equity grants.

We offer a comprehensive benefits package to regular employees including health dental and vision coverage paid time off paid parental leave 401(K) plan with employer matching and wellness benefits among others. Equity opportunities may also be part of your total rewards package. Part-time contract or freelance roles may not be eligible for certain benefits.

About

Jerry is building the first AI-powered advisor to manage all your physical assets.

Your car home and motorcycle arent just purchases theyre the physical embodiment of the life youve worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey buying insuring maintaining repairing selling is fragmented complicated and expensive.

Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price lock in the best insurance rate without you lifting a finger remind you before that service appointment turns into an expensive repair and help you sell at the best price when the time is right. That friend is Jerry.

We started with car insurance in 2019 became one of the top 3 brokers in the U.S. then added driving insights diagnostics and a repair marketplace. Weve reached 5M customers raised $240M and achieved profitability in 2024. Were now expanding into home motorcycle RV and beyond.

Led by serial entrepreneurs and backed by Y Combinator our team comprises talented and big-hearted leaders from places like Nvidia Meta Amazon BCG McKinsey Bain and GEICO. Our culture is the #1 reason people join Jerry and stay we are a small and mighty team of competitive but kind people who think and act like owners care deeply about the quality and impact of our work and are relentless in our pursuit of learning and mastery over our craft.

We are proud to consistently rank as one of Y Combinators Top Companies Forbes and Statistas Best Startup Employers and to have received other accolades in fintech and insurtech innovation workplace culture and leadership.

We support remote work for most roles but if you prefer in-person or hybrid we also have offices in Palo Alto New York City Chicago and Toronto.

Required Experience:

Founder