--- title: 'Founder''s Associate Program (2x YC founder) at Jerry.ai' canonical: 'https://feeny.ai/job/founder-s-associate-program-2x-yc-founder-jerry-ai-palo-alto-r5cgfcexa1ev' type: 'job' last_seen: '2026-10-20' --- # Founder's Associate Program (2x YC founder) at Jerry.ai - **Company:** Jerry.ai - **Location:** Palo Alto, CA - **Employment:** full-time - **Work type:** remote - **Posted:** 2026-10-20 - **Last confirmed live:** 2026-10-20 - **Apply:** https://jobs.ashbyhq.com/jerry.ai/5d397260-4fee-4150-932f-f91facee5b76 ## Job description About us: [Jerry.ai](http://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. Why we exist: Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've 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 we’re 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 painpoints, 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 associates 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 develop the craft of product building, learn how a serial founder/CEO thinks and makes decisions, and see/understand a late stage tech startup’s day-to-day challenges as it goes through a rapid growth phase. You will be exposed to nearly every function at the company (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 likely go on to become a product leader, growth leader, or run a function here or elsewhere. If you’re looking for an opportunity to greatly accelerate your career trajectory, we’d love to hear from you. Who we get excited about: - 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. - First principles thinker: You break ambiguous problems into clear hypotheses, and your instinct is to ask "What are we trying to accomplish here?" before jumping to "What is the solution?". - 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: - 2+ years of experience in management consulting, venture capital, private equity, or a startup environment - Bachelor's degree in a quantitative discipline such as STEM, economics, or similar - 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 $120,000—$160,000 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: [Jerry.ai](http://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. Jerry.ai 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. Jerry.ai 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 recruiting@jerry.ai The successful candidate’s 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 future. In 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.ai Jerry is building the first AI-powered advisor to manage all your physical assets. Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've 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. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're 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 Combinator's Top Companies, Forbes and Statista's 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. ## About Jerry.ai ## Company Overview - **One-liner**: Jerry is an AI-powered AllCar™ app that helps drivers save money on insurance, refinancing, maintenance, and repairs by comparing real quotes from over 100 insurers and providing proactive car care tools. - **Entity Type**: Private (venture-backed) - **Headquarters**: Palo Alto, California, United States - **Founded**: 2017 - **Founders**: Art Agrawal, Musawir Shah, Lina Zhang ## Core Business - **Primary industry**: Insurance technology (InsurTech) / Automotive services - **Target customers**: B2C – individual car owners and drivers in the United States - **Mission**: To make car ownership affordable and accessible. ## Products & Services - **Jerry Insurance Marketplace (PriceProtect™)**: A digital platform that compares real quotes from 100+ insurers for auto, home, motorcycle, and renters policies. Users can buy, bundle, or switch policies directly in the app. Licensed broker in all 50 states and D.C. - **DriveShield™**: A telematics-based driver safety program that rewards safe driving habits with savings. - **GarageGuard™**: Car care suite including maintenance reminders, repair estimator, shop finder, and recall alerts. - **Refinancing**: Helps users find better rates on auto loans. ## Market Standing - **Valuation**: Not publicly available - **Key Metric**: Total funding of approximately $11.1M (per LinkedIn estimate) – note: this figure may be outdated; the company has grown significantly since. - **Notable Investors/Partners**: Y Combinator (Top Companies list), backed by undisclosed venture investors. Partners with 100+ insurance carriers. - **Growth Signals**: Served 5 million customers by 2024 (up from 1 million in 2021). Rated 4.8 on Trustpilot. Headcount of 146 employees (as of mid-2026, -11.5% YoY, though active hiring across many roles). Named to Forbes America’s Best Startup Employers (2022), LinkedIn Top Startups (2021), and Comparably’s Best Company Culture (2022). ## Competitive Advantages - **AllCar™ platform**: Combines insurance, refinancing, driver safety, and car care in a single app – a unique vertical integration. - **Licensed broker with bank-level security**: No spam, no data sharing with third parties for marketing. - **PriceProtect™**: Continuously re-shops policies at renewal to ensure customers always have the best rate. - **High customer trust**: 4.8 Trustpilot rating and over 5 million users. - **Strong engineering and data culture**: Emphasis on AI agents and platform development (multiple product roles focused on agentic AI). ## Strategic Focus - Expanding the AllCar ecosystem beyond insurance into comprehensive car ownership management (maintenance, safety, repairs). - Investing heavily in AI agents and platform capabilities (multiple open roles for AI product managers and engineers). - Scaling remote-first hiring across the U.S. and Canada while maintaining hubs in Palo Alto, Los Angeles, New York, and other cities. - Continuing to grow the licensed insurance agent team to support customer service and sales. ## Why Work Here - **Culture**: Values include Pursuit of Excellence, Sense of Urgency, and Truth Seeking. Employees are given full ownership and encouraged to question the norm. Described as “energetic, diverse, and passionate.” - **Remote/Hybrid**: Most roles have the option to work remotely; offices in Palo Alto, Los Angeles, New York, Nashville, and other U.S. cities. - **Awards**: Recognized as a top workplace by Forbes, Comparably, and Inspiring Workplaces. - **Engineering & Data**: Strong focus on AI, data science, and product ownership. Open roles for data scientists, AI platform managers, and product designers. - **Perks**: Not specified in detail, but the careers page emphasizes impact, growth, and a supportive team environment. ## Sources 1. [jerry.ai/about](https://jerry.ai/about/) 2. [jerry.ai/careers](https://jerry.ai/careers/) 3. [jerry.ai/job-openings](https://jerry.ai/job-openings/) 4. [jerry.ai](https://jerry.ai/) 5. [LinkedIn - Jerry](https://www.linkedin.com/company/jerryinc) ## Other roles at Jerry.ai - [Customer Experience Advocate (Remote, Insurance Tech Startup)](https://feeny.ai/job/customer-experience-advocate-remote-insurance-tech-startup-jerry-ai-san-antonio-0dhxdkrdb9ch) — San Antonio, TX - [Customer Care Associate - Retail & Hospitality Backgrounds Welcome (Remote)](https://feeny.ai/job/customer-care-associate-retail-hospitality-backgrounds-welcome-remote-jerry-ai-1qt2w766ey7y) — Orlando, FL - [Strategic Finance Manager](https://feeny.ai/job/strategic-finance-manager-jerry-ai-remote-74rtf0azfh52) - [Senior Creative Strategist, Growth](https://feeny.ai/job/senior-creative-strategist-growth-jerry-ai-new-york-pk75ytn7s16t) — New York, NY - [HR Generalist](https://feeny.ai/job/hr-generalist-jerry-ai-remote-6ysqg5yn816c) - [People Operations Generalist](https://feeny.ai/job/people-operations-generalist-jerry-ai-remote-rex9ayqtnjcs) - [Senior Associate, Business Operations & Analytics](https://feeny.ai/job/senior-associate-business-operations-analytics-jerry-ai-new-york-ewff1d2em4se) — New York, NY - [Data Scientist](https://feeny.ai/job/data-scientist-jerry-ai-new-york-3xxnvp5debd2) — New York, NY - [Associate Data Scientist](https://feeny.ai/job/associate-data-scientist-jerry-ai-new-york-5aed8bfba8ev) — New York, NY - [Insurance Compliance & Regulatory Senior Lead](https://feeny.ai/job/insurance-compliance-regulatory-senior-lead-jerry-ai-dallas-wdwrpm353jkk) — Dallas, TX