Why we exist:
More than 80% of Americans own a car and see it as a fundamental necessity, yet the experience of owning one is stuck in the 90s. Every part of the user journey (shopping for a car, insurance, repairs, etc) is complicated, fragmented, and time-consuming, and the costs are staggering. In 2025, the cost of owning a car was more than 20% of the average household income, after tax. At Jerry.ai, we are building the first app to manage it all and make car ownership accessible to all.
Why we need you:
Jerry has built a product used by 5 million people, but the real conversations about car insurance and repair aren't happening in our apps—they’re happening on Reddit, Quora, and TikTok. We don’t want to just ‘manage’ these channels; we want to participate in them.
We’re looking for a Community Specialist who can represent Jerry with authenticity and build trust with our current and future users! You’re someone who knows how to provide genuine value in an r/personalfinance thread and can just as easily navigate the high-energy culture of a TikTok comment section.
What you'll own:
Build and grow Jerry's organic presence across key channels like Reddit, Quora, YouTube, and TikTok — the places our customers actually congregate
Develop Jerry's playbook for how to show up in each community: when to post, when to reply, when to stay silent
Grow Jerry’s subreddits into active, trusted communities
Build a content and engagement strategy that scales without losing authenticity, leveraging AI where it helps
Work with Growth and Content teams to ensure consistency across channels
Measure what matters: sentiment, share of voice, referral traffic, and LLM citation
Who you are:
A platform native with a visceral dislike of corporate-speak — you write with a tone that earns upvotes and moves naturally across Reddit, TikTok, and Quora
3+ years in community management or organic social, ideally in fintech, insurtech, or another consumer facing and/or regulated category
A strategic operator who builds systems, not just vibes — you understand SEO and how LLMs cite sources
Proven ability to make "boring" or "stressful" categories feel human, authentic, and worth following
A patient, curious long-game player who values organic trust over quick PR wins
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 is only able to hire employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada. 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 [email protected]
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
Your car and your home are your most expensive assets. And for most people, these 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 or, worse, an accident, and help you sell at the best price when the time is right. That friend is Jerry.
Jerry is building the first AI agent to manage all your physical assets. 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 have been profitable since 2024. We're now expanding into home, motorcycle, RV, and beyond.
We’re fully remote with offices in Palo Alto, New York, Chicago, and Toronto.
Skills Required
- 3+ years in community management or organic social
- Experience in fintech, insurtech, or other regulated consumer-facing categories
- Platform-native writing style that earns upvotes and fits Reddit, TikTok, and Quora
- Strategic operator who builds systems, understands SEO, and LLM citation behaviors
- Proven ability to make technical or stressful categories feel human and authentic
- Patient, curious, long-term approach valuing organic trust over quick PR wins
- Ability to collaborate with Growth and Content teams and measure community KPIs
- Must currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada
What We Do
At Jerry, we’re building a car ownership super app that puts comparison shopping, financing, driving, maintenance and parking solutions at your fingertips and savings in your wallet. We believe drivers deserve better. Why can’t shopping for insurance, financing and maintaining your vehicle be a click, a swipe or a text away? It should be. We’re making that happen. Our custom artificial intelligence, machine learning and bots allow us to provide the best, personalized service for all car ownership needs. The Jerry team’s focus on customer experience results in exceptional transaction speed. With our first product, Jerry redesigned and disrupted the century-old car insurance process, turning stacks of pages and hours of calls into a handful of clicks. That’s why we’re the only car insurance marketplace that gives you the best, customized quotes from more than 55 name-brand insurance carriers in 45 seconds. Jerry helps drivers shop for the best price, compare against current coverage, purchase without a single phone call (unless you want one!) and maintain the best policy for your needs. Led by serial entrepreneurs, tech elite alumni, and fintech, insurtech and auto experts, Jerry attracts people driven to create a customer experience that makes people happy by saving them money and time. And it’s working. Jerry is the #1 rated and most downloaded app in the category. With headquarters in the heart of Silicon Valley, offices in Toronto and Buffalo, and remote team members in four countries, Jerry has removed physical location from recruiting restraints to capture top talent. Join us. Awards: -One of only 50 U.S. startups to be named a LinkedIn Top Startup 2021. -Featured as one of 150 fastest-growing companies to accelerate your career by Otta in 2021. -Included in Forbes and Statista America’s Best Startup Employers 2022. -Ranked on Y-Combinator Top Companies List 2022. -Art Agrawal Named on of The Top 25 InsurTech CEOs 2022.
