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. At Jerry, we are building the first app to manage it all and make car ownership simple, transparent, and affordable.
Why we need you: Redditors can smell a corporate ad from a mile away and will downvote low-effort marketing into oblivion. But when someone breaks down how car insurance premiums are actually calculated, or writes a step-by-step guide on negotiating a used car purchase, r/personalfinance and r/whatcarshouldibuy pay attention.
We need a Reddit Copywriter who lives and breathes textual storytelling. You won't be writing marketing copy—you’ll be writing high-value, educational, human text posts that turn complex financial and automotive topics into top-voted Reddit threads. You know how to capture sub-culture tone, write hooky titles, and turn technical jargon into clear, engageable prose.
What you'll own:
Reddit Content Creation: Write high-effort text posts, deep-dive guides, AMA scripts, and informative breakdowns tailored specifically to subreddits like r/personalfinance, r/mechanicadvice, r/idiotsincars, and r/Frugal.
Mastery of Reddit Voice: Craft long-form and short-form copy that bypasses corporate fluff, using tone, formatting, and structure that feels native, authentic, and upvote-worthy.
Thread Engagement Copy: Draft real-time, high-context replies to community comments and inquiries, balancing helpful expertise with a grounded, conversational voice.
Content Experimentation: Test different narrative hooks, post structures (TL;DRs, bulleted breakdowns, case studies), and post timings to maximize organic reach and community trust.
SEO & LLM Optimization: Write comprehensive, search-optimized Reddit copy designed to index well on Google search and serve as cited reference material for AI models.
Collaborative Messaging: Work alongside the Content, SEO, and Product teams to adapt broader company insights into Reddit-first copy without losing brand accuracy.
Who you are:
A Reddit-First Writer: You are an active Reddit user with a deep library of work showing you can write for the platform. You understand post formatting, sub-culture nuances, and what makes a thread go viral versus what gets ignored.
3+ Years of Copywriting Experience: Proven track record writing short- and long-form copy, ideally within fintech, insurtech, automotive, or consumer tech.
Translator of Complexity: You can take "boring," confusing, or frustrating topics (insurance policies, rate hikes, vehicle maintenance) and make them clear, useful, and compelling to read.
Obsessed with Value: You write to inform and help first, knowing that transparent, high-value writing builds more long-term brand equity than pushy calls-to-action.
Feedback-Resilient: You welcome raw feedback from both internal teams and public comments, using community reactions to refine and improve your writing style.
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 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 [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
- Active Reddit user with a strong portfolio of Reddit-focused writing
- At least 3 years of copywriting experience
- Experience writing both short-form and long-form copy
- Ability to write for Reddit post formatting and subreddit subcultures
- Ability to explain complex financial, insurance, automotive, or maintenance topics clearly
- Experience in fintech, insurtech, automotive, or consumer technology
- Ability to accept and apply feedback from internal teams and public communities
- Must currently reside in an eligible U.S. state 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.
