Comedian + Copywriter

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/Comedian 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: Create genuinely helpful and entertaining content for relevant subreddits such as r/carinsurancehelp, r/mechanicadvice, r/idiotsincars, and r/frugal as well as Jerry's own subreddits.

• 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

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 have been profitable since 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 are a remote-first company, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.