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Jerry is an AI-powered advisor for managing physical assets (cars, homes, motorcycles). The company has grown to 5M+ customers, raised $240M+, and achieved profitability in 2024. They are now expanding beyond car insurance into home, motorcycle, RV, and related services.
You will own Reddit content creation and community engagement for Jerry. Your core responsibilities include:
- Creating genuinely helpful and entertaining long-form and short-form content for relevant subreddits (r/carinsurancehelp, r/mechanicadvice, r/idiotsincars, r/frugal, and Jerry's own subreddits) that educates audiences on complex financial and automotive topics.
- Mastering Reddit's native voice and culture—writing copy that feels authentic, bypasses corporate fluff, and is upvote-worthy through strategic use of tone, formatting, and structure.
- Drafting real-time, high-context replies to community comments and inquiries, balancing helpful expertise with conversational, grounded language.
- Testing different narrative hooks, post structures (TL;DRs, bulleted breakdowns, case studies), and post timings to maximize organic reach and community trust.
- Writing comprehensive, search-optimized Reddit copy designed to index well on Google and serve as cited reference material for AI models.
- Collaborating with Content, SEO, and Product teams to adapt company insights into Reddit-first copy while maintaining brand accuracy.
You will prioritize writing to inform and help first, knowing that transparent, high-value writing builds long-term brand equity more effectively than pushy calls-to-action. You'll welcome feedback from internal teams and public comments, using community reactions to refine your writing style.
Jerry is remote-first but also has offices in Palo Alto, New York City, Chicago, and Toronto. The company is led by serial entrepreneurs backed by Y Combinator and comprises talent from Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. They consistently rank as a Y Combinator Top Company and Forbes/Statista Best Startup Employer.
REQUIREMENTS:
- 3+ years of copywriting experience with a proven track record in short- and long-form copy, ideally within fintech, insurtech, automotive, or consumer tech.
- Active Reddit user with a deep portfolio of work demonstrating ability to write for the platform, understanding post formatting, sub-culture nuances, and what drives viral engagement.
- Ability to translate complex, boring, or frustrating topics (insurance policies, rate hikes, vehicle maintenance) into clear, useful, and compelling prose.
- Feedback-resilient mindset, welcoming raw feedback from internal teams and public comments.
- Obsession with delivering value and helping audiences first.
NOTE: Jerry can only hire full-time salaried employees currently residing in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada.
