Freelance Engine Rebuilding Jobs (NOW HIRING)

Why We Exist
Your car and your home are your most important assets, yet the experience of owning them is stuck in the 90s. Every part of the journey - insurance, repairs, financing, maintenance - is fragmented, complicated, and expensive. Jerry.ai is building the first app to manage it all.
We started with car insurance in 2019, became one of the top three brokers in the country, then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, scaled revenue 70x, and became profitable in early 2024.
Why We're Hiring
Content is how millions of people find Jerry. Every article, guide, and FAQ we publish either earns a click, a citation, and a customer, or it diminishes our online reputation.
The discovery landscape is rapidly evolving. Ranking on Google search is no longer the only thing that matters. When someone asks ChatGPT or Claude how to lower their car insurance after an accident, we want to show up in the answer they get. Most brands that rely on trust and reputation (e.g. financial services, insurance, healthcare, etc) haven't yet figured out how to win in AEO (Answer Engine Optimization). We intend to be among the first.
We're hiring an Editor-in-Chief to lead Jerry's content quality and output (on jerry.ai and on external platforms), and to build and lead the system that makes us authoritative everywhere our customers look for answers.
Why You Will (Or Won't) Like Working Here

• Lean team. You will have one direct report, AI agents, and a freelance bench. The editorial output is dictated by you, and you will set the bar through your own work.
• The metric is customers converted, not page views. You will own traffic and AI-citation targets that directly impact top and bottom line growth, not page visits or impressions.
• We are rebuilding our AI-native content system. You will design and operate the brief-to-publish pipeline including LLM prompts, QA gates, human-edit checkpoints, and be accountable for what ships.
• Insurance content has a zero-tolerance accuracy standard. YMYL finance content cannot be "close enough." Every factual claim needs sourcing; every edge case needs verification. AI drafts require genuine human judgment to clear the bar, not a light read.

What You'll Own

• Content strategy: Own Jerry's editorial engine across jerry.ai and external platforms - roadmap, architecture, resource allocation, and the organic traffic and conversion targets that follow. Define the strategy and hit the numbers.
• AI-native production: Design and run the brief → AI draft → human edit → QA → publish workflow. Manage and develop the prompt libraries, QA gates, and quality-drift metrics that let output scale without degrading. You set the policy on what AI handles and where the human stays in the loop.
• SEO, AEO, and off-domain authority: Build pages and clusters that rank on Google and earn citations from ChatGPT, Perplexity, Gemini, and AI Overviews - structuring content with answer capsules, question-based headings, FAQ schema, and entity optimization. Stay on top of the ever evolving landscape and make sure model updates work in our favor. Track citation presence across search and AI answer engines and own the gap-closure roadmap.
• E-E-A-T and YMYL compliance: Set and enforce Jerry's voice and style guide across writers, freelancers, and AI output. Build the trust infrastructure YMYL finance content requires - named expert authors, sourcing discipline, editorial review processes, and transparent credentials.

Who You Are

• A strong writer with an editor's instincts. You can write a clean, persuasive piece from a blank page and edit an AI draft to a meaningfully higher standard. You also think in systems and can navigate briefs, templates, QA checkpoints effortlessly. You know that taste without process doesn't scale.
• An AI director. You've already shipped a real AI-assisted content pipeline in production. Not a prototype, but a running workflow with guardrails that held quality at scale. You know where AI earns its place and where it creates risk, and you can articulate exactly where the line is.
• An AEO practitioner. You already track how brands appear in AI answer engines and have opinions and examples on what moves the needle. AEO is part of your current practice, not something you've read about.
• A YMYL realist. You've worked in a regulated or high-stakes content category - insurance, personal finance, health, or legal - and you understand that accuracy is the product. Close enough isn't.

What You'll Bring

• 7+ years in content and editorial roles, with 3+ years leading an SEO-driven content program at a consumer, fintech, insurtech, or marketplace brand - or at a content-led media or affiliate site.
• A measurable organic growth result you can point to: sessions grown, publish volume scaled, a topic cluster built, and the dashboard to back it up.
• Hands-on command of LLMs (ChatGPT, Claude, Gemini) for drafting and research, plus SEO and content tools such as Sitefire, Surfer, Clearscope, MarketMuse, or Frase.
• Fluency in GSC, Semrush or Ahrefs, and GA4 - comfortable owning a traffic target, not just reporting on it.
• Experience managing at least one writer and/or a freelance bench, while continuing to produce content personally.
• A portfolio that demonstrates voice, editorial judgment, and accuracy - not only keyword density.

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 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
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.