The posting
Why should you join Jerry?
- Join a pre-IPO startup with capital, traction, and runway ($240M funded | 40X revenue growth in 4 years | $2T market size).
- Disrupt a massive market and help scale us to a $5B business in the next few years.
- Be immersed in a talent-dense environment and accelerate your career growth exponentially.
- Bring sharp visual craft and creative energy to Jerry's video output — from concept through final cut.
About the Role
At Jerry, we are redefining and radically improving how people manage car ownership, one of their most expensive and time-consuming assets. Backed by artificial intelligence and machine learning, Jerry simplifies and automates car ownership while providing personalized services tailored to all car owners' needs. We are the #1 rated and most downloaded app in our category with a 4.7-star rating in the App Store and more than 5 million customers — and we're just getting started.
We're looking for a Creative Director (Video) with a strong visual eye and a genuine curiosity about performance creative. Someone who cares deeply about craft, moves fast, and is excited by how AI and new media are reshaping what great advertising looks like. You'll work closely with senior creative leads to concept, produce, and iterate video ads across TikTok, Meta, YouTube, and CTV — learning and contributing at every stage of the process.
Why you will (or won't) like working here:
Large canvas: You won't inherit a set-in-stone playbook. You'll have real creative input and contribute meaningfully to our brand foundation early in your career.
Hands-on from day one: This isn't a support role. You'll be concepting, editing, and iterating — using AI tools and your own creative instincts to ship work that performs.
Car ownership is not "sexy": Insurance, maintenance, and safety are only topics people think about when they have a bill to pay or a flat tire to change. Can you build enthusiasm and trust around a "dry" topic? That's the creative challenge here.
What You'll Do
- Concept and produce video creative across paid social, CTV, and emerging channels — working end-to-end from brief to delivery under the guidance of senior creative leads.
- Lead a small and nimble team
- Bring a sharp visual eye to every asset: elevating composition, pacing, and storytelling to raise Jerry's brand while keeping performance top of mind.
- Stay on top of platform trends, formats, and cultural shifts to ensure Jerry's creative stays fresh and effective.
- Develop hooks, angles, and visual frameworks rooted in what drives real performance — not just what looks good.
- Edit video directly: fluent in editing tools and comfortable cutting, iterating, and polishing ads at speed.
- Leverage AI tools (for ideation, scripting, editing, asset generation, etc.) to accelerate workflows and expand creative range.
- Collaborate closely with media, growth, and senior creative teammates to turn performance signals into stronger creative work.
What We're Looking For
- 8+ years in video creative, art direction, or production — at a performance agency, in-house growth team, or content studio.
- A growing track record contributing to video creative for paid channels (Meta, TikTok, YouTube, CTV, etc.).
- Strong visual instincts — you have an eye for design, composition, pacing, and brand quality.
- Video editing fluency — you can cut and iterate ads yourself, making them feel polished without heavy direction.
- Performance creative curiosity — you understand (or are actively learning) what makes people stop scrolling: hooks, pacing, CTAs.
- Collaborative and eager mindset — comfortable in fast-paced environments and open to feedback from creative and analytics teams alike.
- AI fluency — you experiment with generative tools to speed up production and expand what's creatively possible.
- Bonus: exposure to both performance and brand creative contexts. You're building a point of view on how craft and conversion can coexist.
Why This Role Matters
Jerry's creative team has proven performance chops — and we're ready to level up. This role is an opportunity to grow fast inside a creative engine that blends craft, data, AI, and media strategy. You'll be hands-on from day one, contributing real work that reaches millions of people — and building the skills and portfolio to grow into a senior creative leader.
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 http://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] [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 achieved profitability in 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 support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
