[Hiring] Creative Director @Jerry.ai

Role Description

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.

Qualifications

• 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.

Requirements

• 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.

Benefits

• Comprehensive benefits package including health, dental, and vision coverage.
• Paid time off and paid parental leave.
• 401(K) plan with employer matching.
• Wellness benefits, among others.
• Equity opportunities may also be part of your total rewards package.

Company Description

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.