[Hiring] Senior Creative Strategist @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 Senior Creative Strategist with sharp performance instincts and elevated visual taste. Someone who’s obsessed with advertising, and excited about how AI and new media are reshaping creative production. You'll own the full creative lifecycle: concepting, producing, and iterating ads that drive measurable results across TikTok, Meta, YouTube, and CTV, while raising the bar on craft and brand quality. You will be a driving force of Jerry’s creative engine with production chops to bring ideas to life yourself.

Qualifications

• 5+ years in performance-driven creative production — ideally at a performance media agency and/or an in-house growth creative team at a DTC or app-based company.
• Proven track record producing or directing high-performing creative for paid channels (Meta, TikTok, YouTube, CTV, etc.).
• Strong performance creative intuition — you understand hooks, pacing, CTAs, and what makes people stop scrolling.
• Elevated visual taste — you have an eye for design, composition, and brand quality.
• Video editing fluency — you can cut and iterate ads quickly yourself.
• Collaborative and entrepreneurial mindset — thrives in fast-paced environments, comfortable bridging creative, media, and analytics teams.
• AI fluency — you actively experiment with generative tools to speed up production, expand creative range, or improve output quality.
• Bonus: experience in both a performance media agency and a brand or design agency, with exposure to brand-level creative craft.

Requirements

• Concept and produce performance creative end-to-end: from ideation and scripting through editing and delivery, across paid social, CTV, and emerging channels.
• Bring a sharp creative eye to every asset: elevating visual quality, pacing, and storytelling to raise Jerry's brand while keeping creative performance-driven.
• Stay on top of platform trends, formats, and cultural shifts: ensuring Jerry's creative stays fresh, relevant, and effective.
• Develop hooks, angles, and creative frameworks rooted in what actually drives performance, not just what looks good.
• Translate performance data into creative direction: partnering with media and growth teams to turn signals into better ads.
• Manage and maximize agency and production partners: writing briefs, providing creative direction, and quality-checking work to ensure external teams deliver at Jerry's standard.
• Edit video directly: you're fluent in editing tools and comfortable cutting, iterating, and polishing ads at speed without sacrificing quality.
• Leverage AI tools (for ideation, scripting, editing, asset generation, etc.) to accelerate workflows and unlock new creative possibilities.

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.
• 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. 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.