Head of Creative

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).

• Work closely with brilliant leaders and teammates from companies like McKinsey, BCG, Nvidia, Better, SoFi, etc.

• 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.

• Own end-to-end creative excellence and be a tastemaker at Jerry - from concepting and production to agency management.

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 Head of Creative 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.

Why you will (or won’t) like working here

• Large canvas: You won’t inherit a set-in-stone playbook. You will contribute meaningfully for our brand foundation. Your creative intuition will direct us to both what performs and what builds brand equity.

• End-to-end ownership: This is a senior level role in scope and impact, but you also will be hands-on: concepting, directing production briefs, writing scripts, editing video, and using AI tools to move fast and unlock the next level.

• Car ownership is not “sexy”: Insurance, maintenance, and safety are only topics people think about when they have a bill to pay, a flat tire to change, or when they get into an accident. Anyone can market something inherently exciting, but can you build enthusiasm and trust around a “dry” topic?

What you'll do

• Lead a team: manage and guide a small, highly-capable team.

• Concept and produce performance creative end-to-end: from ideation and scripting through editing and delivery, across paid social, CTV, and emerging channels. Even as a leader, you're still hands on.

• 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.

What we're looking for

• 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. You can concept ads that convert

• Elevated visual taste — you have an eye for design, composition, and brand quality. You can take performance creative from functional to beautiful without losing effectiveness.

• Video editing fluency — you can cut and iterate ads quickly yourself, making them look premium without needing heavy direction.

• 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.You know how to make ads that perform and ads that feel premium. You don't see those as tradeoffs.

Why this role matters

Jerry's creative team has proven performance chops — but we're ready to level up our creative engine. This role is the key to unlocking exponentially more volume and creative diversity: someone with the taste to raise the bar, the production skills to move fast, and the performance instincts to ensure everything we ship drives results.

You'll be the connective tissue between idea and impact — helping us build a scalable creative system that blends craft, data, AI, and media strategy.

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 [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.