Head of Content Design

Why we exist:

More than 80% of Americans own a car and see it as a fundamental necessity, yet the experience of owning one is stuck in the 90s. Every part of the user journey (shopping for a car, insurance, repairs, etc) is complicated, fragmented, and time-consuming, and the costs are staggering. In 2025, the cost of owning a car was more than 20% of the average household income, after tax. At Jerry.ai, we are building the first app to manage it all and make car ownership accessible to all.

Why we need you:

Since we launched our app in 2019, we’ve reached 5M customers, raised over $240M in funding, scaled our annual revenue more than 70X, and became profitable in early 2024 – just 7 years into our operating history, in spite of challenging macro conditions and in a hyper-competitive $2T U.S. market.

We did this with an exceptionally talented team of analytical thinkers who are brilliant at experimentation and growth optimization. But what we don’t have is someone who obsesses over every single word we put in front of our customers and how we make them feel.

Car ownership is a stressful and emotionally charged topic for most people, and right now, our messaging is very transactional (e.g. click here, shop with us). We need you to change that.

Your job will be to think about what our customers actually need (or want) to hear from us, and how to fundamentally change how we speak to and care for them. Whether you’re crafting in-app copy or email sequences, navigating a subreddit thread, or shaping how we talk about a new feature launch, you will be the definitive voice of Jerry. And you will help us earn our brand and cultivate an enduring community.

We spent the last 9 years building a product that people like, now we need to give them a reason to trust us and a reason to stay.

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

• Blank canvas: You won’t inherit a brand playbook. You will build it in partnership with our CEO, including defining our personality and voice across all organic surfaces.

• Hands-on: This is a senior level role in scope and impact, but you will be an IC with no direct reports on day one. You will personally write the email campaigns, draft the in-app tooltips, and talk to drivers on Reddit.

• 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 own:

We need someone who knows how to talk about a brand in ways that make people feel something and take notice.

• Phase 1: Your sole focus will be overhauling our existing customer communications, including our CRM, email, SMS, and in-app copy. You will take our messaging from functional and direct to value-additive and relationship-driven. You will work closely with our Product, Design, Growth, and Customer Insights team to understand how to build trust, engagement, and as a result, drive long-tail conversion.

• Phase 2: As our brand and voice begins to take shape, you will start taking bigger creative swings to help us stand out online (e.g., pitching and running a campaign where we give away a $150K car to the best driver on our DriveShield platform), own the positioning and messaging for new products like GarageGuard, and build a team to manage organic GTM launches and our social media presence (like Reddit) with native channel expertise.

Who you are:

• A copywriting virtuoso: You know that every word matters. You can translate complex, dry, and even stressful topics (car insurance, loans, repairs) into copy that is engaging, human, and accessible.

• A T-Shaped marketer: Your deep expertise is in copywriting, audience development and product positioning. Horizontally, you have a great sense of the social media landscape and community dynamics (like Reddit).

• A first principles thinker: You avoid making assumptions. You know how to take qualitative data and user pain points and turn them into resonant, empathetic marketing copy.

• Comfortable with discomfort: You’ve weathered fast-growing startups before and can confidently push back on highly analytical, data-first teams to champion the unmeasurable value of a great brand experience.

Ideal experience:

• 7+ years of experience in copywriting, audience development, or product marketing with a heavy focus on brand voice, activation, and retention.

• Experience operating within a B2C growth-stage startup.

• A strong portfolio demonstrating both your writing and creative chops.

• Proven track record of native channel success (e.g. Reddit or another dominant social platform).

• Bachelor's Degree.

While we appreciate your interest and application, only applicants under consideration will be contacted.

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:

Jerry.ai is America’s first and only super app to radically simplify car ownership. We are redefining how people manage owning a car, one of their most expensive and time-consuming assets. 

Backed by artificial intelligence and machine learning, Jerry.ai simplifies and automates owning and maintaining a car while providing personalized services for all car owners' needs. We spend every day innovating and improving our AI-powered app to provide the best possible experience for our customers. From car insurance and financing to maintenance and safety, Jerry.ai does it all.

We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store. We have more than 5 million customers — and we’re just getting started. 

Jerry.ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing.

Join our team and work with passionate, curious and egoless people who love solving real-world problems. Help us build a revolutionary product that’s disrupting a massive market.