Head of Brand

Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.

Sequoia. Goldman. Wachtell. The best services firms have sterling reputations. One of their most durable moats is the incredible brand each has built over decades. At Crosby, we are building a third type of company: neither software nor services, but a neofirm.

Our brand is one of our most important assets. You will own Crosby’s brand as we remake one of the most important industries and build the best AI law firm in the world.

• Brand strategy and positioning: work with the founders, head of marketing, and other stakeholders to build the foundation for what Crosby’s brand stands for. Build a brand that stands out and captures attention, while feeling premium and trustworthy.

• Visual identity and brand system: make Crosby’s brand show up consistently across varied canvases from billboards to conference booths to how our swag feels.

• Signature campaigns and creative direction: partner with the founders and head of marketing to develop Crosby’s next major brand campaign for 2027, building on the recognition created by the “Death of the Billable Hour.” Drive the central idea and its execution across out-of-home, digital, social, and other relevant channels.

• Website and market-facing storytelling: help transform Crosby’s website into a more complete expression of the company, services, and technology. Shape page narratives, visual concepts, headlines, and concise brand copy with product, design, and a dedicated writer.

• Cross functional partnership: work with design, product marketing, events, content, and other teams to consistently build affinity for Crosby’s brand with every interaction a customer or prospect has.

• 4-8 years of experience building a standout brand in tech, consumer, or at an agency. This could be at an admired brand, through a standout campaign or agency project, or while building an emerging company.

• Proven ability to build a brand from the ground up, either as the first or second hire focused on brand.

• Exceptional taste and a clear point of view. Compelling examples of distinctive, high-quality brand work and the ability to explain why creative choices were right for the company, audience, and objective.

• Visual fluency. The judgment to guide identity and visual expression across different formats, plus enough comfort with rough mockups or concepts to communicate direction. Being a production designer is not required.

• Conviction and collaborative judgment. Comfort navigating strong opinions from founders, marketing, Product, Sales, and designers. The ability to defend sound creative decisions, incorporate useful feedback, and move projects forward.

• End-to-end creative leadership. Experience translating a brand idea into campaigns, a website, customer moments, or other shipped work, with clear ownership of concept, feedback, and delivery.

• Resourcefulness and momentum. A bias for shipping high-quality work in an evolving organization, building practical systems, and managing tradeoffs without waiting for perfect resources or direction.

Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.
Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.
Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.