Senior Designer

About Crosby

Crosby is building something new: an AI-powered law firm that combines world-class lawyers with purpose-built AI to deliver faster, more consistent, and more transparent legal services. We're not a legal tech startup selling to law firms. We're the law firm, reimagining the entire model from the inside out.

We're a team of 30 and growing fast. Our founders bring experience from Cooley, Ramp, and Google, and our team includes operators from companies like Stripe, Meta, and Vanta. We're backed by Sequoia, Index, BCV, and Elad Gil, and our clients include some of the fastest-growing companies in tech: Cursor, Clay, Braintrust, Serval, and more. We 10x'd revenue last year and are on track to do it again. Demand is growing faster than we can keep up with.

Legal is one of the last major industries untouched by software. We're building the tools and workflows that will define how AI and humans collaborate on complex knowledge work.

About the role

We’re looking for a Senior Designer to help design and evolve the internal tools that power Crosby’s legal operation. You’ll work closely with our co-founder/CTO, product, and engineering to ship high-quality, workflow-heavy experiences used every day by our lawyers and operators.

This role is focused on internal platforms—systems that sit at the heart of how legal work flows through Crosby. You’ll take ambiguous, complex processes and turn them into clear, fast, and intuitive product experiences.

You’ll collaborate with our founding designer and product lead, contribute meaningfully to design direction and craft, and help raise the bar on how we build—without being expected to define company-wide design standards alone.

You'll be a great fit if:

• You have exceptional visual design taste. Your work makes people want to zoom in. You obsess over typography, visualizations, and color in ways that elevate a product from functional to delightful.

• You're deeply product-minded. You ask "what problem are we solving?" before "what should this look like?" You've shipped features that moved metrics, killed features that weren't working, and can talk about both.

• You're independent and opinionated. You don't wait to be handed a spec. You dig into user problems, form a point of view, and drive toward a solution. When you disagree with a PM or exec, you say so clearly and back it up.

• You thrive in early-stage environments. You've been at a company where you had to figure out the process as you went. You're more excited by a blank canvas than a mature design system.

• You're collaborative without being consensus-driven. You know how to get engineering, product, and stakeholders aligned without watering down the work. You'd rather have a direct conversation than endless comment threads.

• You're excited about AI as a design tool and material. You have a point of view on how AI changes the way we design products. You love leveraging the latest AI tools (Claude Code, V0, and more) for prototyping. You'd rather jump in and play around yourself than wait for eng to build something, and you're eager to push boundaries on what human-AI collaboration can look like.

What you'll do:

• Design and iterate on Crosby’s core internal tool used daily by our legal team

• Own end-to-end design for complex, workflow-driven experiences—from early exploration through shipped product

• Partner closely with lawyers and internal stakeholders to understand real-world workflows and pain points

• Collaborate deeply with engineering to ship high-quality work quickly and pragmatically

• Contribute to evolving design patterns, systems, and shared standards as the product surface grows
Use AI tools to prototype, explore ideas, and move faster—treating AI as a design material, not just an implementation detail

What we're looking for:

• 3+ years of product design experience, with multiple 0 to 1 shipped products you're proud of

• A portfolio that demonstrates strong visual craft and clear product thinking

• Comfort with ambiguity and a bias toward action

• Interest in working with or learning more about AI/ML and the legal space

• Excellent communication skills, both visual and verbal

• Based in NYC or willing to relocate. We are open to hybrid, but value regular in-person collaboration at our light-filled and fun office in downtown NYC.

Nice to have:

• Experience at early-stage startups (Series A/B)

• Experience with complex, workflow-heavy products (B2B, enterprise, or productivity tools preferred)

• Experience building and scaling design systems

• Background working with AI/ML products

Compensation. $190k-$235k salary plus equity.

Note: 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. Pursuant to New York Labor Law Section 194-b, US Pay Range is $190,000 - $235,,000 which represents the base salary we reasonably expect to pay for this position at the time of this posting. Final compensation will be determined based on skills, experience, and qualifications."