Product Designer

About Cassidy

Cassidy is an AI automation platform that helps teams turn their company knowledge into AI-powered assistants, agents, and workflows. We’re building a product that allows non-technical teams to automate complex work without needing to become AI experts or engineers. Today, Cassidy is used across large organizations to automate workflows in sales, operations, insurance, support, marketing, and more. We’re growing quickly and are looking for a Product Designer to help define what the next generation of AI software should feel like.

The Role

We’re looking for an exceptional Product Designer who can own major parts of the Cassidy product from idea through launch.

This is not a role where you’ll be handed perfectly defined requirements and asked to make them look good. You’ll work closely with our founders, product, and engineering teams to understand difficult problems, determine the right product experience, prototype solutions, and ship them.

AI products introduce entirely new design challenges. Users need to understand what an agent is doing, configure complex workflows without feeling overwhelmed, work with probabilistic outputs, debug failures, manage context, and increasingly delegate entire processes to software.

We want someone excited to figure out what these interfaces should look like.

You’ll have a tremendous amount of ownership over the product and a direct impact on how thousands of people interact with AI at work.

What You’ll Do

• Own the end-to-end design of major Cassidy product areas, from early concepts through polished production experiences.
• Work directly with founders, engineers, customers, and the rest of the product team to identify problems and turn them into intuitive product experiences.
• Design interfaces for AI agents, workflows, knowledge management, human-in-the-loop systems, and other emerging AI interaction patterns.
• Take complicated functionality and make it feel simple and approachable for non-technical users.
• Prototype quickly to explore ideas, communicate product direction, and test different approaches.
• Spend time with customers and understand how they actually use Cassidy, where they get stuck, and what would make the product dramatically better.
• Help establish and evolve Cassidy's design system as the product grows.
• Sweat the details. Interaction design, information architecture, visual polish, empty states, onboarding, copy, and the small moments that make a product feel great all matter.
• Ship frequently and continuously improve what you've built based on real usage.

What We’re Looking For

• You have a strong portfolio demonstrating exceptional product thinking, interaction design, and visual craft.
• You’ve designed and shipped real software products, ideally complex B2B, productivity, developer, or prosumer products.
• You are excellent at simplifying complicated systems without removing their power.
• You think beyond individual screens and care deeply about the entire user experience.
• You’re comfortable working from ambiguity and can turn loosely defined problems into clear product direction.
• You move quickly. You know when something needs another week of exploration and when it needs to get in front of users tomorrow.
• You’re highly collaborative and comfortable working directly with engineers throughout the product development process.
• You care about the underlying product problem as much as the design itself.
• You have strong opinions, communicate them clearly, and are equally comfortable changing your mind when the evidence points somewhere better.
• You’re excited about AI and want to help invent interaction patterns that largely don't exist yet.

Bonus Points

• You’ve designed AI-native products or sophisticated workflow/automation tools.
• You’ve worked at an early-stage startup.
• You can build functional prototypes or are comfortable working with tools like Cursor, Claude Code, or similar AI development tools.
• You have experience designing products that serve both highly technical and non-technical users.
• You obsess over products and can explain exactly why the software you love feels great.

How We Work

Cassidy is a small, ambitious team. Designers here are expected to have significant ownership.

We value people who are opinionated, curious, fast-moving, and willing to get close to customers. We care much more about building an exceptional product than protecting strict boundaries between product, design, and engineering.

You’ll work directly with the people building the product, see your work ship quickly, and have a meaningful voice in what Cassidy becomes.

We work together in person from our New York City office five days a week.

Why Cassidy

This is an unusual moment in software. The way people interact with computers is changing rapidly, and many of the conventions for AI-native software have yet to be invented.

At Cassidy, you’ll get to work on those problems at the product level every day.

If you want to design beautiful software, solve genuinely hard interaction problems, move quickly, and help define how people work with AI, we’d love to hear from you.