Founding Product Designer (Contract), Handshake AI Enterprise

About Handshake

Handshake was founded on a simple belief that everyone deserves a path to a great career, regardless of where they went to school or who they know. Today, we power 25 million job seekers, 1 million+ employers, and 1,600 educational institutions. In 2025, we started Handshake AI and built the fastest-growing AI data business in history. We work directly with frontier AI lab researchers to create evaluations, publish benchmarks, and push the boundary of data. We’ve grown from $0 to ~$1B run rate and pay ~$60M to over 30K individuals every month.

Your Role

Handshake AI Enterprise is building the product layer for AI applications deployed directly into the workflows of the world's leading companies. This role begins as a contract engagement with the opportunity to convert to full-time based on mutual fit. We work hand-in-hand with enterprise customers, from Fortune 500s to frontier AI labs, to understand their problems deeply and build solutions that are delightful to use. We're looking for a Founding Product Designer to own the design function from the ground up.

Your Experience

• 5–7+ years of product design experience, ideally on enterprise products, operations tooling, or internal platforms.
• You've designed and shipped production-grade features customers love across complex systems, workflows, and platforms.
• You've worked directly with customers and end users, and know how to connect what you learn to business goals and technical constraints.
• You can walk a customer or executive through a design decision as confidently as you can walk an engineer through a spec.
• You're highly collaborative and a strong communicator; you value diverse perspectives, manage stakeholders well, and understand the nuance of upward and cross-functional communication.
• You're comfortable being the only designer in the room; you don't need a team around you to do great work, and you thrive when the scope is wide and the stakes are high.
• You're deeply motivated by Handshake's mission. Humble, kind, and curious, with a desire to keep learning and help others grow.
• Bonus: experience with multi-sided marketplaces, LLM products in production, operator/workflow management systems, or internal tools at high-growth companies.