Founding Product Designer (Contract), 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.

Why join Handshake now:

• Shape how every career evolves in the AI economy, at global scale, with impact your friends, family and peers can see and feel
• Partner hand-in-hand with world-class AI labs, Fortune 500 partners and the world’s top educational institutions
• Work together with engineers, scientists, operators, and more from Palantir, Meta, Scale AI, and former YC founders
• Build a massive, fast-growing business with billions in revenue

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. You'll be the person who holds the bar, owning design end-to-end across every customer deployment, pairing direct customer impact with founding-team ownership, and helping establish a product that scales with us.

• Collaborate with product, engineering, data, research, sales, and operations to define and build the vision, owning design from early research through high-fidelity, and partnering on demos and prototyping.
• Get close to enterprise customers and operators: run pilots, shadow workflows, uncover pain points, and translate what you learn into clear, simple solutions and prioritized investments.
• Develop strategic product visions, sequence them into pragmatic phases, and tackle complex, ambiguous problems with a strong point of view on craft.
• Operate entrepreneurially: move fast, make decisions with incomplete info, and find creative ways to unblock yourself and your team.
• Raise the bar for design culture and execution through systems thinking, product reasoning, pixel-level precision, and facilitation.

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. Your work reflects that fluency.
• Can walk a customer or executive through a design decision as confidently as you can walk an engineer through a spec.
• 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.
• 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.