Founding Product Designer (Contract), Handshake AI Enterprise

**About Handshake**
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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.