Senior Product Designer II, Handshake AI

Handshake • San Francisco, CA

2d • Hybrid

About The Position

Handshake is the career network for the AI economy, serving 20 million knowledge workers, 1,600 educational institutions, 1 million employers (including 100% of the Fortune 50), and every foundational AI lab. The company powers career discovery, hiring, and upskilling, from freelance AI training gigs to first internships to full-time careers and beyond, experiencing unparalleled growth. Handshake AI specifically focuses on expert-labeled data collection at scale, connecting domain experts with leading AI companies to train frontier models. The Senior Product Designer II will lead significant, high-impact design initiatives, navigating ambiguity with confidence, applying rigor and data-informed thinking to complex problems, and elevating the design organization's standards. This role involves owning substantial parts of the product strategy, driving end-to-end design for complicated, often loosely-defined projects, and serving as a mentor to teammates while staying closely connected to customers, operators, and the overall business to ensure well-grounded decisions.

Requirements

• 6+ years of product design experience, with a track record of designing and shipping products that customers love.
• Proven ability to lead complicated, ambiguous projects with little direction, driving them forward and creating clarity for those around you.
• Strong data-informed thinking. You roll business goals, research, technical constraints, and user needs into well-crafted solutions (mocks, prototypes, flows), and you iterate fast.
• Experience mentoring or coaching peers, and a track record of improving quality beyond your own work.
• Strong communicator who manages stakeholders well — you understand the nuance of upward and cross-functional communication and proactively keep the right people informed.
• Deep visual and interaction design craft, with attention to detail across flows, states, and edge cases.
• Humble, collaborative, and curious. Energized by a complex, evolving product and motivated to keep learning and help others grow.

Nice To Haves

• Experience designing LLM or AI-powered products, or working on enterprise or operations tooling.

Responsibilities

• Lead end-to-end design on significant, high-impact projects, from discovery through production and iteration, often with minimal definition and little precedent to work from.
• Bring a data-informed mindset to every aspect of your work — articulating when data is incomplete or biased, keeping the user at the center of every solution, and holding a high bar for quality and craft before sharing your work.
• Contribute to prioritization, strategy, and process — breaking big ambiguous problems into actionable steps and building clarity for your team and cross-functional partners.
• Use business goals, data, patterns, and industry context to arrive at quick, iterative solutions — avoiding getting stuck in the abstract.
• Proactively identify opportunities to inform, influence, and collaborate across the design org, creating workflow efficiencies and sharing learnings with teammates.
• Serve as a helpful mentor for teammates at earlier career levels, improving craft, communication, and design quality beyond your own area.

Benefits

• Ownership: Equity in a fast-growing company
• Financial Wellness: 401(k) match, competitive compensation, financial coaching
• Family Support: Paid parental leave, fertility benefits, parental coaching
• Wellbeing: Medical, dental, and vision, mental health support, $500 wellness stipend
• Growth: $2,000 learning stipend, ongoing development
• Remote & Office: Internet, commuting, and free lunch/gym in our SF office
• Time Off: Flexible PTO, 15 holidays + 2 flex days
• Connection: Team outings & referral bonuses

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed
• Number of Employees: 501-1,000 employees