Product Designer

About Sailplane

In an unmarked building somewhere in Silicon Valley, a small team of engineers is working on what could become one of the most transformative technologies in enterprise computing: autonomous infrastructure that manages itself. Sailplane, backed by AI kingmaker Khosla Ventures (OpenAI's first investor) and seed specialist True Ventures, is building a "self-driving cloud" - intelligent agents capable of autonomously managing the largest and most advanced AI infrastructure on the planet.

Sailplane is solving one of the most complex challenges in modern computing: autonomous manufacturing and management of massive AI data centers. We are creating intelligent agents that operate rack-scale systems worth millions of dollars. Think Waymo for cloud infrastructure.⁠⁠

"We're building million-dollar agents," explains co-founder Sam Ramji, who previously led product at Google Cloud Platform and brought Linux to Microsoft. "These aren't consumer-grade chatbots - they're sophisticated autonomous systems managing rack-scale hardware worth millions per unit."

About the Role

Sailplane is an early-stage AI infrastructure startup. Expect to wear many hats (product and feature definition, designer, customer confidante). You will bring a Startup Mindset, eager to take ownership of projects, navigate ambiguity, and move quickly to solve challenging problems in a fast-paced environment.

As a Product Designer, you'll shape the entire product experience for Sailplane. This is a senior individual contributor role focused on hands-on craft, systems thinking, and prototyping. You won't manage a team - you will mentor and amplify those around you.

You should be fluent in AI UX, adept at designing agentic workflows, and confident prototyping in Cursor or similar tools. You’re comfortable working in codeand in Figma, and you care deeply about how things work as much as how they look.

This hybrid position reports to the CEO and is expected to work from San Francisco 2 to 3 days per week.

What you will do at Sailplane

• Define and evolve the end-to-end product UX across Sailplane's platform, embodying Sailplane’s product vision

• Prototype AI workflows and build functional prototypes design to code using tools like Claude Code, Cursor, Framer, Storybook, Figma Dev Mode, and other AI development tools

• Inspire the team to explore and improve features and designs through mocks, prototypes, and UX feature designs

• Collaborate closely with customers and engineers through research and workshops, embedding with teams, and leading design critiques and functional reviews

• Set a high bar for design craft and polish, from interaction to visual detail

• Create scalable systems and patterns that unify the product experience

• Explore and shape how AI integrates across user journeys

What you will bring to Sailplane

• 10+ years of experience designing product experiences across platforms

• Strong portfolio showing high-quality, shipped work at scale

• Deep prototyping skills and comfort working in code and design tools, moving from design to code quickly and iteratively

• Experience designing with AI or working on AI-powered products

• Product thinking through user flows, jobs-to-be-done framing, and visual design translating to solutions and outcomes for users

• Systems-level thinking across UX, UI, and design infrastructure scaling design beyond individual features

• Technical product familiarity with developer tools, B2B SaaS, data-heavy UIs, or AI products

• Excellent communication skills with an ability to explain complex AI hardware and agentic concepts to non-experts, and a collaborative approach to working with cross-functional teams and partners

Benefits and Perks

• Comprehensive Health, Dental, and Vision coverage beginning on the first day for employees and their families, paid 100% by Sailplane

• Equity grant participation

• Flexible PTO with no accrual or set annual cap, plus 15 paid holidays per year

• Health and Wellness stipend ($3,000 annually) to help support your personal health goals

• AI tools stipend ($1,200 annually) to encourage hands-on familiarity with emerging tools

• 12 weeks of paid parental leave