Sailplane
Overview
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Base pay range $200,000.00/yr - $300,000.00/yr
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 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 our Senior 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 code and 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.
Responsibilities
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 using tools like Cursor, Framer, Storybook, and Figma Dev Mode
Inspire the team to explore and improve features and designs through mocks, prototypes, and UX feature designs
Collaborate closely with customers and engineers through workshops, embedding with users and engineers, 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
Qualifications
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
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Base pay range $200,000.00/yr - $300,000.00/yr
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 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 our Senior 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 code and 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.
Responsibilities
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 using tools like Cursor, Framer, Storybook, and Figma Dev Mode
Inspire the team to explore and improve features and designs through mocks, prototypes, and UX feature designs
Collaborate closely with customers and engineers through workshops, embedding with users and engineers, 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
Qualifications
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
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