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 (writing code, testing, working with customers and teammates). 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 an AI Engineer, you'll be a technical generalist, designing and shipping the foundational agents, planning systems, and infrastructure to help our customers. This is a technical individual contributor role focused on hands-on coding, systems thinking, and prototyping.

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

What you will do at Sailplane

• Design, implement, and iterate on the agent stack owning how features move from the ADE (UX) into agent logic. Implement agents that must reliably execute complex workflows in real production environments.

• Create simulation and evaluation pipelines to measure task success rates, safety, latency, and cost; build rich traces and observability to debug agent behavior.

• Own features from initial design through deployment, that use the latest in AI and machine learning technologies, working on core areas of the Sailplane platform

• Write clean, maintainable code that solves real customer problems

• Optimize performance and proactively address scale challenges as our platform grows

• Work directly with large language models, natural language processing, and AI systems

What you will bring to Sailplane

• 5+ years working in full stack engineering, preferably in a VC-backed startup environment

• Strong proficiency in tech stack: Typescript(Node JS), Next.js Framework, Python, React

• Shipped at least one system where AI agents or LLMs performed multi-step tasks against real services or production data (not just offline demos)

• Comfortable building production services, APIs, and data pipelines in a cloud environment (GCP/AWS), and working with containers, monitoring, and logs

• Care deeply about correctness, safety, and observability: you design guardrails, fallback paths, and metrics so agents behave predictably

• Thrive with ambiguity, enjoy collaborating directly with founders and early customers, and are excited to own large problem areas end-to-end in a 2–10 person team

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