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