Principal Engineer

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."

Sailplane is an early-stage AI infrastructure startup. Expect to wear many hats (writing code and evaluations, building infrastructure, working with customers). 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 Principal Engineer
, you'll be a first-class generalist and leader moving across Sailplane agents and infrastructure. You are a hands-on technical leader who can turn AI research into a developer-friendly platform for infrastructure and platform teams. This is a senior technical individual contributor role focused on hands-on coding, systems thinking, and prototyping. You will act as a technical multiplier rather than a people manager.

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

• Design and evolve the control plane for agents: planning and execution loops, workflows, callbacks, and state models
• Implement sandboxing, dry-run/preview modes, in variants, approvals, and rollback strategies so agents can safely change real infrastructure and applications
• Take hierarchical planning / agent research prototypes and build production-grade agents, services and APIs around them (auth, rate limits, quotas, retries)
• Anticipate production system needs (security, networking, SLOs/SLAs) and instrument for reliability and usage via observability (logs, traces, guardrails)
• Guide architecture trade-offs and reason about IP boundaries as an engineering design dimension
• Build, deploy, monitor, and operate LLMs in production on-premises in diverse customer environments and implement MLOps best practices (CI/CD pipelines, containerization, continuous monitoring) to ensure reliable performance
• Lead through influence, setting engineering standards for code quality, testing, documentation, and on-call practices
• Partner with founders to prioritize what to build next based on customer needs, market demand and technical implementation
• Conduct interviews and evaluate candidates across engineering, product, and design roles, helping build Sailplane's early team.

• 10+ years of software engineering experience, including time operating at Staff/Principal scope or equivalent
• Deep experience in designing and building AI systems, large-scale distributed systems, infra/devtools, SaaS platforms, or other safety-critical automation domains
• Strong proficiency in at least one backend language (e.g., Go, Rust, Java, C++), plus comfort with Python for glue/ML/agent work
• Hands-on with cloud platforms (AWS/GCP/Azure), containers, CI/CD, and modern deployment practices (Kubernetes or equivalent)
• Track record of building systems and shipping with reliability and safety in mind
• Build a high-trust, inclusive, feedback-driven engineering culture that values autonomy, learning, and accountability
• Experience interviewing and evaluating candidates across engineering, product, and design roles, with a track record of helping build strong teams through thoughtful hiring…