sail

Member of Technical Staff - Monetization

San Francisco
Full-time
Posted Oct 2, 2026

Skills

Large Language Models

Job description

Sail builds the world's most efficient software for inference (processing LLM tokens) and agent hosting (cloud VMs). Together, our technologies allow our customers to deploy AI agents at extreme scale for their most ambitious work.

Own the systems that meter compute and collect revenue at Sail, built to handle many millions (and soon billions) of dollars. You’ll help determine how we sell our products, and build the sustainable systems to execute accordingly. Cost efficiency is a key reason our customers choose Sail, so these systems are critical to the business.

AI infrastructure gives us some unusually interesting pricing problems, with ample opportunity for innovation here. The decisions you make will affect what customers can afford to build, the experience they have with our product, and the economics of Sail itself.

What you’ll do

•Design and operate billing for all of Sail’s current and future offerings, across our smallest self-serve customers, our largest enterprise commits, and our routing partners like OpenRouter.

•Develop new ways to price and package AI infrastructure, plus novel billing features like Supercache.

•Build deep observability for spend and revenue, for both customers and ourselves. Connect revenue to compute costs. Build useful tools and user experiences for customers to monitor their usage and maximize cost efficiency with Sail.

•Build and maintain organization identity, permissioning, authentication, and abuse prevention.

What we’re looking for

•Familiarity with usage-based billing and payments systems, or an interest in learning them.

•Experience owning high-throughput, reliable production systems.

•Solid distributed systems fundamentals.

•Product sense: experience and enthusiasm for building delightful products and user experiences.

•Interest in compute and inference economics.

•Eagerness to work with agents coupled with a healthy dose of skepticism. We start by focusing our attention on the highest-level design decisions first, and try to debate and justify each of decisions. Then, we use our finite review time on the critical pieces of the system that we must build good mental models of to do good work.

•Great interpersonal and technical communication. Please don't use LLMs to write prose. We desk-reject slopful cover letters and resumes.

Interview process

1. Meet Nikki https://www.linkedin.com/in/nicoback, who will ask about your experience, and share as much technical detail about Sail as you want to hear.

2. Share an online whiteboard with a team member and work through a technical problem. We spend a lot of time at whiteboards, building intuition about complex systems together. It's a great way for us to see how you communicate technically, and an even better way for you to see what working at Sail is like.

3. Come in to Sail's SF office for an interview day. Meet the whole team, and work on a bunch of problems that closely simulate the work we do daily. We'll also ask you to give us a 20–30 minute “chalk talk” about an interesting problem you've worked on before.

4. Offer. Once the team decides we want to work with you, we make a strong offer quickly and will be quite persistent over email/text/calls :)

Life at Sail

We work out of a beautiful, sunny office in downtown San Francisco. All meals are on us (and actually great; SF is a food paradise!). Everyone gets a Studio Display (or two) at their desk. We are serious about investing in anything that saves us time or energy. There are six different ways to make coffee or tea in the office. A friendly (hypoallergenic) black cat named Coco visits occasionally.