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Sail builds software for AI inference and agent hosting at scale. As a Member of Technical Staff in Monetization, you will own the billing and revenue systems that meter compute and collect revenue across Sail's customer base—from self-serve users to enterprise customers and routing partners like OpenRouter. These systems handle millions and soon billions of dollars, and are critical to the business.
You will design and operate billing for all current and future Sail offerings, develop new pricing and packaging strategies for AI infrastructure (including novel features like Supercache), and build deep observability tools for spend and revenue tracking. You'll create user-facing dashboards and tools that help customers monitor usage and optimize costs. Additionally, you'll build and maintain organization identity, permissioning, authentication, and abuse prevention systems.
AI infrastructure presents unusually interesting pricing and systems challenges. Your decisions will directly affect what customers can afford to build, their product experience, and Sail's economics. The role requires balancing cost efficiency—a key reason customers choose Sail—with sustainable business models.
Sail is based in downtown San Francisco with a collaborative, technically rigorous culture. The team debates design decisions thoroughly before implementation and focuses review time on critical system components. The office includes meals, Studio Displays, and a friendly office cat named Coco.
REQUIREMENTS:
- Familiarity with usage-based billing and payments systems, or demonstrated 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 AI agents coupled with healthy skepticism
- Great interpersonal and technical communication skills
- Strong written communication (cover letters and resumes will be carefully reviewed)
