Software Engineer, Strategic Projects

This is a fully remote position, open to applicants in United States.

📋 Description

• Collaborate with product-oriented engineers from the outset, designing prototypes (MCP gateways, LLM proxies, sandboxes, remote servers, and similar emerging workloads) to ensure the production pathway is inherently integrated rather than added later.

• Share ownership of the transition from 'demonstration ready' to 'stable in production': focusing on hardening, error management, observability, and operational tools.

• Be responsible for the production standards on prototypes that transition into Tailscale's product offerings, including the security and review procedures surrounding agent-generated code.

• Partner with reference customers to implement Tailscale, both for internal usage (VPN replacement with identity-aware networking) and for incorporation into their products, with special emphasis on reliability, maintainability, and long-term support.

• Identify and resolve the long-tail issues, edge cases, regressions, flaky behaviors, absent tests, and undocumented operational knowledge that distinguish a prototype from a reliable product.

• Create and uphold the review, testing, and security protocols that enable the team to quickly deliver agent-generated code without compromising production standards.

• Light travel required (<10%): mainly for team and company meetings, with optional participation in conferences or customer visits primarily in North America.

⛳️ Requirements

• Expertise in hardening, stabilizing, and maintaining production software; you find fulfillment in detail-oriented tasks and in addressing the long tail of bugs, edge cases, and operational shortcomings.

• Proficiency in Go is essential; familiarity with integrating third-party APIs; basic understanding of networking concepts.

• Frequent daily utilization of coding agents (such as Claude Code, Cursor, or similar) and LLMs within your engineering processes, with insights on their efficiencies, limitations, and particularly on how to incorporate them into the review, testing, and security practices that uphold production standards.

• Enjoy working closely with exploratory, product-oriented engineers and collaboratively take ownership of the process to bring solid solutions into production.

• Comfortable with the pace of a strategy team in a relatively early-stage startup: priorities fluctuate with market signals, prototype-to-production timelines are brief, and the standards for shipping remain high.

• Flourish in working autonomously within a remote setting.

🏝️ Benefits

• An inclusive, flexible environment where you can be your authentic self.

• A competitive total compensation package.

• Comprehensive group benefits with no waiting period.

• Remote-first company—most of our teams work fully remotely.

• Connect with other Tailscalars in real life.

• Support for your personal and professional growth.

• Paid time off and a healthy work-life balance.

• A customizable home office setup.

• Generous parental leave program from your first day.