Software Engineer, Strategic Projects

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

📋 Description

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

• Share ownership of the transition from "operational in a demo" to "stable in production": this includes hardening, error management, observability, and operational tooling.

• Take responsibility for the production standards on prototypes that evolve into Tailscale's product offerings, incorporating security measures and review protocols surrounding agent-generated code.

• Engage with reference customers to facilitate Tailscale integration, targeting both internal use (VPN replacement with identity-aware networking) and embedding within their products, emphasizing reliability, maintainability, and long-term support.

• Identify and address long-tail gaps, edge cases, regressions, unreliable behavior, absent tests, and undocumented operational knowledge that distinguish a prototype from a reliable product.

• Establish and uphold the review, testing, and security procedures that empower the team to swiftly deploy agent-generated code without compromising production standards.

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

⛳️ Requirements

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

• Go programming experience is essential; familiarity with integrating third-party APIs; basic networking knowledge.

• Frequent daily use of coding tools (Claude Code, Cursor, or similar) and LLMs in your engineering workflow, with insights on where they enhance productivity, where they fall short, and particularly how to incorporate them into the review, testing, and security practices that uphold production standards.

• Enjoy close collaboration with exploratory, product-oriented engineers and collectively take responsibility for delivering robust solutions in production.

• Comfortable with the dynamics of a strategy team in an early-stage startup: priorities may shift in response to market signals, prototype-to-production timelines are brief, and the expectations for shipped products remain high.

• Excel at working independently within a remote setting.

🏝️ Benefits

• An inclusive, flexible environment that encourages you to be your authentic self.

• A competitive total compensation package.

• Comprehensive group benefits with no waiting period.

• A remote-first company culture.

• Opportunities to connect with fellow 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 effective from your first day.