Job Overview
Location
Remote (Canada)
Job Type
Full-time
Category
Software Engineering
Date Posted
May 14, 2026
Full Job Description
đź“‹ Description
- • As a Software Engineer on the Engineering Tooling team at Tailscale, you will build and maintain internal tools and services that empower engineering, product, and business teams to work more efficiently and securely. Your work directly enables faster development cycles, improved reliability, and better observability across Tailscale’s distributed systems.
- • Day to day, you will design, build, test, and document core software components; improve CI/CD pipelines and developer tooling; analyze production data to surface issues; collaborate with stakeholders to understand needs and deliver end-to-end solutions; and participate in incident response and customer support escalations to ensure system stability.
- • Tailscale is a fully remote, early-stage company building the new Internet by making secure network access simple and safe for everyone—from individuals to multinational corporations. Backed by top-tier investors and composed of highly technical, collaborative teams, Tailscale values ownership, asynchronous communication, and technical excellence.
- • In this role, you will deepen your expertise in distributed systems, infrastructure as code, observability, and Go-based backend development while gaining impact through tooling that improves engineering productivity across the organization. You’ll grow as a versatile engineer who bridges product needs with platform capabilities.
🎯 Requirements
- • Experience with CI/CD, secrets management, infrastructure as code, and/or observability
- • Experience with developer tooling or developer experience
- • Experience with distributed systems
- • Familiarity with networks (IP addressing, routing, etc.)
- • Experience with Go programming language (a plus)
- • Familiarity with one or more SQL databases (a plus)
- • Ability to give and process constructive feedback, work independently, and adapt to a dynamic startup environment
- • Excellent written and verbal communication skills
🏖️ Benefits
- • Competitive total compensation package including base salary, equity, and variable commission (for quota-based roles)
- • Comprehensive group benefits with no waiting period (health, vision, dental, and more)
- • $1500 USD annual professional development stipend, plus mentorship and coaching opportunities
- • Remote-first work environment with monthly home internet reimbursement and $1000 USD for home office setup
- • Generous parental leave program with top-ups for up to 26 weeks from day one
- • Paid time off supporting work-life integration and flexibility
- • Opportunities to connect in person via annual retreat, team off-sites, and corporate co-working program access
Skills & Technologies
About Tailscale Inc.
Tailscale Inc. provides a zero-config virtual private network built on the open-source WireGuard protocol. It creates secure, encrypted mesh networks that connect devices, servers and users without traditional VPN hardware or complex firewall rules. The software runs on Linux, macOS, Windows, iOS, Android and container platforms, integrating with identity providers like Google Workspace, Microsoft Entra ID and Okta. Organizations use Tailscale to enable remote access to internal applications, SSH, RDP, databases and development environments, while maintaining centralized access controls and audit logs. The company is privately held and headquartered in Toronto, Canada.
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