Software Engineer, Strategic Projects

About the role

Join a team focused on demonstrating the value of Tailscale as a core connectivity solution for developers and organizations. This role involves transforming initial concepts into reliable, production-ready products, with a strong emphasis on AI-assisted development.

Key facts

What you'll do

• Collaborate with product-focused engineers to design and build new features, ensuring they are architected for long-term stability from the outset.
• Take ownership of transitioning software from early prototypes to robust production systems, addressing areas like error handling, observability, and operational support.
• Oversee the quality and security of code generated with AI tools, ensuring it meets production standards through rigorous review and testing.
• Work with key customers to integrate Tailscale solutions, both for internal use and embedding into their own products, prioritizing reliability and maintainability.
• Identify and resolve complex issues, edge cases, and performance bottlenecks that arise in the transition from experimental to dependable software.
• Develop and enforce practices for code review, testing, and security that enable rapid development with AI tools without compromising product quality.
• Travel occasionally, less than 10%, for team gatherings, company events, and potential customer or conference visits primarily within North America.

Requirements

• Proven experience in hardening, stabilizing, and maintaining software in production environments, with a satisfaction in addressing detailed work and long-tail issues.
• Proficiency in Go is essential.
• Experience integrating with third-party APIs and a foundational understanding of networking concepts.
• Extensive daily use of AI coding assistants and LLMs in your development workflow, with a clear understanding of their benefits, limitations, and how to implement effective review, testing, and security practices around them.
• Enjoy working collaboratively with engineers who are exploring new ideas and share ownership in bringing concepts to a production-ready state.
• Adaptable to the fast-paced and sometimes ambiguous nature of a strategy team in a growing company, where priorities can evolve quickly.
• Ability to work effectively and independently in a remote setting.

Nice to have

• Experience managing production services, including observability, incident response, and performance tuning.
• Familiarity with validating code for production use in collaboration with security teams.
• Knowledge of identity infrastructure, including IdP platforms, authentication protocols (OAuth, OIDC, SAML, SCIM), and access control models.
• Experience building applications that utilize LLMs and agentic systems beyond just development tools.
• Familiarity with Tailscale and networking challenges in hybrid or multi-cloud environments.
• Active participation in open-source communities or experience creating public technical content.
• Experience with Python, Rust, or TypeScript.

Skills & tools

• Go
• AI coding agents (e.g., Claude Code, Cursor)
• LLMs
• Third-party API integration
• Networking fundamentals

Practical notes

• Salary Range: $218,420 - $302,840 CAD
• Comprehensive benefits package including health, vision, and dental with no waiting period.
• Employer-matched retirement contributions up to 0.75% of eligible compensation.
• Annual professional development budget of $1500 USD.
• Home office setup support, including company-provided laptop and monthly internet reimbursement.
• Paid parental leave: 20 weeks for birthing parents, 16 weeks for non-birthing parents.
• Tailscale uses AI-assisted tools in its hiring process; all hiring decisions are made by people.
• Be aware of phishing scams; legitimate Tailscale communications will come from @tailscale.com, @greenhouse.io, or @interviews.modernloop.io email addresses.