2 months ago
Remote, CanadaSenior
Responsibilities
- Shape prototypes such as MCP gateways, LLM proxies, sandboxes, and remote servers so production requirements are built in from the beginning.
- Co-own the transition from demos to stable production systems through hardening, error handling, observability, and operational tooling.
- Own the production, security, code review, testing, and operational bar for prototypes that become part of Tailscale’s product surface.
- Work with reference customers on internal Tailscale adoption and embedded product integrations.
- Identify and resolve edge cases, regressions, flaky behavior, missing tests, and undocumented operational knowledge.
- Establish and maintain practices that enable rapid delivery of agent-generated code without compromising quality or security.
- Travel less than 10%, primarily for team and company onsites, conferences, or customer visits.
Requirements
- Go experience is required, along with comfort integrating third-party APIs and basic networking knowledge.
- Experience taking software from prototype to production and hardening, stabilizing, and maintaining production systems.
- Heavy daily use of coding agents such as Claude Code or Cursor and LLMs, with sound review, testing, and security practices.
- Ability to collaborate with product-minded engineers, work independently in a remote environment, and operate effectively amid shifting priorities.
- Experience with production services, observability, on-call, incident response, performance, reliability, security validation, identity infrastructure, or LLM and agentic applications is desirable.
- Familiarity with IdP platforms, identity synchronization and provisioning, directory services, OAuth, OIDC, SAML, SCIM, RBAC/ABAC, session management, MFA, passwordless authentication, Tailscale, multi-cloud or hybrid networking, open source participation, Python, Rust, or TypeScript is desirable.
Benefits
- Fully remote, flexible work environment with asynchronous collaboration.
- Comprehensive health, vision, dental, and other group benefits with no waiting period.
- Equity incentive plan and employer-funded retirement contributions matching employee contributions up to 0.75% of eligible compensation.
- Annual professional development budget of $1,500 USD plus mentorship, coaching, and internal promotion opportunities.
- Flexible paid time off and paid parental leave of 20 weeks for birthing parents and 16 weeks for non-birthing parents.
- Company-provided laptop choice, monthly home internet reimbursement, and $500 USD for workstation customization.
- Annual company retreat, team off-sites, and support for intentional in-person collaboration.
- Fully remote team with light travel required under 10%, primarily for team and company onsites, conferences, or customer visits.
Tech Stack
Categories
About Tailscale
Tailscale builds a software-defined mesh VPN that lets individuals and organizations securely connect devices and services using WireGuard and single sign-on. It sells a subscription SaaS with free and paid plans, offering features like access control lists, device authentication, and admin tooling for teams and enterprises. Founded in 2019 and headquartered in Toronto, the company is privately held and used from hobby projects to corporate networks.