2 months ago
Remote, United StatesSenior
Base Salary
$163k - $226k/yr
Responsibilities
- Partner with product-minded engineers to shape prototypes such as MCP gateways, LLM proxies, sandboxes, and remote servers for production readiness.
- Co-own the transition from demos to stable production software through hardening, error handling, observability, and operational tooling.
- Own the production, security, review, testing, and operational bar for prototypes that become part of Tailscale’s product surface.
- Integrate Tailscale with reference customers for internal identity-aware networking adoption and embedding into customer products.
- Identify and resolve edge cases, regressions, flaky behavior, missing tests, and undocumented operational knowledge.
- Establish practices that enable rapid delivery of agent-generated code without compromising security or production quality.
- Travel under 10% for team and company offsites, conferences, or customer visits, primarily in North America.
Requirements
- Go experience is required, along with comfort integrating third-party APIs and basic networking knowledge.
- Heavy daily use of coding agents such as Claude Code or Cursor and LLMs in the engineering workflow is expected.
- Experience taking software from prototype to production in a startup-like environment is sought.
- Strong production hardening, stabilization, maintenance, debugging, testing, and operational-quality skills are required.
- Candidates should be comfortable collaborating with product-minded engineers, working independently in a fully remote environment, and handling shifting priorities.
- Preferred experience includes operating production services, observability, on-call, incident response, performance and reliability work, and validating prototypes with security teams.
- Preferred identity experience includes IdP platforms, identity synchronization and provisioning, directory services, OAuth, OIDC, SAML, SCIM, RBAC, ABAC, session management, MFA, and passwordless authentication.
- Experience building applications on top of LLMs and agentic systems, familiarity with Tailscale and multi-cloud or hybrid networking, open source participation, and public technical artifacts are beneficial.
- Python, Rust, and/or TypeScript experience is nice to have.
Benefits
- Fully remote work with flexible scheduling and a corporate co-working program.
- Comprehensive health, vision, dental, and family benefits with no waiting period.
- Annual company retreat, team off-sites, and distributed collaboration across Canada, the United States, the United Kingdom, and Singapore.
- $1,500 USD annually for professional development, plus mentorship and coaching opportunities.
- Flexible paid time off.
- Company-owned Mac or PC laptop, monthly home internet reimbursement, and a home-office setup allowance.
- Paid parental leave of up to 20 weeks for birthing parents and 16 weeks for non-birthing parents.
- Light travel required at under 10%, primarily for team and company offsites, with optional conferences or customer visits in North America.
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.