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Software Engineer, Strategic Projects

1 month, 3 weeks ago
Canada
Full-time
Senior
Software Engineer
Software Development
Go LLM OAuth OpenID Connect Python Rust SAML TypeScript
Apply Now
Tailscale

Tailscale

Tailscale is a zero config VPN service that simplifies network security and connectivity for teams of any scale, offering easy deployment, minimal latency, and compatibility with existing services.

Diversified Telecommunication Services
51-250
Founded 2019
$115M raised
View All Jobs 22

Description

  • Build prototypes and proof-of-concepts for AI agents, tooling, and emerging workloads such as MCP gateways, LLM proxies, sandboxes, and remote servers.
  • Work directly with reference customers to integrate Tailscale for internal adoption and product embedding.
  • Create reference architectures and externally visible artifacts through documentation, open source work, community engagement, and conference presentations.
  • Rapidly iterate on customer feedback to turn conversations into shippable prototypes and reference designs.
  • Maintain a production-quality bar on prototypes that may become part of Tailscale's product surface area, including security and review practices for agent-generated code.
  • Collaborate asynchronously with a fully remote team in a fast-moving environment with significant ambiguity.
  • Travel about 10-15% for onsites, conferences, and customer visits, primarily in North America with possible trips to the EU or APAC.

Requirements

  • Experience iteratively developing software in startup-like environments.
  • Strong ability to rapidly prototype, explain technical concepts, and work directly with customers in an exploratory, fast-paced setting.
  • Go experience is required.
  • Comfort integrating third-party APIs.
  • Basic networking knowledge.
  • Heavy daily use of coding agents such as Claude Code, Cursor, or similar, plus LLMs in an engineering workflow.
  • A point of view on where AI tools accelerate work, where they fail, and how to apply review and security practices to keep code production-ready.
  • Comfort with shifting priorities, short prototype-to-production timelines, and high shipping standards in an early-stage strategy team.
  • Ability to thrive independently in a remote environment.
  • Experience building applications on top of LLMs and agentic systems (preferred).
  • Experience with identity infrastructure, including IdP platforms, identity sync/provisioning, directory services, OAuth, OIDC, SAML, SCIM, RBAC/ABAC, session management, MFA, and passwordless auth (preferred).
  • Experience validating prototype code for production use alongside security teams (preferred).
  • Familiarity with Tailscale and networking challenges in multi-cloud or hybrid deployments (preferred).
  • Open source community participation or experience producing public artifacts such as blog posts, talks, or reference implementations (preferred).
  • Experience with Python, Rust, and/or TypeScript (preferred).

Benefits

  • Competitive total compensation package with base salary, equity, and variable commission for quota-based roles.
  • CAN pay range of $218,420 to $302,840 CAD.
  • Comprehensive group benefits with no waiting period, including health, vision, and dental coverage for employees and families.
  • Remote-first work environment with flexibility in where and when you work.
  • Annual $1,500 USD professional development budget plus mentorship, coaching, and internal promotion opportunities.
  • Flexible paid time off to support work-life integration.
  • Home office support including a company-owned laptop, monthly home internet reimbursement, and $1,000 USD for workstation setup.
  • Generous parental leave with top-ups for up to 26 weeks from day one.

Interested in this position?

Apply directly on the company website

Apply Now

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