Software Engineer – Strategic Projects

🕒 Yesterday

🌐 Canada, United States – Remote

🇨🇦 Canada – Remote 🇺🇸 United States – Remote

💵 $218.4k - $302.8k / year

⏰ Full Time

🟡 Mid-level

🟠 Senior

🧑‍💻 Full-stack Engineer

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Tailscale

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2020

☁️ SaaS

🔐 Security

📡 Telecommunications

💰 $100M Series B on 2022-05

SaaS • Security • Telecommunications

Tailscale is a company that provides a modern VPN solution founded on WireGuard technology, simplifying networking by creating secure, software-defined networks that connect users, services, and devices with ease. By eliminating the complexities of legacy VPNs, Tailscale offers secure remote access, site-to-site networking, and multi-cloud networking, all while ensuring user-friendly, quick deployment without complex configurations. Recognized for enabling zero-trust environments and seamless workflows, Tailscale supports robust security features such as automated user onboarding, encryption, and access control lists (ACLs). This tool is particularly popular for both enterprise and personal use, praised for its integration capabilities and ease of use, making secure networking accessible anywhere, regardless of infrastructure.

📋 Description

• Partner with product-minded engineers from the start 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 through hardening, error handling, observability, and operational tooling • Own the production bar for prototypes entering Tailscale's product surface, including security and review practices around agent-generated code • Work directly with reference customers on Tailscale integrations for internal adoption and product embedding • Identify and close edge cases, regressions, flaky behavior, missing tests, and undocumented operational gaps • Establish and maintain review, testing, and security practices for rapidly shipping agent-generated code • Travel less than 10%, primarily for team and company onsites, with optional conferences or customer visits in North America

🎯 Requirements

• Experience taking software from prototype to production in startup-like environments • Strong ability to harden, stabilize, and maintain production software • Go experience is required • Comfort integrating third-party APIs • Basic networking knowledge • Heavy daily use of coding agents such as Claude Code or Cursor and LLMs in the engineering workflow • Ability to establish review, testing, and security practices for agent-generated code • Comfort collaborating with exploratory, product-minded engineers • Comfort with rapidly shifting priorities and short prototype-to-production timelines • Ability to work independently in a remote environment • Nice to have: production service operations, observability, on-call, incident response, performance and reliability work • Nice to have: security validation of prototype code • Nice to have: identity infrastructure, IdP platforms, identity sync/provisioning, directory services, OAuth, OIDC, SAML, SCIM, RBAC/ABAC, session management, MFA, and passwordless authentication • Nice to have: applications built on LLMs and agentic systems • Nice to have: Tailscale and multi-cloud or hybrid networking familiarity • Nice to have: open source participation and publicly visible technical artifacts • Nice to have: Python, Rust, and/or TypeScript

🏖️ Benefits

• Equity incentive plan • Comprehensive group benefits with no waiting period, including health, vision, and dental coverage for you and your family • Flexible remote-first work environment • Corporate co-working program • Employer-funded retirement contributions matching contributions dollar-for-dollar, up to 0.75% of eligible compensation • Annual company retreat and team off-sites • $1500 USD annually for professional development • Mentorship, coaching, and internal promotion opportunities • Flexible paid time off program • Company-owned laptop, with choice of Mac or PC • Monthly home internet reimbursement • $500 USD workstation customization allowance • Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents • Inclusive and accessible hiring process with accommodations available