Software Engineer - Strategic Projects

About the Role

Join our Strategic Projects team, reporting to the team's Engineering Manager and ultimately into our co-founder and Chief Strategy Officer. This team exists to show developers and organizations why Tailscale should be their default connectivity substrate, both for internal infrastructure and for embedding into customer-facing products. Aperture, our identity-aware LLM gateway, is one such initiative.

This is an AI-native team. We use coding agents heavily as a force multiplier and expect every engineer to be a power user. Our customers demand a high bar on code quality, security, and operational rigour, and we treat that as a reason to use every tool available, including LLMs and coding agents, to ship fast without compromising it.

We move fast from idea to prototype, and we're growing the side of the team that's energized by the path from prototype to dependable product. You'll work shoulder-to-shoulder with product-minded engineers from the moment an idea takes shape, shaping how it's built so it holds up later, and co-owning the work of making it production-grade: stable, observable, maintainable, and ready for real customer load. You're the kind of engineer who finds the long tail of development genuinely satisfying, the edge cases, the failure modes, the tests and runbooks, the details that turn a sharp demo into something customers can rely on.

You'll work directly with reference customers on integrations and own the production bar on prototypes that graduate into Tailscale's product surface area, ensuring the security, review, and operational practices that wrap around agent-generated code actually hold in production.

Tailscale is fully remote, this team operates with significant ambiguity, and the shipping cadence is fast. Comfort working asynchronously and collaborating with highly technical customers is essential.

Key Responsibilities

• Partner with product-minded engineers from the start, shaping prototypes (MCP gateways, LLM proxies, sandboxes, remote servers, and similar emerging workloads) so the path to production is built in, not bolted on.
• Co-own the journey from "works in a demo" to "stable in production": hardening, error handling, observability, and operational tooling.
• Own the production bar on prototypes that graduate into Tailscale's product surface area, including the security and review practices that wrap around agent-generated code.
• Work with reference customers to integrate Tailscale, both for internal adoption (VPN replacement with identity-aware networking) and for embedding into their products, with particular attention to reliability, maintainability, and long-term supportability.
• Find and close the long-tail gaps, edge cases, regressions, flaky behavior, missing tests, undocumented operational knowledge, that separate a prototype from a dependable product.
• Establish and maintain the review, testing, and security practices that let the team ship agent-generated code fast without compromising the production bar.
• Light travel required (<10%): primarily team and company onsites, with optional conferences or customer visits concentrated in North America.

What We Are Looking For

Ideal candidates will have experience taking software from prototype to production in startup-like environments. We don't expect expertise with every aspect listed below. Let us know where you feel you have the most experience and where you'd like to keep developing.

• Strong at hardening, stabilizing, and maintaining production software; you take satisfaction in detail-oriented work and in closing the long tail of bugs, edge cases, and operational gaps.
• Go experience is a must; comfort integrating third-party APIs; basic networking.
• Heavy daily use of coding agents (Claude Code, Cursor, or similar) and LLMs in your engineering workflow, with a point of view on where they accelerate work, where they fail, and especially how to wrap them in the review, testing, and security practices that hold the production bar.
• Enjoy collaborating closely with exploratory, product-minded engineers and jointly owning the work of getting something solid into production.
• Comfort with the cadence of a strategy team at an early-ish startup: priorities shift with market signal, prototype-to-production timelines are short, and the bar on what ships stays high regardless.
• Thrive working independently in a remote environment.

Nice to Have

• Experience operating production services: observability, on-call, incident response, performance and reliability work.
• Validating prototype code for production use alongside security teams.
• Identity infrastructure: IdP platforms, identity sync/provisioning, directory services; authentication protocols (OAuth, OIDC, SAML, SCIM); access control models (RBAC/ABAC), session management, MFA, passwordless auth.
• Building applications on top of LLMs and agentic systems (not just using them as dev tools).
• Familiarity with Tailscale itself and with networking challenges in multi-cloud and hybrid deployments.
• Open source community participation; experience producing publicly-visible artifacts (blog posts, talks, reference implementations).
• Python, Rust, and/or TypeScript.

Why You'll Enjoy Working With Us

• Work shoulder-to-shoulder with sharp engineers to turn promising prototypes into products customers depend on.
• Work alongside reference customers on real integrations rather than abstract roadmaps.
• Shape emerging AI connectivity standards and Tailscale's product strategy.
• Collaborate with a small team of motivated, sharp, and fun engineers in a fast-paced, dynamic environment.

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set.

CAN Pay Range 218420 - 302840 CAD