Software Engineer, Strategic Projects

Role Description

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 rigor, and we treat that as a reason to use every tool available, including LLMs and coding agents, to ship fast without compromising it.

You will build prototypes and POCs, work directly with reference customers on integrations, and produce externally-visible artifacts (blog posts, reference repos, conference demos, customer integrations) that demonstrate how Tailscale's emerging platform solves real problems in AI infrastructure, agentic tooling, and identity-aware networking.

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

• Build prototypes and POCs that showcase Tailscale for AI agents and tooling (MCP gateways, LLM proxies, sandboxes, remote servers, and similar emerging workloads).
• Work with reference customers to integrate Tailscale, both for internal adoption (VPN replacement with identity-aware networking) and for embedding into their products to enable secure customer connectivity.
• Create reference architectures and share your work through documentation, open source, community engagement, and conference presentations.
• Rapidly iterate with input from colleagues and reference customers; turn customer conversations into shippable prototypes and reference designs.
• Hold the production bar on prototypes that often graduate into Tailscale's product surface area, including the security and review practices that wrap around agent-generated code.
• Light travel required (~10-15%): primarily team and company onsites, with occasional conferences or customer visits concentrated in North America with potential trips to EU or APAC.

Qualifications

• Strong at rapid prototyping, explaining technical concepts, and working directly with customers in an exploratory, fast-paced environment.
• 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 how to wrap them in review and security practices that hold the production bar.
• 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

• Building applications on top of LLMs and agentic systems (not just using them as dev tools).
• 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.
• Validating prototype code for production use alongside security teams.
• 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.

Benefits

• An inclusive, flexible environment where you can be your authentic self.
• A competitive total compensation package, including a base salary, an equity incentive plan, and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period, covering health, vision, dental, and more for you and your family.
• Remote first company—most of our teams work fully remotely.
• Support for your personal and professional development with $1500 USD annually for professional development.
• Flexible, paid time off program to support any situation life throws your way.
• A build-your-own home office setup with a company-owned laptop and $1000 USD to customize your workstation.
• Generous parental leave program from your first day.