Software Engineer, Strategic Projects

Tailscale

7d•CA$218,420 - CA$302,840•Remote

About The Position

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. 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.

Requirements

Ideal candidates will have experience iteratively developing software in startup-like environments.
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 Haves

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

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.

Benefits

Shape emerging AI connectivity standards and Tailscale's product strategy directly.
Work alongside reference customers on real integrations rather than abstract roadmaps.
Collaborate with a small team of motivated, sharp, and fun engineers in a fast-paced, dynamic environment.
An inclusive, flexible environment where you can be your authentic self.
A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
Remote first company—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you).
Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, and the United Kingdom. We support intentional in-person connection through team travel and distributed collaboration.
Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.
Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!
A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $1000 USD to customize your workstation to make it your own.
Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks.