Software Engineer, Strategic Projects

About Tailscale 

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

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 $218,420 — $302,840 CAD

Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications.  We encourage you to help us break that statistic!

What We Offer

An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.

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). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.

Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.

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, the United Kingdom, and Singapore. 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 $500 USD to customize your workstation to make it your own. 

Paid parental leave program . We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.

Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.

Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness .