Tailscale

Software Engineer, Strategic Projects

Remote (Canada)

Sponsorship not specified$218k-$303kDetected 5 days ago

PythonRustOAuthLLMsAgentic AIStatisticsIncident ResponseCadenceVPNCollaborationMentoring

About the role

From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more.
Job 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.

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.
Establish and maintain the review, testing, and security practices that let the team ship agent-generated code fast without compromising the production bar.
We support intentional in-person connection through team travel and distributed collaboration.
Support for your personal and professional development.
Building applications on top of LLMs and agentic systems (not just using them as dev tools).
Collaborate with a small team of motivated, sharp, and fun engineers in a fast-paced, dynamic environment.

comfort integrating third-party APIs
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.

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.
Open source community participation
experience producing publicly-visible artifacts (blog posts, talks, reference implementations).
Python, Rust, and/or TypeScript.

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.
Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.

An inclusive, flexible environment where you can be your authentic self.
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!
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.
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).

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.
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.

If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.

This listing is sourced directly from Tailscale's careers page and normalized into a canonical job model.