Software Engineer-Infrastructure & Tooling

Remote (Canada)

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.

Job Description

Tailscale is looking for an Infrastructure Engineer to build and maintain the critical systems that power our globally distributed infrastructure. You’ll design and automate systems at scale, write internal tools in Go, and take ownership of the infrastructure that enables every engineering and business function across the company.

This role is ideal for engineers with a traditional ops background who have evolved into software-focused infrastructure roles—someone who thrives in building reliable, observable, self-healing systems in production, and enjoys solving deep technical challenges across cloud platforms.

Key Responsibilities

  • Build and operate the internal infrastructure that supports our engineers, services, and customers.
  • Write internal tools and services in Go to automate manual workflows, enhance developer productivity, and surface operational insights.
  • Design and evolve our multi-cloud infrastructure (primarily AWS, but also GCP, Digital Ocean, etc.) with a focus on security, reliability, and cost-effectiveness.
  • Own our CI/CD pipelines and infrastructure-as-code tooling.
  • Respond to production incidents, contribute to blameless postmortems, and continuously improve system reliability.
  • Instrument systems for observability, proactively surfacing issues through metrics, logs, and traces.
  • Collaborate across engineering, product, and internal teams to ship high-impact projects and provide infrastructure expertise.

What We Are Looking For

  • Have professional experience in infrastructure, SRE, or DevOps roles, especially in production environments.
  • Have strong proficiency in Go, or are comfortable writing production-quality tooling in another systems language and eager to work with Go.
  • Have built or supported high-availability distributed systems at scale.
  • Know your way around cloud platforms (AWS is ideal, but multi-cloud experience is even better).
  • Are fluent in infrastructure as code (Terraform preferred), and have experience with CI/CD systems.
  • Know how to triage and mitigate production issues quickly and effectively.
  • Understand networking fundamentals (TCP/IP, DNS, routing, VPNs).
  • Care deeply about reliability, but also about usability and developer experience.
  • Communicate clearly and thrive in an async-first, remote-friendly culture.

 

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 Ranges

$218,420 - $273,360 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!
  • All-remote with the opportunity to work from anywhere—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/department off-sites, or use your individual travel budget to meet up with team members in Canada, the US, or the UK. 
  • 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. 

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.

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