1,812,230open jobs
104,203companies
275,210added this week
Browse all
Salary
≈ $53k – $103k per year (Estimated)
Location
Remote (Canada)also open in United States
Seniority
Middle · 4+ years exp

Confirmed on the employer's own hiring board on Oct 17, 2026. First seen by Alion on Jun 30, 2026.

Overview
Company
Impact
Profile match
Tailscale is a technology company that provides a zero-config mesh VPN service designed to simplify secure networking for individuals and enterprises. Founded in 2019 by former Google engineers and headquartered in Toronto, Canada, the company builds its solution on the open-source WireGuard protocol to establish direct, end-to-end encrypted connections between devices. Its identity-driven platform eliminates the complexity of traditional networking infrastructure, allowing users to safely connect devices, multi-cloud workloads, and remote teams without managing firewall rules or port forwarding.

Thank you for considering Tailscale. If this job description resonates with you, please apply. 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!

About Tailscale 

Tailscale is making safe connection effortless 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

We’re seeking a talented and motivated full-time Software Engineer to join our growing team. You will work as part of the engineering team to:

  • Develop the Tailscale product, contributing to client code and backend services. The client code is a mix of C#, XAML, and Go. Prior Go expertise is not a requirement. 
  • Bring a special focus on our Windows platform, building and maintaining our Windows client using the modern WinUI/Windows App SDK stack, while contributing to common code that supports macOS, mobile, and other core client platforms.

Because we’re an early-stage and fully remote company, we’re looking for a motivated individual who can help move the product forward. The ability to think on your feet, collaborate with highly technical teams, and comfort working asynchronously are essential.

Key Responsibilities

  • Work with engineers on a native Windows desktop client using Windows App SDK, WinUI, C#, XAML and Go
  • Implement support for the latest Windows platform features while maintaining compatibility with a subset of older versions
  • Develop and optimize product features on Windows, with a focus on UI components and platform integration
  • Develop and maintain unit and integration tests using Microsoft Testing Platform v2 and xUnit
  • Contribute to common, cross-platform Tailscale code

What We Are Looking For

  • Four or more years of experience in software development
  • Strong understanding of software development principles, capabilities, and limitations of the Windows platform
  • Proficiency in C# and modern native UI frameworks (WinUI/UWP/WPF)
  • Experience with general networking concepts - DNS, VPNs, IP Networking, routing, etc.
  • Excellent written and verbal communication skills
  • Ability to give and process constructive feedback, as well as work independently
  • Flexibility to adjust to the dynamic nature of a startup

Nice to Have

  • Experience with WinUI 3 and Windows App SDK
  • Experience developing native Windows applications and services
  • Familiarity with Windows networking stack and Windows Filtering Platform
  • Familiarity with Windows security model, session isolation, access tokens and related concepts
  • Proficiency in Go

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

$191,620—$239,860 CAD

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.

Free account
Stop reading job ads. Get the ones that fit.
One free account turns this page into a shortlist built around your stack, your level and your pay.
Match on every job. Stack, seniority, pay and location, scored against your profile.
1,812,230 open roles. Read straight off company career pages, refreshed every day.
Unlimited applications. Every one you send is tracked in one place, on-site or on a company board.
3 tailored CVs a month. Rewritten for the exact job you are applying to. Included free.
Create a free account Continue with Google
Free forever. No card. Under a minute.

Your match

How well do you fit this role?
Two answers are enough for a real match. No account needed.
Check my fit
Answers stay in this browser until you create an account.

Recommended for you based on this role

Industrial Engineering
Similar stack
Same company
Canada
Mechanical Engineer 18 days ago
$70k – $86k per year • In office • 8+ years exp • Toronto
Apply
≈ $94k – $178k per year (Estimated) • Remote (United States) • 12+ years exp • Bachelor's Degree • Austin
Python
Java
SQL
AI/ML
Claude Code
LLM
DevOps
Splunk
Terraform
Puppet
Ansible
GCP
Istio
CloudFormation
Prometheus
Azure
CI/CD
Git
AWS
Docker
Kubernetes
Grafana
Service Mesh
Configuration Management
Amazon EC2
Linux
Unix
Apply
≈ $92k – $174k per year (Estimated) • Remote (United States) • Full-Time • 7+ years exp • Bachelor's Degree • United States
Python
Apply
$70k – $95k per year • In office • 7+ years exp • Bachelor's Degree • Calgary
Design
AutoCAD
Apply
$89k – $109k per year • In office • 10+ years exp • Bachelor's Degree • Toronto
Apply
≈ $85k – $172k per year (Estimated) • In office • Top Secret • Full-Time • 4+ years exp • Bachelor's Degree • El Segundo
SQL
DevOps
Red Hat
VMWare
Debian
Windows Server
Linux
Windows
DNS
DHCP
Cybersecurity
Active Directory
Management
Agile
Apply
Software Engineer 1 day ago
≈ $99k – $210k per year (Estimated) • Hybrid • Full-Time • Olivette
JavaScript
TypeScript
SQL
C#
C#
.NET
Entity Framework Core
Databases
MS SQL
AI/ML
AI Agents
Frontend
Angular
Mobile
MVVM
DevOps
Rest API
CI/CD
Git
Apply
Software Engineer 1 day ago
≈ $123k – $225k per year (Estimated) • In office • Secret • Full-Time • 5+ years exp • Bachelor's Degree • Las Cruces
Python
Java
SQL
PowerShell
C++
Ada
DevOps
GitLab CI
CI/CD
Git
Configuration Management
GitLab
Windows
Cybersecurity
Wireshark
Management
Jira
Agile
Waterfall
Apply
$80k per year • Hybrid • 2+ years exp • Bachelor's Degree • Moscow
JavaScript
TypeScript
SQL
C#
C#
.NET
Frontend
React.js
DevOps
Rest API
Vercel
Management
Agile
Apply
≈ $37k – $79k per year (Estimated) • Equity • In office • 1+ year exp • High School Diploma • Phoenix
DevOps
Windows
Management
Outlook
Apply
$115k – $144k per year • Equity • Remote (United States) • PhD • United States
Python
DevOps
CI/CD
Kubernetes
Windows
TCP/IP
DNS
VPN
Wi-Fi
Apply
≈ $53k – $111k per year (Estimated) • Equity • Remote (Canada) • PhD • Canada
Python
DevOps
CI/CD
Kubernetes
Windows
TCP/IP
DNS
VPN
Wi-Fi
Apply
Windows Engineer 18 days ago
$143k – $179k per year • Equity • Remote (United States) • 4+ years exp • PhD • United States
Go
C#
DevOps
Windows
DNS
Wi-Fi
Apply
≈ $67k – $127k per year (Estimated) • Equity • Hybrid • 2+ years exp • PhD • Vancouver • Toronto
DevOps
Wi-Fi
Apply
$181k – $226k per year • Equity • Remote (United States) • PhD • United States
DevOps
CI/CD
AWS
Kubernetes
Wi-Fi
Apply
$42k – $56k per year • Equity • In office • Full-Time • Bachelor's Degree • Canada
Apply
Area Manager II 9 hours ago
$53k – $74k per year • Equity • In office • Full-Time • 2+ years exp • Bachelor's Degree • Canada
Apply
$50k – $59k per year • Equity • In office • Full-Time • Bachelor's Degree • Canada
Apply
Area Manager II, YOW3 9 hours ago
$53k – $74k per year • Equity • In office • Full-Time • 2+ years exp • Bachelor's Degree • Canada
Apply
≈ $51k – $91k per year (Estimated) • Hybrid • 10+ years exp • Canada
Management
Confluence
Jira
Agile
Scrum
Waterfall
Apply
See all jobs
This is one of many
1,812,230 more open roles from verified company boards, updated every day.