IT Manager

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

We’re seeking a talented and motivated IT Manager to join us at Tailscale! 

As the IT Manager at Tailscale you will lead day-to-day operations which will include providing end-user support, making key technical decisions and being the escalation point for our HelpDesk. You will collaborate with HR and Technical Leadership to enforce policies, manage vendor relationships and implement standard operating procedures. 

Key Responsibilities

  • Hands-On IT Leadership: Take an active role in troubleshooting, supporting end-users, and leading the implementation of IT projects
  • HelpDesk & Project Management: main point of contact for all Tailscale users for any and all HelpDesk related issues. 
  • Tech-Stack Decision Making: Oversee tech decisions in coordination with Engineering Leadership, ensuring alignment with company-wide IT standards
  • Platform Expertise: Proficiency in supporting TailScale’s key platforms including Google Workspace and Active Directory 
  • Device Management: Troubleshoot and manage macOS, Linux, and Windows laptops
  • Cybersecurity Ambassador: Maintain a security-first mindset and act as the local ambassador for Cybersecurity by following corporate governance guidelines and assisting with security audits
  • Team Collaboration: Maintain close communication with leadership and business units to ensure customer satisfaction and timely response to business needs
  • Asset and Vendor Management: Assist in managing IT assets, procurement, and vendor relationships

What We Are Looking For

  • Education & Experience:
    • Bachelor’s or Master’s Degree in Computer Information Systems, Information Technology, or related experience 
    • 5+ years of IT management experience
    • 4+ years of HelpDesk management experience
  • Fast-Paced Environment Experience: Experience working in fast-growing, ambiguous environments
  • Technical Expertise:
    • Proficiency with Google Workspace, macOS (MBP), and serverless SaaS environments
    • Experience in vendor management and contract lifecycle management
  • Project Management: Strong ability to prioritize tasks, manage multiple projects, and effectively oversee change control processes
  • Communication Skills: Excellent written, oral, and interpersonal communication skills
  • Team-Oriented: Self-starter who thrives in a collaborative environment and knows when to ask for help

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

$161,000 - $196,700 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! We encourage all Tailscalars to take 4-6 weeks of vacation annually. 
  • 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. 

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