IT Manager

Summary

Join Tailscale as our talented and motivated IT Manager! Lead day-to-day IT operations, providing end-user support and making key technical decisions. Collaborate with HR and Technical Leadership to enforce policies, manage vendor relationships, and implement standard operating procedures. You will be the escalation point for our HelpDesk and oversee tech decisions, ensuring alignment with company-wide IT standards. This role requires proficiency in supporting Tailscale’s key platforms and managing various devices. Maintain a security-first mindset and act as the local ambassador for Cybersecurity. We offer a competitive compensation package and comprehensive benefits.

Requirements

• Hold a Bachelor’s or Master’s Degree in Computer Information Systems, Information Technology, or related experience
• Possess 5+ years of IT management experience
• Have 4+ years of HelpDesk management experience
• Demonstrate experience working in fast-growing, ambiguous environments
• Show proficiency with Google Workspace, macOS (MBP), and serverless SaaS environments
• Have experience in vendor management and contract lifecycle management
• Possess a strong ability to prioritize tasks, manage multiple projects, and effectively oversee change control processes
• Exhibit excellent written, oral, and interpersonal communication skills
• Be a self-starter who thrives in a collaborative environment and knows when to ask for help

Responsibilities

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

Benefits

• Competitive total compensation package including base salary, an equity incentive plan and variable commission (for quota-based roles)
• Comprehensive group benefits with no waiting period. Coverage for health, vision, dental, and more for you and your family!
• All-remote work with the opportunity to work from anywhere
• Opportunity to participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you)
• Annual company retreat, team/department off-sites, or individual travel budget to meet up with team members in Canada, the US, or the UK
• $1500 USD annually for professional development, mentorship, coaching, and internal promotion opportunities
• Flexible, paid time off program
• Encouragement to take 4-6 weeks of vacation annually
• Company-owned laptop (Mac or PC), monthly home internet reimbursement, and $1000 USD to customize your workstation
• Generous parental leave program from your first day, with parental leave top-ups for up to 26 weeks