Customer Support Team Lead - Remote & Mentorship

Bilinguallink; Montreal (administrative region); Remote; CAD 193,000 - 236,000; Full time

Benefits offered by this job

Remote-first culture

Equity & base salary as part of total:

Professional development budget

Home office stipend

Annual company retreat

Comprehensive benefits

Parental leave

WeWork/ coworking options

Job summary

Tailscale is seeking a Team Lead, Customer Support to guide a team of 8–10 Support Engineers, bridging frontline troubleshooting with strategy. You will mentor, manage performance, and ensure timely responses while aligning activities with the VP of Customer Engineering.

This remote-first role focuses on scaling support quality and workflows across platforms. We value data-driven thinking, strong communication, and the ability to navigate a fast-paced SaaS environment.

Qualifications

• 4+ years in a technical SaaS support role
• 1+ year in leadership, management, or mentoring
• Strong networking and security knowledge (incl. TCP/IP, DNS, firewalls, routing)
• Experience with identity management and SSO integrations (Okta, Azure AD, Google)
• Ability to improve support workflows across processes and tooling
• Data-driven mindset with metrics like CSAT, TTFR, and TTR

Responsibilities

• Manage day-to-day operations for a team of 8–10 Support Engineers
• Lead onboarding, mentoring, and career coaching for direct reports
• Conduct regular 1:1s and performance reviews
• Oversee SLA/SLO adherence and resolve escalations
• Align team activities with the VP of Customer Engineering's roadmap
• Improve workflows with Jira, Incident.io, and PagerDuty
• Perform QA reviews on tickets to ensure accuracy and brand voice
• Report trends to leadership based on CSAT data

Skills

Leadership

Networking fundamentals

Identity management

OS support (Linux, MacOS, Windows)

Data-driven

Excellent communication

Prioritization/multi-tasking

CSAT/TTFR/TTR analytics

Tools

Jira

Incident.io

Kapa.ai

PagerDuty

Job description

Tailscale is seeking a Team Lead, Customer Support to guide a team of 8–10 Support Engineers, bridging frontline troubleshooting with strategy. You will mentor, manage performance, and ensure timely responses while aligning activities with the VP of Customer Engineering.

This remote-first role focuses on scaling support quality and workflows across platforms. We value data-driven thinking, strong communication, and the ability to navigate a fast-paced SaaS environment.