Remote Team Lead, Customer Support

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

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 are seeking a Team Lead, Customer Support to serve as a player-coach responsible for the daily operations and professional growth of a team of 8-10 Support Engineers. You will bridge the gap between frontline technical troubleshooting and strategic alignment, ensuring Support Engineers are engaged and delivering high quality customer support to all of our users. Reporting directly to the VP of Customer Engineering, you will align your team’s performance with departmental goals, manage technical escalations, and help serve as a voice of the customer to the broader organization.

Key Responsibilities

• Manage day-to-day support operations for a team of 8-10 Support Engineers.
• Lead the onboarding, technical mentoring, and career coaching for all direct reports.
• Conduct regular 1:1s and performance management reviews to ensure team alignment and growth.
• Oversee the support queue to ensure SLA/SLO adherence, including response and resolution times.
• Act as an internal escalation point for both complex technical issues and difficult customer situations.
• Align team activities and outcomes with the strategic roadmap set by the VP of Customer Engineering.
• Partner with Support and CX Operations to refine workflows and improve internal tooling like Jira, Incident.io, Kapa.ai, and PagerDuty.
• Perform regular QA reviews on tickets to maintain technical accuracy and brand voice.
• Analyze support data and customer feedback (CSAT) to identify and report trends to leadership.

What We Are Looking For

• 4+ years of experience in a technical support role within a SaaS environment
• 1+ years of experience in a leadership, management, or formal mentoring capacity
• Strong technical background in networking fundamentals (TCP/IP, DNS, firewalls, and routing)
• Proficiency with networking and security concepts (k8s a plus)
• Experience with identity management and SSO integrations such as Okta, Azure AD, and Google
• Previous experience in supporting customers across OS’s (Linux, MacOS, Windows, etc)
• Proven ability to manage and optimize support workflows across processes and tooling
• Data-driven mindset with the ability to track and act on metrics like CSAT, TTFR, and TTR
• Excellent communication skills for translating technical concepts to both customers and internal stakeholders
• Ability to thrive in a fast-paced environment while managing multiple competing priorities

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

$214,400 – $214,400 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!
• 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.
• 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, and the United Kingdom. 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 $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.