Team Lead, Customer Support

Tailscale

1d • $214,400 - $214,400 • Remote

About The Position

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.

Requirements

• 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

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.

Benefits

• 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).
• 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.
• 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.
• Flexible, paid time off program
• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed