Customer Support Team Lead, Tailscale
$160k
+ Equity
More information about location
A zero config VPN for building secure networks
Be an early applicant
A zero config VPN for building secure networks
201-500 employees
Be an early applicant
$160k
+ Equity
More information about location
201-500 employees
Company mission
To remove overhead and complexity from the “long tail” of software and operational problems that people face every day.
Role
Who you are
- 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
- 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 the job involves
- 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
- 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
Our take
The internet is a global phenomenon, but often online activity is unprotected which leaves users vulnerable to hackers on public networks. Additionally certain sites are inaccessible or censored depending on the users location. Use of a VPN enables a secure connection through an encrypted virtual tunnel which also disguises IP addresses. Traditional VPN's tunnel all network traffic through a central gateway server which can affect reliability, and VPN's almost always slow connection speed.
Tailscale is a VPN service built on top of a secure network fabric, which is unlike a traditional VPN provider as it ensures encrypted point-to-point connections by using the open source WireGuard protocol. Tailscale is configured, on average, in a matter of minutes, while other solutions take weeks to fully implement and then require several hours a week of maintenance.
The product has been well received, with reviewers agreeing that it is easy to set up and a great tool for developers. The company plans to develop its product further by tackling the complexity of software and confronting operational problems that people face daily. Off the back of impressive 2025 funding, Tailscale is expanding its engineering, product and sales teams as well as its global reach, all to empower small teams to build systems that scale, without scaling overhead.
Steph
Company Specialist at Welcome to the Jungle
Insights
81% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Apr 2025
$160m
SERIES C
May 2022
$100m
SERIES B
Total funding: $275m
Company benefits
- Flexible (and reasonable) working hours—work/life balance is exceptionally important to us
- Competitive compensation, stock options and 401(k) (for United States-based employees)
- Comprehensive medical/dental/vision benefits, and more
- 4 weeks of paid vacation (standard across the company) + 12 company holidays per year
- An allowance for equipment to help you personalize your workspace
Company HQ
King West Village, Toronto, ON
Leadership
Avery Pennarun
(Co-Founder & CEO)A range of experience in software engineering including Senior Staff Software Engineer at Google Fiber. They co-founded EQL Data in 2009.
David Crawshaw
(Co-Founder & CTO)Previous experience includes working as a Staff Software Engineer at Google before co-founding Tailscale.
David Carney
(Co-Founder)Co-founded Format in 2012, working as a Full Stack Developer, COO and CFO. Also co-founded Form & Method and The Navarra Group.
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