Tailscale

Tailscale is a software company that provides zero-configuration virtual private networks (VPNs) for secure connectivity.

51-100 employees

Founded 2019

$100.5M series b

Infrastructure

Private Company

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Infrastructure Information Technology Cyber Security Network Security

Remote-First Company

This company operates with a remote-first culture, allowing team members to work from anywhere.

Open Positions18

Remote (United States)Full-TimeSoftware, SaaSPosted

Customer Support Engineer

Serve as the primary escalation point for technically complex tickets raised by paying customers, taking full ownership through to resolution.
Diagnose and troubleshoot advanced Tailscale-specific issues like ACL misconfigurations, subnet routing/exit node configurations, and integration with identity providers.
Manage a ticket queue with a consistent focus on SLA adherence, ensuring timely first responses and resolutions.
Drive positive user outcomes and maintain high CSAT scores by providing clear, helpful, and accurate technical guidance.
Balance a high volume of daily ticket replies while maintaining the technical depth required to troubleshoot complex networking issues.
Partner cross-functionally to identify recurring friction points and advocate for improvements to the user experience.
Own escalations of technically complex tickets from Tier 1, ensuring issues beyond Tier 1's scope are resolved efficiently.
Mentor and support Tier 1 colleagues through ticket reviews, escalation guidance, and documentation contributions.

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Showing 1 of 18 positions

About Tailscale

Tailscale is building the new internet, simplifying private networks with secure, identity-based connectivity. They replace legacy VPNs, SASE, and PAM solutions. You can easily connect remote teams, multi-cloud environments, and even AI workloads. Tailscale streamlines connectivity for DevOps, IT, and Security teams, minimizing latency and improving reliability. Founded in 2019, Tailscale is headquartered in Toronto, Ontario, Canada.

How We Work

Tailscale embraces a remote-first philosophy, empowering you to work from almost anywhere with Wi-Fi. This inclusive environment values diverse voices and backgrounds, recognizing their impact on product and company growth. You will find flexibility in how and when you work, integrating work and life. Tailscale believes in real people solving concrete problems, focusing on decentralization, encryption, and scalability as tools for effective solutions. They foster a culture of curiosity, accountability, and customer empathy. They encourage clear communication and constructive feedback.

Engineering at Tailscale

Engineers at Tailscale are pioneering a new internet, making secure connectivity simple and transparent. They build on WireGuard's Noise protocol encryption, a trusted, peer-reviewed standard. Their solutions address the complexity of traditional VPNs, which often lead to performance issues and security vulnerabilities. Tailscale focuses on direct device-to-device connections, avoiding centralized bottlenecks for higher throughput and lower latency. This approach improves stability and reliability by reducing single points of failure. Tailscale's technology is infrastructure-agnostic, supporting diverse operating systems and cloud environments.

Why Join Us

Shape the future of internet connectivity, building an easier, more sensible, and safer online experience.
Work in a fully distributed team across Canada, the United States, and the United Kingdom, connecting in-person at annual company retreats.
Grow your career with $1500 USD annually for professional development, mentorship, and internal promotion opportunities.
Customize your workstation with a company-provided laptop, monthly internet reimbursement, and a $1000 USD home office setup bonus.
Benefit from a generous parental leave program with top-ups for up to 26 weeks, demonstrating care for your life outside of work.

Benefits & Perks

Competitive total compensation package including base salary and equity incentive plan.
Comprehensive group health, vision, and dental benefits with no waiting period.
Flexible paid time off program and 12 paid company holidays, plus holiday closures between December 24th - January 1st.
Monthly home internet reimbursement.
$1000 USD to customize your home workstation.
Up to 26 weeks of parental leave with top-ups.
$1500 USD annually for professional development.
Corporate co-working program for access to WeWork or similar spaces.
Employee assistance programs.

Tech Stack

mobileframework

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