Tailscale

Tailscale

Senior Customer Support Engineer (Tier 3), Customer Escalations

Remote (Canada) · Senior

Sponsorship not specified$154k-$193kDetected 5 days ago
PythonGoNode.jsKubernetesCI/CDLinuxStatisticsCustomer SupportTCP/IPDNSFirewallVPNCollaborationMentoring

About the role

  • From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more.
  • You'll take ownership of our most complex, ambiguous customer escalations, solving issues where the root cause is not always obvious.
  • You will work these issues to resolution or alternatively a fully-documented handoff that engineering can act on without delay.

Responsibilities

  • Own high-severity, post-sales technical escalations from intake through resolution or engineering handoff. This includes deep-dive investigations and reproduction of difficult-to-isolate bugs.
  • Build engineering handoff packages that require minimal follow-up questions: reproducible case, log evidence (timestamps, node IDs), version matrix, impact scope, what's already been ruled out, and a proposed engineering team to own the fix.
  • translate what you learn into product improvements, tooling, and runbooks that raise the technical bar for the whole Support org.
  • Partner with Support, CSE, and Product/Eng, while staying within this team's scope
  • 4+ years in a technical support or escalation role at a SaaS or infrastructure company, with demonstrated ownership of escalated/enterprise-tier accounts.
  • Comfortable owning a live, high-stakes customer call: staying calm, building trust, and communicating clearly with a frustrated or technical customer under pressure.
  • Own high-severity, post-sales technical escalations from intake through resolution or engineering handoff.
  • Monitor for patterns across escalations to catch recurring or systemic issues early; translate what you learn into product improvements, tooling, and runbooks that raise the technical bar for the whole Support org.
  • Track record of independently building reproducible test cases and clear, evidence-backed bug reports engineering can act on directly.
  • We support intentional in-person connection through team travel and distributed collaboration.

Requirements

  • Proficiency with programming/scripting in Go, Python, JSON
  • Experience with packet-level analysis

Skills

  • About Tailscale
  • Strong systems administration skills as well as troubleshooting across Linux, macOS, and Windows.

Compensation

  • 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.
  • Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore.
  • Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.

Benefits

  • An inclusive, flexible environment where you can be your authentic self.
  • 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!
  • Employer-funded retirement contributions.
  • Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
  • 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 $500 USD to customize your workstation to make it your own.
  • Paid parental leave program.
  • We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

Company info

  • Get on calls with customers, pull logs, and communicate with the customer about leading theories
  • What We Are Looking For
  • Investigative mindset; curious to analyze root cause, and evaluate all options to get customers to the best solution
  • As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels.

Equal opportunity

  • If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.
Apply directly at Tailscale →Create a free account for alerts like thisView Tailscale immigration profile

This listing is sourced directly from Tailscale's careers page and normalized into a canonical job model.