Note: The job is a remote job and is open to candidates in USA. Tailscale is a company dedicated to building a secure and interconnected Internet for users of all sizes. They are seeking a Senior Customer Support Engineer (Tier 3) to manage complex customer escalations, ensuring effective communication between customers and engineering teams to resolve technical issues efficiently.
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
- Get on calls with customers, pull logs, and communicate with the customer about leading theories
- 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
- File and track issues for confirmed bugs, keeping the ticket/issue link intact so engineering retains full customer context
- 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
- Partner with Support, CSE, and Product/Eng, while staying within this team's scope
Skills
- 4+ years in a technical support or escalation role at a SaaS or infrastructure company, with demonstrated ownership of escalated/enterprise-tier accounts
- A genuine problem-solver who gets energy from untangling hard, ambiguous technical issues
- Comfortable owning a live, high-stakes customer call: staying calm, building trust, and communicating clearly with a frustrated or technical customer under pressure
- Hands-on networking experience in production or homelab environments: TCP/IP, routing, DNS, firewalls, NAT, VPNs, load balancers
- Deep familiarity with overlay networking concepts — WireGuard, UDP hole punching, STUN — and comparable VPN/networking products
- Code-level debugging capability: can read Go source, reason about goroutines/locks/channels, read pprof CPU/heap profiles, and understand network interface semantics
- Comfortable with infrastructure concepts: cloud IaaS, CI/CD pipelines, containerized applications, and Kubernetes debugging
- Strong systems administration skills as well as troubleshooting across Linux, macOS, and Windows
- Track record of independently building reproducible test cases and clear, evidence-backed bug reports engineering can act on directly
- Strong technical storytelling: able to distill highly technical, ambiguous issues into clear narratives for both engineers and non-technical stakeholders
- Investigative mindset; curious to analyze root cause, and evaluate all options to get customers to the best solution
- Proficiency with programming/scripting in Go, Python, JSON
- Experience with packet-level analysis
Benefits
- An inclusive, flexible environment where you can be your authentic self.
- 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.
- 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.
- 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, the United Kingdom, and Singapore. 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 $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 Overview
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