Senior Customer Support Engineer – Customer Escalations

This is a fully remote position, open to applicants in United States.

📋 Description

• Take ownership of high-severity, post-sales technical escalations, guiding them from initiation to resolution or handoff to engineering. This involves conducting thorough investigations and reproducing challenging bugs.

• Engage in calls with customers, gather logs, and communicate leading theories with them.

• Create engineering handoff packages that minimize the need for follow-up inquiries: these should include a reproducible case, log evidence (timestamps, node IDs), a version matrix, scope of impact, exclusions already considered, and a proposed engineering team to address the fix.

• Log and monitor confirmed bugs, ensuring the ticket/issue link remains intact for engineering to maintain full customer context.

• Analyze patterns in escalations to identify recurring or systemic issues early; leverage insights gained to drive product enhancements, tooling, and runbooks that elevate the technical standards for the entire Support organization.

• Collaborate with Support, CSE, and Product/Eng, while remaining focused on this team's responsibilities.

⛳️ Requirements

• A minimum of 4 years' experience in a technical support or escalation role within a SaaS or infrastructure company, showcasing ownership of escalated or enterprise-tier accounts.

• A true problem-solver who thrives on unraveling complex, ambiguous technical challenges.

• Proficient in managing high-pressure customer calls: maintaining composure, building trust, and communicating effectively with frustrated or technical customers.

• Practical networking experience in production or homelab settings: TCP/IP, routing, DNS, firewalls, NAT, VPNs, load balancers.

• Strong understanding of overlay networking concepts, including WireGuard, UDP hole punching, STUN, and similar VPN/networking solutions.

• Capable of code-level debugging: able to read Go source, understand goroutines/locks/channels, interpret pprof CPU/heap profiles, and grasp network interface semantics.

• Familiarity with infrastructure concepts: cloud IaaS, CI/CD pipelines, containerized applications, and Kubernetes debugging.

• Solid systems administration skills and troubleshooting experience across Linux, macOS, and Windows.

• Proven ability to independently create reproducible test cases and clear, evidence-backed bug reports that engineering can promptly act on.

• Exceptional technical storytelling skills: capable of translating complex, ambiguous issues into clear narratives for both technical and non-technical audiences.

• An investigative mindset; eager to analyze root causes and explore all options to guide customers toward optimal solutions.

• Proficient in programming/scripting with Go, Python, and JSON.

• Experience with packet-level analysis.

🏝️ Benefits

• An inclusive and flexible work environment where you can express your authentic self.

• A competitive total compensation package that includes a base salary, equity incentive plan, and variable commission (for quota-based roles).

• Comprehensive group benefits with no waiting period, offering coverage for health, vision, dental, and more for you and your family.

• A remote-first company culture—most teams operate fully remotely. Enjoy the flexibility of working from various locations with Wi-Fi, participate in virtual and in-person social events, and utilize our corporate co-working program to access WeWork or similar spaces nearby. Some positions may require in-office collaboration, which will be explicitly stated in the job description.

• Employer-funded retirement contributions. Tailscale matches your retirement contributions dollar-for-dollar, up to an annual maximum contribution equal to 0.75% of your eligible compensation.

• Opportunities to connect with other Tailscalars in real life. Attend our annual company retreat, join team off-sites, and collaborate in person with colleagues across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person interactions through team travel and distributed collaboration.

• Support for your personal and professional growth. Cultivate your career thoughtfully with an annual budget of $1500 USD for professional development, or benefit from mentorship, coaching, and internal advancement opportunities.

• Paid time off and a healthy work-life balance. Our flexible paid time off program accommodates various life situations, whether you're moving homes or traveling the globe.

• A customizable home office setup. You can choose your own company-owned laptop (Mac or PC), receive monthly home internet reimbursement, and $500 USD to personalize your workstation.

• Paid parental leave program. We value your life beyond work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).