Tailscale logo
Tailscale

Simple, secure networks for teams of any scale. Built on WireGuard.

Senior Customer Support Engineer – Customer Escalations

Support EngineerSupport EngineerFull TimeRemoteSeniorTeam 51-200Since 2020H1B No SponsorCompany SiteLinkedIn

Location

United States

Posted

6 days ago

Salary

$115K - $144K / year

Seniority

Senior

Job Description

Senior Customer Support Engineer – Customer Escalations

Tailscale

• 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

Job Requirements

  • 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).

Related Categories

Related Job Pages

More Support Engineer Jobs

EverCommerce logo

Technical Support Specialist

EverCommerce

Software that Powers the Service Economy

Full TimeRemoteTeam 1,001-5,000Since 2016H1B Sponsor

• Provide exceptional support to customers via phone, chat, email, and customer portal. • Diagnose, troubleshoot, and resolve application, workflow, and configuration issues. • Serve as a trusted advisor by helping customers maximize the functionality of our solutions. • Escalate complex issues to the appropriate internal teams while providing complete documentation. • Collaborate cross-functionally with Product, Engineering, Billing, and other internal departments to resolve customer issues. • Document all customer interactions and troubleshooting steps accurately and thoroughly. • Represent the voice of the customer by providing feedback that helps improve our products and services. • Identify opportunities to improve support processes and customer experience. • Utilize internal knowledge bases and support tools to research and resolve issues. • Demonstrate empathy, professionalism, and strong communication during every customer interaction. • Contribute to the development and maintenance of internal knowledge base articles. • Meet or exceed departmental performance metrics, including customer satisfaction, quality, productivity, and SLA goals. • Continuously expand product knowledge and stay current on new features and enhancements.

United States
$19 - $21 / hour
Job Closed
Full TimeRemoteTeam 501-1,000H1B No Sponsor

• Atuar no suporte técnico para clientes utilizando a plataforma de folha de pagamento digital • Identificar e solucionar problemas técnicos relacionados à folha de pagamento digital • Interagir com os clientes para entender suas necessidades e oferecer suporte personalizado • Documentar e reportar incidentes técnicos para a equipe de desenvolvimento

Brazil
NetBox Labs logo

Senior Customer Support Engineer

NetBox Labs

We make it easier to build and manage complex networks.

Full TimeRemoteTeam 11-50Since 2023H1B No Sponsor

• Be the technical anchor for your customers • Participate in architecture reviews, planning sessions, and Business Reviews alongside Customer Success Managers • Help customers translate their network management goals into NetBox workflows and adoption paths • Serve as the bridge between what customers need and what the product can do • Meet SLAs for response and resolution while keeping customers informed throughout • Escalate proactively when revenue, stability, or customer trust are at risk

Australia
A$115.5K - A$130.5K / year
GitLab logo

Support Engineer – U.S. Government

GitLab

Build software faster. The One DevOps Platform enables your entire org to collaborate around your code. We're hiring.

Full TimeRemoteTeam 1,001-5,000Since 2014H1B No Sponsor

• Collaborate closely with public sector customers, including U.S. government agencies, the Department of War, and Intelligence Community organizations, to diagnose, troubleshoot, and resolve complex issues in GitLab deployments operating under strict security, compliance, and operational constraints. • Perform deep, hands-on technical investigations using Linux command-line tooling and GitLab internals to analyze logs, system performance, and application behavior, often with limited telemetry or incomplete datasets. You will trace issues across infrastructure, application, and code paths to identify root causes, recommend mitigations, and drive durable fixes; frequently partnering with GitLab Product, Development, and Infrastructure teams to ensure outcomes that meet both mission and platform reliability requirements. • Create and update clear, reusable documentation and support content based on real customer interactions to improve self-service and reduce repeated issues. • Participate in regular pairing sessions with other Support Engineers and act as a stable counterpart to cross-functional teams to share knowledge and improve support processes. • Contribute to building and refining internal support tools and workflows, including automation and troubleshooting utilities, to make diagnosing and resolving issues more efficient. • Participate in weekday and weekend on-call rotations, providing timely emergency support for self-managed customers operating in restricted and compliance-focused environments. • Support the growth of the team by reviewing applications and assessments, and participating in interviews and hiring decision discussions.

New York
$95.2K - $160.8K / year