[![Image]() Meet Jobicy Copilot — free AI autofill for job applications + remote job alerts ›](#) [All remote jobs](https://jobicy.com/jobs.md)Open role[![Tailscale logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/d3fa2e99-221.png)](https://jobicy.com/company/tailscale.md)Remote opportunity at[Tailscale](https://jobicy.com/company/tailscale.md) # Customer Support Engineer (Tier 2) Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/tailscale.md)Share6 Sep 2026Published41Listing views3Application actions6 Oct 2026Apply before Opportunity details ## About this role. AI SummaryTailscale is hiring a Tier 2 Customer Support Engineer to own escalated technical cases for customers using its secure networking platform. The role requires advanced troubleshooting across networking, identity-provider integrations, operating systems, logs, and basic Kubernetes environments. This engineer will manage SLA-sensitive ticket queues, communicate complex solutions clearly, partner with Product and Engineering on recurring issues, and mentor Tier 1 colleagues. It is a remote US full-time role for a support professional with at least four years of SaaS technical-support experience. The position offers a disclosed base-salary range plus equity and benefits. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 4/5EasyHard ### Pace & Pressure 4/5RelaxedFast-paced ### Autonomy Level 4/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThe role handles escalated cases involving routing, ACLs, NAT traversal, SSO, cross-platform diagnostics, and Kubernetes, requiring strong applied infrastructure knowledge. High ticket volume and SLA/CSAT ownership add operational pressure while maintaining technical depth. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job medianMarket rate$109,000US market range$90k–$130k0$143k AI insightThe disclosed US yearly base-salary range is $97,000 to $121,000 USD, with a midpoint of $109,000. This is broadly competitive for a Tier 2 technical support engineer with SaaS networking, identity, and infrastructure troubleshooting expertise; an estimated US market range is $90,000 to $130,000 annually. Equity and benefits are mentioned separately and are not included in the base-salary figures. ## Core skills Skills and capabilities most closely associated with this opportunity. [Technical Support](https://jobicy.com/jobs?search_keywords=Technical%20Support.md)[SaaS](https://jobicy.com/jobs?search_keywords=SaaS.md)[Networking](https://jobicy.com/jobs?search_keywords=Networking.md)[TCP/IP](https://jobicy.com/jobs?search_keywords=TCPIP.md)[DNS](https://jobicy.com/jobs?search_keywords=DNS.md)[VPN](https://jobicy.com/jobs?search_keywords=VPN.md)[WireGuard](https://jobicy.com/jobs?search_keywords=WireGuard.md)[SSO](https://jobicy.com/jobs?search_keywords=SSO.md)[Kubernetes](https://jobicy.com/jobs?search_keywords=Kubernetes.md)[Customer Success](https://jobicy.com/jobs?search_keywords=Customer%20Success.md) Sample interview questionsHow would you investigate a customer report that devices cannot reach a subnet router through Tailscale?I would first clarify the topology, affected devices, expected destination ranges, recent changes, and exact error behavior. I would verify device connectivity and authorization, advertised and approved routes, ACL policy, IP forwarding and firewall rules on the subnet router, then inspect relevant client and service logs. I would test reachability hop by hop, document findings, and provide the customer with a clear remediation plan or escalate with reproducible evidence if needed. Explain how you would troubleshoot an ACL misconfiguration without compromising the customer's security posture. I would review the intended access model before proposing any policy change, then compare it with the active ACL rules, group definitions, tags, and test identities. I would identify the smallest rule adjustment that enables the required traffic, validate it with a limited test where possible, and explain the impact in plain language. I would avoid broad allow rules unless they are explicitly intended and would document the final policy rationale. What information do you gather when an SSO or identity-provider integration is failing? I gather the identity provider, protocol and configuration details, affected users, timestamps, exact errors, recent changes, and whether the issue affects authentication, provisioning, or authorization. I validate redirect URLs, certificates or signing settings where applicable, domain and group mappings, and audit logs from both systems. I then isolate whether the failure is caused by IdP configuration, user assignment, policy, or the application integration. How do you maintain quality when working through a high-volume, SLA-driven ticket queue? I triage by severity, customer impact, SLA risk, and whether an issue is blocking access or has a known workaround. I use concise but complete initial responses, set expectations early, maintain structured case notes, and use reusable diagnostic checklists for recurring issues. For complex cases, I communicate progress regularly and escalate with a clear problem statement, evidence, and actions already taken. Describe how you would mentor a Tier 1 support colleague on a networking escalation. I would review the ticket with them to understand their reasoning and recognize what they handled well. Then I would walk through a repeatable diagnostic framework, such as validating connectivity, configuration, policy, routing, and logs, while explaining why each step matters. I would help them create customer-ready documentation and identify what signals should trigger escalation in similar future cases. About Tailscale Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We’re building a future for the Internet that’s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we’re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital. ### About the Role If you’re passionate about solving technical issues and providing high-quality support to a diverse community of users, this is the role for you. We’re seeking a motivated Support Engineer (Tier 2) to join our growing team of support professionals. You will serve as the face of the company for teams and companies using Tailscale, handling a broad range of tickets that will help flex your technical muscles. As a Tier 2 engineer, you’ll be part of a distributed team focused on delivering excellent support to our customers and proactively solving friction by partnering with our broader CX team and Product/Eng. This role reports directly to the Support Team Lead and will play a key role in our journey. ### Key Responsibilities * 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 (e.g. Okta, Azure AD). * 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, including those originating from free-tier users, ensuring issues beyond Tier 1’s scope are resolved efficiently and thoroughly. * Mentor and support Tier 1 colleagues through ticket reviews, escalation guidance, and documentation contributions. ### What We Are Looking For * 4+ years of experience in a technical support role within a SaaS company, with demonstrated experience handling escalated or enterprise-tier accounts. * Hands-on familiarity with Tailscale or comparable networking/VPN products (i.e. WireGuard, traditional VPNs) strongly preferred. * Display a natural tinkerer’s mindset and a deep curiosity for how things work, likely demonstrated through personal projects, homelabs, or open-source contributions. * Strong working knowledge of networking fundamentals – TCP/IP, DNS, subnetting, firewalls, NAT traversal, and routing – with the ability to apply this knowledge to real-world troubleshooting scenarios. * Show proficiency in troubleshooting across multiple operating systems such as macOS, Windows, Linux, and mobile platforms. * Experience working with identity providers and SSO integrations (e.g. Okta, Google Workspace, Azure AD) as they relate to device or user authentication. * Basic experience troubleshooting Kubernetes environments, including familiarity with pod networking, namespaces, and common CLI tools such as kubectl. * Familiarity with log analysis and CLI-based diagnostic tools to independently investigate issues before escalating. * Excellent written communication skills, with the ability to explain complex technical concepts with empathy and clarity. * Familiarity with Jira and Slack to manage internal workflows and collaborate effectively across distributed teams * Maintain a proactive approach to learning new technologies and staying current with evolving infra tools. As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. 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. Individual offers may vary based on experience and skill set. US Pay Range $97,000—$121,000 USD Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic! What We Offer * An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life. * 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). Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter. Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people. Please be aware that legitimate emails from Tailscale’s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit [https://tailscale.com/scam-awareness](https://tailscale.com/scam-awareness). 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