Customer Support Engineer

Remote from: UK
Salary, yearly, GBP: 76,630 - 95,590
Department: Technical Support
Employment type: Full Time,
Job posted: 20 Jul 2026
Apply before: 20 Aug 2026
Experience level: Midweight
Views / Applies: 131 / 10

Tailscale makes your network work like a single secure computer, so you can connect devices anywhere in the world easily and safely.

Computer & Network Security
2019

AI Summary

Tailscale is hiring a Tier 2 Customer Support Engineer to handle complex technical tickets for its VPN/ networking product. The role requires deep knowledge of networking fundamentals (TCP/IP, DNS, NAT) and experience with identity providers and Kubernetes. You'll own escalated issues, mentor Tier 1 staff, and collaborate with product teams. The company is fully distributed and offers a competitive salary.

Role DNA

Job Complexity

Easy Hard

Pace & Pressure

Relaxed Fast-paced

Autonomy Level

Guided Full Ownership

Communication Load

Independent Highly Collaborative

AI Insight The role demands 4+ years of support experience, advanced networking expertise, and familiarity with enterprise tools, making it challenging for typical support professionals.

Salary Analysis

AI Insight The offered salary of £86,110 median is well above the UK market average for support engineers, reflecting the specialized skills required in networking and cloud-native environments.

Core Skills Required

Customer Support Tier 2 Networking TCP/IP VPN WireGuard Kubernetes Identity Providers SSO Troubleshooting

Cover Letter Sample

Dear Hiring Manager,

I am excited to apply for the Customer Support Engineer (Tier 2) position at Tailscale. With over five years of technical support experience at SaaS companies, I have developed a strong foundation in networking and a passion for troubleshooting complex issues. My hands-on experience with WireGuard and other VPN technologies aligns perfectly with Tailscale's mission.

In my previous role, I handled escalated tickets involving ACLs, DNS, and identity providers, ensuring high CSAT scores. I also enjoy mentoring junior team members and contributing to knowledge bases. I am eager to bring my technical depth and customer-focused mindset to Tailscale.

Thank you for considering my application. I look forward to discussing how I can support Tailscale's customers and growth.

Sincerely,
[Your Name]

Sample Interview Questions

Describe a time you debugged a complex networking issue. What steps did you take?

I once helped a customer whose VPN connections were dropping intermittently. I started by gathering logs and reviewing network configurations. I discovered a misconfigured MTU size causing fragmentation. After adjusting the MTU and testing across different OSes, the issue was resolved. I documented the solution for future cases.

How would you handle a frustrated customer whose critical issue is not resolved quickly?

I would first acknowledge their frustration and reassure them I'm focused on their problem. I'd provide a clear update on what I've found and the next steps, setting realistic expectations. If needed, I'd escalate internally while keeping the customer informed every step of the way.

Explain how you would troubleshoot a Tailscale ACL policy that is not working as expected.

I would verify the ACL syntax by checking the admin console and using the tailscale status command. I'd test connectivity with a simple allow rule to isolate the issue. Then I'd check for typos, tag mismatches, or overlapping rules. Using the debug logs would help confirm the packet flow.

What experience do you have with identity providers like Okta or Azure AD?

I have configured SSO integrations with Okta and Azure AD for user authentication in VPN products. I'm familiar with SCIM provisioning, OIDC, and SAML. I've troubleshooted login failures by checking token expiration and attribute mappings.

How do you prioritize multiple high-severity tickets at once?

I assess the impact on the customer and the urgency. I communicate with stakeholders to set expectations and, if needed, seek help from teammates. I also use a ticketing system to track SLAs and organize my queue, ensuring no ticket falls through the cracks.

About Tailscale

Tailscale is building the new Internet 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.

Job Description

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.

UK Pay Range

£76,630—£95,590 GBP

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.

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