At a Glance
- Tasks: Help users solve technical issues and provide top-notch support.
- Company: Join Tailscale, a forward-thinking tech company revolutionising internet security.
- Benefits: Enjoy competitive pay, remote work, and comprehensive health benefits.
- Other info: Flexible work environment with great career growth and personal development opportunities.
- Why this job: Make a real difference by supporting diverse users and solving complex problems.
- Qualifications: 4+ years in technical support with strong networking knowledge.
The predicted salary is between 40500 - 49500 £ per year.
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.
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.
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.
- 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).
- 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.
- 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 tailscale.com/scam-awareness.
Customer Support Engineer (Tier 2) employer: Tailscale
Tailscale is an exceptional employer that champions a fully distributed work culture, allowing you to thrive in a flexible environment while contributing to the future of Internet security. With a strong focus on employee growth and development, Tailscale offers unique opportunities to engage with cutting-edge technology and collaborate with a diverse team of professionals. Join us in our mission to make the Internet safe and sensible, all while enjoying the benefits of a supportive and innovative workplace.
StudySmarter Expert Advice🤫
We think this is how you could land Customer Support Engineer (Tier 2)
✨Get to Know the Company Culture
Before jumping into applications, it’s super helpful to understand the vibe at Tailscale. Check out their social media, read reviews on sites like Glassdoor, and see how they engage with customers. It'll give you clues on their values and help tailor your conversation during interviews.
✨Join Customer Support Communities
Dive into online communities like those on Reddit or LinkedIn where customer support pros hang out. Participating in discussions or asking questions can make you more visible to potential recruiters and help you learn about job openings at companies like Tailscale before they even post them.
✨Attend Job Fairs or Networking Events
Look out for local job fairs or events specifically for customer support roles. This is your chance to meet hiring managers face-to-face, and you might even get the opportunity to interview on the spot!
✨Show Off Your Skills with Customer Interactions
In the customer support world, showcasing your communication skills is key. Consider creating a short video introducing yourself or even doing a mock call to showcase your abilities. It's a memorable way to stand out, especially if you can share this during your interview process!
We think you need these skills to ace Customer Support Engineer (Tier 2)
Some tips for your application 🫡
Show Off Your Communication Skills:In customer support, clear communication is key. Make sure your CV highlights any experience you've had in customer-facing roles and your ability to resolve issues. Don't shy away from including specific examples of how you've gone above and beyond to help customers – this really shows your potential in the role.
Tailor Your Cover Letter to Tailscale:Your cover letter is your chance to shine! Tell us why you want to work at Tailscale specifically. Mention any unique aspects of our company that resonate with you and how your skills can enhance our customer support. This personal touch will set your application apart from the rest!
Highlight Any Relevant Tools or Tech Skills:If you've used customer support software like Zendesk or Freshdesk or have experience with CRM systems, make sure to mention these in your application. Being familiar with industry-standard tools can be a big plus for us when we’re reviewing applications, as it shows you can hit the ground running!
Demonstrate Your Problem-Solving Skills:Customer support roles often require a knack for problem-solving. In your application, share examples of past experiences where you've tackled tough situations or resolved conflicts effectively. This will give us a good sense of how you handle challenges—an essential skill for success at Tailscale!
How to prepare for a job interview at Tailscale
✨Show Off Your People Skills
In customer support, it's all about communicating effectively. Prepare to share instances from your past experiences where you handled difficult customers or resolved conflicts. We want to hear how you empathised and found the best solutions, so think of specific examples to back up your stories!
✨Know the Tools of the Trade
Familiarise yourself with common customer support tools like Zendesk or Freshdesk, and make sure to review how you’ve used any similar systems in the past. During the interview, being able to discuss your hands-on experience with software or ticketing systems can really set you apart from the competition, so don’t skip this prep!
✨Show Genuine Enthusiasm
As this is a full-time role, employers want someone who isn’t just looking for any job, but wants to grow within customer support. Make sure to express your enthusiasm for helping customers and your desire to develop your skills. Show them why you're passionate about this field!
✨Practice Common Scenarios
Be prepared for role-playing scenarios where you might have to reassess a solution with a frustrated customer or explain a complex process in simple terms. Practising these common scenarios can help us feel more confident and demonstrate our practical skills effectively during the interview.
