At a Glance
- Tasks: Solve complex technical issues and build trust with customers in a dynamic environment.
- Company: Join Tailscale, a forward-thinking tech company revolutionising Internet security.
- Benefits: Enjoy competitive pay, remote work flexibility, and comprehensive health benefits.
- Other info: Inclusive culture with opportunities for personal growth and professional development.
- Why this job: Make a real impact by resolving high-stakes customer escalations and improving products.
- Qualifications: 4+ years in technical support, strong problem-solving skills, and networking experience required.
The predicted salary is between 90850 - 113760 £ per year.
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.
If you're passionate about solving complex technical problems and helping build trust between customers and engineering, this is the role for you. We're seeking a motivated Senior Customer Support Engineer (Tier 3), Customer Escalations to join our Escalation Engineering team. You'll take ownership of our most complex, ambiguous customer escalations, solving issues where the root cause is not always obvious. You will work these issues to resolution or alternatively a fully-documented handoff that engineering can act on without delay. As a Senior Customer Support Engineer (Tier 3), Customer Escalations, you'll partner closely with Support and Product/Engineering to close the gap between "customer has described a problem" and "engineering has what it needs to fix it." This role reports directly to the Customer Escalations Team Lead.
Key Responsibilities
- 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.
What We Are Looking For
- 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.
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 £90,850 - £113,760 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.
Senior Customer Support Engineer (Tier 3), Customer Escalations 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 Senior Customer Support Engineer (Tier 3), Customer Escalations
✨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 Senior Customer Support Engineer (Tier 3), Customer Escalations
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.
