Senior Customer Support Engineer, Tailscale
Tier 3, Customer Escalations
£90.8-113.8k
+ Equity
A zero config VPN for building secure networks
Be an early applicant
A zero config VPN for building secure networks
201-500 employees
Be an early applicant
£90.8-113.8k
+ Equity
201-500 employees
Company mission
To remove overhead and complexity from the “long tail” of software and operational problems that people face every day.
Role
Who you are
- 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
- 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 the job involves
- 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
- 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
Our take
The internet is a global phenomenon, but often online activity is unprotected which leaves users vulnerable to hackers on public networks. Additionally certain sites are inaccessible or censored depending on the users location. Use of a VPN enables a secure connection through an encrypted virtual tunnel which also disguises IP addresses. Traditional VPN's tunnel all network traffic through a central gateway server which can affect reliability, and VPN's almost always slow connection speed.
Tailscale is a VPN service built on top of a secure network fabric, which is unlike a traditional VPN provider as it ensures encrypted point-to-point connections by using the open source WireGuard protocol. Tailscale is configured, on average, in a matter of minutes, while other solutions take weeks to fully implement and then require several hours a week of maintenance.
The product has been well received, with reviewers agreeing that it is easy to set up and a great tool for developers. The company plans to develop its product further by tackling the complexity of software and confronting operational problems that people face daily. Off the back of impressive 2025 funding, Tailscale is expanding its engineering, product and sales teams as well as its global reach, all to empower small teams to build systems that scale, without scaling overhead.
Steph
Company Specialist at Welcome to the Jungle
Insights
81% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Apr 2025
$160m
SERIES C
May 2022
$100m
SERIES B
Total funding: $275m
Company benefits
- Flexible (and reasonable) working hours—work/life balance is exceptionally important to us
- Competitive compensation, stock options and 401(k) (for United States-based employees)
- Comprehensive medical/dental/vision benefits, and more
- 4 weeks of paid vacation (standard across the company) + 12 company holidays per year
- An allowance for equipment to help you personalize your workspace
Company HQ
King West Village, Toronto, ON
Leadership
Avery Pennarun
(Co-Founder & CEO)A range of experience in software engineering including Senior Staff Software Engineer at Google Fiber. They co-founded EQL Data in 2009.
David Crawshaw
(Co-Founder & CTO)Previous experience includes working as a Staff Software Engineer at Google before co-founding Tailscale.
David Carney
(Co-Founder)Co-founded Format in 2012, working as a Full Stack Developer, COO and CFO. Also co-founded Form & Method and The Navarra Group.
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