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Jobs at Tailscale (Now Hiring) — 19 open

Tailscale logoTailscale

Customer Support Engineer

United Kingdom · Remote OK

$77k–$96k/yr

Senior$276M raised

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, …

Skills: TCP/IP, DNS, Subnetting, Firewalls, NAT Traversal

Tailscale logoTailscale

Customer Support Engineer

United States · Remote OK

$97k–$121k/yr

Senior$276M raised

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, …

Skills: TCP/IP, DNS, Subnetting, Firewalls, NAT Traversal

Tailscale logoTailscale

Customer Support Engineer

Canada · Remote OK

$130k–$162k/yr

Mid level$276M raised

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, …

Skills: TCP/IP, DNS, Subnetting, Firewalls, NAT Traversal

Tailscale logoTailscale

New Business Account Executive

Vancouver, British Columbia, Canada · Hybrid

$134k–$168k/yr

Mid level$276M raised

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, …

Skills: Prospecting, Closing, Pipeline Management, Sales Forecasting, Multi-threading

Tailscale logoTailscale

Senior New Business Account Executive

Denver, Colorado, United States · Hybrid

$120k–$150k/yr

Mid level$276M raised

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, …

Skills: Prospecting, Closing, Pipeline Management, Sales Forecasting, Technical Sales

Tailscale logoTailscale

Customer Account Executive

Denver, Colorado, United States · Hybrid

$100k–$125k/yr

Mid level$276M raised

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, …

Skills: Prospecting, Closing, Upselling, Renewals, Pipeline Management

Tailscale logoTailscale

Senior Customer Account Executive

Denver, Colorado, United States · Hybrid

Mid level$276M raised

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, …

Skills: Closing, Account Management, Upselling, Renewals, Pipeline Management

Tailscale logoTailscale

Software Engineer, Strategic Projects

Canada · Remote OK

$218k–$303k/yr

Senior$276M raised

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, …

Skills: Go, Rapid Prototyping, LLM Integration, Networking, API Integration

Tailscale logoTailscale

Software Engineer, Strategic Projects

United States · Remote OK

$163k–$226k/yr

Senior$276M raised

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, …

Skills: Go, Rapid Prototyping, LLM Integration, Networking, API Integration

Tailscale logoTailscale

Solutions Engineer - Commercial (Expansion Sales)

United States · Remote OK

$150k–$200k/yr

Senior$276M raised

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, …

Skills: Technical Discovery, Solution Architecture, TCP/IP, DNS, Routing

Tailscale logoTailscale

Solutions Engineer - Commercial (Expansion Sales)

Canada · Remote OK

$201k–$268k/yr

Senior$276M raised

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, …

Skills: Technical Discovery, Solution Architecture, TCP/IP, DNS, Routing

Tailscale logoTailscale

Senior Product Designer

United States · Remote OK

$146k–$183k/yr

Senior$276M raised

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, …

Skills: Product Design, B2B Design, Infrastructure Design, User Discovery, GUI Design

Tailscale logoTailscale

Senior Product Designer

Canada · Remote OK

$196k–$245k/yr

Senior$276M raised

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, …

Skills: Product Design, User Experience (UX), User Interface (UI), B2B Design, Infrastructure Product Design

Tailscale logoTailscale

Backend Engineer, Identity

United States · Remote OK

$163k–$204k/yr

Senior$276M raised

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, …

Skills: OAuth2, OIDC, SAML, WebAuthn, SCIM

Tailscale logoTailscale

Backend Engineer, Identity

Canada · Remote OK

$218k–$273k/yr

Senior$276M raised

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, …

Skills: OAuth2, OIDC, SSO, SAML, WebAuthn

Tailscale logoTailscale

Frontend Engineer

United States · Remote OK

$181k–$226k/yr

Senior$276M raised

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, …

Skills: React, Frontend Architecture, Browser Security, HTTP Semantics, Authentication Flows

Tailscale logoTailscale

Frontend Engineer

Canada · Remote OK

$243k–$303k/yr

Senior$276M raised

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, …

Skills: React, Frontend Architecture, Browser Security, HTTP Semantics, Authentication Flows

Tailscale logoTailscale

Software Engineer, Networking (Features)

Canada · Remote OK

$218k–$303k/yr

Senior$276M raised

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, …

Skills: Go (Golang), Application-Layer Networking, Distributed Systems, Socket Programming, Routing Tables

Tailscale logoTailscale

Software Engineer, Networking (Features)

United States · Remote OK

$163k–$226k/yr

Senior$276M raised

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, …

Skills: Go (Golang), Networking Internals, Distributed Systems, Socket Programming, Routing Tables

Tailscale logo

Customer Support Engineer

Tailscale

United Kingdom • Remote OK

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Senior

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  • $77k–$96k/yr
  • Full-time
  • Equity Incentive Plan, Health Insurance, Vision Insurance, Dental Insurance, Remote Work, Annual Company Retreat
  • Posted 1d ago
  • ~40 hrs/week
  • Remote in United Kingdom

Responsibilities

Serve as the primary escalation point for complex technical tickets, diagnosing issues related to ACLs, subnet routing, and identity providers. Partner cross-functionally with Product and Engineering teams to reduce user friction and mentor Tier 1 support staff.

Requirements

Requires 4+ years of technical support experience in a SaaS environment with strong networking fundamentals and proficiency across multiple operating systems. Candidates should have experience with SSO integrations, Kubernetes basics, and a passion for technical tinkering.

Full job description

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.
  • 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, and the United Kingdom. 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 $1000 USD to customize your workstation to make it your own. 
  • Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks. 

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.

Related keywords

TailscaleSaaSVPNWireGuardTCP/IPDNSSubnettingFirewallsNAT TraversalRoutingmacOSWindowsLinuxKubernetesKubectlOkta

About Tailscale

LinkedInVisit site

Simple, secure networks for teams of any scale. Built on WireGuard.

Industry
Software Development
Company size
201-500 employees
Founded
2019
Headquarters
Toronto, Ontario
LinkedIn followers
37,988
Total funding
$276M

For teams who want secure, private networks without weeks of setup and configuration, Tailscale makes it easy. Unlike existing corporate VPNs, Tailscale has no upfront cost, minimal latency, and works with their existing services.

Offices: Toronto, Ontario M6K 3S5, CA · Berkeley, CA 94705, US

SecurityPrivacyLog ProcessingConnectivityRemote Access2FA/MFAWireGuardComputer NetworkingComputer NetworksWireGuard
View all jobs at Tailscale

About Tailscale

LinkedInVisit site

Simple, secure networks for teams of any scale. Built on WireGuard.

Industry
Software Development
Company size
201-500 employees
Founded
2019
Headquarters
Toronto, Ontario
LinkedIn followers
37,988
Total funding
$276M

For teams who want secure, private networks without weeks of setup and configuration, Tailscale makes it easy. Unlike existing corporate VPNs, Tailscale has no upfront cost, minimal latency, and works with their existing services.

Offices: Toronto, Ontario M6K 3S5, CA · Berkeley, CA 94705, US

SecurityPrivacyLog ProcessingConnectivityRemote Access2FA/MFAWireGuardComputer NetworkingComputer NetworksWireGuard
View all jobs at Tailscale

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