Customer Support Engineer, Tailscale

$97-121k

+ Equity incentive plan

Slack
Mid and Senior level
Remote in US
Tailscale

A zero config VPN for building secure networks

Open for applications

Tailscale

A zero config VPN for building secure networks

101-200 employees

B2CB2BSecurityContentSaaSAPICyber Security

Open for applications

$97-121k

+ Equity incentive plan

Slack
Mid and Senior level
Remote in US

101-200 employees

B2CB2BSecurityContentSaaSAPICyber Security

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 experience in a support role within a SaaS company
  • 1+ years experience with network troubleshooting. You should know what NS lookup and IP tables are. Extensive experience with Tailscale is even better!
  • Interpersonal communication skills and the ability to work effectively on a team
  • Excellent written communication skills. Much of the role is via email and async slack conversations
  • A strong desire to work with customers and partners in solving problems

What the job involves

  • We’re seeking a new full-time Technical Support Engineer to join our growing team
  • In this role, you will be responsible for providing technical support for individuals, teams, and companies using Tailscale
  • You’ll be part of a growing team of engineers focused on delivering excellent support and proactively solving friction through partnering with our Sales, Product, and Engineering teams
  • Become an expert in the use of the Tailscale product, including Access Control, Authentication, and Routing features
  • Handle support requests from customers regarding issues occurring in their use of the product
  • Work closely with Customer Success, Sales, and Engineering to help users successfully deploy the Tailscale product
  • Collaborate with our Engineering team to debug and fix customer issues

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Insights

Top investors

81% employee growth in 12 months

Company

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

Funding (last 2 of 4 rounds)

Apr 2025

$160m

SERIES C

May 2022

$100m

SERIES B

Total funding: $275m

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 plan to develop its product further by tackling the complexity of software and confront operational problems that people face daily. The company continues its expansion by empowering small teams to build systems that scale, without scaling overhead.

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Steph

Company Specialist at Welcome to the Jungle