Outliers and outperformers wanted

Outliers and outperformers wanted

Uncork Capital-backed companies are building kick-ass teams in engineering, marketing, sales, operations and more.

Uncork Capital-backed companies are building kick-ass teams in engineering, marketing, sales, operations and more.

Customer Support Engineer



Customer Service
Canada · Remote
Posted on Tuesday, January 31, 2023


If you’re passionate about solving networking issues and providing high-quality support, this is the role for you! 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.

Because we’re an early-stage and fully remote company, we’re looking for a motivated individual who can think on their feet, enjoys collaborating with highly technical teams, and is comfortable working asynchronously. This doesn’t mean we are going to give you more work than you can handle– we want to understand your special, niche skills and enable you to bring them to work with you.

You will:

  • 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.

Ideally, you have:

  • 4+ years experience in technical support roles.
  • 1+ years experience with networking. You should know what a subnet is and what routing does. CCNA or equivalent is a plus. 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 forum-based conversations.
  • A strong desire to work with customers and partners in solving problems.

Please keep reading...

Research shows that candidates from underrepresented backgrounds often don't apply for roles if they don't meet all the criteria — unlike majority candidates meeting significantly fewer requirements.

We strongly encourage you to apply if you’re interested: we’d love to know how you can amplify our team with your unique experience!

About Tailscale

Tailscale builds software that makes it easy to connect and secure devices, no matter where they are. Every day, banks and multi-national companies use Tailscale to protect their corporate networks. Hobbyists and start-ups trust Tailscale to collaborate and share access to tooling. We're building a future for the Internet that's easy, small and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, HeavyBit, and Uncork Capital.