Software Engineer, Tailscale
Engineering Tooling
£143-178.5k
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
£143-178.5k
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
- Experience with CI/CD, secrets management, infrastructure as code, and/or observability
- Experience with developer tooling or developer experience
- Experience with distributed systems
- Experience with one or more SQL databases
- Familiarity with networks (IP addressing, routing, etc.)
- Most of the non-front-end portions of the system are developed in the Go programming language. Experience with Go is a plus
- Ability to give and process constructive feedback, as well as work independently
- Flexibility to adjust to the dynamic nature of a startup
- Excellent written and verbal communication skills
- 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
- We’re seeking a skilled and diligent full-time software engineer to join our growing team. You will work as part of the engineering team to:
- Support and enable internal business units through shared engineering services and functionalities, building the tools and processes for those teams to succeed
- Build relationships with multiple stakeholders across the organization to understand and meet their needs with projects you'll own end to end
- Work directly with internal customer-facing teams to empower their mission and take pride in making their day-to-day lives easier. Work with product engineering to extract the data needed to drive business decisions
- Example deliverables in this role might include:
- Introducing new developer tooling to increase engineering productivity
- Improving existing tools, such as CI/CD
- Using information from production data to surface potential issues
- Creating tooling for dev and staging environments
- Work as part of a team of engineers to design, build, test, and document core software components
- Exhibit ownership over the running services that comprise Tailscale’s product by building for observability, participating in incident response, and fielding customer support escalations
- Analyze and improve efficiency, scalability, and stability of various system resources
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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