Security Infrastructure Engineer, Tailscale
CA$218.4-273.4k
+ 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
CA$218.4-273.4k
+ 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
- Expertise in the security of cloud platforms (e.g., AWS), especially securing multi-cloud networks and infrastructure, and designing cloud agnostic systems
- Familiarity with container security, orchestration security, and authentication/authorization
- Familiarity with internet/web security fundamentals: WAF’s, TLS, PKI, DNS security, etc
- Proficiency developing in at least one programming language (Tailscale uses Go) and Infrastructure as Code tooling (e.g. Terraform, Ansible)
- Prior experience in a safety-related technical role, e.g.:
- Infrastructure security
- Security operations
- Threat modeling and prioritization
- Digital forensics and incident response
- Knowledge of operating system internals and security mechanisms
- Knowledge of common networking protocols
- Act as a Subject Matter Expert during security incidents, focusing on infrastructure-level containment and remediation
- Ability to give and process constructive feedback
- Ability to work independently and collaboratively
- Flexibility to adjust to the dynamic nature of a startup
- Take a risk-based approach to building security controls, balancing your security expertise and broad technical skillsets with practical, usable solutions
- 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 talented software engineer, specializing in security and infrastructure, to help grow our product security team. We’re looking for people who can move Tailscale forward while making it safer to use. The abilities to think on your feet, collaborate with highly technical teams, and be comfortable working asynchronously are essential
- Design and build security controls across diverse layers (e.g., cloud platforms, OS, Kubernetes, networks, CI/CD) to defend against sophisticated adversaries and insider threats
- Improve the security properties of Tailscale by identifying opportunities for security and privacy features, bug fixes, defense-in-depth, and implementing them across our codebase
- Audit Tailscale infrastructure for technical security weaknesses, identifying mitigations or solutions, and driving them towards resolution
- Support engineering decisions with threat modeling and security analysis and expertise
- You will spend 25-50% of your time in this role writing software vs purely operational or governance security responsibilities
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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