Engineering Manager, Tailscale
Backend - Control Plane
CA$309.5-387.3k
+ Equity incentive plan and variable commission (for quota-based roles)
A zero config VPN for building secure networks
Job no longer available
A zero config VPN for building secure networks
101-200 employees
Job no longer available
CA$309.5-387.3k
+ Equity incentive plan and variable commission (for quota-based roles)
101-200 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
- Because we’re an early-stage and fully remote company, we’re looking for a motivated individual who can help move the product forward. The ability to think on your feet, collaborate with highly technical teams, and comfort working asynchronously are essential
- Experience as a people manager: we are not yet at a size and level of maturity as an engineering org to provide the training and support for someone new in the management role
- Demonstrated leadership with substantial experience in managing and mentoring Engineering teams, including performance evaluations, career development, and fostering a collaborative work environment
- Background in one or more of the skillsets used within Tailscale Engineering; management benefits from having the context to understand the work of the team. At this time, expertise in one of the following would be especially relevant:
- Networking including L4-L7 connectivity, browser and DNS behaviors, BGP and related protocols
- Data Engineering including Snowflake, dbt, Rudderstack, and similar tools
- Design and maintenance of distributed systems and highly available services
- Experience developing in Go, used for much of the system. Previous experience in #golang makes ramping up quicker
- Ability to give and process constructive feedback, as well as work independently
- Flexibility to adjust to the dynamic nature of a startup
What the job involves
- We’re seeking a talented and motivated full-time Software Engineering Manager to join our growing team. You will work as part of the engineering team to:
- Provide guidance, mentorship, and career development for a team of software engineers
- Contribute toward the success of our Product organization which includes Engineering, Product Management, and Design. We operate in Pods of 2-4 engineers plus a Product Manager and Designer, and each Engineering Manager handles 2-3 such Pods
- Pods work across the codebase to implement features, address shortcomings, and answer customer requests
- Provide technical direction in projects as needed, as well as growing the technical leadership capabilities of the engineers reporting to you
- Help in growing the organization: interviewing and recruiting, guiding the development of the engineering culture, developing processes as we grow
- Achieve significant business outcomes through cross-functional collaboration with product managers, data scientists, and designers
- Help your team to improve their performance, the quality of their work; make major design decisions
- Hire, nurture, and oversee a team of engineers while fostering an atmosphere of psychological well-being, embracing diversity and promoting inclusion
- Lead a team responsible for managing a critical production service, including operational concerns (monitoring, alerting, on call, etc)
- Manage healthy conflict by moderating design discussions and cultivating a positive culture of feedback with candor and kindness
- Collaborate with interdisciplinary teams across the organization to complete complex projects spanning multiple technical domains
- Drive planning across multiple time horizons, from immediate tactical needs to long-term strategic direction
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.
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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