Engineering Manager, Tailscale
$205-255k
+ Equity
A zero config VPN for building secure networks
Job no longer available
A zero config VPN for building secure networks
201-500 employees
Job no longer available
$205-255k
+ 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
- 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
- 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
- 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. Pods have substantial agency in choosing what to work on
- 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
- 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
- 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
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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