Product Design Manager, Tailscale
$189-236k
+ An equity incentive plan
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
$189-236k
+ An equity incentive plan
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
- We’re seeking an experienced Product Design Manager to lead the design function within the EPD organization at Tailscale
- Extensive experience as an IC Product designer and a leader of design teams
- Experience working on B2B software in highly technical domains where customer problems are unfamiliar to you
- Ability and willingness to lead new processes and activities by example, helping your team adopt new practices with hands-on demonstrations
What the job involves
- Design plays a critical role in making Tailscale accessible and trustworthy to a wide audience, and you will help foster a user-centered culture within the EPD team by partnering with Engineering and Product leaders to advocate for the quality and thoughtfulness of the end user experience
- You will help Product Designers perform their best, and work with them to define and maintain high quality standards across our product and its features, both existing and new
- You will also collaborate closely with UXR and Brand Design to ensure we carry a consistent presentation, voice, and brand image across the Tailscale experience, from our product all the way into our marketing
- Manage a team of 4+ Product Designers, fostering an inclusive and supportive culture. Lead team rituals like crits and offsites
- Support cross functional collaboration in all directions. Help our team interface with other disciplines, and help other disciplines engage effectively with our team
- Advocate for the end user experience in the building of new features and the prioritization of improvements to existing workflows
- Identify gaps in systems and processes that reduce Design Team efficacy, and recommend improvements
- Define and champion standards for quality and consistency
- Help designers on your team improve their craft and grow, by practicing coaching, mentorship, and sponsorship
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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