People Business Partner, Tailscale
$129-177k
+ Equity
A zero config VPN for building secure networks
Open for applications
A zero config VPN for building secure networks
201-500 employees
Open for applications
$129-177k
+ 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
- 5+ years of experience in a People Partnership role, with at least 3+ years in a fast-paced, ever evolving startup environment working with GTM teams
- A passion for program development and improvements, and continuous iteration
- Ability to manage effectively through ambiguity, juggle multiple projects with deadlines and to prioritize in a rapidly changing environment
- Strong coaching and judgment skills with experience navigating sensitive or complex situations with objectivity and confidentiality
- Working knowledge of employment laws and ability to accurately advise your partners
- Proficiency in Google Workspace, HRIS administration, benefit administration, and ATS platforms
- Natural curiosity - you’re a problem solver, well-organized, and a strong effective communicator who has expert partnership skills cross-functionally
- High attention to detail - noticing the small things is a strength
- Global experience, in particular US, Canada, and the UK
- Living our values & principles every day
What the job involves
- We’re looking for an experienced People Business Partner to join our small but mighty People Experience team. In this role, you’ll help to build, optimize, and scale organizational effectiveness and employee experience that supports our rapidly growing company
- You’ll be responsible for offering high-touch support, effective coaching, and manager enablement, and act as a trusted advisor to individual contributors and managers.
- Design and implement People Programs that strengthen performance, leadership, engagement, and organizational health across the company
- Design and deliver scalable training, coaching, and guidance to managers and equip them with the tools to effectively drive feedback, performance, and growth with their teams. Partner with leadership to embed and strengthen organizational capacity for high-performing teams and high talent density
- Collaborate with managers to implement structured processes for defining, tracking, and reviewing goals that align with individuals and team objectives with the company's overall strategy, ensuring accountability and measurable outcomes
- Partner with management to develop and evolve career leveling and paths, effectively facilitating career progression between managers and ICs
- Sensitively manage confidential employee relations and interpersonal conflicts, acting as a confidential advisor to ICs and managers
- Operationalize stay and exit interview processes, leverage qualitative and quantitative feedback into actionable insights. Use trend analysis to recommend and drive initiatives that strengthen engagement, retention, and organizational health
- Drive succession planning and bench strength initiatives to highlight areas of weakness and appropriate steps to support aggressive growth
- Manage involuntary exit processes, including risk mitigation, documentation, and execution, partnering with Legal, Finance, and People Operations
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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