People Operations Partner, Tailscale
CA$171.5-214.4k
+ Equity incentive plan and variable commission (for quota-based roles)
More information about location
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$171.5-214.4k
+ Equity incentive plan and variable commission (for quota-based roles)
More information about location
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
- You like to create solutions for issues that arise and thrive in an ever-changing, fast-paced startup environment
- You are extremely organized, have a keen eye for details, and have strategic prioritization skills. You also utilize the utmost discretion and care when handling employee information and addressing any concerns that may arise
- 6+ years of experience in a People Operations role
- Expert business acumen and analytical skills
- Working knowledge of federal, state, and local employment laws, including California, in order to build and lead compliant practices
- Familiarity with global benefit best practices in various geographic regions, particularly in the US, UK, and CAN
- Ability to manage effectively with ambiguity, manage multiple projects through completion on time and on budget, and to prioritize in a rapidly changing environment
- Startup experience is strongly preferred
- Strong situational adaptability in both written and verbal communication
- Passion for program development and policy improvements!
- Proficient in Google Workspace
- Proficiency in HRIS, benefit administration, and ATS platforms
- High level business acumen, discretion, and analytical/technical skills
- Naturally curious problem solver, well-organized, and a strong effective communicator
- Strong partnership skills within People org as well as with cross-functional teams and partners
- You notice the small things; paying attention to detail is your strength
- You live our values, every day
What the job involves
- The People Operations Partner will be a key member of our small but mighty People Operations team. As our People Operations Partner, you will be a trusted advisor to new hires and employees
- Our programs are essential for attracting and retaining top talent and empowering individuals to do their best and most meaningful work
- The ideal candidate will be knowledgeable in employee relations and will act as a thought partner to build out new processes and people programs while informing how best to scale programs and practices informed by data as well as internal demographic and market trend insights
- As a People Operations Partner, you’ll execute our People Operations strategy in partnership with the People Operations team
- Collaborate with People team leadership to build and maintain processes related to the following: talent acquisition, employee lifecycle, learning and professional development programs, talent management, and onboarding-related IT processes. Recommend and implement process changes that positively impact the business
- Ensure employees receive required training and development
- Serve as an internal resource to assist employees and managers in meeting employee development needs, using outside resources when appropriate
- Provide guidance to management for developing professional & managerial talent, soliciting advice from outside consultants as appropriate
- Help drive the strategic evolution and execution of our benefits programs to ensure we're constantly innovating in the space, and providing benefits are top of market
- Support day-to-day administration of our People programs (including but not limited to employee life cycle support from onboarding to offboarding, etc.)
- Support in identifying and implementing effective and efficient benefit administration and HR/PO processes to ensure a positive employee experience
- Automate reporting to keep our business informed and enlightened on employee trends, while partnering with People Ops leadership to story tell using data and analytics
- Act as a first-line of support for employees regarding people programs
- Lead new hire orientations/onboarding process
- Any other ad-hoc People Ops/Benefits projects and tasks as needed
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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