People Operations Generalist, Tailscale
$87-135k
+ An equity incentive plan
More information about location
A zero config VPN for building secure networks
Be an early applicant
A zero config VPN for building secure networks
101-200 employees
Be an early applicant
$87-135k
+ An equity incentive plan
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
- If you thrive in a dynamic, fast-paced startup, love creating operational efficiency, and want to deliver an exceptional employee experience, we’d love to hear from you!
- 6+ years of experience in a People Operations role, with at least 4+ years in startups
- Working knowledge of federal, state, and local employment laws in the US, UK, and Canada and familiarity with with benefit practices in these regions
- Ability to manage effectively through ambiguity, juggle multiple projects with deadlines, and prioritize in a rapidly changing environment
- Strong situational adaptability in both written and verbal communication
- A passion for program development, policy improvements, and continuous iteration
- 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
- Living our values, every day
What the job involves
- We’re looking for a People Operations Generalist to join our small but mighty People Ops team
- In this role, you’ll build, optimize, and scale core processes that support our rapidly growing company—from onboarding to offboarding, and everything in between
- You’ll be responsible for day-to-day People Operations tasks such as managing employee data, handling leaves, and maintaining compliance with employment laws
- Develop, refine, and document processes related to the employee lifecycle
- Provide a high-touch experience to new hires, managing orientations, onboarding, and offboarding processes
- Identify areas for automation and efficiency improvements; create SOPs to ensure clarity and consistency, and continuously evolve workflows
- Create and deploy automation and workflows to handle repetitive questions and seize opportunities to educate and inform where appropriate
- Participate in the planning, coordination, and execution of People team initiatives, as needed, such as company events, employee experience projects, and various other enablement initiatives
- Serve as the primary contact for benefits and all people-related inquiries, providing guidance and managing escalations
- Administer accommodations & leaves programs, ensuring compliance with applicable regulations
- Liaise with vendors and brokers to manage enrollments, changes, and compliance
- Coordinate annual 401(k) compliance testing and audits, ensuring all data and documentation meet regulatory standards
- Ensure data integrity through regular audits and maintain accurate records for changes to employee information
- Oversee the secure handling of sensitive information in line with data protection laws
- Maintain documentation related to compensation cycle changes
- Keeping us current on employment legislation; proactively update policies and processes to align with legal requirements
- Conduct routine compliance reporting 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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