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People Operations Generalist

Remote (Canada)

About Tailscale 

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

Job Description

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. 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!

Key Responsibilities

Build & Scale People Ops Processes

  • 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.

Manage Benefits, Leave of Absence, and Accommodations

  • 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.

Maintain Employee Data & Records

  • 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.

Ensure Corporate Compliance

  • Keeping us current on employment legislation; proactively update policies and processes to align with legal requirements.
  • Conduct routine compliance reporting as needed.

What We Are Looking For

  • 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

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set.

CAN Pay Ranges

$116,580 - $180,900 CAD

Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!

What We Offer

  • An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
  • A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
  • Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
  • Remote first company—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
  • Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team/department off-sites, or use your individual travel budget to meet up with team members in Canada, the US, or the UK. 
  • Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities. 
  • Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world! 
  • A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $1000 USD to customize your workstation to make it your own. 
  • Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks. 

Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.

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