People Operations Generalist

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.

US Pay Ranges$87,000—$135,000 USD

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