[Remote] People Operations Generalist at Tailscale

Canada

Tailscale Logo
Not SpecifiedCompensation
Mid-level (3 to 4 years), Senior (5 to 8 years)Experience Level
Full TimeJob Type
UnknownVisa
Biotechnology, Software Development, Internet ServicesIndustries

Requirements

Candidates should possess over 6 years of experience in People Operations, including at least 4 years in startup environments. A strong understanding of US, UK, and Canadian employment laws and benefit practices is required, along with proficiency in Google Workspace, HRIS, benefits administration, and ATS platforms. The ideal candidate is adaptable, organized, detail-oriented, and an effective communicator with strong cross-functional partnership skills.

Responsibilities

The People Operations Generalist will build, optimize, and scale core HR processes from onboarding to offboarding, manage employee data and records, and ensure compliance with employment laws in the US, UK, and Canada. Responsibilities include administering benefits and leave programs, liaising with vendors, coordinating 401(k) compliance, maintaining data integrity, and updating policies to align with legal requirements. This role also involves creating SOPs, automating workflows, and participating in People team initiatives and company events.

Skills

People Operations
Onboarding
Offboarding
Employee Lifecycle
HRIS
Compliance
Benefits Administration
Leave of Absence
Process Improvement
Automation
Workflow Development
SOP Creation
Employee Experience
Startup Environment

Tailscale

Secure VPN for remote resource access

About Tailscale

Tailscale offers a secure networking solution that allows users to access remote resources like virtual machines and databases from anywhere using a WireGuard-based Virtual Private Network (VPN). Its service is designed for businesses and individuals needing to manage private resources remotely, with a focus on simplicity and minimal setup. Tailscale's freemium model attracts a wide user base, allowing users to start for free and upgrade for additional features. The company aims to enhance data security while providing an easy-to-use remote access solution.

None, CanadaHeadquarters
2019Year Founded
$111.9MTotal Funding
SERIES_BCompany Stage
Enterprise Software, CybersecurityIndustries
51-200Employees

Benefits

Health Insurance
Dental Insurance
Vision Insurance
Flexible Work Hours
Remote Work Options
Unlimited Paid Time Off
Parental Leave
Professional Development Budget
Home Office Stipend
Phone/Internet Stipend
Company Equity

Risks

A critical vulnerability in Windows client poses remote code execution risk.
Cooling venture funding may impact Tailscale's future investment opportunities.
Scalability challenges may arise with rapid enterprise adoption of zero-trust solutions.

Differentiation

Tailscale uses WireGuard's Noise protocol for trusted encryption standards.
It integrates with existing identity providers like GSuite and Office365 for easy setup.
Tailscale offers over 100 integrations, fitting into almost any tech stack.

Upsides

Tailscale's zero-trust solution meets growing demand for enterprise security.
The $100 million Series B funding boosts product expansion and market reach.
Integration with Mullvad enhances privacy with a global VPN server network.

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