Full-Time

People Operations Partner

Updated on 3/13/2025

Tailscale

Tailscale

51-200 employees

Secure VPN for remote resource access

Compensation Overview

CA$144.7k - CA$187.6kAnnually

Senior

Remote in Canada

Candidates must be based in Canada.

Category
Human Resources
People & HR
Required Skills
Data Analysis
Requirements
  • 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
  • Strong situational adaptability in both written and verbal communication
  • 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
Responsibilities
  • 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
Desired Qualifications
  • Startup experience is strongly preferred
  • Passion for program development and policy improvements!

Tailscale offers a secure networking solution through a WireGuard-based Virtual Private Network (VPN) that allows users to access remote resources like virtual machines and databases from anywhere. Its service is particularly beneficial for businesses and development teams needing to connect to private networks securely. Tailscale stands out for its simplicity, requiring minimal setup, and supports over 100 integrations, making it versatile for various tech environments. The company's goal is to provide an easy-to-use and secure way for users to manage and access their resources remotely.

Company Size

51-200

Company Stage

Series B

Total Funding

$111.9M

Headquarters

Canada

Founded

2019

Simplify Jobs

Simplify's Take

What believers are saying

  • Tailscale's zero-trust solution is easy to deploy in existing infrastructures.
  • Partnership with Mullvad expands Tailscale's global VPN server network.
  • Viral adoption among developers indicates strong product-market fit.

What critics are saying

  • Increased competition from other zero-trust startups could impact market share.
  • A critical vulnerability in the Windows client poses a security risk.
  • Cooling venture funding may limit Tailscale's expansion capital.

What makes Tailscale unique

  • Tailscale uses WireGuard's Noise protocol for trusted encryption.
  • It integrates with existing identity providers like GSuite and Office365.
  • Tailscale offers over 100 integrations, fitting into diverse tech stacks.

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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

Growth & Insights and Company News

Headcount

6 month growth

1%

1 year growth

0%

2 year growth

3%
BetaKit
Jan 14th, 2025
Tailscale Hits 10,000 Paid Business Clients After Doubling Customer Base In 10 Months

Corporate VPN startup has seen rapid growth amid strong demand from AI companies

Arun Blog
Sep 3rd, 2024
SSH setup of the future

About two weeks, Tailscale announced a fantastic SSH experience as well: Tailscale SSH that allows one to establish SSH connections with devices on my tailnet without having to generate and distribute keys.

Tailscale
Sep 7th, 2023
Mullvad on Tailscale: Privately browse the web

Tailscale has partnered with Mullvad to make its global network of VPN servers available for our customers.

Tailscale
Jun 27th, 2023
Prerequisites

Tailscale recently introduced Tailscale SSH, which allows you to use Tailscale to authenticate to your devices over SSH instead of having to rely on passwords, key rotation, copying over authorized keys and more.

Benzinga
Jun 6th, 2023
Despite Quantitative Tightening, Vcs Are Investing In Devops And Ai Security

DevOps shifts security left. “Architecture and development shifts create new opportunities for security,” says James Green, General Partner at CRV and a Forbes’ 30 under 30 honoree in 2022. The startups best positioned to land funding are those with defensible moats that usually go in hand with solving tough problems others haven’t addressed. One example is integrating security with DevOps, which empowers developers to prioritize security issues and expedite remediation. “Existing Source Code Analysis solutions are not sufficient,” Green notes. CRV’s investments in Project Discovery and Tailscale put security in the hands of developers, reducing silos and remediation time.The result of this cloudification of work is a diverse landscape of cybersecurity offerings extending protection from on-premises basics to newer terrain - developer and firmware environments, and even AI algorithms