People Operations & Benefits Partner

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

The Global People Operations & Benefits Partner will be a key member of our small, but mighty, Global People Operations team. As our Global People Operations & Benefits Partner, you are a trusted advisor for new hires and employees. Our benefit programs are essential for attracting and retaining top talent and empowering individuals to do their best and most meaningful work.

The ideal candidate will be knowledgeable in global benefits and administering leave programs and be a thought partner to build out new processes and people programs while informing how best to scale programs and practices informed by data as well as internal demographic and market trend insights. You like to create solutions for issues that arise and thrive in an ever-changing fast paced startup environment.

As a Global People Operations & Benefits Partner you’ll be executing our Global People Ops & Benefits strategy in partnership with the Global People Ops team.

You are extremely organized, have a keen eye for detail, strategic prioritization skills, and utilize the utmost discretion and care when handling employee information and addressing any concerns that may arise. 

If this sounds like you, keep reading!

Key Responsibilities

  • Help drive the strategic evolution and execution of our global benefits programs to ensure we’re constantly innovating in the space, and providing benefits that are top of market
  • Recommend global benefits programs by assessing Tailscale’s direction, reviewing competitor & general industry practices, and supporting analyzing cost impact/effectiveness
  • Support day-to-day administration and compliance of benefits, leaves, and accommodations in partnership with the People, Legal, and Payroll teams
  • Support day-to-day administration of our Global People & Benefit programs (including but not limited to employee life cycle support from onboarding to off-boarding,  etc.)
  • Lead Open enrollment and regularly schedule benefits-related meetings
  • Support in identifying and implementing effective and efficient benefit administration and HR/PO processes to ensure a positive employee experience
  • Collaborate with People team leadership to build and maintain global system 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.
  • Review benefit compliance with applicable federal, state, and regional provider rules, regulations, and policies, and record/report benefit compliance in an accurate way
  • 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
  • Process and administer all leave of absence requests and disability paperwork for teams across our regions: medical, personal, disability, ADA, and FMLA
  • Act as first line support for employees regarding their people program and benefits needs for leave and/or modified work schedules/leave planning
  • Participate in new hire orientations/onboarding process and off-boarding
  • Any other ad-hoc People Ops/Benefits projects and tasks as needed

Requirements

  • 4+ years of experience in global benefits (inclusive of planning, compliance, and administration from a high-growth, technology company)
  • Familiarity with global benefit best practices in various geographic regions, particularly in US, EU, & CAN (more is a plus!)
  • Experience with global benefits compliance and communications for programs at scale
  • Experience administering benefits plans, especially in troubleshooting enrollment data processes and answering advanced employee questions
  • Ability to manage effectively with ambiguity, manage multiple projects through completion on time and on budget and to prioritize in a rapidly changing environment
  • Startup experience 
  • Passion for benefit program development and policy improvements!
  • 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
  • You live our values, everyday
  • Working knowledge of US federal, state, and local employment laws, in addition CAN & UK employment & benefits compliance regulations to support compliant practices
  • Strong situational adaptability in both written and verbal communication

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. We use San Francisco market data to establish our pay ranges.

CAN Pay Ranges

$171,520 - $214,400 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!
  • All-remote with the opportunity to work from anywhere—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). 
  • 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! We encourage all Tailscalars to take 4-6 weeks of vacation annually. 
  • 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. 

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