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 [lead?] new hire orientations/onboarding process and offboarding
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 is needed/preferred/required [especially at scale point]
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.

Tailscale

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