We are seeking a Senior Global Benefits Manager to play a key role in our Total Rewards & broader People teams.

Our Total Rewards team ensures that our compensation philosophy & benefits offerings are globally competitive, strategically aligned, & designed to meet the evolving needs of our workforceboth today & in the future.

Our benefits & perks are designed to support holistic well-being & provide peace of mind, enabling our employees worldwide to focus on what they do best. As our Senior Global Benefits Manager, you will be instrumental in advancing this mission, ensuring our programs are innovative, scalable, & aligned with our global workforce needs.

You will report to the Head of Total Rewards, manage a team of three Benefits Analysts, & be based in our New York office in a hybrid role (3 days per week in-office).

You'll Get To

• Define & establish our global benefits philosophy, creating a clear brand identity & strategic roadmap to effectively operationalize all program elements in collaboration with our People Centers of Excellence.
• Provide strategic & operational leadership in the design, development, implementation, administration, & communication of our global benefit programs, including: medical, dental, vision, life, & disability insurance coverage; Flexible Spending Accounts (FSA), retirement & pension plans, onsite & remote wellness programming, COBRA, & legislated leaves of absence & statutory provisions.
• Drive the annual global benefit renewal processes & recommend a go-forward approach taking into consideration feedback from internal stakeholders, market research, & cost analysis.
• Manage global vendor relationships & demonstrate your ability to leverage these partnerships to ensure the company is getting the best return on investment.
• Lead the annual U.S. benefits open enrollment process to include; systems administration, communication & training including open enrollment meetings, vendor management
• Oversees Global leaves of absence programs & policies. Ensure compliance with FMLA & other statutory regulations.
• Develop simple, logical processes that make it easy for employees to access & understand their benefits.
• Conduct regular audits to ensure compliance with local legislation for benefits, absence, & time-off administration.
• Continuously improve the employee experience by simplifying benefits communication, FAQs, & self-service tools.
• Maintain & frequently update benefit information & policies on internal communications resources, & develop new materials, strategies, & project plans to enhance employees' understanding of benefits offerings & policy changes.
• Manage retirement & pension plans, including vendor & platform management, 401(k) Committee, & annual compliance & testing.
• Ensure plan compliance with regulatory filings & guidelines for health & welfare, & 401k plans to include ERISA, IRS, 5500, non-discrimination testing COBRA & to lead any plan audits.
• Proactively partners with key stakeholders in People, Finance & Legal. Develop & work in partnership to monitor service level agreements & performance of all service providers & brokers & hold them accountable for performance measures, including evaluating the ROI & recommending changes to leadership as appropriate.
• Lead, motivate, & develop a team of service oriented benefit professionals to ensure competence & expertise, ensuring seamless administration & compliance with regional regulations.

Who We're Looking For

• 10+ years of benefits experience, with 7 years overseeing multiple areas of benefits including domestic & international program modeling, design, & implementation
• Proactive delivery of communication & follow-up, & highly-effective verbal & written communication skills to collaborate, develop partnerships & instill trust of vendors, managers, & employees.
• Strong collaboration & stakeholder management skills, with the ability to navigate & align competing priorities across diverse teams.
• Proven ability to influence without authority, building consensus & driving initiatives forward in a complex, global environment.
• Skilled in managing multiple stakeholders, balancing strategic objectives while addressing competing needs effectively.
• Adept at fostering cross-functional partnerships, ensuring alignment between benefits strategy & broader business goals.
• Thorough working knowledge of regulatory requirements in the US & international markets, including COBRA, HIPAA, ACA, ERISA, FMLA, & statutory leaves.
• Proven ability to develop clear, structured processes that improve efficiency & employee understanding related to benefits, absence & time off, ensuring alignment with organizational goals & compliance with global regulations.
• Strong proficiency in Workday Benefits administration with the ability to optimise workflows & resolve process-related issues,
• Proficiency in Google Workspace (Docs, Sheets, Slides, etc.), Experience in process simplification & benefits programme optimisation.
• Experience collaborating with payroll teams to ensure accurate benefit deductions & seamless leave management administration.
• Strong technical skills in benefits administration systems, with the ability to optimize workflows & troubleshoot issues.

Benefits & Perks

• A choice between medical plans with an option for 100% covered premiums
• Fertility & adoption benefits
• Access to supplemental insurance plans for additional coverage
• Headspace mindfulness app subscription
• Global Employee Assistance Program
• Retirement benefits with employer match
• Flexible paid time off
• 20 weeks for parental leave & up to 12 weeks to care for an ill family member
• Pretax commuter benefit
• Education reimbursement
• Employee donation match to community organizations
• 6 Global Employee Resource Groups (ERGs)
• Dog-friendly workplace
• Free lunch & snacks
• Private rooftop
• Hack week twice per year

Cash Compensation Range: $178,500 - $250,000 USD

The base salary for this position will vary based on job-related criteria including relevant skills, experience, & location, among other factors.

In addition to the cash compensation above (which includes base salary and, where applicable for eligible roles, may include on-target commissions or overtime pay), Squarespace employees are eligible to be granted an option to purchase our common stock.

About Squarespace

Squarespace is a design-driven platform helping entrepreneurs build brands & businesses online. We empower millions of customers in more than 200 countries & territories with all the tools they need to create an online presence, build an audience, monetize, & scale their business. Our suite of products range from websites, domains, ecommerce, & marketing tools, as well as tools for scheduling with Acuity & creating & managing social media presence with Bio Sites & Unfold. Our team of more than 1,500 is headquartered in bustling New York City, with offices in Dublin, Ireland, Aveiro, Portugal, & coworking spaces in the UK, Netherlands, & Australia. For more information about our company culture, visit https://www.squarespace.com/about/careers.

Our Commitment

Today, more than a million people around the globe use Squarespace to share different perspectives & experiences with the world. Not only do we embrace & celebrate the diversity of our customers, but we also work toward the same in our employees. At Squarespace, we are committed to equal employment opportunity regardless of race, color, ethnicity, ancestry, religion, national origin, gender, sex, gender identity or expression, sexual orientation, age, citizenship, marital or parental status, disability, veteran status, or other class protected by applicable law. We are proud to be an equal opportunity workplace.

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