Senior Global Benefits Manager

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

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

Our benefits and perks are designed to support holistic well-being and 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, and aligned with our global workforce needs.

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

You'll Get To…

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

Who We're Looking For

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

Benefits & Perks

• A choice between medical plans with an option for 100% covered premiums
• Fertility and 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 and 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 and 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, and 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 and businesses online. We empower millions of customers in more than 200 countries and territories with all the tools they need to create an online presence, build an audience, monetize, and scale their business. Our suite of products range from websites, domains, ecommerce, and marketing tools, as well as tools for scheduling with Acuity and creating and managing social media presence with Bio Sites and Unfold. Our team of more than 1,500 is headquartered in bustling New York City, with offices in Dublin, Ireland, Aveiro, Portugal, and coworking spaces in the UK, Netherlands, and 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 and experiences with the world. Not only do we embrace and 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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