Senior People Operations & Benefits Lead

We are seeking a Senior People Operations & Benefits Lead to join our People Operations team. In this role, you will be the go-to expert for People Operations and Benefits across Ireland and Portugal. Beyond providing essential support, you will apply deep functional knowledge to make significant improvements to the team's productivity and influence the work product of the broader team. You will move beyond execution to build and shape the team's deliverables and strategy, collaborating with cross-functional partners to drive outcomes that align with the department's long-term strategy.

This is a hybrid role working from our Dublin office 3 days per week. You will report to the Senior Manager, People Operations.

You'll Get To…

Data Analysis & Reporting:

• Take on project leadership roles and own projects of broad, diverse scope and complexity, such as major system implementations and change management initiatives.

• Identify opportunities to enhance and refine existing methodologies and processes for the entire employee lifecycle, ensuring solutions are creative, scalable, and effective.

• Demonstrate comfort with ambiguity by determining the methods and procedures required to manage new, unbounded assignments without needing detailed instruction.

• Support with benefits program design and rollout of new plans or updates, ensuring alignment with global strategy and local needs.

People Process & Support:

• Apply knowledge and experience to ensure data integrity in Workday and provide high-level support for strategic decision-making in collaboration with People Partners.

• Design and oversee the People/Benefits-Payroll data handoff processes, ensuring high-quality execution and preventing downstream errors.

• Oversee relationships with benefits brokers, carriers, and providers, managing RFPs, contracts, and service delivery.

• Manage leave of absences, including general administration globally, and compliance with applicable laws and regulations in each country.

• Serve as an escalation point for unbounded problems and complex queries that go beyond Tier 1 and Tier 2 scope.

• Coordinate the activities of others in a Lead capacity, helping to develop their skills and improve work outcomes.

Compliance & Policy:

• Use influence to resolve competing priorities and negotiate differing points of view regarding People Operations policies and procedures.

• Partner with key contacts outside the immediate function (Finance, Legal, and Payroll) to ensure policies on the company intranet are aligned with legislation and cross-functional business needs.

• Drive the development and communication of People policies, ensuring they are not just accurate, but optimized for the global employee population.

• Proactively research, monitor, and ensure compliance with applicable country specific laws, including data protection and local labor requirements, for health, retirement, and leave of absence plans.

Who We're Looking For

• Bachelor’s degree in Human Resources, Business Administration, or related field or related experience. Master’s degree preferred but not required.

• 6+ years of experience in People Operations, Benefits, or a related HR analyst role, with a broad and deep understanding of benefits and people operations functions.

• Exceptional analytical skills with the ability to solve unbounded problems and interpret complex data.

• Effective communicator with the ability to influence stakeholders and collaborate across teams to drive results.

• Proficiency in HRIS systems (e.g., Workday) and data management tools, with sound judgment in selecting methods and techniques to achieve outcomes.

• Proven ability to coordinate the work of others and manage multiple high-priority initiatives effectively.

Benefits & Perks

• Health insurance with 100% covered premiums for you, your spouse or partner and your dependent children including medical, dental, and vision

• Life and Income Protection

• Fertility and adoption benefits

• Headspace mindfulness app subscription

• Global Employee Assistance Program

• Pension benefits with employer match

• Flexible paid time off

• 26 weeks paid maternity leave & 12 weeks paid paternity leave

• 2 weeks paid family care leave

• Education reimbursement

• Employee donation match to community organizations

• 8 Global Employee Resource Groups (ERGs)

• Free lunch and snacks

• Close proximity to cultural landmarks such as Dublin Castle and St. Patrick's Cathedral

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 1,700 is headquartered in New York City, with offices in Dublin, Ireland, and Aveiro, Portugal. For more information about our company, 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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