Senior Benefits Analyst

Our mission at Greenhouse is to make every company great at hiring – so we go to great lengths to hire great people because we believe that they’re the foundation of our success. At Greenhouse, you’ll join a team that collaborates purposefully, fosters inclusivity, and communicates with transparency and accountability so we can help companies measurably improve the way they hire. 

Join us to do the best work of your career, solving meaningful problems with remarkable teams.

Greenhouse is looking for a Senior Benefits Analyst to join our team!

Working directly with the Manager, Global Benefits, the Senior Benefits Analyst oversees the operations, analysis, and optimization of the company’s benefits programs across the US, Ireland, Canada, the UK, and APAC in partnership with Deel, while also supporting benefits administration and compliance as the company expands into new countries. This role ensures programs remain competitive, compliant, cost-effective, and clearly communicated to employees.

This highly collaborative role partners cross-functionally with Finance, Legal, People, and global external vendors while leading a growing team dedicated to supporting every Greenhouse employee through key life moments.

Who will love this job

• A collaborator - you thrive on building strong cross-functional relationships and enjoy working with diverse teams across the globe.
• An analyst - you love diving into data, reconciling invoices, and ensuring accuracy in every detail.
• A problem solver - you approach challenges with empathy and creativity, always keeping the employee experience top of mind.
• A communicator - you excel at translating complex benefits information into clear, accessible communications for employees at all levels.

What you’ll do

• Manage daily operations of global benefits programs, including vendor relationships, compliance, and employee communications
• Lead monthly auditing and reconciliation of benefits invoices, ensuring 100% accuracy between Workday, vendors, and payroll
• Build foundational infrastructure and reporting for self-funded readiness and global renewal cost tracking
• Deliver accurate and timely compliance filings (Form 5500, ACA, PCORI, international pension filings) and establish a compliance calendar
• Support the creation and launch of a Benefits Portal in collaboration with Internal Communications and Marketing
• Provide operational support for global mobility cases, including relocation and visa coordination
• Collaborate with cross-functional partners in Finance, Legal, HRIS, and People Partners to ensure seamless benefits operations
• Drive improvements in employee experience and satisfaction through enhanced communications and case resolution
• Additional projects and responsibilities as business needs require

You should have

• 4+ years of progressive benefits experience in global benefits administration
• Proven track record managing benefits across multiple countries, including program implementation and compliance
• Experience leading benefits administration and compliance during new country expansions
• Strong knowledge of US benefits regulations (ERISA, ACA, COBRA, HIPAA, Section 125) and retirement plan compliance requirements
• Familiarity with statutory benefits and compliance obligations in other regions (e.g., Canada, Ireland, UK, APAC)
• Demonstrated vendor management skills, including contract negotiations and renewal processes
• Proficiency with HRIS and benefits administration systems (Workday, strongly preferred)
• Strong analytical abilities with experience building cost models and delivering data-driven recommendations
• Collaborative approach, partnering effectively with People Partners, Finance, Legal, and external vendors
• Empathy-driven problem solving, keeping employee needs central while balancing compliance, cost, and business priorities
• Excellent written and verbal communication skills with the ability to explain complex benefits concepts to diverse audiences
• Comfort in a fast-paced, high-growth environment; comfortable managing shifting priorities and ambiguity
• A global perspective; you embrace cultural differences and ensure benefits remain competitive, compliant, and cohesive company-wide
• Experience supporting global mobility, relocation, and immigration case management, strongly preferred
• Your own unique talents! Your background has given you a unique perspective and set of transferable skills that aren't always in alignment with