Benefits Lead - United States

dss+•Houston, TX

2d•Remote

About The Position

We are seeking an experienced Benefits Lead to own and evolve our benefits programs across the United States and Canada. This role is responsible for the full lifecycle management of benefits, blending operational excellence with strategic insight to deliver a best-in-class employee experience. The Benefits Lead will serve as the primary subject matter expert and point of contact for all employee benefits matters, manage vendor partnerships, oversee benefits systems and analytics, and provide thoughtful, data-driven recommendations to leadership. This role will also play a key part in M&A-related benefits analysis and integration, supporting growth initiatives across North America. In addition, the role will be cross-trained in payroll and serve as a backup to the Payroll Lead for the same employee population. This role will report directly to the People & Culture Leader of North America.

Requirements

7+ years of progressive experience in benefits administration and strategy, preferably in a multi-country or professional services environment
Demonstrated experience supporting M&A activity, including benefits due diligence, analysis, and post-acquisition integration
Strong working knowledge of US benefits programs and regulatory requirements. A strong candidate will have similar knowledge of Canadian benefits
Experience managing benefits systems, vendors, and analytics
Payroll experience or exposure strongly preferred
Excellent communication skills with a high level of discretion, problem-solving and attention to detail

Nice To Haves

A proactive, collaborative team member who sees benefits as both a business lever and an employee experience driver
Comfortable operating independently while partnering cross-functionally and doing so remotely
Data-driven, organized, and able to manage complexity with confidence
Passionate about delivering a thoughtful, inclusive, and high-quality employee experience
Excitement to be part of a growing, fast-paced team and organization with strong project management skills, systems knowledge, and innovative ways of working

Responsibilities

Own end-to-end administration of all employee benefit programs for the US and Canada, including health and welfare, retirement, leaves, wellness, and related offerings
Lead annual renewal processes, plan design evaluations, and cost-management strategies
Develop and present strategic recommendations based on market trends, employee feedback, and data insights
Ensure programs are competitive, compliant, and aligned with organizational goals
Support mergers, acquisitions, and other growth initiatives through benefits due diligence, cost modeling, and risk assessment
Evaluate acquired companies’ benefits programs and develop integration strategies aligned with organizational philosophy and compliance requirements
Partner with internal stakeholders and external advisors to execute smooth benefits transitions during post-merger integration
Support employee communications and change management related to benefits during M&A activity
Act as the primary point of contact for employee questions, concerns, and escalations related to benefits
Deliver a high-touch, employee-centric experience with clear communication and timely resolution
Partner closely with People & Culture colleagues to support employee lifecycle moments (onboarding, leaves, life events, offboarding)
Own benefits-related systems, integrations, and data accuracy
Produce and analyze benefits metrics, reports, and insights to inform decision-making
Ensure compliance with all applicable US and Canadian regulations and manage audits, filings, and documentation
Manage relationships with brokers, carriers, administrators, and external partners
Oversee vendor performance, contracts, renewals, and service delivery
Collaborate with Finance, Legal, and external advisors as needed
Cross-train on payroll processes for the US and Canada
Serve as backup support to the Payroll Lead, ensuring continuity and accuracy during absences or peak periods
Collaborate closely with payroll to align benefits and payroll data