Benefits & People Operations Lead

Job Summary

RLDatix is seeking a Chicago-based Principal Analyst, Benefits & People Operations to join our People Operations team. This role will involve owning, strengthening, and strategically advancing our benefits programs across North America.

About the Role

The Principal Analyst will serve as RLDatix's trusted benefits expert and data custodian, driving operational excellence, audit readiness, and employee-centred program design to ensure every member of TeamRLD is protected, informed, and well-served.

Responsibilities

• Leading end-to-end benefits administration across the US and Canada, covering medical, dental, vision, life, disability, retirement (401(k), RRSP/DPSP), and ancillary programs, to deliver seamless, compliant, and high-quality benefits experiences at scale.

• Managing all benefits records, vendor file feeds, eligibility data, enrolment, and payroll reconciliation to ensure zero downstream errors and maintain full audit readiness across monthly, semi-monthly, and quarterly audit cycles.

• Shaping the strategic direction of our benefits programs by translating market intelligence, regulatory changes, and broker benchmarking data into prioritized recommendations for senior stakeholders and long-term EVP planning.

• Redesigning and streamlining benefits administration workflows, open enrollment processes, and vendor file management to build consistency and efficiency across a growing, multi-entity organization.

• Responding to a high volume of employee benefits enquiries, including eligibility questions, claims escalations, life events, and open enrollment support, to deliver outstanding employee experience within established SLAs.

• Crafting clear and compelling benefits communications, including open enrollment campaigns, employee education materials, total rewards statements, and policy updates, to ensure employees fully understand and utilize their benefits.

Requirements

• Significant experience (10+ years) in end-to-end benefits administration in the US and Canada, ideally within organizations of 1,500 or more employees across multiple states.

• Proven success in acting as a benefits thought leader, with the ability to shape plan design, lead vendor and broker negotiations, and inform EVP strategy using data-driven market and regulatory insight.

• In-depth knowledge of US and Canadian benefits compliance frameworks, including ERISA, ACA, COBRA, HIPAA, IRS Section 125, provincial Canadian legislation, non-discrimination testing, and statutory filings.

• Demonstrated understanding of the connection between benefits administration and payroll accuracy, including experience reconciling benefits data against HRIS and payroll systems; hands-on experience with Dayforce/PeopleHub is a significant plus.

• A knack for working both independently and collaboratively within a high-volume, fast-paced, globally matrixed environment, engaging effectively with employees, people partners, payroll teams, brokers, and senior leadership.

• Sincere interest in driving meaningful improvements to the employee experience through benefits education, process excellence, and a genuine commitment to getting the details right.