People Operations Specialist

Morgan Street Holdings•Chicago, IL

3d•Hybrid

About The Position

This is a high‑ownership role for someone who excels at executing and managing compliance‑driven people programs with precision and accountability. You will own program operations end‑to‑end—driving execution, managing communications, ensuring accurate reporting, and partnering closely with stakeholders to keep programs running smoothly and compliantly. This role is ideal for someone who takes pride in operational excellence and leading work through disciplined execution. The People Operations Specialist, Policy & Programs focuses on policy execution and compliance-driven programs, including leave of absence administration, immigration support, workers compensation, benefit invoicing and vendor coordination, and related reporting support. This role blends operational execution with governance and cross-functional partnership. You are critical in ensuring people processes and programs are implemented seamlessly while maintaining compliance with internal and external regulations, which requires helping employees navigate sensitive situations through empathy and expertise. This role drives the operational excellence of policy and program execution and strategically partners with multiple centers of excellence across the People team and other key functional areas by leveraging technology and automation where possible. Additionally, this role will support the continuous improvement activities that drive operational efficiency, internal controls, and accurate management of the employee lifecycle in partnership with operational centers of excellence, including Talent Acquisition, Talent Management, Total Rewards, Human Resources Business Partners, and Finance and Legal functions. You will drive enhanced ways of working through ideas and thought partnership to improve the overall employee experience.

Requirements

3-5 years of demonstrated experience in people operations or a related discipline with a strong emphasis on executing and administering established people programs.
Proven ability to own complex, compliance-driven processes end-to-end, including execution, issue resolution, documentation, and reporting.
Exceptional attention to detail and accuracy, particularly related to employee data, system transactions, and audit-ready documentation
High level of discretion and professionalism when handling sensitive employee maters and confidential information.
Strong written and verbal communication skills, with the ability to clearly explain policies, processes, and next steps to employees and stakeholders.
Ability to track, monitor, and report on program activity, risks, and exceptions to support compliance and leadership visibility.
Advanced technical skills, particularly in Microsoft Excel, with experience producing operational reports and reconciliations.
Experience managing multi-step programs involving external vendors, internal partners, and multiple handoffs.

Nice To Haves

A strong sense of personal accountability – you naturally take ownership of work and see it through to completion.
Experience executing leave management, benefits administration, or other compliance-heavy people programs.
Experience with SAP SuccessFactors and/or UKG payroll systems.
Continued curiosity that challenges the status quo and a passion for people with a drive to enhance the overall employee experience.
Experience with multiple HCM or payroll systems
Advanced technical skills and experience with system integrations

Responsibilities

Own the end‑to‑end execution of assigned people programs, ensuring accurate administration, timely processing, and consistent application of established policies and procedures. Including Leave of Absence, Immigration, Benefit Invoicing & Vendor Management,
Serve as the primary point of accountability for program communications, including employee guidance, stakeholder updates, and executive‑level reporting.
Monitor program activity, resolve issues, and escalate risks appropriately to ensure continuity, compliance, and a positive employee experience.
Maintain system accuracy through timely updates, audits, and reporting support (e.g., PTO, LOA, Gradifi, Breeze PTO, UKG, and related tools).
Support annual handbook updates and ensure ongoing alignment between documented policy and operational execution.
Respond to complex employee inquiries requiring sound judgment, discretion, and clear interpretation of established policies.
Provide operational backup support to the Global People Solutions team as needed.
Execute compliance‑driven programs (e.g., workers’ compensation, tuition reimbursement, relocation, unemployment, immigration coordination) in accordance with defined policies, controls, and regulatory requirements.
Ensure required documentation, approvals, and audit trails are complete, accurate, and maintained in line with governance standards.
Partner closely with Legal, Finance, Payroll, and HR Centers of Excellence to support compliance obligations and resolve execution‑related issues.
Identify execution risks, process gaps, or control issues and communicate findings clearly to program owners and leadership.
Produce accurate, timely program reporting and dashboards to support leadership visibility, decision‑making, and compliance monitoring.
Track program metrics, trends, and exceptions, ensuring data integrity across systems and vendors.
Support operational improvements by identifying opportunities to improve execution efficiency, clarity, and reliability—while operating within established program frameworks.
Act as a trusted operational partner to HR, Payroll, Finance, Legal, and external vendors to ensure seamless execution of people programs.
Translate complex requirements into clear, consistent operational practices for employees and stakeholders.
Bring discipline, organization, and follow‑through to complex, multi‑step processes with competing priorities.