Description

Summary

Middleburg is a vertically integrated real estate investment, development, and construction firm specializing in attainable rental housing across the southeastern United States since 2004.

As the Benefits and Payroll Manager, you will lead and optimize our payroll and benefits programs for a multi-state workforce. The Benefits and Payroll Manager is responsible for the management, administration, compliance, and continuous improvement of all payroll and employee benefits programs. This role provides leadership and oversight of payroll processing, benefits administration, regulatory compliance, reporting, audits, and vendor management. This position requires demonstrated expertise and hands-on experience with UKG Ready.

This position will be full-time, in person, located in the Vienna, VA office and will report directly to the SVP, People & Culture.

Essential Duties and Responsibilities:

Payroll Management

• Oversee and manage accurate and timely multi-state payroll processing (bi-weekly or semi-monthly as applicable).
• Ensure compliance with all federal, state, and local wage and hour laws.
• Manage payroll tax filings, reconciliations, W-2 processing, and year-end reporting.
• Ownership, administration, and optimization of UKG Ready, including system configuration, payroll processing, benefits integration, reporting, compliance setup, and end-user support.
• Lead payroll audits and ensure internal controls are in place and effective.
• Partner with Finance & Accounting on allocation reconciliation, accruals, and reporting.
• Manage payroll systems and processes to ensure accurate calculation of wages, overtime, variable compensation, reimbursements, and wage garnishments

Benefits Administration

• Administer all employee benefit programs, including medical, dental, vision, life, disability, 401(k), and voluntary benefits.
• Serve as primary contact for benefits vendors and brokers.
• Oversee annual open enrollment process, including system setup & integration, vendor coordination, employee communications, and compliance.
• Ensure compliance with ERISA, ACA, COBRA, HIPAA, FMLA, and other applicable regulations.
• Manage benefit audits, testing, and required reporting (e.g., 5500 filings).
• Evaluate and recommend benefit plan enhancements aligned with organizational goals.
• Serve as the primary point of contact for brokers, carriers, and third-party administrators.
• Analyze utilization, costs, trends, and employee feedback to inform renewals and long-term strategy.
• Support and evaluate benefits offerings, including health and wellness programs, and voluntary benefits, to ensure market competitiveness.
• Bring fresh ideas to support the promotion and communication of benefits and wellness to our workforce, looking at new avenues to communicate and engage team members.

HRIS/UKG Ready Management & Optimization

• Serve as the system owner and subject matter expert for UKG Ready.
• Configure and maintain payroll, benefits, timekeeping, onboarding, and reporting modules.
• Manage system updates, enhancements, and releases.
• Ensure accurate system configuration for taxes, deductions, earnings codes, workflows, and approvals.
• Develop and maintain custom reports and dashboards.
• Lead system integrations with benefits carriers and third-party vendors.
• Troubleshoot system issues and serve as primary liaison with UKG support.
• Continuously evaluate and improve system utilization and automation opportunities.

Compliance & Reporting

• Maintain compliance with all applicable employment, payroll, and benefits regulations.
• Develop and document policies and procedures related to payroll and benefits administration.
• Prepare internal and external reporting for leadership, audits, and regulatory agencies.
• Ensure data integrity and confidentiality of employee information.
• Maintain strong documentation, procedures, and internal controls

Requirements

Knowledge and Experience:

• Bachelor’s degree in Human Resources, Business Administration, Accounting, or related field (or equivalent experience).
• 5+ years of progressive payroll and benefits management experience.
• 3+ years of hands-on, advanced experience with UKG Ready, including payroll and benefits configuration.
• SHRM-CP, SHRM-SCP, PHR, or SPHR certification.
• Demonstrated expertise in payroll compliance and benefits regulations.
• Experience managing payroll audits and year-end processing.
• Strong analytical skills and advanced reporting capabilities within UKG Ready
• High level of accuracy, attention to detail, and ability to manage confidential information.
• Experience in multi-state payroll environments.
• Ability to meet critical payroll deadlines.
• Ability to think strategically while executing operationally
• Clear, confident communicator across all levels of the organization
• Strong organizational skills