Senior Paralegal & Projects Operations Lead

Winston Staffing; Chicago (IL); On-site; USD 120,000 - 180,000; Full time

Job summary

Winston Staffing in Chicago seeks a Senior Manager to lead the paralegal and project assistant department. You will guide team performance, staffing, development, and workflow to support the firm’s needs.

You will oversee day-to-day operations, staffing forecasts, recruitment, onboarding, training, and performance management, ensuring strong attorney relationships and efficient resource use.

Qualifications

• Experience leading a paralegal department.
• Strong staffing and performance-management experience.
• Excellent communication and coaching skills.

Responsibilities

• Lead the day-to-day operation of the Chicago paralegal and project assistant department (32 total), including direct supervision of the paralegal supervisor.
• Forecast staffing needs and develop strategies with department leadership, practice group heads, and Human Resources.
• Participate in recruiting, interviewing, and selecting paralegal and project assistant staff.
• Oversee onboarding, integration, training, and ongoing employee development, including Project Assistant training programs.
• Lead performance and compensation processes, including gathering attorney feedback, preparing appraisals, recommending compensation, and conducting review meetings.
• Coach and develop staff, address employee relations concerns, resolve conflicts, and support performance improvement plans.
• Build strong working relationships with attorneys, staff, firm administration, and fellow managers.
• Monitor feedback, productivity, morale, utilization, and workloads; recommend engagement and recognition initiatives.
• Manage paralegal and project assistant technology programs, including graphics, trial, hearing, arbitration, and specialty practice support.
• Prepare regular productivity and hours reports to support workflow coordination and resource allocation.
• Oversee timekeeping and attendance records in accordance with firm policies and applicable wage-and-hour requirements.

Skills

People leadership

Staff development

Workforce planning

Legal operations

Job description

Winston Staffing in Chicago seeks a Senior Manager to lead the paralegal and project assistant department. You will guide team performance, staffing, development, and workflow to support the firm’s needs.

You will oversee day-to-day operations, staffing forecasts, recruitment, onboarding, training, and performance management, ensuring strong attorney relationships and efficient resource use.