Paralegal Ops Leader, National Project Assistant Program

Winston Staffing; Chicago (IL); On-site; USD 130,000 - 190,000; Full time

Job summary

Winston Staffing seeks a senior leader to run one of the firm's largest paralegal organizations—32 paralegals and project assistants supporting ~500 attorneys across Chicago practice groups. The role partners with firm leadership nationwide and drives staffing strategy, onboarding, and career development to build a high-performing team.

The ideal candidate has 10+ years in professional services and 5+ years managing large teams, with strong executive presence to influence partners and

Qualifications

• 10+ years in professional services and 5+ years managing 15+ direct/indirect reports.
• Legal industry experience strongly preferred; candidates from legal tech consulting or legal ops with prior law firm exposure will be considered.
• Strong executive presence capable of influencing partners and stakeholders.

Responsibilities

• Lead the firm's national Project Assistant program end-to-end, including recruiting, onboarding, and training.
• Own staffing strategy, recruiting, onboarding, performance management, compensation, and career development.
• Forecast staffing needs and resolve complex, competing priorities with attorneys and firm administration.
• Drive engagement and retention through coaching, mentorship, and building a unified team culture across practice groups.
• Balance strategic leadership with hands-on operational oversight, including a direct report managing timekeeping and administrative functions.

Skills

Leadership

Staffing strategy

Recruiting

Performance management

Coaching

Stakeholder management

Executive presence

Legal ops experience

Tools

ATS

HRIS

Job description

Winston Staffing seeks a senior leader to run one of the firm's largest paralegal organizations—32 paralegals and project assistants supporting ~500 attorneys across Chicago practice groups. The role partners with firm leadership nationwide and drives staffing strategy, onboarding, and career development to build a high-performing team.

The ideal candidate has 10+ years in professional services and 5+ years managing large teams, with strong executive presence to influence partners and