Paralegal Manager

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

Lead one of the firm's largest paralegal organizations — 32 paralegals and project assistants supporting ~500 attorneys across every Chicago practice group.

• High-visibility leadership role with direct partnership with firm leadership, practice group heads, and peer managers nationwide.
• Own the full talent lifecycle: staffing strategy, recruiting, onboarding, performance management, compensation, and career development.
• Run the firm's national Project Assistant program end-to‑to‑end, from annual recruiting (interviews Jan/Feb, offers March, start dates June/July) through onboarding and training.
• Drive engagement and retention through coaching, mentorship, and a strong, unified team culture across practice groups.
• Balance strategic leadership with hands‑on operational oversight, including a direct report managing timekeeping and administrative functions.
• Partner closely with attorneys and firm administration to forecast staffing needs and resolve complex, competing priorities.
• Built for growth: this role has a clear path to expand into a broader Litigation Practice Support Senior Manager position.
• Join a top-tier global platform known for collaborative culture, strong financial performance, and real investment in business support functions.
• Ideal for a current paralegal leader at a large Am Law firm — or a manager/supervisor ready to step up — with 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 also be considered.
• Strong executive presence required — proven ability to influence partners, manage stakeholders, and build trust across all levels of the firm.