Demo

Chief of Staff

Winston Staffing
Chicago, IL Full Time
POSTED ON 10/15/2026
AVAILABLE BEFORE 11/13/2026

Position Summary

As a "Chief of Staff" you will serve as a trusted strategic partner and extension of the Principal's practice to help drive growth of practice area. In this high-impact role, you will leverage deep knowledge of the Principal’s ( Rainmaker's) priorities and key client relationships to proactively drive coordination, communication, and relationship management. You will play a critical part in ensuring all administrative and client engagement activities are executed with exceptional quality, discretion, and alignment with Firm standards.


Essential Functions and Responsibilities

Strategic Calendar & Logistics Management

  • Proactive Scheduling: Manage the Principal’s complex calendar seamlessly by anticipating needs, prioritizing competing demands, and aligning schedules with critical client and business priorities.
  • Travel Coordination: Organize end-to-end travel arrangements, including detailed logistics, materials, and comprehensive itinerary management.

Client Engagement & Relationship Support

  • Relationship Management: Develop a deep understanding of key clients, matters, and priorities to proactively support and enhance client engagement.
  • Outreach & Tracking: Maximize client connection opportunities by aligning meetings with travel plans, prompting strategic outreach, and tracking critical follow-ups.
  • Contact Database: Maintain and regularly update a comprehensive, strategic list of key client contacts and relationships.
  • Matter Intake: Support ongoing client matters, including opening new matters and assisting with conflict-related inquiries.

Communication & Stakeholder Relations

  • Primary Point of Contact: Serve as the gatekeeper and primary liaison for internal and external stakeholders, including high-profile clients, using sound judgment to prioritize communications.
  • Correspondence: Draft, review, and handle correspondence on behalf of the Principal, ensuring polished and timely responses.
  • Materials Preparation: Create highly accurate and professional client-facing materials, presentations, and documents..


Meeting & Records Administration

  • Meeting Logistics: Coordinate video conferences, conference calls, room reservations, material preparation, and visitor hosting.
  • File Maintenance: Organize and maintain electronic and paper files according to the Firm's records retention policies.


Salary.com Estimation for Chief of Staff in Chicago, IL
$245,075 to $371,583
If your compensation planning software is too rigid to deploy winning incentive strategies, it’s time to find an adaptable solution. Compensation Planning
Enhance your organization's compensation strategy with salary data sets that HR and team managers can use to pay your staff right. Surveys & Data Sets

What is the career path for a Chief of Staff?

Sign up to receive alerts about other jobs on the Chief of Staff career path by checking the boxes next to the positions that interest you.
Income Estimation: 
$258,641 - $455,625
Income Estimation: 
$884,710 - $2,266,655
Income Estimation: 
$258,641 - $455,625
Income Estimation: 
$884,710 - $2,266,655
Employees: Get a Salary Increase
View Core, Job Family, and Industry Job Skills and Competency Data for more than 15,000 Job Titles Skills Library

Job openings at Winston Staffing

  • Winston Staffing Newark, NJ
  • Remote role but will need to go to Newark, NJ to pick up equipment and orientation one day General Information This position is responsible for conducting ... more
  • 13 Days Ago

  • Winston Staffing Northampton, MA
  • Locum Tenens Anesthesiologist – Western Massachusetts | $385–$400/Hour Winston Locums is seeking an experienced Anesthesiologist for a high-paying locum te... more
  • 1 Day Ago

  • Winston Staffing Manhattan, NY
  • About the Company Winston Resources, a Search & Staffing firm founded in Midtown Manhattan in 1967 is an industry leader, with an unparalleled reputation a... more
  • 1 Day Ago

  • Winston Staffing Lewisburg, PA
  • Non-Invasive Cardiology Physician – Locum Tenens Lewisburg, PA | $370–$385 Per Hour | Ongoing Opportunity Winston Locums is seeking an experienced Non-Inva... more
  • 2 Days Ago


Not the job you're looking for? Here are some other Chief of Staff jobs in the Chicago, IL area that may be a better fit.

  • Coinbase Chicago, IL
  • Ready to do the most impactful work of your career? At Coinbase, we are uncompromising on our mission to increase economic freedom. The bar is high, the en... more
  • 18 Days Ago

  • The Equus Group Chicago, IL
  • Chief of Staff/Executive Assistant to the CEO Private Equity | Chicago, IL | On-Site, 5 Days per Week About the Opportunity A successful private equity fir... more
  • Just Posted

AI Assistant is available now!

Feel free to start your new journey!