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Executive Assistant - Operations and Client Support; Part-Time

Remote / Online - Candidates ideally in
Chicago, Cook County, Illinois, 60601, USA
Listing for: FreedUp
Part Time, Remote/Work from Home position
Listed on 2026-11-05
Job specializations:
  • Administrative/Clerical
    Business Administration, Office Administrator/ Coordinator
  • Business
    Business Administration, Office Administrator/ Coordinator
Salary/Wage Range or Industry Benchmark: 34000 - 55000 USD Yearly USD 34000.00 55000.00 YEAR
Job Description & How to Apply Below
Position: Executive Assistant - Operations and Client Support (Part-Time)
About Freed Up

Freed Up places talented Executive Assistants with founders and executives at growing US companies. We free leaders up by saving them time and effort so they can focus on the work only they can do. For our EAs, we aim to be one of the best US companies for LATAM and Filipino talent, with a supportive environment and real room to grow.

About the role

We’re looking for a proactive, organized Executive Assistant to support the US-based co-founder of a growing leadership coaching and development firm. The firm helps founders and leadership teams at companies of 5 to 100 employees grow their people through one-on-one coaching, group leadership development programs, strategic planning and coach training. It also serves nonprofits and ministries, and is built around a values-driven, people-first approach to leadership.

The business has doubled its revenue this year and is now growing fast, and the founder is spending too much of his time on admin and coordination. You’ll take ownership of the operational backbone of the firm: scheduling, the coaching management system, client and coach communication, course administration and sales support. This is not a task-taker role. The founder wants someone who will own responsibilities, notice when something doesn’t make sense, and come to him with a proposed solution.

The firm is small and still evolving, so things won’t always be perfectly defined. You’ll help build and refine the processes as you go.

This is a part-time, remote position that requires strong written communication, organizational excellence, and accountability.

Location: Fully Remote

Job Type: Part-Time

What you’ll do
Scheduling and coordination (Main Priority)
  • Manage the founder’s calendar and schedule calls, coordinating availability across clients, coaches and internal team members.
  • Handle the back-and-forth of aligning multiple people for meetings, sessions and programs so the founder doesn’t have to.
Coaching operations
  • Run administration in the firm’s coaching management system, including onboarding new clients, offboarding finished engagements, and keeping coach records up to date.
  • Keep clients, coaches and the internal team informed and aligned. For example, after the founder delivers a group coaching session, send a summary to all the coaches involved.
  • Own internal communication so updates go out on time, every time.
Course and program administration
  • Set up and manage the logistics for the founder’s coaching courses and group leadership programs.
  • Support students and participants so they stay on track and succeed.
Sales support
  • Prepare client proposals using the firm’s existing templates, and help improve those templates over time.
  • Build and format materials in Canva and Google Slides.
Process and partnership
  • Lead a weekly check-in meeting with the founder to review how things are going and agree on changes.
  • Create and maintain living SOPs for the responsibilities you own, updating them as feedback comes in.
  • Spot gaps, inefficiencies and things that don’t add up, and propose practical fixes.
Must-haves
  • At least 3 years of experience as an Executive Assistant, Operations Assistant, Virtual Assistant or in a similar support role.
  • Excellent written and spoken English (C1 or above).
  • Strong experience with calendar management and multi-party scheduling.
  • Comfortable learning and administering new software systems, such as a CRM, client management tool or learning platform.
  • Working knowledge of Canva and Google Slides.
  • Clear, professional written communication for both clients and internal teams.
  • Proactive and solution-oriented: you ask good questions, flag what doesn’t make sense, and suggest what to do about it.
  • Comfortable working with some ambiguity in a small, growing business.
  • Responsive and…
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