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Lead Facilitator and Coach Education Leaders

Remote / Online - Candidates ideally in
Charlotte, Mecklenburg County, North Carolina, 28245, USA
Listing for: Tracey A. Benson Consulting
Full Time, Part Time, Contract, Remote/Work from Home position
Listed on 2026-01-12
Job specializations:
  • Education / Teaching
Job Description & How to Apply Below
Position: Lead Facilitator and Coach for Education Leaders (Contract to Full-Time)

The Role

This is a contract to permanent full-time position.

This role begins as a 1099 contractor position where the individual will be paid for training and work completed (an estimated 5-10 hours per week). The initial contracting period will serve as an opportunity for the employer and candidate to evaluate whether the candidate is a great fit for the full-time role.

If the evaluation of the contractor's work is satisfactory, a full-time (exempt) salaried offer will be made, tentatively, in quarter 3 of 2024.

This role will report directly to the CEO.

The Lead Facilitator will serve as a critical member of the programming team. In collaboration with senior leadership, the role will help hone the professional learning experience for our clients - education professionals; execute a significant portion of in‑person and virtual workshop facilitation; evaluate the effectiveness of workshops to provide ongoing feedback; provide executive coaching to clients; and enhance the services of the organization by ongoing strategizing with the senior leadership team.

  • Facilitator
  • Anti‑Racist Executive Leadership Coach (for educators)
  • Client relationship manager

The role in its full‑time iteration requires a significant amount of travel.

Responsibilities and Duties Workshop Facilitation
  • Facilitates the curriculum of the Anti‑Racism Leadership Institute through in‑person and virtual workshops for the organization’s clients
  • Executes on associated administrative work for each workshop (including during and both pre and post‑workshop to include finalizing workshop dates, ensuring materials are ordered, conducting any make‑up sessions etc.)
  • Coordinates with other team members to determine best scheduling of workshops to ensure all agreed upon engagements are delivered on time and in a high‑quality manner
Coaching
  • Regularly, serves as the 1:1 leadership coach for multiple clients after the conclusion of their workshop series
  • Serves as 1:1 leadership coach for additional clients as needed
  • Completes up to 100 hours of coaching/monthly
Client Relationship Management
  • Maintains a portfolio of accounts/clients
  • Serves as the primary contact for those in the portfolio
  • Provides services as needed (and outlined in the contract) to portfolio accounts
  • Assists in the renewal of portfolio accounts
Strategic Guidance
  • Provides feedback and strategic guidance to the senior leadership with regards to the organization’s professional learning services
  • Collaborate with CEO and COO to develop standards and measures to determine efficacy of coaches
Role Requirements
  • Willingness to perform the role as a contractor with no guarantee of a full‑time offer
  • Willingness to serve a facilitator understudy and co‑facilitator in preparation for eventual solo facilitation
  • Willingness to travel for up to several weeks at a time between multiple sites, domestically and internationally
  • Willig and able to coach up to 100 (1)‑hour coaching sessions monthly
  • Understands the ebbs‑and‑flows of the educational consultancy field and is amicable to moving at a fast pace during high season and maintains productivity during low season
Qualifications
  • Three or more years of experience as an assistant principal, principal / head of school, assistant superintendent, or superintendent.
  • Experience facilitating workshop or professional development/learning sessions.
  • Engaging public speaker
  • An adult learner able to receive frequent, critical feedback on facilitation methods with grace and gratitude
  • Ability to implement suggested improvements willfully and immediately
  • Demonstrated project Management skill set
  • Comfortable learning new technologies
Benefits

If invited to transition to a full‑time role, the full‑time role comes with the following organization sponsored benefits:

  • Healthcare Reimbursement Arrangement – A set dollar amount available to you each month for reimbursement for healthcare premiums (if you are not covered via your spouse’s plan) and any other qualified medical expenses
  • 401K Option
  • Monthly Remote Work Stipend
Applying

Along with your application, please provide a cover letter that addresses the three items below.

  • Throughout your career in education, in what ways has systemic racism/white…
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