Lead Facilitator and Coach for Education Leaders (Contract to Full-Time) - Tracey A. Benson Consulting - Remote

Mon, 23 Feb 2026 20:00:33 -0600

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.

The Lead Facilitator will assume the duties of:

- 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

- Willing 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.

1. Throughout your career in education, in what ways has systemic racism/ white supremacy shown up? Please provide a specific example of how you addressed a situation of racial equity that was affecting students or share in hindsight how you would have hoped to address it.

2. Describe your facilitation style.

3. How might you motivate a reluctant adult learner towards self-improvement?

About the Anti-Racism Leadership Institute

The Anti-Racism Leadership Institute strives to be the launching pad for meaningful change and improvement toward racial equity for individual school systems. Our firm specializes in designing comprehensive equity audits, custom needs analysis, diagnostic racial equity evaluation, strategic planning and implementation, and anti-racist leadership development.

Our flagship program, The Anti-Racism Leadership Institute is designed to help education leaders build knowledge, skills, and ability, while concurrently developing a concise, high-yield plan of action to increase racial equity. This program, which includes a 40 hour educator, anti-racist master class and ongoing coaching and support, is a unique approach to racial equity consulting. In this model, leaders in education institutions not only build their knowledge and set goals, but also implement the strategies over a 18 week period with the support of an expert anti-racist leadership coach.

Through our domestic and international collaborations with state agencies, school districts, colleges and universities, and education-based organizations, we have improved the lifetime outcomes of students of color by being laser-focused on solving the most intractable, contemporary racial equity issues. Learn more at TraceyABenson.com.

EEO Statement

Tracey A. Benson Consulting, as a firm and Minority Business Enterprise (MBE), has an unyielding commitment to equity as part of our mission and in our workplace. We are an equal opportunity employer that invites individuals from a diverse set of backgrounds to join us in our mission. All considerations for employment, promotion and termination are made without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status. Come as you are.