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Executive Assistant to the CEO

Position Overview

The Executive Assistant will support our busy CEO while she leads two separate ventures, Enrollment Builders and Briar Hill Stables. This position is an in-person role, reporting Monday - Friday at Briar Hill Stables in Lexington, Kentucky.  

  • Enrollment Builders is a higher education admissions company, providing contact center services for institutions like The University of Alabama, Missouri Baptist University, and Rocky Mountain College.
  • Purchased in May 2021, Briar Hill Stables is located on 15+ acres in the heart of horse country. This horse farm will soon be home to 10-12+ hunter/jumper horses and is currently under construction. 

The mission of the Executive Assistant (EA) is to stay five steps ahead of the CEO, tracking all of the administrative details and clearing the path to help her focus on the most important parts of our business.

The Executive Assistant is a key asset to the CEO, anticipating needs at an exceptionally high level and allowing her to develop vision and strategy for all aspects of operations in alignment with revenue and profitability goals.

While repetitive tasks are certainly part of this position, duties assigned vary from week to week based on the CEO’s needs and the needs of business.


The Executive Assistant has the following primary responsibilities:

  • Acting as the gatekeeper to keep the CEO focused on priorities, rerouting and delegating incoming issues as needed
  • Maintaining the CEO’s project calendar, tracking her task schedule, keeping tasks on target by communicating important deadlines and priorities, and keeping everyone aligned so that things move smoothly and get done
  • Managing and prioritizing email on behalf of the CEO, helping her respond to important or time sensitive emails in a timely manner
  • Completing hands-on invoicing, payables, and weekly expense reporting
  • Executing a variety of personal and professional administrative assignments including, but not limited to, booking appointments, conducting research projects, coordinating travel, making purchases, paying bills, and more
  • Managing meetings, building and preparing in-depth agendas, and taking and distributing notes,
  • Creating financial reports and driving accountability throughout the business.
  • Communicating on the CEO’s behalf both internally and externally
  • Analyzing and documenting internal processes, identifying opportunities for improvement
  • Proofing material for grammar, spelling and errors as needed
  • Acting as the CEO’s proxy in dealings with vendors and in other situations as directed


  • Quality Communication
    The EA must be an excellent communicator, in both written and oral form. This includes proficiency in spelling, grammar, and punctuation. They must also be responsive, and highly-organized, able to respond quickly to communication across multiple channels. 
  • High Level of Discretion
    The EA regularly works with confidential information; discretion and sensitivity regarding financial, operational, and personal information is a must. In addition to working directly with the CEO, the EA works with other leaders and teams across the businesses. The EA must collaborate and communicate well with these team members, always representing the CEO with the highest degree of professionalism.
  • Anticipating Needs
    Strength in technical problem solving based on expertise and experience, and a strong commitment to efficiently achieve high quality results is required. The EA must stay five steps ahead of the CEO, clearing the path for her to make her greatest contribution.
  • Affinity for Technology
    The EA is a savvy technology user and readily learns and adopts new technology. Proficiency in the following basic tech platforms is a minimum expectation: Slack, Zoom, Google Workspace, HubSpot, Trello, and Microsoft Office.
  • Financial Knowledge
    The CEO’s EA must have a high attention to detail and accuracy, using their existing experience dealing with financial and accounting information, their experience supporting Executives, and their ground-level understanding of accounting terminology to provide informed administrative support.


  • Candidates local to Lexington, KY are strongly preferred
  • Education: Bachelor’s degree, preferred.
  • Experience supporting small business executives, dealing with personal and financial information.
  • Experience in a marketing organization, technology firm, and/or small business start-up environment is preferred
  • Experience around horses, preferred
  • Experience with project management, preferred
About Enrollment Builders:
One enrollment equals one story. The heart of Enrollment Builders is filled with stories of real people fulfilling their dream of earning a college degree. Through experience, empowerment, and science Enrollment Builders helps higher education institutions grow enrollment one story at a time.
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