Chief Operating Officer

Chief Operating Officer

The Classical Academy of Sarasota

 

Job Description

 

Exempt

 

Job Summary

 

As the COO of The Classical Academy (TCA), you will play a pivotal role in shaping the operational strategies and processes that drive our organization's growth and success. This is an extraordinary opportunity for a results-oriented and strategic leader with a passion for operational excellence and a commitment to a highly complicated financial and fiscal cycle. You will collaborate closely with the Executive Leadership Team and interface with the Board of Directors to ensure operational excellence, performance monitoringreporting, HR compliance and execution, ownership of capital budgets and projects, and overall financial management thereby enhancing our overall performance. The ideal candidate will possess an understanding of non-profit governance, finances, facilities, human resources, legal compliance matters, including current technology and applications that can streamline those processes, and will be dedicated to implementing innovative solutions that ensure financial stability and operational excellence. Your ability to build strong relationships with stakeholders, manage resources efficiently, and lead high performing teams and functional areas will be crucial in achieving our strategic objectives. As Pre-K-12 private, tuition-based, enterprise, TCA is a beneficiary of the Florida Empowerment Scholarships and complements State of Florida support with private fundraising through events, individual and corporate donors.

 

Job Relationships

 

Reports to: Headmaster

Supervises: Finance, HR, Operations

 

Responsibilities and Qualifications 

 

As the Chief Operating Officer (COO) of The Classical Academy (TCA), you will play a pivotal role in shaping and executing the operational strategies that drive our organization’s growth and long-term success. This position offers an exceptional opportunity for a results-driven, strategic leader with a deep commitment to operational excellence and strong financial stewardship within a complex fiscal environment.

 

Reporting to the Headmaster and working closely with the Board of Directors, the COO will oversee and strengthen all core operational functions, including:

 

• Organizational performance management, monitoring, and reporting

• Human resources compliance and execution

• Capital budgets, project ownership, and facilities oversight

• Financial management and fiscal strategy

 

The ideal candidate will have 10-15 years or more of demonstrated experience in non-profit governance, financial and facilities management, HR, and legal compliance, with a strong skill set with metrics, KPI’s and reporting. You may have served as a CFO in a previous role. A strong understanding of modern technologies and systems that streamline operations will be essential. This leader will bring an innovative mindset to ensure continued financial stability and operational excellence while fostering a culture of accountability, efficiency, and collaboration.

 

Success in this role requires exceptional relationship-building skills, resource management expertise, and the ability to lead high-performing teams across multiple functions.

 

Communication Skills

 

Must have excellent interpersonal and communication skills using the English language. Demonstrates the ability to: read, analyze, and interpret documents; respond effectively to the most sensitive inquiries or complaints; communicate effectively at multiple levels within the organization; manage communications professionally and with respect; know when to escalate issues to upper management (or the BOD if appropriate); communicate to various contractors and suppliers in a simple and timely manner.

 

Application Instructions

 

Location of position: The Classical Academy, 8000 Bee Ridge Rd. Sarasota, FL 34241

 

Contract Details:

 

This is a full-time, on-site, two-year contract position that also offers seasonal flexibility based on the school schedule. At the conclusion of the second year, the role will be evaluated to determine whether ongoing full-time support is needed or if responsibilities may transition to a fractional role as TCA’s capital construction projects are completed and operations move into a steady state.

 

Compensation and Benefits:

 

$175,000 - $225,000. The Classical Academy offers competitive health and other benefits. A relocation advance may be provided, as appropriate. Tuition Discount, if applicable. Flexible work schedule based on school schedules.

 

To apply, please submit:

 

• Cover Letter

• Resume/CV

• Three References

 

Submit Applications to: TCAJobs@outlook.com

 

Additional project assignments will be required for finalist interviews.

 

Application Deadline: We are seeking to fill this position immediately. Candidate evaluation and assessment will begin immediately upon the presentation of materials. Candidates are asked to submit their materials no later than January 5, 2026.