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Robert Land Academy - Headmaster (FT)

Robert Land Academy (RLA) is seeking an exceptional individual to be Headmaster.

The Headmaster is responsible for leading a broad and dynamic military-themed educational program, to include the development, review, and delivery of initiatives in accordance with the strategic plan. The ideal candidate is an accomplished and compassionate leader who models the military ethos and has worked in an educational setting.

As CEO, the Headmaster reports directly to the Board of Directors and is responsible for the day-to-day leadership in all operational and administrative aspects of the school. As an effective manager, the Headmaster must effectively hold those staff accountable to whom he or she delegates in order to mitigate risk and deliver on the Academy's promise to develop young men to enable their success in life.

Implementing the a strategic plan, leading day-to-day operations, managing staff, overseeing enrolment, ensuring the financial health of the school – including marketing and fundraising, are key components of the role. The Headmaster leads a small leadership team and will be responsible for ensuring effective staff training and evaluation. As a key coordinator, the individual will consider the most efficient use of Academy resources.


  • Lead the Academy, including teaching and operational staff, and student body
  • Inculcate and apply the Academy's values in order to promote, protect, and lead others
  • Ensure the consistent application of the military theme within the context of the overall RLA program, in concert with the Adjutant
  • Recognize and promote the military ethos within the Academy program, understanding that RLA students are not soldiers but young men who attend RLA to effect positive life changes
  • Contribute to and ensure a safe and healthy workplace and school environment for all

Specific Duties

Note that these accountabilities are not exhaustive and are intended to represent the cross-section of work and responsibilities undertaken by the Headmaster.

  • Formulate the Annual Plan (in accordance with the Strategic Plan), designed to achieve the Academy's objectives
  • Provide appropriate and timely advice and background to the Board of Governors to enable effective governance. The Headmaster ensures that Board members are kept apprised of all relevant information regarding Robert Land Academy activities.
  • Act as a role model and example of the Academy’s military theme
  • Communicate with staff to ensure mission integrity with regard to the military theme
  • Lead the hiring and training of operations and academic staff
  • Support all functions and events at the Academy; including but not limited to the Raider Challenge, Bataan Death March, Annual Inspection, and Open House
  • Support and liaise with outside organizations
  • In conjunction with the Academy Sergeant Major and Company Commanders, lead day-to-day management of Operations staff and students
  • Validate the design of staff development programs and ensure their effective execution (e.g. NCO course)
  • Provide supervisory support on some weekends throughout the academic year
  • Other administrative and supervisory functions as required
  • Create a culture of continuous improvement, whereby staff are given the opportunity to achieve their full potential
  • Ensures discipline is undertaken within the bounds of school guidelines, which are communicated to cadets, faculty, staff and parents
  • The Headmaster is responsible for the revenues and expenditures of the Academy, and for meeting financial goals

Required qualifications

  • Proven business and military acumen
  • A Bachelor’s degree in education, business, finance, or a related field and/or equivalent experience
  • Purchasing and business operations management experience
  • Knowledge of accounting, procurement, finance, operations management, and modern management principles and practices
  • Exceptional oral and written communication skills
  • Demonstrated ability to plan and direct multiple programs and projects
  • Strong analytical skills
  • Significant supervisory experience
  • Strong customer service skills with diverse groups, such as students, staff, administrators, community leaders and vendors
  • Has held responsibilities for hiring decisions
  • Experience with the development and delivery of training
  • Possess a valid First Aid certificate

Preferred qualifications

  • Master’s degree in education, business administration, finance or related field
  • Graduation from and experience working at a Military Academy would be considered an asset
  • Graduation from the Canadian Armed Forces Joint Command and Staff Programme (JCSP) or equivalent would be considered an asset

As with all other components of the Headmasters job, relations with personnel are required to be professional at all times and intended to build morale and a culture of service, while ensuring mission integrity.

Instructions to Prospective Candidates

The Headmaster has a considerable impact on the success of students who attend the Academy. We anticipate that the successful candidate can commence Summer 2020; however, this timeframe could be modified to accommodate the successful candidate. Candidates should be eligible to work in Canada. Only those selected for an interview will be contacted and we thank all those who apply. Please email your expression of interest and CV to Ms. Sarah Whittaker at [email protected]. A more detailed packet will be sent to screened, prospective applications.

References will be solicited from candidates who are successfully screened. As the selected candidate will work with youth, a vulnerable sector check is required as a pre-condition to hire.

About Robert Land Academy

Robert Land Academy’s mission is to "Develop the whole boy and produce the best possible citizen."

Robert Land Academy is a highly structured, character driven and military themed living and learning environment focused on supporting boys (grades 5 through 12) to reach their potential and aimed at preparing them for post-secondary education. Located in Wellandport, RLA is the only private, pre-university-level military-themed boarding school in Canada. Founded in 1978, Robert Land Academy has developed a strong reputation as an ideal choice for boys who may be exhibiting difficulties with motivation and self-discipline in conventional educational systems. For more information, please visit

Enrolment at Robert Land Academy is approximately 125 boys in residence - capacity is 150.  Applications are received from across Canada, the United States, Asia, Europe and elsewhere around the globe.  The Academy is located in a country setting on 168 acres in the heart of the historic Niagara Peninsula, 60 minutes southwest of Toronto, Ontario and 45 minutes north of the U.S./Canada Border.

Robert Land Academy is committed to providing accommodation for persons with disabilities. Please notify us when an employment interview time is scheduled if you require accommodation during the interview process.

Accessible Customer Service Plan
Robert Land Academy is committed to excellence in serving all customers including people with disabilities. This policy is reflective of the Accessibility for Ontarians with Disabilities Act, 2005 (AODA) and the Accessibility Standards for Customer Service, Ontario Regulation 429/07. [ Full Policy ]

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