Career Center

Executive Assistant to Head of School

2022-2023

About Cascades Academy

Cascades Academy is an independent PK-12 day school with ~235 students located in the beautiful mountain town of Bend, Oregon.  The school was founded in 2003 and resides on an award-winning 53-acre campus located on the Deschutes River. The school’s unique mission weaves challenging academics with experiential learning within an engaged, vibrant community.

Cascades Academy values employees who are committed to our mission, are prepared to engage fully in a learning community, and are excited to bring their authentic selves to work. Cascades Academy’s culture is highly collaborative and puts what is best for students at the center of the work. Regularly named one of the Best Nonprofits to Work for in Oregon, our faculty and staff see each other as teammates and feel motivated to do their best work here. 

Cascades Academy strives to cultivate and maintain a supportive, inclusive community for all employees and actively promotes a commitment to diversity, equity, inclusion, and anti-racism.  

Studies have shown that women and people of color are less likely to apply for jobs unless they believe they meet every one of the qualifications as described in the job description. We are most interested in finding the best candidate for the job and are eager to consider applications from groups traditionally underrepresented in independent school communities.

 Cascades Academy seeks an Executive Assistant to the Head of School. The role requires a desire to participate in a community of colleagues who can collaborate and enjoy their work in a joyful yet busy and demanding school environment. The role suits a person who takes initiative and is well organized and who shows kindness and poise with colleagues, parents, and children. The role requires a person with project management skills as well as the ability to follow through on the day-to-day and month-to-month items of an active and dynamic school community.  

The Executive Assistant to the Head of School provides a full range of administrative and strategic support to the head. The Executive Assistant also holds the responsibility for oversight of the head’s office, functioning as both an extension of the head and ensuring both responsiveness, efficiency, and warmth, so that everyone feels welcomed, respected, and well served. In addition, the Executive Assistant provides administrative support to the Board of Trustees, limited support to administrators, and manages a variety of special projects.

This person must be exceedingly well organized, detail oriented but flexible, and enjoy the challenges of working with a variety of situations and circumstances. The ability to interact with staff and external stakeholders at all levels while remaining diplomatic, professional, proactive, resourceful, and efficient. A high level of professionalism, sound judgment, and absolute confidentiality is critical to this role.

 Essential Duties and Responsibilities

 Head of School Support

• Manages the Head’s business communication (phones, email, and mail) applying necessary judgment to determine priorities and importance.
• Maintains the Head’s calendar; prioritizes requests for the Head’s attention by managing the scheduling of meetings and appointments, coordinates activities and agendas, and uses tact and diplomacy to resolve appointment conflicts due to unforeseen circumstances.
• Maintains a strong understanding of the school’s mission, vision, values, and strategic priorities in order to appropriately filter and prioritize incoming information and meeting requests.
• Establishes systems to ensure the Head is provided with the necessary background information and briefing materials for meetings, events, and speaking engagements; researches, organizes, prepares, and presents information in a clear and concise manner.
• Assists with monthly credit card reconciliation for the Head’s credit card by procuring and attaching appropriate original receipts.
• Maintains and manages an organized and logical filing system for all electronic and paper documents.
• Makes and manages all travel arrangements for the Head, including airline and hotel reservations, conferences and meeting registrations, transportation, etc. 
• Works with the Administrative and Leadership Team to coordinate workflow, facilitate projects, assist and coordinate Crisis Management plans, and plan meetings and retreats. Maintain vacation request dates for all administrators.
• Post and manage all job openings, review and handle application materials, coordinate and schedule interviews, and arrange for campus visits. 
• Oversees and manages the annual professional development budget for both the Head and the Division Heads.  Oversees collection of documentation and schedules for accreditation.   

• Track professional development on a regular basis throughout each school year for the administration, faculty, and staff.
• Prepares professional development proposals for Title grants from the Bend LaPine School District
• Works with the Business Office to ensure PD budget reconciliation

• Serves on the Self-Study Leadership team and coordinates the school’s accreditation process.

 Board of Trustees Support

• Assist the Board Chair in all Board-level communications.
• Coordinate, schedule, and plan all Board meetings, Board retreats, Board Committee meetings, and events.
• Maintain files for all meeting minutes, charters and objectives, confidentiality statements, bylaws, and other Board and Board Committee materials.  Load documents to the Board Google drive.
• Assist with the preparation for Board Meetings. Provide administrative assistance with drafting agendas.
• Assist with the production of accurate Board minutes at each meeting.
• Provides administrative support to the Board of Trustees, including correspondence, agendas, and all logistics for meetings, retreats, and events.
• Annually update all materials and build packets for new Board members’ orientation. 

Front Office Team Oversight

• Ensure the smooth operational function of the front office team including managing the school’s front office coordinator

COVID-19 Compliance

• Stay current on compliance with all relevant state and local health requirements.
• Provide the health and safety team with logistical and organizational support.

  Qualifications

• Three - five years of experience as an executive assistant or office manager responsible for executing a variety of administrative processes 
• Exceptional project management skills including the ability to think independently and critically, manage multiple tasks simultaneously, and meet deadlines in a fast-paced, stressful environment.
• Strong oral, written and interpersonal communications skills, both in person and over the phone. Ability to communicate professionally, with tact and diplomacy.
• Ability to work independently and prioritize workload; proven experience maintaining confidential information.
• Manage highly-sensitive, confidential information with the highest level of discretion and expediency
• Flexible, organized, and able to accurately work under time constraints and deadlines
• Ability to anticipate and resolve complex and/or confidential administrative issues with excellent judgment and little or no supervision.
• Proven success at working collaboratively and effectively on team
• Demonstrated understanding of cultural competence and its impact on the role
• Appreciation and respect for diversity in all of its forms
• A sincere commitment to the school’s mission and the willingness to be a visible, enthusiastic brand ambassador. Passion for what is good for children and families.
• Knowledge of common tech platforms used in education, such as Blackbaud, Google Suite, Microsoft Office, etc.
• Clean driving record and valid driver’s license

Physical Requirements

• The person in this position must be able to work at the school.
• Requires mobility to traverse campus.  This may include moving between buildings multiple times throughout the workday and bending, squatting, stooping, and kneeling.

Position Details

Application Instructions

To apply, please complete the application on our website, including your resume, cover letter, and at least 1 letter of recommendation. No phone calls, please.

It is the policy of Cascades Academy to provide equal employment opportunity, regardless of race, color, sex, age, national origin, religion, physical or mental impairment, sexual orientation, veteran’s status or any other status protected by applicable law. Specifically, employment opportunities are and shall be open to all qualified applicants solely on the basis of their experience, aptitudes, abilities and training; advancement is and shall be based on the individual’s achievement, performance, ability, attitude and potential for promotion. 

 Qualifications

• Three - five years of experience as an executive assistant or office manager responsible for executing a variety of administrative processes 
• Exceptional project management skills including the ability to think independently and critically, manage multiple tasks simultaneously, and meet deadlines in a fast-paced, stressful environment.
• Strong oral, written and interpersonal communications skills, both in person and over the phone. Ability to communicate professionally, with tact and diplomacy.
• Ability to work independently and prioritize workload; proven experience maintaining confidential information.
• Manage highly-sensitive, confidential information with the highest level of discretion and expediency
• Flexible, organized, and able to accurately work under time constraints and deadlines
• Ability to anticipate and resolve complex and/or confidential administrative issues with excellent judgment and little or no supervision.
• Proven success at working collaboratively and effectively on team
• Demonstrated understanding of cultural competence and its impact on the role
• Appreciation and respect for diversity in all of its forms
• A sincere commitment to the school’s mission and the willingness to be a visible, enthusiastic brand ambassador. Passion for what is good for children and families.
• Knowledge of common tech platforms used in education, such as Blackbaud, Google Suite, Microsoft Office, etc.
• Clean driving record and valid driver’s license

Physical Requirements

• The person in this position must be able to work at the school.
• Requires mobility to traverse campus.  This may include moving between buildings multiple times throughout the workday and bending, squatting, stooping, and kneeling.