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Executive Assistant to Assistant Head of School ID-8343

March 19, 2025

Brentwood School, a vibrant and diverse K-12 independent school, is seeking an Executive Assistant to the Assistant Head of School (AHS), who serves as the chief advancement officer and liaison to the school’s robust Veteran partnership. The Executive Assistant’s professional expertise supports these areas of responsibility: Fundraising, VA Community Partnership (VCRE), Constituent Relations, Conditional Use Permit (CUP) and Neighbor Relations, Board of Trustees Governance Committee, and Events. The position handles sensitive and confidential information regularly; therefore diplomacy, tact, and discretion are essential skills.

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Under the general direction of the AHS, the Executive Assistant also supports the Director of Giving and the Assistant Director for Annual Fund in their fund development roles, so the ability to anticipate needs while working in a fast-paced environment with multiple, and sometimes, competing priorities, is a must. A strategic problem-solver with sound judgment and a collaborative style will thrive in our close knit, professional, and productive team.

Duties and responsibilities include, but are not limited to:

Fundraising Operations

Collaborates with Constituent Database Manager to organize and oversee all prospect research
Assists with donor and prospect management database and related systems
Identifies opportunities to streamline operations, including donor acknowledgement and engagement
Supports the Director of Giving and Assistant Director for Annual Fund in tracking and reporting on status of fundraising goals
Creates invitations and forms to manage RSVPs, and prepares supporting materials as needed
Handles routine customer service requests on behalf of Director of Giving and Assistant Director for Annual Fund staff working on major gifts and Brentwood Annual Fund
Drafts Brentwood Annual Fund communications for publications, website and annual Report on Philanthropy
During an active campaign, drafts letters, produces proposals, and prepares briefing packets as requested
Post-campaign, drafts and manages pledge reminders and acknowledgements

Veteran Partnership and VCRE (Veterans Center for Recreation and Education)

Facilitates process for annual launch of VA Scholarships to Summer at Brentwood application and supports application process as requested
Assists with special events for Veterans and their Families, including staffing VCRE booths, helping with meals and distributing other products
Serves as relief VCRE tour guide
Attends VCRE department meetings
May assist with and/or teach classes or seminars for Veterans
As needed, offers the Director of Veteran Education support in the areas of coordination and logistics of educational programming for Veterans

Administrative Support

Brings joy and a good sense of humor to the workplace
Partners with Advancement and Communications Coordinator and Alumni Engagement Associate on varied tasks for the Advancement Office, including inventory management and ordering of supplies, occasional mailings, work order submissions, ensuring tidiness of common area and storage spaces, and birthday celebrations.
Processes correspondence, donation documentation, invoices, and check requests
Creates an annual process to archive Advancement Office work product
Supports planning, tracking and logistics for major events (i.e., Hutson Lecture, Stand Down, Adaptive Sports Day, Commencement, Emeritus, Anniversaries, etc.)
Takes, prepares, and shares notes from staff meetings
Assists with additional Advancement functions as requested by AHS, including occasional evening and weekend events.
Other duties as assigned by AHS or Senior Administrative Team

Skills and Qualifications:

Bachelor's Degree or at least 5 years work experience in an administrative support role, preferably at the executive level
Well-developed interpersonal skills to establish and maintain effective working relationships and interact with individuals from a range of backgrounds
Data-driven and digital first mentality
Fluent in Google Suite, MS Word, Excel, PowerPoint. Adobe Creative Cloud is a plus
CRM experience required (Raiser’s Edge NXT and Research Point preferred)
Talent managing simultaneous projects and deadlines with flexibility and adaptability, while maintaining calm under pressure
Ability to maintain complete confidentiality
Articulate in oral and written communication with excellent proofreading and organizational skills
Ability to work independently and follow through on assignments with minimal direction
Skill in managing a complex calendar, prioritizing well, and resolving conflicts

Other Expectations

Engage in professional and personal development and commit to growth in the areas of diversity, equity and inclusion
Participate and initiate opportunities that demonstrate one's growth, knowledge, and skills

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...

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Executive Assistant to Assistant Head of School ID-8343

Other Jobs You May Be Interested In

Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

5. HOW DO YOU PROCESS INFORMATION?

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

8. HOW TO PRIORITIZE WORK?

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?