Organization Summary

Founded in 1986, Chesapeake Bay Outward Bound School’s (CBOBS) mission is to change lives through challenge and discovery. Outward Bound is an international educational movement, founded by Kurt Hahn, dedicated to the idea that people are capable of far more than they know. The Chesapeake Bay Outward Bound School (CBOBS) is a non-profit, outdoor educational organization with programs that deliver character development and self-discovery in the wilderness, in the city, and in school. CBOBS operates programs in Baltimore City, the District of Columbia, the Appalachian Trail in MD and PA, the Potomac River, the Dolly Sods Wilderness Area in WV, and the Eastern Shore of the Chesapeake Bay.

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Position Summary

The Executive Assistant (EA) facilitates the efficient functioning of the Executive Director (ED) by offering crucial administrative support, including scheduling, coordinating with staff and external contacts, and preparing meeting materials. The EA liaises with various stakeholders on behalf of the ED and collaborates closely to advance strategic initiatives. Additionally, the EA oversees daily office operations, manages administrative tasks, and supports the smooth functioning of the CBOBS office.

Essential Duties & Responsibilities

The essential functions include, but are not limited to the following:

Executive Director Support (60%)

  • Act as a point of contact between ED, employees, clients, and external partners.
  • Coordinate and schedule ED meetings, including preparing agendas, taking minutes, and following up on action items.
  • Arrange and manage logistics for ED meetings, board meetings, and other events.
  • Serve as liaison to the Board of Trustees; schedule all board and committee meetings, create meeting packets, take minutes, and be the point of contact for all board members.
  • Assist with special projects, research, and reports as needed at the request of the ED.
  • Prepare and edit correspondence, communications, presentations, and other documents.
  • Handle incoming and outgoing communications, including emails, phone calls, and mail.
  • Organize and maintain confidential files and records.

Office Management (40%)

  • Greet visitors, answer and direct phone calls, and manage incoming and outgoing correspondence.
  • Maintain office equipment, manage supplies, handle vendor relationships, and schedule repairs.
  • Maintain office and kitchen supply inventory by monitoring stock, placing orders, and verifying deliveries.
  • Manage all space and infrastructure planning, including common area maintenance, workstation changes, and providing requested resources and solutions.
  • Scan checks as assigned by the Chief Operating Officer.
  • Identify process and office management improvement opportunities, and design and implement new systems.
  • Develop office policies and procedures, and ensure they are implemented appropriately with the support of the Chief Operating Officer,
  • Prepare the annual budget for office services and executive and board expenses with support from the Chief Operating Officer.

Minimum Qualifications (Knowledge, Skills, and Abilities)

This job operates in a professional office environment.

  • Strong organizational skills and attention to detail.
  • Ability to make timely decisions and demonstrate good judgment.
  • Exceptional customer service orientation.
  • Strong written and verbal communication skills.
  • Ability to tailor approach toward the perspective of others.
  • Excellent team player with demonstrated successful working relationships with staff at all levels of an
  • Ability to maintain confidentiality.
  • Proficiency in Microsoft Office, with interest and aptitude to learn new software and systems, required.
  • Two or more years of office management experience preferred.
  • Experience with Salesforce or similar CRM software preferred.

Physical Demands and Work Environment

  • Ability to sit at a desk or computer 90% of the time or greater.
  • Ability to carry weights up to 15 pounds.


This job description in no way states or implies that these are the only duties to be performed by the employee(s) of this position. Employees will be required to follow any other job-related instructions and to perform any other job-related duties requested by any person authorized to give instructions or assignments. All duties and responsibilities are essential functions and requirements and are subject to possible modification to reasonably accommodate individuals with disabilities.

To perform this job successfully, the employee(s) will possess the skills, aptitudes, and abilities to perform each duty proficiently. Some requirements may exclude individuals who pose a direct threat or significant risk to the health or safety of themselves or others. The requirements listed in this document are the minimum levels of knowledge, skills, or abilities. This document does not create an employment contract, implied or otherwise, other than an at-will relationship.

This is a full-time, exempt position.  Applicants should expect sporadic evening and weekend work.


Salary Range: $46,000-$56,000; commensurate with experience.


  • Employer contribution of 75% for Medical, Dental, & Vision insurance through CareFirst BlueChoice for the employee and their children, if applicable.
  • Fifteen (15) days of Paid Time Off (PTO) which accrue per pay period.
  • Up to Eight (8) weeks of paid Family/Medical leave
  • Eleven (11) paid holidays.
  • 401(k) with a match. Employees are eligible for participation after 6 months of employment. Current match is 6% of the employee’s salary.
  • Long-term disability, short-term disability, AD&D insurance, and a $25,000 life insurance policy.
  • Pre-tax Saving Cafeteria Plan: Healthcare Flexible Spending Account (FSA), Dependent Care Flexible Spending Account (FSA), Health Savings Account (HSA).
  • Pre-tax Commuter/Transit Benefits.
  • Employee Assistance Program (EAP).
  • Mutual of Omaha Supplemental Insurance.
  • Pro Deals: Discounts from outdoor industry vendors for outdoor professionals.

Chesapeake Bay Outward Bound School prohibits discrimination against any student or applicant because of race, color, religion, sex, gender, ethnic or national origin, sexual orientation, qualified individuals with disabilities on the basis of disability, or any other category which may be protected by applicable state or federal law. Chesapeake Bay Outward Bound School also promotes respect for all people and will not tolerate harassment based on any of these characteristics nor on differences based on gender identity or expression.

Outward Bound has a zero-tolerance policy for incidents of child abuse and neglect and will report any suspected abuse or neglect.