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 dedicated to the idea that people are capable of far more than they know. As the first urban Outward Bound school in the United States, CBOBS is committed to providing transformational experiences to a diverse group of youth and adults through one-day programs, virtual programs, and multi-day expeditions.

To meet this goal, CBOBS raises over 2 million dollars annually to increase the accessibility and reduce the cost of programming for schools and students in our community. CBOBS has an established location in Baltimore, MD and is developing a location in Washington, DC.

Position Summary

Over the last decade, CBOBS has been committed to being an exceptional resource to our partner schools, providing a suite of Character Development programs over the course of each school year that include: in-class curriculum, teacher training and support in experiential education, challenge course days, and wilderness expeditions. CBOBS is searching for a dynamic, collaborative, outcome-focused, research-motivated, and safety-oriented leader to oversee all aspects of our growing programming.

The Program and Safety Director supervises 5 direct reports who manage numerous seasonal staff members, across both locations, in the execution of programs that serve students throughout the Chesapeake Bay region. The Program and Safety Director is a member of CBOBS’ Leadership Team and reports dually to the Executive Director and the Chief Operations Officer.

The ideal candidate has a passion for CBOBS’ mission, a penchant for creative problem-solving, and an entrepreneurial mindset. They possess strong organizational, communication, and management skills. They are resourceful and thrive in a fast-paced, supportive, team environment. They love managing and leading people; value relationships and accountability; and strive to empower others to achieve superior results. No work is ‘beneath’ them and they are eager to serve others, rolling up their sleeves when necessary. They have at least 7 years of leadership experience and are committed to using research and evaluation to inform ongoing innovation and development of CBOBS programs. Management experience in wilderness expeditions, challenge course operation, and/or K-12 experiential education is required.


Overseen by: Executive Director

Safety Management

  • Manage and ensure compliance with all OBUSA National Safety Policies & Standards, Charter Operating Procedures, and Association of Challenge Course Technology (ACCT) management standards.
  • Manage annual OBUSA Safety Audits and/or Safety Reviews.
  • Conduct annual internal Safety Audit and lead the creation of annual safety goals.
  • Maintain annual updates/edits to the Emergency Response Plan (ERP) including training staff on their role(s) in an emergency scenario and managing and evaluating ERP training.
  • Establish Safety KPIs with Executive Director annually and manage implementation and monitoring.
  • Review, manage, and audit internal safety systems and processes for, but not limited to, technical equipment, vehicle inspection systems, and base facilities.
  • Organize and lead (with the Committee Chair and Associate Program Directors/Program Managers) the CBOBS Program and Safety Committee including scheduling monthly meetings and planning agendas and discussion topics.

Incident Management, Investigation, and Reporting

  • Lead and/or manage incident investigations and analysis; recommend action based on findings to leadership.
  • Maintain oversight of the incident reporting database for quality control and integrity of data.
  • In collaboration with Instructional Designer, perform annual assessment of training needs and direct curriculum for safety, judgement, and risk management for all departments.
  • Serve as single point accountability for the CBOBS transportation program.
  • Analyze and report on local, national Outward Bound, and industry incident and safety trends.
  • Prepare and distribute monthly, trimester and annual safety reports, including incident root-cause analysis.

Overseen by: Chief Operations Officer

Program Delivery Management:

  • Oversee the safety and front-line management of all operations of CBOBS programs, and ensure they remain true to the mission, values, and principles of CBOBS.
  • Ensure all programs adhere to the OBUSA and CBOBS safety policies and procedures as well as Charter Operating Policies and Procedures (COPPs), and administrative directives. Update COPPs annually.
  • Manage the ongoing evaluation of programs to meet organizational social-emotional outcomes and lead the ongoing development of programs to meet those outcomes.
  • In collaboration with the Development Team, ensure all requirements and reporting responsibilities are met for grant-funded programs.
  • Oversee the program calendar and staffing system of all programs.
  • Oversee all logistics, safety, and program resources.
  • Develop and maintain relationships with local land managers, public agencies, and partners to secure and maintain operating and site-use permits.
  • Ensure the timely completion and review all required program record-keeping including, but not limited to pre-program paperwork, course reports, employee licensure and training records, and post-course staff evaluations.
  • Strengthen communication and promote understanding among student families, schools, and communities by articulating the role of safety, risk, and training in our mission and building character.

Staff Development & Management:

  • In collaboration with the Instructional Designer, evaluate CBOBS training plan to ensure appropriate safety and program training for all staff.
  • Support and direct recruitment staff on the hiring, on-boarding, screening, and scheduling of all CBOBS field staff.
  • Ensure the timely initiation of investigations of policy violations and/or failures to meet expectations by field staff, the completion of appropriate documentation, and the delivery of appropriate discipline for infractions.
  • Evaluate the performance and professional development of department staff. Make and/or recommend decisions related to advancement, seasonal re-hiring, and separation.
  • Oversee staff housing, including the selection of the seasonal Staff House Manager.


  • Responsible for budget forecast/tracking and annual budget development for Programs. Manage program within defined budgetary constraints with an eye for fiscal responsibility, adjusting appropriately as revenue and expenses fluctuate throughout the year.
  • Coordinate with all CBOBS departments to ensure successful execution of programs.
  • Other duties as assigned.


  • 7+ years program leadership experience required with management experience in youth-focused wilderness expeditions, challenge course operations, and/or K-12 experiential education.
  • Additional background or experience in business, education, non-profit management, or another related field a plus.
  • Entrepreneurial, results-driven work style with the ability to identify and develop areas of growth and opportunity.
  • Ability to perform under tight deadlines and meet financial goals.
  • Strong planning and execution skills.
  • Compassionate and effective communicator, written and oral, with the interpersonal skills and versatility to effectively build relationships across a broad spectrum.
  • Ability to represent yourself and CBOBS positively and effectively with strong presence in diverse public settings.
  • Ability to have open, honest, and difficult conversations, including the ability to give and receive feedback with direct reports and colleagues.
  • Comfort working independently and cooperatively as a team member in a group environment that requires team building, flexible multi-tasking, and careful time and expense management.
  • Personal and professional values consistent with the CBOBS mission, values, and principles.
  • Must be able to lift 60 pounds and participate in vigorous to moderate physical activity including, but not limited to, backpacking, paddling, ropes courses, and rock climbing.
  • Proficient in Microsoft Office 365 and Google Apps, as well as strong presentation and writing skills. Experience with Salesforce or another CRM a plus.
  • State and Federal background check and Motor Vehicle Records check required. Must complete Outward Bound driver training.

Compensation & Benefits

  • Compensation: The hiring range for this position is $65,700-$80,300. Pay will be 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.
  • Ten (10) paid holidays.
  • Up to eight (8) weeks of paid Family/Medical Leave.
  • 401(k) with a match. Employees are eligible for participation after 1 year of employment. Current match is 6% of the employee’s salary.
  • Long-term disability, short-term disability, AD&D insurance, as well as, a $25,000 life insurance policy at no cost to the employee.
  • 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).
  • Aflac Supplemental Insurance.
  • Pro Deals: Discounts from outdoor industry vendors for outdoor professionals.

How to Apply

Please send a cover letter and resume addressed to Hiring Committee to or apply online at Resume review will begin on Monday, February 8, 2021.


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.

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