Executive Assistant

Who We Are:

Outward Bound USA (OBUSA) is a national non-profit educational organization in the United States, in operation for more than 60 years. Outward Bound’s mission is to change lives through challenge and discovery. While ambitious and bold, our vision is a more resilient and compassionate world, with more endurance in response to change and more courage in the face of challenge.

Outward Bound programs provide increased access for today’s youth to develop social-emotional skills and build their capacity to navigate the future with confidence, compassion, and curiosity. Programs are far-reaching – inside city and suburban classrooms and outside in rugged backcountry settings – lasting anywhere from one day to an entire semester. Outward Bound staff are positive, fun, passionate, mission-driven change makers who uphold a high standard of quality and commitment to our students.

We strive to provide educational experiences that are inclusive and relevant for all participants and are committed to organizational improvement in support of an equitable and just society. Learn more about us.

Position Impact:

Outward Bound USA aims to support, amplify, and grow the capacity of our network schools, where students are prepared with 21st-century skills to be ready for work, life, and civic leadership in an evolving world. Our work is guided by an unwavering commitment to our students, equity, adventure, and safety.

Guided by a strategic Vision for Impact 2030 between 2023 and 2030, OBUSA supports this work through targeted initiatives designed to: create new and expanded capacity in regional schools by positioning OB as an educational partner to parents, schools, and corporations; accelerate access to the outdoors for underrepresented communities; provide a leading-edge research and development engine that will continuously improve program outcomes; and cultivate a workplace that attracts, develops, and retains the best outdoor educators and administrative professionals in the US.

Reporting to the CEO, the Executive Assistant (EA) provides high-level administrative, operational, and strategic support to ensure the CEO can focus on advancing the mission, vision, and priorities of Outward Bound. This role requires exceptional attention to detail, proactive initiative, sound judgment, and the ability to operate with professionalism in a fast-paced nonprofit environment. The EA will work closely with the Board of Directors, senior leadership team, donors, community partners, and key stakeholders.

Our Culture:

As a leading non-profit educational organization, Outward Bound is designed to embrace challenges. Thriving here requires compassion, a learning mindset, and a deep desire to do meaningful work that achieves our goals. At Outward Bound, we are crew, not passengers. Everyone is on the crew, and we all contribute. We share success and view challenges as opportunities for growth. From the office to the wilderness, we grow together. You belong here.

Functions and Responsibilities:

Executive Support

• Manage the CEO’s daily schedule, appointments, meeting logistics, and travel.
• Anticipate needs and ensure the CEO is fully prepared for meetings, presentations, and events.
• Draft, edit, and proofread communications, presentations, reports, and other materials with accuracy and attention to detail.
• Maintain confidential documents and sensitive information with discretion.
• Serve as the primary point of contact for internal and external inquiries directed to the CEO.
• Support cross-organizational projects, timelines, and priorities in collaboration with staff and leadership.
• Strengthen day-to-day office operations, systems, and administrative processes to improve efficiency and organizational impact.

Board & Donor Engagement

• Serve as liaison to the Board of Directors, maintaining strong, trust-based relationships.
• Support all Board activities, including meeting planning, materials preparation, minutes, follow-up, and recordkeeping.
• Coordinate communication between the CEO, Board members, committee leads, donors, and key stakeholders.
• Support donor engagement efforts, including correspondence, tracking interactions, and preparing materials for fundraising meetings.

Event & Meeting Planning

• Plan, organize, and execute internal and external events, including Board meetings, retreats, fundraising events, and special initiatives.
• Manage logistics such as venue selection, catering, travel arrangements, materials, agendas, technology needs, and on-site coordination.

Competencies:

• Cultural Competence: You recognize and appreciate cultural differences and commonalities, and build strong, respectful relationships across diverse identities and organizational cultures.
• Collaboration: You work effectively across teams and support collaborative problem-solving, ensuring alignment and shared success.
• Communication: You communicate with clarity and impact in all situations, producing polished written materials and adapting your style for executives, board members, donors, and staff.
• Conflict Management: You independently manage and resolve conflict, even in high-stakes or time-sensitive situations, while maintaining professionalism and discretion.
• Self-Management: You can set, prioritize, and follow through on goals and commitments independently; you anticipate roadblocks and take proactive steps to address them.
• Attention to Detail / Accuracy: You demonstrate exceptional accuracy, organization, and follow-through in all aspects of your work.
• Stakeholder Management: You understand who the key stakeholders are and can effectively engage, balance, and leverage those relationships, especially within a federated network.
• Entrepreneurial Mindset: You develop and implement process improvements and creative solutions that strengthen organizational efficiency and effectiveness.
• Instills Trust: You exemplify the highest standards of trustworthiness, integrity, reliability, and cross-cultural appreciation.
• Project Management: You manage multiple projects simultaneously, demonstrating strong planning, organization, and attention to detail from start to finish.
• Customer Service: You assess stakeholder needs, deliver high-quality service, and ensure a positive, mission-aligned experience for internal and external partners.
• Analytical Skills: You quickly analyze information, recognize patterns, resolve problems, anticipate needs, and respond proactively using strong critical-thinking skills.

Work Experience:

• 4–7 years of executive-level administrative support, ideally to a CEO/Executive Director or senior leader.
• Proven ability to manage complex executive calendars, competing priorities, and multi-time-zone scheduling.
• Experience preparing board-ready materials (agendas, packets, minutes, briefings).
• 2+ years supporting board or governance work, including committee coordination and follow-up.
• Hands-on experience planning high-level meetings or events (board meetings, retreats, donor events).
• Experience serving as a liaison to donors or senior external stakeholders, including drafting correspondence and preparing meeting materials.
• Demonstrated ability to improve or maintain administrative systems and workflows.
• Successful experience working independently in a remote or hybrid environment.
• Proficiency with CRM systems (Salesforce preferred) and project management tools.
• Ability to support basic budgeting and expense tracking.
• Experience working within a federated or networked organization, navigating multi-stakeholder communication.
• Experience supporting leaders through organizational change or growth (preferred).
• Familiarity or interest in outdoor education or youth development (preferred).

Location and Physical Requirements:

• Permanent work authorization in the United States is required to apply for this position.
• This is a remote position. We welcome applications from the following states: AZ, CO, CT, FL, IA, ID, IL, IN, MA, MD, ME, MI, MN, NC, NM, NY, OR, PA, VT, and WA.
• Up to 5% of work time may be spent traveling. Occasional in-person attendance at meetings and collaboration sessions may be required
• Ability to work at a desk and on a computer for most of the day. Repetitive motions, such as typing on a keyboard, are part of daily tasks. Strong visual acuity is essential for reading and analyzing data on a computer screen.

Compensation & Benefits:

• Salary Range: $28.12 - $34.37 ($58,500-71,500). This is a non-exempt role.
• In the interest of transparency and pay equity across our team, a candidate can expect to be offered in the lower third of the range.
• OBUSA offers a competitive benefits package, including health/dental/vision insurance, short-term and long-term disability, life insurance, plus a retirement plan with an employer match.
• OBUSA offers 15 days of PTO per year, plus 10 federal holidays and paid time off for the last week of the year.

Application:

Please apply via the link by submitting a resume and cover letter (the cover letter may be addressed to Ginger Naylor, CEO). Applications will be accepted through January 28, 202

• Fully Remote position - Must be located in AZ, CO, CT, FL, IA, ID, IL, IN, MA, MD, ME, MI, MN, NC, NM, NY, OR, PA, VT, or WA.
• OBUSA offers a competitive benefits package, including health/dental/vision insurance, short-term and long-term disability, life insurance, plus a retirement plan with an employer match.
• OBUSA offers 15 days of PTO per year, plus 10 federal holidays and paid time off for the last week of the year.