Experiential Education Staff Supervisor

Location: Portland, Oregon (Hybrid: 3 days in-office, 2 days remote)
Employment Type: Full-Time (Includes Health Benefits)
Salary Range: $70,000 - $80,000 (Depending on Experience)
Travel: Some travel required

About Us

We are a small, mission-driven business based in Portland, Oregon, dedicated to delivering high-quality experiential education programs. We are seeking an Experiential Education Staff Supervisor to lead and support our part-time cohort employees, ensuring seamless program execution and operational efficiency.

Position Overview

The Experiential Education Staff Supervisor will oversee and support a newly developed team of eight cohort employees who work flexible schedules to deliver programs. This role requires strong leadership, scheduling expertise, and a background in experiential education. The ideal candidate is a proactive manager with experience in training, logistics, and performance oversight.

As this is the first year implementing the cohort staffing model, this role will evolve to meet emerging needs. We are looking for someone adaptable and committed to continuous process improvement. This is an ideal role for a dynamic leader who thrives in a collaborative and evolving environment.

Key Responsibilities

Cohort Employee Management

• Supervise cohort employees, ensuring alignment with program goals and company policies.

• Conduct performance evaluations, provide feedback, and support professional development.

• Manage scheduling and ensure adequate staffing for programs.

• Track and approve timesheets, monitor hours, and oversee expense approvals.

• Gather and analyze program feedback to improve staff performance and program quality.

• Ensure completion of pre- and post-program evaluations by staff.

• Oversee debrief reporting, including:

• Uploading program photos, surveys, evaluations, & participant agreements.

• Sharing program narratives for social media.

• Completing program paperwork, thank-you notes, and incident reports.

Program Operations & Coordination

• Work closely with the Program Coordinator to ensure smooth program execution.

• Contribute to program design and content development as needed.

• Lead program kick-off calls to align staff on expectations and logistics.

• Oversee program budgets, track expenses, and optimize cost efficiency.

• Ensure proper documentation of program logistics, SOPs, training materials, and reports.

• Be on-call during program delivery to support facilitators and troubleshoot issues.

• Provide onsite supervision for larger programs to ensure quality execution.

Training & Development

• Design and facilitate training programs for new and existing cohort employees, including an annual multi-day training.

• Support ongoing professional development initiatives to enhance facilitator skills.

• Ensure all staff are well-versed in program materials, logistics, and expectations.

• Provide one one-on-one training and support for cohort staff as they prepare for the delivery of new or challenging programs.

Program Facilitation

Facilitating Experiential education programs is the key service that GutMonkey provides. In this role, a staff supervisor would, from time to time, facilitate their own programs, lead the staff at a larger scale program, or cofacilitate with other staff at a larger program to provide performance feedback. Key responsibilities around program facilitation include:

• Deliver experiential programs, which spark dynamic participant experiences and encourage continued engagement. Programs delivered by the cohort facilitators are typically designed by full-time GutMonkey staff, but some adjustments and customization may be needed pending the program and partner needs.

• Engage and connect with patients during programs outside the hours of facilitation. Have conversations with curious parents during a teen program, take extra time to connect with partner staff upon arrival and departure to the site, and be willing to connect with community members as a representation of GutMonkey. 

• Ensuring program integrity, creativity, and adherence to GutMonkey’s curriculum.

• Lead participant groups between 5 and 300 teens and/or adults impacted by chronic health conditions (the majority of participants navigate living with a bleeding disorder).

• Practice Positive Youth Development and positive strategies with teens and youth participants, many of whom come from diverse and varied backgrounds.

• Ensure program agendas and program supplies are well organized physically and digitally, and communicate needs to have the necessary tools, materials, and training to successfully implement programming.

• Data Collection and Reporting: Document program outcomes and lessons learned, collect participant data, take photos, and compile program highlights.

• Implementing risk management procedures and exercising sound judgment in real-time situations.

Additional Responsibilities

• Assist with operational and administrative tasks during slower program periods.

• Support hiring and onboarding of additional program staff as needed.

Required Skills & Qualifications

• Minimum 3 years of managerial experience, preferably in experiential education, training, or a related field.

• High proficiency with independent & team work environments, national travel for program delivery and team management, and managing logistics around travel and program delivery.

• Background in experiential education or hands-on learning environments.

• Strong leadership and staff supervision skills, including coaching and performance management.

• Excellent organizational and scheduling abilities.

• Experience with budget management, expense tracking, and payroll approvals.

• Proficiency in Google Suite (Docs, Sheets, Slides, Calendar, Drive) and other relevant software.

• Strong verbal and written communication skills for team coordination and stakeholder engagement.

• Ability to problem-solve in real time and remain flexible in dynamic situations.

• Experience facilitating dynamic, hands-on education programs for teen and adult populations.

• Strong group management skills for working with diverse audiences over multiple hours or days.

• Experience managing curriculum development, activity execution, or educational programs.

• Positive and solution-focused attitude. 

• Ability to thrive in an ever-changing environment. 

Preferred Qualifications

• Experience in event coordination, program logistics, or operations management.

• Familiarity with HR functions, including onboarding, training, and policy implementation.

• Background in budget forecasting and financial oversight.

• Experience in outdoor education, community-based art education, or creative health education. (If applicable, please outline your specialty in your application.)

• Experience facilitating adult education programs.

• Spanish language proficiency.

• Experience with public health community engagement.

• Background in conflict resolution and group dynamics.

• Equity and Inclusion training and experience.

Why Join Us?

• Work with a passionate team making an impact through experiential education.

• Hybrid work environment (balance of in-office and remote flexibility).

• Competitive salary with health benefits.

• Opportunity to shape staff leadership, training, and program operations in a growing organization.

Application Instructions

To apply, please submit:

1. Your resume, highlighting relevant experience in staff supervision, program operations, budget management, and experiential education.

2. A written statement, short video, or audio file (instead of a formal cover letter) answering the following:

• What is your experience with experiential education?

• What is your definition of a great supervisor? Provide examples of how you’ve demonstrated these skills.

• How has your contribution to staff supervision positively impacted the organizations where you’ve worked?

• How do you bring energy to a role? What’s your style of engaging with people?

• Provide examples of how in a leadership or supervision position you’ve adjusted your approach to better support an employee or team.

• What strategies do you use to motivate your team, especially during challenging stretches of time?

• How do you build trust and rapport within a team?

• Share examples of challenging situations with staff and the steps you took to support both the staff member, the organization, and the projects or programs that were being led.

📩 Email your application to info@gutmonkey.com
📅 Application Deadline: March 31, 2035
🚫 No phone calls, please. Direct all inquiries only to the email above.

About GutMonkey

GutMonkey is a Portland-based company specializing in outdoor and experiential education programs that empower communities affected by rare and chronic conditions. Our programs range from keynotes and workshops to multi-day immersive experiences for youth and adults.

Our team is passionate about relationship-building, community engagement, and health advocacy. We are committed to equity and inclusion, working to dismantle systemic barriers that impact the health of the communities we serve.

Company Structure

GutMonkey currently has:

• 3 full-time employees (CEO, Sales Manager, Communications Director)

• 1 part-time employee (Program Coordinator)

• 8 seasonal cohort staff supporting program delivery

• 2 remote contract employees (Business Manager, Finance Manager)

• 2 new full-time hires in progress (Experiential Education Staff Supervisor and Director, Business & Operations)

This role will lead and support the cohort facilitators while collaborating closely with the CEO and the internal team to ensure quality program delivery across all of GutMonkey’s program offerings.