Director of Educator Development & Staffing

Job Title

Job Description

Responsibilities

Lead the staffing strategy for Field Education so programs are well-supported across campuses, seasons, and changing daily needs

Lead annual workforce planning, hiring projections, staffing allocations, and personnel forecasting to ensure Field Education has the capacity and talent needed to meet program goals

Create clear systems for scheduling, coverage, time off, staff assignments, and communication

Balance program needs with staff capacity, educator growth, team culture, and financial sustainability

Support personnel budget planning, staffing forecasts, and workforce allocation decisions in partnership with the Head of Field Education

Partner with HR and Field Education leadership to recruit, hire, onboard, and prepare year-round and seasonal staff

Supervise and coach Field Education team members through regular feedback, clear expectations, and meaningful professional development

Lead annual performance review processes and support employee growth, accountability, retention, and advancement across the Field Education team

Directly supervise designated Field Education staff and lead systems for performance management, coaching, evaluation, accountability, and professional growth across the educator team

Guide educator development through mentorship, field observations, performance feedback, and ongoing training

Support instructor advancement pathways, leadership development, and succession planning efforts within Field Education

Partner with the Head of Field Education to implement staff training, onboarding, and professional learning systems

Support Field Education leadership through annual planning, staff meetings, retreats, debriefs, and cross-team collaboration

Ensure staffing and training systems align with TSS operating guidelines, academic pillars, risk management practices, and program goals

Serve as a member of the Field Education leadership team and contribute to strategic planning, departmental initiatives, and organizational priorities

Support the development and supervision of a diverse team of year-round, seasonal, and AmeriCorps educators

Strengthen relationships with internal teams and external partners to support smooth program delivery

Foster a team culture rooted in trust, inclusion, accountability, learning, and care for people and place

Qualifications

Bachelor's degree required; master's degree or equivalent experience preferred

Minimum of four years of experience teaching or leading programs in formal, informal, outdoor, environmental, or place-based education settings

Minimum of two years of experience coaching, supervising, developing, or managing educators or staff teams

Experience managing complex schedules, staffing systems, seasonal hiring cycles, or multi-site team operations

Strong organizational, prioritization, and systems-building skills

Demonstrated ability to lead teams, communicate clearly, and manage competing priorities in a dynamic environment

Ability to make sound decisions related to staffing, risk, program quality, and staff support

Experience with budget management, payroll processes, workforce planning, or program operations preferred

Familiarity with Google Workspace, spreadsheets, scheduling tools, and database systems

Ability to build strong relationships with internal teams, external partners, educators, and seasonal staff

Experience in the Greater Yellowstone Ecosystem, residential education, AmeriCorps programs, or outdoor program operations preferred

Working Conditions & Physical Requirements

Position is based in Jackson, Wyoming with regular work across TSS campuses and program locations

Work occurs in both office and field settings, including time at a computer, in meetings, outdoors, and supporting active programs

May require evening, weekend, or irregular hours to support programs, staffing needs, trainings, retreats, and emergencies

Ability to work outdoors in variable weather conditions, including cold, heat, wind, snow, rain, and arid conditions

Ability to hike over uneven terrain and support field-based programming as needed

Ability to carry a backpack of 20 or more pounds for extended periods as needed

Ability to drive or become approved to drive TSS vehicles, including 15-passenger vans, according to organizational policies

Successful applicants must pass required background checks and driving record review prior to start date