Job Posting

Program Director

Trails Youth Initiatives

Title: Program Director (contract, full-time)

Immediate Supervisor: President

Contract: Maternity leave contract, starting June 2021 – January 2023 with possibility of extension 

Hours: 40 hours/Week (with adjusted schedule includes working two weekends per month September – June, and Extended hours during summer sessions July – August)

Salary: $35,000 – $45,000

Application Deadline: May 2, 2021 


About the Charity


Trails Youth Initiatives became a registered charity in 1992 and offers a safe haven for youth from the GTA who encounter barriers to success. Our mission is to challenge and equip vulnerable youth to become contributing members of society. We offer participants a feeling of belonging and our Four Seasons, Four Years, For Life outdoor program helps them develop life skills and build confidence through high school credits, bursaries and mentorship. Our vision is to break the cycle of poverty by teaching kids practical skills, fostering a sense of community, developing emotional intelligence and facilitating academic performance, all of which translates to employability. In the process, we forge lasting connections and each child becomes a unique branch on our family tree of graduates. We celebrate together as they reach a turning point and surpass all expectations – society’s as well as their own.


About the Position


Reporting to the President, the Program Director is responsible for delivering ‘The Trails Way’ to each participant, ensuring that programming aligns with the Charity’s mission. The incumbent oversees the Facilitators, through whom the Weekend/Summer Program is delivered and who are responsible for teaching lessons, supervising participants and for the management of all gear and equipment. This position directs the day-to-day program and carries out its mandate within parameters set by the President. Key requirements include contributing to a positive, healthy and safe work environment; inspiring staff to provide and deliver world-class youth programs; supporting, coaching and inspiring team members and holding direct reports accountable for performance. Crucially, you will be passionate about the Charity’s mission to challenge and equip vulnerable youth to become contributing members of society.


Key Responsibilities


  • Co-direct summer and weekend program with other Directors, running pre and post-meetings, and writing reports
  • Plan, deliver and evaluate all programs including, but not limited to, summer, weekends, March Break program, Graduation and Holiday Celebration 
  • Co-manage 30 part-time Facilitators, provide guidance, feedback and direction over summer/weekends periods
  • Commit to working in an overnight educational setting, which includes extended hours throughout the year with emphasis in the peak summer period with the potential of leading wilderness out-trips
  • Ensure the overall safety of participants through implementation of Trails risk management protocols
  • Ensure the program is always physically and emotionally safe for all staff, participants, and families
  • Monitor and ensure the behavior management strategies and intervention tools that support program participants are used consistently
  • Act as a year-round resource for participant families, which may include home visits and follow up as per the need for additional support
  • Manage all aspects of pre and post-summer/weekend Facilitator briefings and evaluations and follow-up reports


Human Resources, Supervisory


  • Oversee Facilitators who deliver Program 
  • Review calendar plan, communicate key information to the Facilitator team, send preparation materials and field questions
  • Review culture, routines, policies and procedures with Facilitators
  • Participate actively in attracting and inspiring capable Facilitators 
  • Assist in the on-boarding and training of Facilitators 
  • Provide ongoing feedback to Facilitators and help set standards and expectations
  • Make recommendations to President on hiring and termination decisions, salaries and raises


Planning, Evaluation


  • Review program curriculum, rubrics and other assessments 
  • Participate actively in end-of-summer review session with Directors
  • Work with Director of Education to ensure summative projects for credits are completed on site as per weekend, and follow up with participants who were absent 
  • Lead final debrief with Facilitators at end of each session 




  • Ensure the safe and effective delivery of all programs in accordance to policies 
  • Ensure Facilitators are briefing participants according to Trails safety guidelines
  • Monitor, assess, and ensure all accident/incident reports are managed appropriately
  • Supervise all emergency procedures 


Certifications and Requirements 


  • One of either Wilderness Advanced First Aid or Wilderness First Responder (will be required or willingness to obtain)
  • Bronze Cross
  • Police Check with Vulnerable Sector Screening
  • Post-secondary degree or equivalent certification
  • Valid Ontario ‘G’ driver’s license free of serious offenses under Highway Traffic Act, F-Class to be obtained 
  • At least 3 years of relevant experience working with youth 


Experience and Qualifications


  • Ability to connect with people from all backgrounds and varying degrees of experience
  • Flexibility in responding to shifting priorities and refocus after interruptions
  • Comfort in asking for support from President and others while working in collaboration on program objectives
  • Ability to work outside of regular business hours as needed


Note: as the Charity grows and legal requirements as well as our participants’ needs change, management may change tasks assigned to this role accordingly. 


Please send a resume and cover letter to 



April 16, 2021

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