Ontario Works Training Programs In Toronto Jobs in Toronto, ON

THE ROLEThe Ontario Regional Program Lead is based out of Don Valley Brickworks Park in Toronto and trains and mentors instructors while coordinating program design and delivery for the range of OBC's programming from short local to remote and longer. This position involves travel to remote locations within Ontario, such as Algonquin Park, for approximately 30% of the time. The Program Lead position is responsible for coordinating logistics, staffing and risk management as well as hands-on facilitation and instruction of both day programs and multi-day backcountry trips. The Ontario Program Team is a fun hands-on team that is committed to building a culture of outdoor excellence and connection to each other. You will work closely with the Senior Regional Principal & Program Manager to support leadership development, technical skills training and program development.WHAT WE OFFER Location: Don Valley Brickworks Park, Toronto, ON (base), with regular travel to program locations across Ontario. Salary: $55,000 - $60,000 Benefits: OBC provides a comprehensive benefits package that includes three weeks of paid time off, additional sick and wellness days, and extended health and dental care. Term: Full-time Supervisor: Senior Regional Principal & Program Manager Start Date: August 2026, with flexibility on start date and schedule for the right candidate DUTIES AND RESPONSIBILITIES Coordinates the creation and execution of program plans to ensure seamless program delivery across both Brickworks-based and Ontario multi-day backcountry programming. Supervises the development of instructors and the delivery of OBC curriculum aligned with organizational mission and vision. Integrates risk management, group facilitation, technical skills, coaching, and mentorship into field experiences in both urban and backcountry settings. Creates a positive learning environment, adapting to the unique needs of each instructor, program, and student. Along with the Program Manager, organizes the recruitment, hiring, training, and evaluation of instructional staff, fostering a positive workplace culture. Participates in national team meetings and retreats, providing regional leadership and representation when required. Provides direct customer care for participants and their families, teachers, or agencies - this can include completing aspects of the sales cycle with specific groups. Coordinates the transfer of course information from key sources to instructors, including for courses delivered away from the Toronto base. Organizes and facilitates program evaluation processes and paperwork. Travels to operating areas across Ontario (approximately 30% of time) to provide course delivery support - including field presence, staffing coverage, logistics troubleshooting, and instructor mentorship - backcountry and urban programs. Program Delivery & Instruction Instructs and leads Outward Bound courses directly in the field modeling the technical skills, group facilitation, and leadership standards expected of all instructors. Delivers OBC curriculum on assigned courses, adapting programming to the needs of each group of students and the demands of the environment, whether urban or backcountry. Serves as the lead field presence on courses, making real-time decisions on program pacing, group dynamics, and safety, including on multi-day backcountry courses. Balances a direct instructional course load with the training, mentoring, and coordination responsibilities below, this is a delivery role first, not purely a supervisory one. Training & Mentoring Instructors In consultation with the Program Manager, assesses instructors' growth, offering feedback on leadership, risk management, and group management skills. Delivers high-quality training for instructors, focusing on leadership, technical skills, risk management, group facilitation, and environmental education across all program contexts. Provides one-on-one coaching and feedback to support the professional development of instructors. Facilitates training sessions in field-based settings and offers ongoing mentorship, including during on-site visits to program areas Supports instructors in managing challenges related to group dynamics and personal leadership development. Risk Management Supports the Regional Safety Officer (RSO) to ensure that all courses and programs are led in accordance with OBC's national risk management policies and protocols. Shares responsibility for briefing students and instructors on safety expectations and course participation requirements. Coordinates logistics, food management, transportation, route planning, staffing, and emergency response plans to ensure robust risk management systems are in place on a scheduled basis. Works closely with the Regional Safety Officer to ensure the ongoing safety and security of programs - while the RSO holds primary responsibility for the safe delivery and planning of programs, this role is a key partner in maintaining that standard day to day, including while supporting courses in the field away from Toronto. QUALIFICATIONS, SKILLS & EXPERIENCERequired Certifications Standard first aid with willingness to complete Wilderness First Responder (80 hour) before open enrolment season Bronze Cross or NLS Post-secondary education in one of the following fields: education, recreation (asset) G Class Driver License Willingness to travel to operating areas across Ontario (approximately 30% - 40% of time) Required Skills & Experience Communication & Coaching: Ability to mentor and coach individuals from diverse backgrounds, providing clear, constructive feedback. Commitment to Inclusion: Proven commitment to fostering inclusive environments and disrupting dominant narratives in outdoor spaces. Ability to model and teach outdoor travel and living skills in urban environments. Experience delivering journey-based expedition programming (e.g., canoe tripping, backcountry hiking, or similar multi-day expedition travel), with comfort leading and supporting courses away from a home base. Well-practiced in communicating effectively with a high level of professionalism. Experience working with youth in an outdoor setting. Ability to facilitate and lead both youth and adults of various abilities. Experience in adventure and experiential educational module delivery. Understanding and application of Outward Bound methods and philosophy. Skilled in behaviour management, crisis intervention, and problem-solving. Focus on providing high levels of customer service. Strong organizational skills, ability to prioritize, and multitask under deadline, including when coordinating logistics for courses running at a distance from the Toronto base. High level of cross-cultural competence, in recognition that Outward Bound Canada works with students and partners from a diversity of communities and backgrounds. Passionate about the Outward Bound Canada mission, an interest in outdoor pursuits, and a desire to help get young people outdoors for transformative experiences. Assets Experience in program development and evaluation. Trauma-informed care or mental health first aid training. Ability to facilitate and program ground initiatives, low ropes, rock climbing, and high ropes elements.