Manager, My Path Forward

Job Posting: Manager, My Path Forward
Salary: $57,000 to $60,000/year
Type: Full-Time
Location: Winnipeg
Start Date: September or October 2025
Reports To: Director of Programs

Executive Summary
Career Trek Inc. is seeking collaborative, resourceful, dynamic, creative individual who thrives in a space of innovation, growth, change, and out-of-the-box thinking to serve as Manager, My Path Forward.
Reporting to the Director of Programs, the Manager of My Path Forward is responsible for implementing a career education program to meet the needs of youth in care. Working with youth on a one-to-one basis, this role aims to build relationships and provide the opportunity for participants to explore careers, understand the pathways, identify their skills, likes and talents, develop or enhance employability skills, support the navigation of online education, volunteer, or job applications, connect with industry, and visit post-secondary institutions. This Manager will also provide information to youth and families on how they can save for their child’s post-secondary education and assist them, or their child, in the application process. The Manager practices and role-models Career Trek’s core values of Equity, Inclusion & Belonging; Respect; Balance & Wellness; Truth & Reconciliation; and Caring in all aspects of their work.

Who Are We Looking For?
Career Trek seeks a proactive individual with a hands-on approach, eager to tackle tasks as needed, and keen on learning and forming connections with youth in care. The ideal candidate will engage with the community, stakeholders, and families, while directing a team to empower youth, fostering self-esteem, confidence, and understanding of educational and employment opportunities and obstacles. Some of the responsibilities of this role include:
1. Responsible and accountable for the development, implementation, management, supervision and evaluation of all programming activities related to My Path Forward.
2. Establishing relationships with participants and their families, schools, community members, businesses, and other organizations that align with Career Trek’s Mission and Vision.
3. Ensuring high-quality, high-impact one-on-one and group program delivery that provides participants with engaging and immersive career exploration lessons and skill development opportunities.
4. Coordinate and implement engaging programming that provides the opportunity for learning, growth and development of employability skills.
5. Lead field trips and welcome guest speakers that align with career lessons.
6. Complete all administrative tasks to ensure Career Trek can report to its funders and the community at large.
7. Provide guidance, support and mentorship to a group of Part-Time Program Delivery staff.
8. Oversee and ensure proper use of PPE and any safety protocol required at partner locations.

Skills & Qualification
• A combination of education, experience (work, volunteer, self-taught or lived) and professional development that demonstrates your knowledge and understanding of community development, program planning, implementation, evaluation and stakeholder relations.
• 1 to 2 years of experience working with children & youth from equity-deserving groups.
• 2 to 3 years in a leadership role, managing and coaching a team of staff.
• Familiarity with and working knowledge of Microsoft applications, including Word, Power Point, Excel, Teams, Outlook and Shared Point.
• Experience with public speaking or program/workshop facilitation.
• Familiarity or experience with planning and implementing events or programs.
• Ability to work under pressure, manage simultaneous priorities, meet deadlines and be accountable for results.
• Excellent organizational, leadership, interpersonal and time management skills, with the ability to pay attention to detail.
• Demonstrated oral and written communication skills.
• Ability to manage personal and professional boundaries.

Assets (Desirable Skills)
• Knowledge of barriers that marginalized and underserved youth may face.
• Experience working with Indigenous communities and organizations.
• Experience working with youth in care with Winnipeg General Authority or similar organizations.
• Experience administering scholarship programs or assisting youth and families to access financial support.
• Experience writing programming narratives, partner correspondence, and funding reports.
• Experience designing, leading or delivering Career Development programs or initiatives.
• Knowledge of Indigenous worldviews, teachings, language, or land-based education, with a commitment to ongoing learning in the space of truth and reconciliation.
• An understanding of Canada’s history and relationship with Indigenous Nations, with a commitment to ongoing learning in the space of truth and reconciliation.
• Graduate of Career Trek.

Additional Information
• Work will be a combination of work from home and in-person, in accordance with Career Trek’s Remote & Flexible Work Policy.
• A stable internet connection is required to work from home.
• Travel within Manitoba including Northern and rural communities will be required.
• Valid Driver’s License and access to a reliable vehicle are required.
• Must be willing to undergo a Criminal Record Check and Child Abuse Check.
• Must provide or be willing to acquire a current First Aid CPR C certificate.
o Cost will be reimbursed by Career Trek.
• Training, ongoing support, and professional development will be provided.
• Some weekend and evening work is required.

If, after reading the posting and learning about some of the key responsibilities, you’re still interested in applying, as mentioned, please forward a detailed cover letter highlighting your experience along with your resume to: [email protected]. Please include ‘Manager, My Path Forward’ in the subject line. Applications will be reviewed on a rolling basis until the position is filled. Career Trek thanks everyone who applies. Only those selected for an interview will be contacted.

Career Trek is committed to employment equity practices that achieve a workforce reflective of the community at large and the participants it supports through its programming. We encourage applicants to self-identify as Indigenous, Two-Spirit, Black, a Member of a Racialized Community, A Person with a Disability, or LGBTQQIA+.

For more information about Career Trek, please visit: www.careertrek.ca

IMPORTANT NOTE: While there are no current public health orders or vaccination mandates in place as it pertains to COVID-19, should this change, Career Trek will reinstate its mandatory COVID vaccination policy, which requires all staff to be fully vaccinated and provide proof as such as a condition of employment.