Enterprise Job Training & Community Outreach Educator

Title :Enterprise Job Training & Community Outreach Educator

Reports To :Director of Business Operations

Hours : 1 Position – Full Time (40 Hours a Week) Some evenings and weekends may be required

Salary Range: $48,000-$52,000

Divisions Served :Development Department & Community Engagement Division

AI Disclosure :No AI tools will be used to screen or assess candidates for this position

Summary of Position

The Enterprise Job Training & Community Outreach Educator leads, develops, and expands our Enterprise Job Training Program while championing public education and community outreach. This multifaceted role is responsible for full program facilitation – including participant recruitment, curriculum delivery, and operational tracking – as well as leading public education initiatives regarding homelessness, addiction, and poverty. Additionally, the Educator actively cultivates third party fundraising events, corporate sponsorships, and strategic community partnerships to secure long-term financial sustainability and foster regional empathy.

Expected Outcomes

- Successful execution of at least 8 high-quality vocational training sessions annually, maintaining a minimum of 10 participants per cohort.
- Increased participant retention and graduation rates, evidenced by documented technical skills gained and positive employment outcomes.
- Fundraising and third-party event targets consistently met or exceeded, ensuring full financial independence for the program.
- Increased regional awareness and reduced social stigma through public presentations delivered to schools, businesses, and civic groups.
- Establishment of a robust pipeline of self-sustaining, community-led third-party events (e.g., community food drives, independent fundraisers, workplace campaigns).
- Sustainable recruitment and transition pathways secured via active partnerships with local agencies, the City of Windsor and regional employers.
- Maintenance of a rigorous tracking database detailing program metrics, financial milestones, and outreach efficacy for stakeholder reporting.
- Seamless transition management achieved via proactive onboarding and training of the Manager of Mission Promotional Products and program successors.

Education,



Knowledge and Experience

- College-level training or verified professional experience in Human Services, Education, Public Relations, or Business Development.
- Specific credentials in fundraising or public relations are highly valued; a Certified Fund-Raising Executive (CFRE) designation is an asset.
- A service-first philosophy deeply aligned with the mission, vision and core values of The Downtown Mission of Windsor.
- Nuanced understanding of the structural causes of homeless, mental health complexities, and substance-use recovery journeys.
- Proven experience managing income/expenditure budgets, driving fundraising campaigns, or executive corporate sales/marketing initiatives.
- Advanced proficiency in Microsoft Office 365, database tracking systems, and presentation software.
- Valid Driver’s License with a clean Driver’s Abstract and access to reliable personal transportation.

Skills and Qualities Required

- Relationship Building: Proven capacity to inspire trust, build authentic rapport, and cultivate lasting connections with donors, corporate sponsors, and grassroots organizers.
- Public Speaking & Pedagogy: Exceptional communication skills with the ability to confidently present complex social issues to diverse audiences, from classrooms to corporate boardrooms.
- Event Development: Resourceful, creative, and entrepreneurial mindset capable of conceptualizing, pitching, and guiding independent third-party campaigns.
- Multitasking & Organization: Demonstrated ability to manage multi-layered projects, educational schedules, and event timelines simultaneously without compromising accuracy.
- Inclusive Engagement: Global or local experience working within diverse community networks.

Duties and Responsibilities

Job Training Program Facilitation

- Session Delivery: Plan,



organizer and execute a minimum of 8 annual Enterprise training sessions in partnership with the City of Windsor or independently through the Mission
- Team Coordination: Synchronize efforts with specialized instructors, support staff, and volunteers to ensure an inclusive, high-impact learning environment.
- Metric Tracking: Manage comprehensive participant files, document individual milestones, and generate performance reports for leadership review.
- Leadership Onboarding: Provide hands-on training to the current Manager of Mission Promotional Products and future program successors.

Community Outreach & Public Engagement

- Stigma Reduction Campaigns: Design and deliver educational presentations breaking down common myths and stereotypes surrounding regional homelessness, poverty, and mental illness.
- Mission Advocacy: Actively educate the public on the comprehensive ecosystem of The Downtown Mission, including its Sanctuary (overnight shelter), Hot Meals program, Wellness/Phoenix Recovery infrastructure and the Windsor Youth Centre.
- Civic Engagement: Conduct targeted outreach at regional high schools, post-secondary institutions, faith groups, and corporate offices to build empathy and drive volunteer engagement.
- Content Creation: Collaborate on the development of physical and digital informational materials used to clearly articulate the Mission’s localized data, systemic needs, and community impact.

Third-Party Event Cultivation & Resource Development

- Grassroots Cultivation: Actively scout, pitch, and incentivize local businesses, schools, and community groups to host independent third-party fundraisers (e.g., third-party donor runs, donation drives, corporate matches).
- Organizer Toolkits: Develop and distribute promotional “toolkits” and logistical guidance to empower external organizers to execute compliant, successful events on behalf of the Mission.
- Revenue Diversification: Work directly with the Development team to identify, cultivate, and write proposals for corporate partnerships, community grants, and foundational sponsorships.
- Financial Tracking: Monitor, evaluate, and report on the financial yields of all public outreach efforts and third-party events against established annual budget goals.

Pay: $48,000.00-$52,000.00 per year

Work Location: In person

📌 Enterprise Job Training & Community Outreach Educator (Canada)
🏢 Downtown Mission of Windsor
📍 Canada