In October 2022, Alex, a seasoned educator transitioned from the classroom to a new role as a success coach with United Way. After seven years as a teacher, she saw firsthand how challenges students faced extended far beyond academics. The pandemic amplified these struggles, revealing the urgent need for holistic support for students and their families.
Her journey to this role was serendipitous. “I had my eye on this job for a while,” she shares. “It was a family movie night — we were watching The Lion King for the 17th time — when I saw the posting again. I thought, ‘This is it. I’m going for it.’” Now, she feels privileged to work with United Way, helping students succeed academically and beyond.
United Way: A Personal Connection
Alex has been a donor since 2006, long before she joined the staff. “I was drawn to the idea that every dollar raised in Windsor stays in Windsor. It felt personal,” she says. Inspired by a former colleague who championed local giving, she realized the importance of contributing to a community she loved. Today, she channels that passion into her role, embodying the spirit of “local love.”
A Day in the Life
No two days are the same in her role. Her day typically unfolds in three parts:
- Morning: Administrative tasks like tracking student progress, coordinating with teachers and community supports, and planning programming events.
- Afternoon: Student-focused activities such as arranging tutoring sessions, addressing financial barriers, and providing direct support.
- Evening: Overseeing academic support sessions, where students receive tutoring, decompress, and connect with peers in a supportive environment.
Flexibility is key, as the program is tailored to meet each student’s unique needs. “We focus on pillars of support: academics, mentorship, financial assistance, and family support,” she explains. “Whether it’s helping with basic needs or providing bursaries for post-secondary education, everything we do is about breaking barriers.”
Challenges and Triumphs
Navigating the complexities of students’ barriers is challenging. Many face issues rooted in financial insecurity, social anxieties, or limited access to support and resources. “Coming from outside their experience, I strive to listen, empathize, and show them it’s okay to ask for help,” she reflects. Despite these challenges, the rewards are immeasurable.
“Watching students grow, set goals, and achieve them is incredible,” she says. Success isn’t always measured in scholarships or grades; sometimes, it’s a student who is at a turning point in their education journey and is showing up to school consistently after years of absenteeism. “It really shows the power of meeting students where they are and providing that personalized support.”
Collaboration and Community Impact
The program thrives on partnerships with students, parents, and the community. “We’re not here to replace the support system at home,” she emphasizes. “We’re here to collaborate, filling gaps and building bridges.”
A Message to Donors
To the donors, she offers heartfelt gratitude: “Your contributions go far beyond financial support. You’re giving these kids skills, relationships, and opportunities that change their lives.” For non-donors, she extends an invitation: “Learn about our impact. We’re working to address issues some youth face by prioritizing educational success, and your support can make all the difference.”
Looking Ahead
As she reflects on her journey, one thing is clear: the work being done by United Way is transformative. “It’s about much more than academics,” she concludes. “It’s about empowering students to reach their full potential and creating lasting positive change in our community.”
Click here to learn more about the On Track To Success program.
Last updated on December 9, 2025