Assiniboine Alumni to recognize education, community, and future leaders at annual advancement dinner

Assiniboine College’s Alumni Association is proud to recognize four outstanding members of the Assiniboine alumni community whose achievements, leadership, and commitment to learning have made a lasting impact on their professions, communities, and fellow graduates.

The 2026 Alumni Award recipients are:

• Kevin Bailey, recipient of the Distinguished Alumni Award
• Sydney Huston, recipient of the One to Watch Alumni Award
• Brandy Robertson, recipient of the Excellence in Education Award
• Rich Little, recipient of the Excellence in Education Award

“These recipients exemplify leadership, innovation, service, and a commitment to helping others succeed,” said Theresa Elton, Chairperson of the Alumni Association at Assiniboine College. “Whether they are inspiring students in the classroom, strengthening their communities through volunteerism, or building successful careers in their industries, each of these award recipients demonstrates the profound and lasting impact of an Assiniboine education.”

Distinguished Alumni Award: Kevin Bailey

A 1985 Business Administration graduate, Kevin Bailey enjoyed a 36-year career in the insurance industry, including 35 years with Wawanesa Mutual Insurance Company. Since his retirement, he has dedicated much of his time to community service, serving on the Assiniboine College Alumni Association Board and continuing his leadership with United Way Westman.

Bailey credits Assiniboine with helping shape both his career and personal success.

“Applying to attend Assiniboine was one of my best decisions I have made. It truly helped shape the person I am and allowed me to have such a great career and quality of life,” said Bailey.

Reflecting on receiving the award, Bailey said, “I was almost in shock and then had a few tears. It's still hard to believe I was even in the conversation for this award. I feel very blessed and grateful. Assiniboine will always be in my heart.”

One to Watch Alumni Award: Sydney Huston

A 2024 graduate of Assiniboine’s Media and Communications program, Sydney Huston has already established herself as an emerging leader in Manitoba’s business community. After beginning her career in marketing, she transitioned to a rapidly growing Winnipeg technology startup, Taiv, where she works as an account executive and contributes to building workplace culture while supporting business growth.

During her time at Assiniboine, Huston developed the communication, collaboration, and leadership skills that continue to drive her success today.

“At Assiniboine I really got to figure out what I was good at and what I wasn't,” said Huston. “It helped me realize that coordination and people were where my passion and skills lied. I love working with a hard-working group of people to achieve the same goal and to build something together.”

Excellence in Education Award: Brandy Robertson

A 2004 graduate of Assiniboine’s Business Administration program, Brandy Robertson has dedicated her career to supporting student success in post-secondary education. Over the past two decades, she has worked in advising, administration, leadership, and teaching, including as an instructor in the Peters School of Business and the School of Health & Human Services. She currently serves as a Student Success Advisor.

Robertson’s commitment to education is rooted in helping others realize their potential.

“I love seeing the positive impact that one person can have on another human,” said Robertson. “I've had good people in my corner and on my side and I want to be one of those good people for others,” she added.

Upon learning she would receive the award, Robertson reflected on what recognition means to her career as an educator. “It’s validating! when students I've worked with are asked to think of an educator that made a positive difference in their lives, I am the person that comes to some of their minds. For me, that's winning.”

Excellence in Education Award: Rich Little

A business instructor at Assiniboine since 2011, Rich Little is recognized for his innovative approach to teaching, blending active learning, technology, and what he describes as “Ludic Pedagogy” to create engaging and effective learning experiences. A recipient of the 2022 ACBSP Teaching Excellence Award for Canada, Little has become a leader in experiential learning and educational innovation.

His teaching philosophy centres on creating meaningful opportunities for students to learn through experience.

“I want students to have opportunities to practice, fail, get feedback, reflect, and live to learn another day,” said Little. “The classroom should be a place where they can take some risks before the stakes get high.”

Receiving recognition from former students makes the award especially meaningful.

“This award means a tremendous amount to me because it comes from alumni,” said Little. “When a student with an established career remembers you and what they learned in your classroom, to me that's proof of concept.”

The Alumni Association will celebrate these deserving award recipients at the Assiniboine Advancement Dinner on November 19 at the Backyard on Aberdeen. For ticket information visit assiniboine.net/alumniawards or email [email protected].