Signature Events

Find out more about upcoming BBBST events!

Big Night Out

Big Night Out is BBBST’s annual gala! Guests wear their finest threads to enjoy an evening of food, drinks, and fun, all in support of BBBST.

Music that Moves

This special evening features a headline performance by Crash Test Dummies with Tim Magwood & The Riffers opening the show. Enjoy a full concert experience at one of Toronto’s most iconic venues, complete with food stations and an open bar throughout the night.

Big on Bay Scavenger Hunt

Big on Bay is a fun event occurring in the Toronto downtown core on September 18th, 2025, at 5:00 pm for Big Brothers Big Sisters of Toronto Day to raise critical funds to support youth mentorship.

Big Open House

Big Open House event box language: The Big Open House is a yearly event held at our Yonge/Eglinton location for members of the community to meet Big Brothers Big Sisters of Toronto staff and volunteers to see what being a mentor is all about! Learn more about our programs, speak with current Big Brothers, Big Sisters, and Big Siblings to feel what it is like to be a part of our community.

Date: TBD

For questions about Big Open House, please contact Barbro Boungou at barbro.boungou@bigbrothersbigsisters.ca.

Mentors’ Corner

Mentors’ Corner aims to bring mentors across all programs together to network, connect, and share their experiences on being a Big Brother, Big Sister or Big Sibling. It a quarterly initiative developed and supported by BBBST staff that focuses on a pre-determined topic driven by volunteer feedback.

Date: TBD

For questions about Big Open House, please contact Barbro Boungou at barbro.boungou@bigbrothersbigsisters.ca.

Siobhan Calderbank's Bio

Siobhan Calderbank is an award-winning keynote speaker, leadership strategist, and Talent & Human Resources Executive with more than 20 years of experience transforming organizations, building inclusive cultures, and developing diverse leadership pipelines. Currently serving as Vice President, Talent & Performance Management at Element Fleet Management, she is recognized for leading large-scale organizational transformation, advancing talent and leadership strategies, and helping organizations build high-performing, future-ready teams.

Recognizing the need for greater access to mentorship and leadership development, Siobhan is dedicated to empowering women and youth, particularly those from underrepresented communities, through coaching, career development, networking, financial aid, and leadership-building opportunities. Her commitment to creating pathways for others to succeed is reflected in her extensive mentorship, community leadership, and advocacy efforts focused on supporting youth, women, newcomers, and emerging leaders.

As a globally recognized speaker, Siobhan has inspired audiences from more than 70 countries through conferences, corporate events, and leadership forums. She is a published author and contributor featured alongside influential thought leaders including Oprah Winfrey, Maya Angelou, John Lewis, and Deepak Chopra. Her thought leadership on leadership, change management, inclusion, and talent development has been featured across numerous publications and media platforms. Her voice has been featured on ABC, CBS, NBC, FOX, and CW, and she has appeared on Reuters and Nasdaq billboards in Times Square, as well as Planet Hollywood in Las Vegas.

Siobhan has held several leadership and advisory roles supporting diversity, inclusion, mentorship, and community development initiatives. Her contributions have been recognized through numerous honours, including being named one of the Top 100 Accomplished Black Canadian Women, receiving the Women of Inspiration Award for Diversity and Inclusiveness, and being recognized as one of the Top 100 Black Women to Watch in Canada.

She holds a Master of Arts in Leadership from Royal Roads University, a Certificate in Advanced Human Resources from Queen’s University, and a Bachelor of Commerce in Information Technology Management from Toronto Metropolitan University. Through her professional leadership and community service, Siobhan remains committed to helping individuals realize their potential and creating opportunities that enable future generations to thrive.