Presented by: Scotiabank
At Big Brothers Big Sisters of Toronto (BBBST), we build thriving communities by empowering lives through mentorship. Many young people in our city face adversities in their lives, resulting in toxic stress that can negatively impact their development. With the support of a mentor, young people see positive results in mental health, education, career opportunities and civic engagement.
On Thursday, June 12th, we invite you to join us at this year’s Big Night Out! We are returning for another incredible event experience, wearing your finest threads, and enjoying an evening of food, drinks, and fun for all in support of BBBST.
Be a part of Big Night Out 2025! For general information, please contact: events.toronto@bigbrothersbigsisters.ca
For details on being a part of the night, to purchase a table or to be become a sponsor, please contact: lisa.limarzi@bigbrothersbigsisters.ca
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.
Gisela Carere, MBA
With over 30 years of experience and a deep passion for group benefits, Gisela Carere has dedicated her career to meeting the unique needs of executives, employees, and organizations across industries.
As the President of Benchmark Benefits, she combines unparalleled expertise in benefit plan design, group underwriting, and cost-containment strategies to help businesses create stronger, healthier teams. Her background includes a degree from the University of Toronto, a CEBS designation, and an MBA from Ivey Business School—a foundation that blends technical precision with strategic leadership.
Gisela’s journey began early, gaining hands-on experience in the nuances of group employee benefits while working with actuaries and underwriters. Over the years, she honed her skills, earned key credentials, and ascended to leadership roles—all while building a reputation as a trusted partner in the industry.
Today, Gisela is not only a leader but also a strategic visionary, leveraging her extensive industry relationships and insights to deliver exceptional results for Benchmark clients. Under her leadership, Benchmark Benefits has become synonymous with innovation and excellence in employee benefits.