Power of Possibility

A conversation with entrepreneurial women to explore the possibilities in ideas, opportunities, connections & change.

DFS Toronto is thrilled to present The Power of Possibility, an exceptional fundraising event to celebrate International Women’s Day.

The Power of Possibility features inspiring women who live the definition of embracing change and have the courage to move an idea through to action and into impact. The event supports DFS Toronto’s mission, programs, and, most importantly, the remarkable women we serve.

We are thrilled to introduce you to our incredible panel for this year’s event:

Jenn Harper, CEO & Founder of Cheekbone Beauty
Anna Sinclair, Founder & CEO of Total Mom Inc & Sinclair Creative Agency Inc
Jody Steinhauer, President & CBO (Chief Bargains Officer) of The Bargains Group

Event Details

March 25, 2025 • 6 PM – 9 PM
Hosted at the Toronto Reference Library
$100 / Ticket, including a $25 Tax Receipt
250 Guests in Attendance

Event Overview

The Power of Possibility offers guests an evening of inspiration, reflection & connection featuring:

An intimate Fireside Conversation featuring three entrepreneurial women who embrace fear, aspire to grow & aim to try new things
A networking reception

Together, let's create a transformative experience that showcases the power of women's empowerment and economic independence.

Interested in sponsoring this event? Click here to download our Sponsorship Snapshot!

Jenn Harper

Founder & CEO, Cheekbone Beauty

An award-winning social entrepreneur, Jenn Harper is the founder and CEO of Cheekbone Beauty Cosmetics INC. Cheekbone Beauty aims to help every Indigenous person see and feel their value in the world while developing sustainable colour cosmetics that won’t end up in a landfill.

Jenn Harper is an Anishinaabe woman and is a member of the Northwest Angle #33 First Nation in Kenora, ON. Throughout her life, Jenn has struggled with accepting her Indigenous roots. She was estranged from her Indigenous family for much of her child and adult life. After learning about her grandmother’s experience in residential school, she understood how her family was affected by generational trauma.

Harper has been making a name for herself in the beauty industry for a number of years but gained popularity quickly after appearing on CBC’s hit show, Dragon’s Den in 2019.

Anna Sinclair

Founder & CEO, Total Mom Inc & Sinclair Creative Agency Inc

Anna is an award-winning entrepreneur, angel investor, content creator, and super mom of three. Recognizing a lack of support systems for modern-day working women, Anna responded by building a career and professional platform designed to empower founders personally and professionally.

Known as a super-connector and for her impressive network of contacts and relationships, Anna founded the Canadian Women Entrepreneur Industry Awards Gala, which unites Canada’s top brands, marketers, founders, creators, and media to open doors for diverse women entrepreneurs through the power of social capital.

As an angel investor and agency owner, Anna finds the most joy in strategic consultation through her impact agency, Sinclair Creative Agency Inc. Anna supports, connects, funds, and empowers those around her to thrive as founders and build a life and brand just as unique as they are.

Jody Steinhauer

President of The Bargains Group & Kits For A Cause

As President and CBO (Chief Bargain Officer) of the Bargains Group, Jody has mobilized her award-winning discount wholesale and promotional products company to revolutionize the social impact landscape.

A winner of the Canadian Woman Entrepreneur of the Year Award, Canada’s Top 40 Under 40 and other notable awards, Jody uses her network of resources and leveraged buying power to aid every company and NFP agency/charity that she touches to maximize their buying dollar. Since 1988, Jody has grown the Bargains Group from her apartment living room to a multi-million dollar-a-year business.

Recognized widely as a thought-leader, Jody is a frequent speaker at conferences on the topic of employee engagement and engaged philanthropy. She is also an award-winning author, contributing to the recent Amazon best-seller Women of Purpose: Creating a Better World.

Jennifer Hsiung

Co-Anchor, CP24 Breakfast

As the co-anchor of CP24 BREAKFAST, Jennifer Hsiung helps viewers in Toronto and the GTHA begin their day, weekdays from 5:30 a.m. to 9:30 a.m. ET. With more than a decade of international broadcasting experience, the Toronto native first joined CP24 in September 2020, and soon became a fill-in anchor on CP24 BREAKFAST. She officially joined the team on a full-time basis in November 2021.

Hsiung also maintains a lifelong passion for performance arts, and she began pursuing stand-up comedy in Beijing in 2015. She made her televised comedy debut on Season 3 of Comedy Central’s Stand Up Asia! alongside Montreal’s Sugar Sammy. It premiered in August 2018 in 19 countries across Asia. She also competed in the 2017 Hong Kong International Comedy Competition, and was the only woman to reach the finals. In 2020, Hsiung won the iHeart Comedy Award for Best Newcomer Comic in Toronto.

Thank You to Our Sponsors

Presenting Sponsor

Signature Sponsors

Sponsor Logos (Web Format) - Salesforce 2

Event Sponsors

Event Participants

Sponsor Logos (Web Format) - Rakuten Kobo

Beverage Sponsors

Print Media Sponsors

Impact Agency Sponsor

In-Kind Partners

Your support can make a difference.

Our purpose is to offer long-lasting solutions.

At Dress for Success Toronto, our mission is made possible because of the generosity of our community. By making a financial contribution, you are making an investment in not only the individuals we serve, but also their families and our community as a whole.

With your support, we can provide our services to those in need, at no cost. Through our programs, Clients get a fresh start, empowering them to actively define their life and change the trajectory of their future.