Meet the Experts
Real Experience. Practical Insight. Powerful Connections.
The Gig to Grow Business Summit brings together accomplished speakers, experienced entrepreneurs, and trusted professionals who know what it takes to start, grow, and lead.
They're not coming to share vague theories.
They're coming to share real lessons, practical strategies, honest experiences, and ideas you can use in your business.
You'll hear from people who have built businesses, led teams, solved problems, embraced change, and helped others move forward.
And this time, you get to hear them in person.
Sylvia Calleri
Event Co-Host & SpeakerSylvia Calleri is the founder of Authentically Evolving and a certified Life Mastery Consultant with more than 32 years of experience in corporate sales, marketing, and business growth. Through coaching, workshops, retreats, and community initiatives, she helps people break through limitations, step into their power, and create lives filled with purpose, success, and spiritual fulfillment. Sylvia is also a serial entrepreneur, published author, and founder of the International Women's Day Conference.
Speaking Focus
Personal Growth & Transformation
Laura Connor
Event Co-Host & SpeakerLaura Connor is the founder of The Media Seen Corporation and an AI Growth Consultant who helps small businesses use practical AI to save time, improve customer follow-up, and grow with greater confidence. A dynamic speaker, trainer, and community builder, she is known for making technology easy to understand, relatable, and immediately useful.
Speaking Focus
Practical AI Growth
Roger Caesar
Event EmceeRoger Caesar is an internationally recognized speaker, Certified World Class Speaking Coach, author, and communication expert. A Top Three finalist in the 2021 World Championship of Public Speaking, he has worked with organizations including Toyota, Dell Technologies, TD, and Desjardins and is known for his engaging stage presence, warmth, and ability to connect with audiences.
Dr. Jude Joseph
Featured SpeakerDr. Jude Joseph is a project management consultant, corporate trainer, and adjunct professor with more than 20 years of experience leading IT projects and digital transformation initiatives. He holds a PhD in Project Management with a minor in Artificial Intelligence and helps organizations connect emerging technology with practical leadership and business strategy.
Speaking Focus
Artificial Intelligence and Leadership
Nadine Zeinoun Khoury
Featured SpeakerNadine Zeinoun Khoury is an award-winning inspirational speaker, Master Certified Coach, and executive leadership coach with more than 15 years of corporate leadership experience and over 3,000 coaching hours. She helps leaders strengthen emotional intelligence, build trust, and guide their teams through change with greater clarity, alignment, and confidence.
Speaking Focus
Leadership & Emotional Intelligence
Jady Nugent
Featured PanelistJady Nugent is a licensed insurance agent with HUB Financial Inc., serving families and business owners across Ontario. As an independent agent with access to leading Canadian insurance carriers, she helps clients choose life insurance strategies that protect what matters most and support long-term wealth planning. Her background in real estate and healthcare allows her to consider how a client's health, home, and finances work together.
Speaking Focus
Funding & Financial Readiness
Alan Luk
Featured PanelistAlan Luk is a Small Business Consultant with the Richmond Hill Small Business Enterprise Centre and a Business Coach with Seneca HELIX. A former digital marketing agency owner, he has helped entrepreneurs across a wide range of industries strengthen their websites, reach more customers online, and grow their businesses. Alan brings both public-sector economic development experience and firsthand knowledge of what it takes to build and support a small business.
Speaking Focus
Digital Marketing and Small Business Growth
Winston Stewart
Keynote SpeakerWinston Stewart is the President and CEO of Wincon Security, a company he founded in 1992 and grew from one client and one employee into a multimillion-dollar organization serving more than 100 clients with over 250 employees. A respected entrepreneur and community leader, Winston is also Chair of the Board of Governors at Seneca Polytechnic and has served on numerous boards and advisory committees throughout the GTA. He brings more than three decades of firsthand experience in entrepreneurship, leadership, business growth, and community impact.
Speaking Focus
Entrepreneurship, Leadership & Business Growth
Chantel Escoffery
Featured PanelistChantel Escoffery is a marketing strategist, entrepreneur, educator, and mentor with more than 25 years of experience helping businesses build strong brands, attract customers, and create meaningful connections. As Founder and Principal Consultant of CE Marketing Solutions Inc., she has worked with entrepreneurs, nonprofits, corporations, and community organizations across a variety of industries. A small business owner and professor at Durham College, Chantel brings practical, real-world experience to marketing strategy. She is passionate about helping entrepreneurs make smarter marketing decisions and use actionable strategies to grow their businesses with confidence.
Speaking Focus
Marketing Strategy & Business Growth
Judy Stewart
Featured PanelistJudy Stewart is the Founder and CEO of Trèsolz, a premium women's footwear brand creating stylish shoes in sizes 11–16. Inspired by her own experience, she built Trèsolz to serve a market often overlooked by the fashion industry. A successful contestant on CBC's Dragons' Den, Judy has used pitching to gain visibility, funding, mentorship, and new business opportunities. She brings practical insight into helping entrepreneurs clearly communicate their value and confidently pitch their ideas.
Speaking Focus
Pitching & Business Storytelling
Rina Winston
Featured PanelistRina Winston is a Certified Professional Coach and Project Management Professional with more than a decade of experience supporting executive teams. She helps professionals and entrepreneurs strengthen self-leadership by identifying the patterns that shape how they focus, decide, work, and follow through, blending psychological insight with systems thinking to support sustainable success.
Speaking Focus
Money Management, Mindset and Self-Leadership for Entrepreneurs
Zehra Mahoon
Featured SpeakerZehra Mahoon is a leadership and business coach, author, and speaker who helps entrepreneurs and professionals communicate their ideas with greater clarity, confidence, and impact. Drawing on decades of business, leadership, and speaking experience, she helps people use their voice, message, and thought leadership to build credibility, create opportunities, and grow their business.
Speaking Focus
Speaking for Business Growth & Thought Leadership
Bill Hutton
Featured PanelistBill Hutton is an Employee Benefits Consultant with Norbram Group, with more than 15 years of experience helping small businesses and start-ups design practical, cost-effective health and dental benefit programs. As the exclusive advisor for the Chambers of Commerce Group Insurance Plan in the Markham area, he helps business owners understand their benefit options, manage costs, and provide competitive coverage for themselves and their teams.
Speaking Focus
Employee Benefits & Small Business Coverage
Edith Taki
Expert CoachEdith Taki is a technology strategist, entrepreneur, and founder of Altimex Consulting, where she helps businesses and organizations use technology to modernize, grow, and work more effectively. With experience in digital transformation, fintech, e-commerce, and emerging technologies, she focuses on making AI practical, accessible, and easier to understand for entrepreneurs and business owners.
Coaching Focus
Artificial Intelligence, Digital Transformation and Emerging Technology
Lisa Watts
Expert CoachLisa Watts is a brand translator, creative strategist, and artistic consultant who helps businesses align who they are with how they communicate, connect, and grow. With a Fine Art degree and more than 20 years of experience in newspaper and media, she blends art, psychology, language, strategy, and technology to turn complex ideas into clear, cohesive brands and digital experiences that feel both intentional and human.
Coaching Focus
Brand Strategy, Messaging, Creative Direction and Digital Experience
Kat Ostroumova
Expert CoachKat Ostroumova is an award-winning women's wellness coach, hormonal health specialist, entrepreneur, keynote speaker, and Founder & CEO of Kat International Wellness. She helps ambitious women build sustainable success by strengthening the connection between health, energy, leadership, boundaries, and business performance.
Coaching Focus
Women's Wellness, Sustainable Success, Leadership and Work-Life Balance
More Participants Coming Soon
We're continuing to build a strong lineup of speakers and panelists who can bring real value to the Gig to Grow community.
New participants will be announced as they're confirmed.
Check back often and follow Gig to Grow for the latest announcements.
Meet Them in the Room
A website bio can tell you what someone has accomplished.
But there's something different about hearing their story, learning from their experience, and connecting with them face-to-face.
- • One presentation could give you a new idea.
- • One panel conversation could answer a question you've been carrying.
- • One introduction could lead to your next client, collaborator, mentor, or opportunity.
Get in the room.
Gig to Grow Business Summit: From Start-Up to Scale-Up
Saturday, October 3, 2026
Monte Carlo Inn, Warden Avenue, Markham, Ontario