Jon Montgomery
Speaker, Host of The Amazing Race Canada; Olympic Champion
About Jon Montgomery
Jon Montgomery is a Canadian Olympic Gold Medalist who won the skeleton event at the 2010 Vancouver Winter Games, a five-time Canadian champion, and the award-winning host of The Amazing Race Canada.
As an in-demand keynote and inspirational speaker, he has spent over a decade delivering high-energy presentations to audiences around the world, helping individuals and organizations build confidence and develop self-efficacy — the belief that achieving one's goals is truly possible.
Jon's talks blend authentic storytelling and humour with a powerful message of embracing your roots and believing your dreams are within reach.
Jon Montgomery's Expertise
- Jon Montgomery is a Canadian Olympic Gold Medalist, keynote speaker, and television host best known for winning gold in men's skeleton at the 2010 Winter Olympics in Vancouver/Whistler and for hosting The Amazing Race Canada, a role that earned him two Canadian Screen Awards.
- With over 20 years of experience in leadership, learning and development, mentoring, and coaching, he delivers sought-after keynote presentations on topics including "Dreaming Big: Living Bigger," the importance of teamwork, and his personal Olympic journey — connecting powerfully with both youth and corporate audiences.
- Beyond athletics and broadcasting, Montgomery brings real-world business credibility as a former sales consultant, automobile auctioneer, entrepreneur, and small business owner. He is also a committed philanthropist, contributing to clean water initiatives and youth sports programs, making him a well-rounded and influential public figure across sports, business, media, and community leadership.
Jon Montgomery's Bio
Jon Montgomery is a Canadian Olympic Gold Medalist, renowned speaker, and engaging host of The Amazing Race Canada. Born and raised in Russell, Manitoba, he is as proud of his prairie roots as he is of his Canadian identity – something he expands on in his keynotes.
Montgomery’s athletic achievements include winning a gold medal on home soil in the men’s skeleton event at the 2010 Winter Olympics in Vancouver/Whistler. His diverse professional background encompasses roles as a sales consultant and automobile auctioneer, entrepreneur and small business owner, showcasing his versatility and business acumen.
As a speaker, Montgomery has captivated audiences with his compelling and inspirational talks. With over 20 years of experience in leadership, learning and development, mentoring, and coaching, he has become an innovative leader and consultant. His speaking engagements cover a wide range of topics, including “Dreaming Big: Living Bigger,” “The Importance of Teamwork,” and “Jon Montgomery’s Olympic Journey.” His ability to connect with both youth and corporate audiences has made him a sought-after speaker for a variety of events. +
Residing on the west coast of Canada on Vancouver Island with his wife and former team-mate Darla Deschamps Montgomery and their two children, his commitment to his family and his ability to balance his professional and personal life reflect his strong work ethic and dedication.
In addition to his speaking engagements, Montgomery has also gained recognition as the host of The Amazing Race Canada, earning him two Canadian Screen Awards, further showcasing his talent as a versatile and engaging television personality. His popularity extends beyond his athletic and television career, making him a well-respected and influential figure in the public eye and contributor to several philanthropic movements in clean water and youth-sports initiatives.
Overall, Jon Montgomery’s journey from Olympic success to becoming a multifaceted professional and a compelling speaker is a testament to his resilience, passion, and ability to inspire others. His impact on diverse audiences and his continued success in various fields solidify his status as a respected and influential figure in the public sphere. --
Contact Us for Jon Montgomery's speaker fees, and date availability.
Jon Montgomery's Presentation Topics
Dreaming Big: Living Bigger
While Jon always wanted to be a Canadian National Team athlete, he didn’t know which sport it would be in! Keeping his eyes wide open, living outside his comfort zone, trying new things and accepting the challenges that presented themselves enabled him to find his passion and his opportunity to realize his dreams. Jon’s story will inspire others to go after what they are looking for, no matter how daunting a task it may seem.
Innovation and Realism
While we must be realistic about the things in life we cannot change, there are always ways in which we can optimize ourselves and our situations through creative thinking and innovation.Unless you’re moving forward, you’re getting left behind!
Jon’s Olympic Journey
The story of how a small town boy from Manitoba, who grew up playing hockey and idolizing his home town hero, Theo Fleury (the smallest guy to ever play in the NHL) inspired him to become an Olympic Champion.
Self-efficacy
Whether you think you can, or you think you can’t... you’re 100% correct! Learning this nugget-of-wisdom the hard-way, very early in his development as a skeleton athlete, illuminated a fundamental truth for Montgomery - the greatest differentiator between realizing a goal and falling short is rooted in the individuals personal belief that they will achieve that which they seek. Jon will relive the dramatic experience that revealed the toughest hurdle he would have to overcome to realize his dream... his ability to believe in himself!
Teamwork
Skeleton racing is an individual sport - but you are never alone! Whether you find yourself piloting a skeleton sled at 140kph down a frozen track or working on a project late at night at work, you have resources!
When we lean into the resources, human or otherwise, that are around us, we are more! Together our growth and development can be amplified and expedited - and it is through this collaborative approach that we can benefit from the invaluable experience of others. Preparation is the key to seizing your moment when the time comes; “pre-pair”, “pre-pair”, “pre-pair”... then “pre-form”!
Book Jon Montgomery to speak at your next conference or corporate event.
Frequently Asked Questions About Jon Montgomery
Who is Jon Montgomery? +
Jon Montgomery is a Canadian Olympic Gold Medalist who won the men's skeleton event at the 2010 Vancouver Winter Olympics, a five-time Canadian champion, an award-winning television host of The Amazing Race Canada, and one of Canada's most in-demand inspirational keynote speakers. --
What does Jon Montgomery speak about? +
Jon delivers keynote presentations on confidence, self-belief, leadership, teamwork, and resilience. His signature talks include "Dreaming Big: Living Bigger," "Jon's Olympic Journey," and "Innovation and Realism" — each tailored to inspire both corporate and youth audiences. --
How do I book Jon Montgomery as a keynote speaker? +
Jon Montgomery is directly represented in Canada and the USA by K&M Productions, a Toronto-based speakers bureau and corporate event planning agency. To book Jon Montgomery, submit an event inquiry --
What types of events is Jon Montgomery available for? +
Jon is available for corporate conferences, leadership summits, sales kickoffs, association events, youth programs, and virtual keynotes. He has spoken for organizations including TD, PwC, Home Hardware, BC Assessment, Aviso Wealth, Tire Discounter Group and Equitable Life. --
Is Jon Montgomery available for virtual keynotes? +
Yes. Jon Montgomery is available for both in-person and virtual speaking engagements, making him a flexible option for hybrid corporate events and online conferences. --
What is Jon Montgomery best known for? +
Jon Montgomery is best known for his dramatic Olympic gold medal win in skeleton at the 2010 Vancouver Winter Games — celebrated by his now-iconic victory walk through Whistler — and for hosting The Amazing Race Canada, for which he won two Canadian Screen Awards. --
How much does it cost to book Jon Montgomery as a keynote speaker? +
Jon Montgomery's current speaking fee range is $15,001–$20,000. Final fees depend on event format, location, travel requirements, and whether the engagement includes additional services such as workshops or coaching. Contact K&M Productions directly for a personalized quote and to confirm Jon's availability for your event date. --
Where is Jon Montgomery based and does he travel for events? +
Jon Montgomery is based in Vancouver Island, British Columbia, Canada and is available for events across Canada, the United States and internationally. He has presented at conferences and corporate events on multiple continents and is an experienced international speaker comfortable with travel-intensive engagements. For events outside of Canada, contact K&M Productions to discuss travel logistics and any applicable travel fees. --
Is Jon Montgomery represented by a speaker's bureau in Canada and how is the contract handled? +
Jon Montgomery is represented by K&M Productions Speakers & Shows Canada for booking coordination and contract agreement management. Keynote speakers in Canada often work through a speakers bureau to handle support requests, contracts, logistics, billing and payments. Booking the speaker through K&M Productions Speakers & Shows is like an "insurance policy" for your conference in the unlikely occurrance of speaker illness or cancellation. We step into action to find you an acceptable replacement speaker at equal or greater fee - all at no additional cost to you. --.
How do I contact Jon Montgomery to check his date availability and begin the booking process in for events in Canada or the USA? +
Jon Montgomery is contacted through K&M Productions Speakers & Shows to confirm availability and event details. Event planners and meeting planners typically schedule a pre-event call to clarify format, objectives, and expectations. The booking process begins once the event requirements are sorted .Written confirmation follows contract-agreement execution. --
What Clients are Saying About Jon Montgomery
Jon delivered a truly inspirational message at our national leader conference earlier this year. His message was right on the mark… inspiring leaders to take responsibility for challenging goals in the face of an uncertain path and really demonstrating how to take ownership for developing your full potential and that of your team. Jon is skilled at communicating his message in a way that resonates across a diverse audience with just the right blend of humour and candour. Jon Montgomery was the perfect keynote speaker for setting the stage at our national conference.
–Great-West Life
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Jon delivered a truly inspirational message at our national leader conference earlier this year. His message was right on the mark… inspiring leaders to take responsibility for challenging goals in the face of an uncertain path and really demonstrating how to take ownership for developing your full potential and that of your team. Jon is skilled at communicating his message in a way that resonates across a diverse audience with just the right blend of humour and candour. Jon Montgomery was the perfect keynote speaker for setting the stage at our national conference.
–Great-West Life
Jon Montgomery gave a first class professional presentation to an audience of over 200 independent retailers, hardware vendors and TruServ Canada staff at the TruServ Canada Spring Market. His presentation was very well received and cited by audience members as the best pre-market function ever. Jon is friendly, unpretentious and a captivating speaker with a great Canadian story. He connects with his audience and is a real crowd pleaser. I highly recommend Jon as a motivational speaker in any context.
–Truserv Canada
Jon was a wonderfully energetic and infectiously enthusiastic speaker. He spoke from the heart, and very naturally, about his journey to his Olympic dream, and kept our group captivated and entertained the entire time. He is a true Canadian spirit.
–Canadian Security Traders Association, Inc.