Meet Charley
“After being in sales for 25+ years, I firmly believe sustainable sales performance is built from within. Sales is both Mindset and process. As we move into a new generation of Sales in an AI augmented world, the true Trusted Advisor Sales Rep will be more important now than the ones that chase the SPIFF’s. If you treat a customer like a transaction, they will treat you like one.”
Hailing from beautiful Cape Breton Island, Nova Scotia, on the East Coast of Canada, I turned small town humble beginnings into a career of significant achievement, continually surpassing expectations. I hold a Bachelor of Business Administration from St. Francis Xavier University and have excelled in enterprise sales for 25+ years, engaging with the boardrooms of global technology leaders like IBM, Siemens, HPE, and NTT. I have assisted Canada’s largest companies implement their strategies with expertise in Healthcare, the Big Banks, and Manufacturing.
Transitioning from a 25+ year career in enterprise sales to sales consulting is the ultimate value-add, transforming decades of frontline experience into actionable strategic guidance.
My journey moves from consistently hitting high-stakes quotas and navigating complex corporate landscapes to a role focused on architecting predictable growth for multiple organizations. This shift leverages my proven expertise in relationship management, advanced negotiation, and sales cycle optimization, effectively converting operational wisdom into a consulting framework.
Not a large Enterprise? I’ve got you covered. I have also assisted SMB and Emerging Technology Companies.
Beyond the corporate world, I have applied that same drive to my passion for sport, becoming a NCCP Triathlon Canada Licensed Coach while actively learning, racing, and continually growing with every mile on my own triathlon journey competing in Ironman races. Anything really is possible.
I’m Charley, and I started Train.Sell.Win. because I saw a gap in how modern sales teams operate. I help companies and salespeople perform at their peak. I focus on turning drive into measurable outcomes — increasing sales effectiveness, closing more deals, and building long-term client trust — so success isn’t just achieved, it’s sustainable.
With a “big-firm” pedigree and years of real-world execution, I’ve learned that top-tier revenue growth isn’t an accident. It’s the result of elite discipline, data-driven strategy, and the mental stamina to see a complex deal through to the finish line.
I’m glad you found your way. I share what I’ve learned about all things sales to help you reach your goals and potential. Let’s build something extraordinary.
Charley Chiasson
Industry experience
