By Charley Chiasson, Founder & Principal, Train.Sell.Win. I was at the RBC Amphitheatre in Toronto on Wednesday night. GODSMACK, with Stone Temple Pilots and Dorothy opening. Waterfront, summer air, the kind of night that reminds you why live music exists. I went there for one reason — a night out with a friend. An escape. …
Adding more structure to sales doesn’t lower burnout. From working at some of the biggest, most respected companies out there, it can actually make burnout worse in sales. The rapid adoption of AI can also increase pressure if it’s layered on top of existing processes rather than used to simplify work. Long-term success relies on …
Read more “Tighter processes won’t save your sales team from Burnout. These three drivers will.”
Punching above your weight isn’t about pretending to be bigger. It’s about understanding how the giants think — and acting where they hesitate. Most SMBs lose before the fight even starts. Why? Because they try to copy the giants: If you’re small and slow, you’re just small. The real advantage of SMBs: strategic agility Big …
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If you are a sales leader, you are likely being sold that more structure is good. Optimize your processes. Here’s what I have learned and observed 25+ years in Enterprise SalesA process mindset is important, however too much structure is usually a tax to a sales rep not a benefit. What structure should do for …
Read more “Structure should be a weapon for a sales rep, not a chore.”
I absolutely love this quote from Mark Allen. The similarities in triathlon and sales are undeniable. “Triathlon is never only about Triathlon. The swim teaches you how to stay calm when you can’t control the conditions. The bike teaches patience when the payoff is far away. The run teaches you how to keep moving when …
Read more “What Triathlon Taught Me About Developing Sales People Who Actually Last”
Relationship-based selling used to be enough to secure a seat at the table. Today, with shifting trade policies and complex buying committees, it takes more than a brand name to navigate the labyrinth—it takes a total recalibration of your sales DNA. In 2026, the shift from “who you know” to “what you solve” has reached …
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I chuckle when I see Sales Consultants and their cheat sheets and playbooks saying how easy sales is if you follow these tidbits of advice on prospecting, outreach, building pipeline, and how you are going to knock it out of the park. That is only one small aspect of sales. After close 30 years of …
Read more “Why Focus is the New Competitive Advantage in Sales.”
We all watched the magical and inspiring Toronto Blue Jays run to the World Series in the fall. In a time of economic uncertainty and turbulent times they united a country. They were a team in every sense of the word; no egos, injured, vulnerable and all stepped up at different times. The thing that …
Training for a triathlon taught me far more than how to swim, bike, and run. It taught me about discipline, leadership, and perseverance in every part of life and business. The lessons I learned on early morning rides, long training runs, and in the open water translate directly to achieving success in enterprise sales. Here …
Read more “10 Key Takeaways From Triathlon for Enterprise Sales”