Train.Sell.Win.

Punching Above Your Weight: The SMB Advantage in Interprovincial & Global Markets

by charley.chiassonLeadership, Sales Leadership, Sales Training, Strategy February 26, 2026March 4, 2026No Comments

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 …

Empowering Sales Teams with Financial Acumen | Driving Revenue Growth through Customer Insight

by charley.chiassonLeadership, Sales Leadership, Sales Training, Strategy February 17, 2026February 17, 2026No Comments

Your biggest competitor in Enterprise Sales isn’t another vendor—it’s the CFO’s spreadsheet. Before I jumped into Enterprise Sales, I was in Finance. I worked at a manufacturer that was evaluating SAP. That background gave me an edge: understanding customers’ financials changes the game. Why should sales reps care about financial statements? Because it turns you …

Leaders Coach. AI Analyzes.

by charley.chiassonLeadership, Sales Leadership, Sales Training, Strategy February 3, 2026February 4, 2026No Comments

Imagine the locker room speech. Leaders coach. AI analyzes. The Gold lies somewhere in between. After 25+ years in the trenches, here’s the truth:Data doesn’t win Gold Medals or close $1M deals. Intuition does. The real job of a sales leader? Coaching. Yet, most managers are laser-focused on sales metrics—and not on coaching. I hear …

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Structure should be a weapon for a sales rep, not a chore.

by charley.chiassonLeadership, Sales Director, Sales Leadership, Sales Training, Strategy February 3, 2026February 3, 2026No Comments

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 …

What Triathlon Taught Me About Developing Sales People Who Actually Last

by charley.chiassonLeadership, Sales Leadership, Sales Training, Strategy January 27, 2026January 27, 2026No Comments

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 …

The Shift from “Who you know” to “What you solve”

by charley.chiassonLeadership, Sales Leadership, Strategy January 26, 2026February 19, 2026No Comments

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 …

Why Focus is the New Competitive Advantage in Sales.

by charley.chiassonUncategorized January 20, 2026No Comments

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 …

Augmented Selling: Transitioning from Transactional Rep to the AI-Enhanced Trusted Advisor

by charley.chiassonLeadership, Sales Director, Sales Leadership, Sales Training, Strategy January 12, 2026January 12, 2026No Comments

Early in my Sales Career I was taught one of the most important lessons in my entire career. It wasn’t by a Sales Manager. It was by my customer. I politely asked a CEO if he would sponsor an executive briefing so we could present our strategy for healthcare to an entire province. His …

Thoughts on Fractional Sales Leadership

by charley.chiassonSales Director, Sales Leadership, Sales Training January 5, 2026January 8, 2026No Comments

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 …

Rethinking What it Means to Lead

by charley.chiassonLeadership, Sales Leadership, Sales Training, Strategy January 4, 2026January 7, 2026No Comments

Prior to the holidays, one of the great CEO’s in Corporate History passed away. Lou Gerstner led one of the most significant turnarounds in history at the helm of IBM from 1993-2002. The stock grew by 800% in his time as leader. He was the first outsider to be the leader of IBM with no …