5 Ways Sales Leaders Fail Their Teams (And How to Create the Culture They Deserve

5 Ways Sales Leaders Fail Their Teams (And How to Create the Culture They Deserve

Here's something that might surprise you: the biggest threat to your sales team's success sometimes isn't the competition, market conditions, or even bad delivery. Sometimes it’s their sales manager.

In the past 10 years of running Pitch Lab, I've watched countless well-intentioned sales leaders hurt their teams through misguided kindness, conflict avoidance, and a fundamental misunderstanding of what good leadership actually looks like.

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Why Roleplaying is a Waste of Time (and What Comedy Can Teach You About Real Sales Practice)

Why Roleplaying is a Waste of Time (and What Comedy Can Teach You About Real Sales Practice)

Your salespeople hate roleplaying.

You know this. I know this.

But here's the thing: your team still needs practice. They just don't need fake practice.

During my time as a stand-up comedian, I learned something crucial about getting better at anything that requires real-world performance.

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Why 95% of Businesses Fail at AI (And How You Can Be in the 5%)

Why 95% of Businesses Fail at AI (And How You Can Be in the 5%)

Just months ago, AI dominated every news cycle. Promises of transformation here, warnings about falling behind there. Now we're hearing a completely different story: "95% of businesses see no ROI from AI," "We're in an AI bubble," and concerns about reliability and sustainability.

If you're an entrepreneur or running a growth-stage company, this creates one massive question: Should you invest in AI or wait it out?

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10 Questions for CEOs: Can Your B2B Sales Team Navigate the Economic Uncertainty Ahead?

10 Questions for CEOs: Can Your B2B Sales Team Navigate the Economic Uncertainty Ahead?

2025 has proven so far that B2B sales is getting tougher.

The companies that will survive have sales infrastructure strong enough to adapt when the ground keeps shifting.

Answer these ten questions honestly. The more questions you answer with "yes," the stronger your foundation for scaling revenue through whatever uncertainty lies ahead.

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Learning the Secret to Sales Success from Ron Swanson

Learning the Secret to Sales Success from Ron Swanson

In this 2-minute video, Nick Offerman talks about how he was able to remain patient and happy while waiting for his big break on Parks and Recreation.

After watching this video I thought about how much of my own happiness I’m withholding until after I’ve “closed this next deal”.

I hope it also inspires you to take some time for yourself this summer and put happiness first.

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Why Your Sales Team Needs Their Own Open Mic: Practice Tips from Comedians

Why Your Sales Team Needs Their Own Open Mic: Practice Tips from Comedians

One thing that's always stuck with me during my time as a stand-up comedian is the way comedians practice. They're out there night after night, sometimes multiple times a night at different open mics, honing their skills, trying out new material, and perfecting their timing. They're constantly improving regardless of who's watching.

So why don't salespeople have an open mic like comedians do?

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Beyond Lip Service: 3 Signs Your Sales Team Is Embracing Change

Beyond Lip Service: 3 Signs Your Sales Team Is Embracing Change

While most change initiatives fail, there's a critical moment when the tide turns. I've spent years guiding companies through this terrain, and there are three unmistakable signals that reveal whether your team is truly embracing change or merely telling you what you want to hear in team meetings.

I'm grateful to my client and friend, Tom Hurst, CRO at ACA Group, for sharing these insights that are worth putting into print and sharing with you.

 

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7 Essential Elements of a Winning B2B Sales Pitch

7 Essential Elements of a Winning B2B Sales Pitch

Recently, I watched a promising enterprise deal slip away when a top performer made a critical mistake: jumping straight into capabilities before establishing value. The most successful sales organizations win at premium prices by following a proven framework that positions value before investment.

Let's explore the seven essential elements that will help your sales team deliver winning pitches and close more deals:

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The Truth About Sales Transformation: How CEOs Survive the Turnover Storm

The Truth About Sales Transformation: How CEOs Survive the Turnover Storm

After 25 years in sales and eight years as a consultant and trainer, I've learned that overhauling a sales culture is not for the faint of heart.

If you're a CEO considering this type of endeavor, you need to understand one thing upfront: this is a commitment that requires nerves of steel, decisive leadership, and most importantly, the courage to face significant team turnover.

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Lessons Learned from Scaling a Distributed Sales Team

Lessons Learned from Scaling a Distributed Sales Team

Are you looking to expand your sales force across the nation? Scaling a distributed sales team comes with unique challenges. At Pitch Lab, we've learned valuable lessons about fast growing sales teams from both our successes and mistakes.

Here are five critical tips to help you grow your remote sales organization effectively:

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