Building Scalable Sales Systems: David Weiss on Root Cause Analysis and Effective Coaching

Overview

In this episode of The Gap, we chat with David Weiss, Chief Revenue Officer at The Sales Collective. David brings street-smart insights from his sales leadership roles at Outreach and Seismic, plus hands-on experience helping over 300 B2B startups last year alone.

What makes this conversation refreshing is David's honesty about his early career stumbles:

"I'm the person who's messed up everything. I totally bombed my first few sales jobs. I didn't even know if I was going to stay in sales."

This raw authenticity sets up a practical conversation about what actually works in sales leadership and why most training falls flat.

Key Takeaways

From Flunking to Flying: How David's Failures Shaped His Approach

David's philosophy comes straight from his personal journey. After crashing and burning in his first two sales roles, he made a critical decision at job number three.

"I will do whatever they tell me to do. They trained me. I will do it."

The result? He shot to the top 5% among 300 sellers in just one year. His leadership path followed the same pattern. Initial faceplants taught him what not to do.

"I failed at every aspect of leadership. I tried to create mini-mes. I focused on command and control. It wasn't until I embraced leadership as its own science that I actually became somewhat good at it."

Forget Silver Bullets, Build Complete Systems

David pulls no punches when talking about quick fixes:

"I don't believe in silver bullets. There's no one piece of tech or process or hiring that's a silver bullet."

Instead, he champions building three interconnected systems:

1. Hiring the right people
2. Creating effective processes
3. Implementing proper training

"I geek out about building all of that stuff. Independent systems that combine into a master system."

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Find the Real Problem: The Root Cause Revolution

David's team has assessed 2.4 million salespeople with 92% accuracy in predicting top performers. This data reveals how often companies misdiagnose their own problems:

"We have a hiring problem. No, you've got a culture and compensation, and onboarding problem. Oh, we have a closing problem. No, you don't have a closing problem. You have a discovery problem. You have a business case problem."

This explains why 72% of sales training initiatives crash and burn. They're solving the wrong problems.

Will Beats Skill: The Hidden Success Factor

David breaks success into three buckets, with an unexpected emphasis:

• Will: Your desire, commitment, outlook, responsibility, and motivation
• Beliefs: What you think about money, rejection, approval
• Skills: Your tactical sales abilities

Most training programs obsess over skills while ignoring will. David flips this on its head:

"If you lack will, you do not have the ability to take advantage of your skill. It's just like a race car with no gas."

He brings this to life with a relatable example:

"I have a ton of desire to lose weight. I don't go to the gym. Low commitment. It's that concept."

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Surgical Coaching: Individual Development Plans

David avoids vague improvement talk. He prefers laser-focused coaching:

"We build what we call IDPs - Individual Development Plans. That's literally someone's name, the behavior we want changed, and four to five actions they'll take in the next 30 days."

The secret sauce? Weekly follow-up:

"Every week, look for those behaviors, have them demonstrate them to you, role play, record calls, watch calls, join them in the field."

This transforms fuzzy coaching into measurable growth.

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AI Makes Great Coaching Scalable

David advises AI companies like Replayz (led by CEO Dave Kennett) that are changing how coaching works:

"They've analyzed hundreds of thousands of calls and created a framework for what good calls look like. Then they're doing spider graphs that show 'you did these things well, missed these things, and might want to consider these things' - all in seconds."

This tackles the classic leadership excuse: "I don't have time to coach everyone."

Real Enablement: Beyond Content Libraries

David doesn't mince words when critiquing typical enablement:

"They are managing content on a platform, doing flavor-of-the-month spot training."

He pushes for enablement that truly supports frontline leaders:

"Enablement can't replace the frontline sales leader. They can teach them to be better coaches and give them visibility into areas needing attention. But ultimately, it's still the job of the frontline sales leader to coach their damn people."

Frequently Asked Questions About Sales Systems and Coaching

What makes up an effective sales system?

According to David, you need three essential pieces working together: hiring systems to get the right people, process systems to guide their work, and training systems to build their skills. When these three gears mesh properly, you accelerate what David calls "speed to revenue."

How is competency-based training different from regular sales training?

Traditional training takes a one-size-fits-all approach. Competency-based training first assesses each person across 25 core areas, then creates a personal learning path based on their specific gaps. This targeted approach explains why 72% of old-school training programs fail. They're simply not aligned with what each person actually needs.

Why does David emphasize "will" so much in sales performance?

Will is your internal engine. It includes your desire, commitment, outlook, responsibility, and motivation. David explains it simply: without will, skills are useless. "It's like a race car with no gas." Even highly skilled salespeople will sputter out without internal drive. The Sales Collective can now identify will-based gaps and provides targeted help created by PhD psychologists.

How exactly can AI improve sales coaching?

AI tools analyze calls, emails, and interactions in real-time to provide instant feedback. Companies like Replayz use AI to check calls against proven frameworks, creating visual maps of performance and suggesting specific improvements. This technology makes coaching scalable by handling the heavy lifting of analysis, freeing leaders to focus on the human side of coaching.

What makes Individual Development Plans (IDPs) effective?

An IDP focuses on one specific behavior at a time, lists 4-5 concrete actions to take over 30 days, and includes regular check-ins. Rather than vague "get better" advice, IDPs create a clear path with measurable progress. Sales leaders use these plans to structure weekly coaching, observe specific behaviors during calls, and track improvement over time.

Why do companies miss their actual sales problems?

Most organizations jump to conclusions without proper diagnosis. What looks like a "closing problem" is usually a discovery issue, weak business case, or poor executive communication earlier in the sales process. The Sales Collective uses their assessment method (tested with 2.4 million salespeople) to find the true issues before implementing fixes.

How should sales enablement work with frontline managers?

Sales enablers should support frontline leaders, not replace them. Good enablement gives leaders the tools, reports, and processes to coach effectively while helping them spot areas needing attention. As David plainly puts it, "It's still the job of the frontline sales leader to coach their people"—enablement is there to make that job easier and more effective.