Navigating Sales Leadership with Scott Leese: From Surfing to Strategic Enablement

Overview

This episode of The Gap features Scott Leese, a sales leader with an extraordinary story. Scott spent four years in hospitals, survived nine surgeries, and overcame opioid addiction before launching his sales career at 27. Today, he's one of the most respected voices in sales leadership. Our conversation explores what real enablement looks like, how sales is evolving, and finding the sweet spot between tech tools and human connection.

Takeaways

• Redefining Enablement: Tools aren't enough. Scott believes true enablement needs a personal touch. "The biggest problem is you load people up with a bunch of tools and think, 'Oh, they should be able to succeed. I don't have to spend time with them,'" Scott explains. Enablement must include developing talent and creating a coaching culture.

• The Role of Sales Leadership: Want successful reps? Slow down to speed up. Scott's 30-day onboarding covers four critical areas: industry knowledge, product mastery, process understanding, and effective messaging. "If you don't ace these things, you don't advance past go, you don't collect $200," he insists. Skip this foundation, and reps aren't ready for customer conversations.

• Tech as an Ironman Suit: Tech tools are like an "Ironman suit" for sales teams. They enhance capabilities but can't replace human judgment. "Right now, the marriage of the two things is the season that we're in where people are getting the most advantage and winning the most," Scott shares. This balance between automation and personal touch separates top performers from those struggling to adapt.

• Future of AI in Sales: AI is coming for sales jobs, but not immediately. Scott predicts that within 6-7 years, AI will be 256 times more powerful than now. "You think an SDR role is still gonna be necessary? If you're not looking ahead and planning for that moment, you're an ostrich with your head in the sand."
• Innovative Approach to Sales Education: Traditional conferences with 50,000 attendees aren't Scott's style. His Surf & Sales Summit combines morning learning with afternoon surfing in Costa Rica. "What sounds more interesting is going somewhere cool where you can get half a day of content, and then do something fun like take surf lessons or go zip-lining." Attendees leave with 19 real connections instead of 100 useless badge scans.
• Evolution of Sales Processes: Rigid sales processes are dying. Scott recently advised a client to share pricing upfront when asked. "Buyers have more access to information than they've ever had before. They have more alternatives to you than they've ever had before. You're not paying attention to how buyers want to buy? You're going to lose right now."

The Sales Leader's Journey

Scott's battle with illness shaped his leadership style. Starting his career late taught him to value efficiency and remove obstacles. "My job is to help you get where you want to go, period. If I do that, I've done my job." This philosophy guides how he supports his teams. He'll even fetch coffee to save reps 15 minutes if that helps them succeed.

The Swiss Army Knife Definition of Enablement

Asked about his ideal enablement function, Scott offers a simple definition: "The simplest definition I've come up with would be a Swiss army knife to eliminate inhibitors and blockers amongst all the people on my team." This means addressing everything that stands between reps and success. From onboarding issues to tool adoption to business acumen, sales enablement should clear the path.

Frequently Asked Questions

What is the biggest gap in sales enablement today?‍

It's the belief that sales enablement tools can replace coaching. Many leaders invest in technology but skip the personal development work. Real enablement needs both.

What's a good 30-day onboarding framework for sales?‍

He focuses on four areas: learning the industry, mastering the product, understanding the sales process, and developing effective messaging. Reps can't skip to customer conversations until they nail these basics.

What is the future of AI in sales?‍

He believes AI will replace many sales roles within 6-7 years as it becomes better at understanding emotions and context. The SDR role will likely disappear first.

How should sales leaders adapt to changing buyer behaviors?

Stop forcing buyers through rigid processes. Be transparent with pricing when asked. Recognize that sales cycles aren't linear anymore. Adapt to how buyers want to buy instead of how you want to sell.

What skills will salespeople need as AI advances?

Business acumen will become more valuable. As AI handles routine interactions, the ability to have meaningful business conversations and provide strategic guidance will separate successful salespeople from the rest.

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