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In this episode, Patrick sits down with sales legend Scott Leese to trace the unconventional journey that brought him to the top of the startup sales world. Scott’s path is anything but typical—far from the kid running lemonade stands or flipping sneakers, he spent four years in and out of hospitals battling life-threatening health issues before he ever picked up a phone to cold call. That adversity gave Scott a unique sense of perspective—and a relentless drive—that became the foundation for a career built on resilience, leadership, and a passion for helping others succeed.
Over the course of their conversation, Scott breaks down the mental frameworks that have guided his success, the systemic issues plaguing sales leadership today, and what founders actually need to do to scale effective go-to-market teams. He also offers a candid take on how AI is changing the future of sales—and why human authenticity is more valuable than ever.
Scott Leese didn’t set out to be in sales. In fact, before 27, he’d never had a real job. After nearly half a decade battling chronic illness, major surgeries, and opioid addiction, he emerged determined to make up for lost time. Sales, as he saw it, was the only career path where results could outpace experience—and startups were the only places moving fast enough to match his urgency.
That unique origin story gave Scott something most sales reps don’t have: unshakable perspective. “Do you think I care about somebody hanging up on me after what I’ve been through?” he says. “I’ve already faced the hardest thing in my life.” That mindset allowed him to push through rejection and failure in ways others couldn’t—and it made him hungry to grow, fast.
But that hunger eventually shifted. Six months into his AE role, the personal wins felt hollow. “It was kind of a selfish quest,” he admits. So he started coaching colleagues. Watching them succeed lit a new fire. From there, Scott began to climb into sales leadership roles—not for the title or the check, but because helping others win felt more meaningful than chasing another closed deal.
Scott’s take on sales leadership is direct: if you care more about closing your own deal than seeing your teammate win, you’re not ready to lead. And the problem? Too many people get promoted without asking that question.
This, Scott says, is the root of one of the biggest issues in sales today: managers who can sell but can’t coach. “The number one complaint reps have is they don’t get enough training or support from their managers,” he says. And that’s not because managers don’t know the numbers—it’s because many don’t actually care about developing their team.
Scott believes great leaders share one thing in common: they’re teachers at heart. Whether it’s early morning trainings or late-night one-on-ones, they create a culture of development that reps can opt into—not because it’s required, but because they want to get better. At one company, Scott ran three daily training sessions (all optional) to ensure every rep, regardless of schedule or experience level, had a way to keep learning. That kind of culture, he says, is rare—but when it exists, it’s powerful.
One of Scott’s sharpest critiques is reserved for startup founders who expect junior reps to figure out sales messaging. “You can’t hire kids and expect them to optimize your go-to-market motion,” he says. “That’s your job.”
In Scott’s view, early-stage growth stalls when messaging is unclear—or worse, inconsistent. Without a clear articulation of the problem you solve, why it matters, and why it needs to be solved now, no volume of cold calls or email spam will save you. “You combine bad messaging with medieval tactics, and you’re dead in the water.”
Scaling, then, is a matter of unlocking key inflection points. First, founders have to nail the messaging. Then, they need to teach it—repetitively and consistently—to every rep. Only then does process matter. Miss any one of those stages, and you hit a ceiling. “You can’t get to your first million without messaging. You won’t hit five million if you can’t teach it. You won’t get to ten without a system.”
Over decades of selling, Scott developed a simple framework rooted in both human psychology and his own recovery journey: find pain, build value, create urgency, then present the solution. Whether you’re pitching a prospect or helping someone into rehab, Scott believes the psychology is the same—no one changes unless they feel the consequences of inaction.
It’s not just a presale framework either. For every new stakeholder who enters the deal, Scott believes in re-running the whole process. CFOs, for example, care about ROI. End users care about ease of use. “If I pitch everyone the same way,” he says, “I lose.”
And above all, you have to shut up and listen. Scott aims for a 40/60 talk-to-listen ratio in every sales call. “Most reps are talking 82% of the time,” he says. “And then they wonder why no one buys.”
Scott is bullish on real-time AI coaching. He’s bearish on AI-driven sales content. Why? Because he’s seen how easily humans exploit new tools into the ground. We did it with dialers. We did it with email. And we’re about to do it with AI-generated messaging. The result? A tidal wave of mediocre outreach, and no one able to tell what’s real anymore.
So what survives? According to Scott, it’s two things: trusted networks and deeply human experiences. Whether that’s referrals or in-person gatherings, the future belongs to those who prioritize authenticity over automation. That’s the philosophy behind Surf & Sales, Scott’s anti-conference for sales pros, where 50-person meetups in Costa Rica replace giant, impersonal events like Dreamforce.
As AI continues to reshape sales, Scott’s advice is simple: lean into what makes you irreplaceably human—empathy, trust, and lived experience. Because while AI might help you scale faster, it won’t build relationships for you.
Want more from Scott? Follow him on LinkedIn, where he shares daily insights and answers every DM. And if you’re looking for a one-of-a-kind sales experience, check out Surf and Sales—because not every playbook has to be written in a boardroom.
