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Insights from sales advisor Elliot Grossbard on building high-performing sales teams in the age of AI
Elliot Grossbard has seen it all. From cutting his teeth during the Windows 95 era to leading modern revenue teams, he’s spent 30+ years navigating the highs and lows of B2B sales. Today, as the founder of GrowthListic, Elliot works directly with startups and SMBs to help them scale smarter, faster, and with fewer painful missteps.
In this conversation with Patrick Monnot, CEO of Pod, Elliot shares what’s top of mind for sales leaders in 2025—from how to adopt AI tools without losing your human edge, to building a culture of coaching and likeability. If you’re a founder or growth leader trying to scale your B2B sales motion this year, Elliot’s advice is gold.
For Elliot, the rise of AI in sales isn’t something to fear—it’s something to figure out. A year ago, he was skeptical. Then he did the homework. He went down YouTube rabbit holes, took Stanford courses, and started experimenting. Now? He’s building apps in his free time and embedding AI tools into how he works with clients.
But here’s the catch: most SMBs are doing it wrong.
The mistake? Over-prioritizing automation at the expense of the buyer experience. AI shouldn’t be a shortcut to spam. It should be a thought partner that gives sellers superpowers—surface deal risks, prep for meetings, reduce admin drag. Think: a thousand Donnas from Suits or a personal Jarvis from Iron Man, doing the research, organizing data, teeing up what matters—so reps can spend more time building actual relationships.
It’s not about replacing salespeople. It’s about helping the good ones be great.
There’s a growing obsession with automating every part of the sales process, but Elliot sees diminishing returns when you let tools talk to prospects for you.
He recalls getting a cold email addressed to “Brendan” from a founder at an AI outreach startup. Wrong name, no context, followed by a generic follow-up. “If your entire value prop is cold outreach,” Elliot says, “you better at least get the name right.”
This is where most AI-enabled sales tools fall short—they remove the very nuance that makes people want to buy. That’s why Elliot believes the real power of AI isn’t in writing emails or taking actions for you. It’s in surfacing insights that help sellers make better decisions. What’s the real decision-maker title in similar accounts? Which deals should I prioritize today? How does this buyer typically engage?
That’s what Elliot calls undervalued AI: contextual intelligence that helps humans win, not lazy automation that turns off buyers.
When it comes to scaling a sales team, AI tools and training programs are table stakes. But the difference between good and great teams? Culture.
Elliot talks about the shift from sales as an individual sport to a team game. When reps coach each other, share feedback, and celebrate wins together, they don’t just close more—they enjoy the ride. He’s implemented peer-to-peer coaching incentives, ride-alongs, and even startup-style pitch rooms where reps riff and refine together. “When the team buys in,” he says, “the whole engine moves faster.”
Of course, that culture starts at the top. Leaders can’t just push metrics—they have to model curiosity, coach in real time, and give their teams the space to try, fail, and grow. Elliot’s view? Sales enablement isn’t a static onboarding doc. It’s a living, breathing system of support that blends process with empathy.
Elliot’s take on hiring is refreshingly simple: you can train on methodology, but you can’t teach someone how to be likable.
He shares a great litmus test: “If your flight gets delayed, and you’re stuck next to this person for two hours—no phone, no WiFi—would you enjoy the conversation?” If yes, that’s someone worth betting on. Because in B2B sales, especially in SMBs, trust still trumps tactics.
And once you’ve hired the right people? Onboarding them isn’t about drowning them in product decks. It’s about giving them a core foundation and adapting the delivery to who they are. “You’re not managing robots,” Elliot says. “You’re managing people.”
That’s where personalization matters—not just in outbound emails, but in how you train, coach, and support your team.
What ties all of Elliot’s advice together is this: great sales teams are built by people who are curious, coachable, and committed to connecting. AI can accelerate those things. But it can’t replace them.
Want to close more deals in 2025? Build a culture where people want to help each other. Use AI to make your reps smarter, not lazier. And above all, hire people your prospects will actually enjoy talking to.
As Elliot puts it: “Sales is easy if you listen, you learn, and you’re open to using tools that help you sell better. Don’t complicate it.”
Thanks to Elliot Grossbard for the candid insights. To learn more about his work, check out GrowthListic and connect with him on LinkedIn. And if you’re building a modern B2B sales team, learn how Pod helps reps and managers turn insight into action at www.workwithpod.com.
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