"Most sales teams don’t need more tech or training—they need coaching. Because when reps show up curious, authentic, and prepared, they become trusted partners—not pitch machines. It’s not just about knowing your product—it’s about knowing your buyer, earning their trust, and helping them feel safe saying yes." - Lee Levitt In this episode of Revenue Boost: A Marketing Podcast, The Real Pipeline Fix: How Coaching, Curiosity, and Authenticity Close More Deals, I sit down with Lee Levitt, veteran sales coach, former Oracle and Google sales enablement leader, and founder of Acelera Group. We explore why most sales organizations don’t have a tech or training problem—they have a coaching problem. Lee shares the sales effectiveness habits that separate top performers from the rest: Why training alone doesn’t work—and what coaching really looks like How to develop curiosity and authenticity as sales superpowers What deliberate practice means (and why most teams skip it) How sales leaders can drive better prep, follow-through, and customer trust Why sales enablement needs a seat at the strategic planning table Whether you're a CRO, VP of Sales, or sales enablement leader, this episode will help you refocus your team on what actually drives pipeline momentum: authentic preparation, emotional intelligence, and trusted conversations—not just activity volume.
The Real Pipeline Fix: How Coaching, Curiosity, and Authenticity Close More Deals
Most sales teams don’t need more tech or training. They need coaching. Because when reps show up curious, authentic, and prepared, they become trusted partners—not pitch machines. That’s a quote from Lee Levitt and a sneak peek at today’s episode. Hi there, I’m Kerry Curran, B2B Revenue Growth Executive Advisor, industry analyst, and host of Revenue Boost: A Marketing Podcast.
Every episode I sit down with top experts to bring you actionable strategies that drive real results. If you’re serious about business growth, hit subscribe and stay ahead of your competition today.
In The Real Pipeline Fix: How Coaching, Curiosity, and Authenticity Close More Deals, I sit down with Lee Levitt. He’s a sales effectiveness coach and founder of the Accelerate Group. We uncover why most teams miss quota and what leaders can do to fix it. From deliberate practice to buyer psychology, Lee shares how small behavior shifts lead to bigger sales wins.
Be sure to stay tuned to the end, where Lee shares how sales enablement leaders can earn a strategic voice—and why it’s your unfair advantage for long-term growth. Let’s go.
Kerry Curran, RBMA (00:01.249)
So welcome, Lee. Please introduce yourself and share your background and expertise.
Lee Levitt (00:06.53)
Thanks, Kerry. I appreciate you having me on. I run my own podcast, so it’s a little different being the guest instead of the host. Usually, I ask the question “Who is Kerry?” and today you’re asking “Who is Lee?”
I’m a coach at heart. I’m here to help people transform—personally and professionally. My view is that I help salespeople help their customers succeed. For example, if I’m coaching a rep calling on Cincinnati Children’s Hospital, I’m thinking about how they can improve patient outcomes.
I’ve been in the tech world for a long time. I’ve run marketing and sales, been an analyst, and led sales enablement at Oracle and Google. I’ve started companies, closed companies, and after leaving Google a couple of years ago, I returned to my roots in sales productivity and coaching. Today, I work with organizations that want to improve sales effectiveness, and I also coach individuals who want to have more fun selling.
Kerry Curran, RBMA (01:18.805)
I love that. And one of the key differentiations you make is that you’re not a sales trainer—you’re a coach. Talk about the difference.
Lee Levitt (01:31.47)
Here’s my secret: I’m not really a sales coach. I’m a life coach for salespeople. Most reps come in with head trash—an inner critic telling them “I’m not good enough” or “I have to act a certain way.” When they’re not authentic, their results suffer.
Training is the transfer of information: “Here’s version 3.2 of our widget—go tell customers about it.” Coaching is different. Coaching helps people discover new ways of being and doing.
A big part of that is deliberate practice. Some people call it role play; I call it deliberate practice. Salespeople don’t get enough time to practice in a safe space, so they end up practicing in front of customers. That’s the worst time to practice. I even joined an improv group myself—it’s great practice for listening, being present, and responding authentically in the moment.
Kerry Curran, RBMA (03:00.437)
I can see those skills translating well. And you’re right—salespeople are bombarded with new tech and scripts, but if they’re just told to “go implement this,” they won’t see long-term value. Leaders need to shadow reps and often find they aren’t using the technology in a way that drives ROI. How are you helping managers and teams address this?
Lee Levitt (04:24.45)
Here’s a story. About 10 years ago, I was in strategic sales for a marketing analytics company. I had four major accounts—IBM, GE, and others. When I joined, the CEO handed me a 100-slide deck and said, “Learn this and deliver it.”
I told him, “My customers are smart. I sell using a whiteboard. I start empty, sketch out their issues, and co-create the ‘as-is’ and ‘to-be’ states.” He said, “That’s nice, but use the deck.”
The point is: sometimes leadership isn’t aligned with what works in the field. But sometimes salespeople miss the mark too, like when a team ignores updated messaging. It has to be a partnership—leadership providing useful tools, and reps using them effectively. You can’t blame one side; both must adjust.
Kerry Curran, RBMA (06:10.197)
Agreed. Without that coaching partnership, you don’t uncover the real issues. So what skills do you see leaders lacking most?
Lee Levitt (06:50.616)
Leaders run the gamut. Some have high EQ and coach effectively; others are drill sergeants barking “make more calls.” It depends on the organization’s goals. Companies focused only on short-term revenue often tolerate bad leadership behaviors. But organizations focused on adding value for customers tend to develop better leaders—and see better long-term results.
Kerry Curran, RBMA (07:48.331)
And what about sales reps? What are they missing?
Lee Levitt (07:58.168)
Most reps lack coaching. Their managers inspect pipelines and deals but don’t develop skills. Many frontline managers were lone wolves promoted into management. They know how to sell but not how to coach.
What I look for in reps are two attributes:
It’s like networking. If you show up just to get leads, you’ll be standing alone. If you show up to help others, people flock to you. Enterprise selling works the same way.
Kerry Curran, RBMA (10:04.897)
Absolutely. So how do you coach sellers on those attributes?
Lee Levitt (10:34.538)
Through deliberate practice and diagnostics. For example, I coach a young SDR who was booking meetings but having no-shows. We discovered he wasn’t engaging prospects with clear value. We practiced how to frame the meeting so prospects actually wanted to attend.
Another client was calling on two longtime insurance execs. I had her ask, “Why have you stayed at this company so long?” That one question built trust and got her a meeting with the head of strategy.
Coaching is about pattern recognition and facilitating discovery. It’s not about giving information—it’s helping reps uncover better ways of selling authentically.
Kerry Curran, RBMA (13:34.241)
That’s powerful. And another area you mentioned is lack of preparation. How should reps improve here?
Lee Levitt (14:11.81)
Sales leaders push call volume, but without preparation, calls don’t convert. Think of painting a room—90% of the work is prep. Selling is the same.
For SDRs, even five minutes of prep per call can make a difference. For enterprise reps, it could be hours. I walk through prep with them—using LinkedIn, researching tenure, identifying patterns. At first, I guide them. By the fourth time, they’re doing it themselves.
AI helps with research but it’s just a tool. If reps rely solely on AI outputs without internalizing them, they can’t lead authentic conversations. Use AI for inputs, but think through what it means for your conversation with the buyer.
Kerry Curran, RBMA (17:17.579)
Exactly. Another challenge you see is buyer paralysis. How can reps address that?
Lee Levitt (17:54.86)
Buyers often prefer the devil they know. Change feels risky. Sellers who push a migration or upgrade are asking them to move from a known to an unknown unknown, which spikes perceived risk.
The key is to lower that risk perception. That means keeping promises—big and small—showing up prepared, being consistent. It also means helping buyers reprioritize. Don’t pitch product features. Show them how retention improves 8% or productivity improves 5%. Connect your solution to meaningful business outcomes. That reframes the risk.
Kerry Curran, RBMA (21:43.607)
That’s smart. So for sales leaders listening today who know their sellers need help, where should they start?
Lee Levitt (22:09.528)
Start with sales enablement. If you have 10+ sellers, you should have a sales enablement function. Empower them with a strategic advisory board—leaders from sales, marketing, HR, finance, operations. Meet monthly, align priorities, and identify areas for improvement.
At Google, I saw how lack of enablement planning nearly derailed a major integration. With enablement at the table earlier, we could have avoided massive attrition. Sales enablement looks beyond this quarter. They plan skills and systems for long-term growth.
Once you’ve done the internal diagnosis, bring in external experts for targeted help—SDR onboarding, account planning, or coaching.
Kerry Curran, RBMA (24:42.976)
Great advice. For people ready to bring in an expert, how can they reach you?
Lee Levitt (24:56.494)
Visit aceleragroup.com—that’s A-C-E-L-E-R-A group.com. You can also find me on LinkedIn (Lee Levitt, L-E-V-I-T-T) or on my blog and podcast at thoughtsonselling.com.
Kerry Curran, RBMA (25:16.567)
Perfect. Thank you, Lee—I’ll include all that in the show notes. I appreciate your time and wisdom today.
Lee Levitt (25:24.536)
Thanks, Kerry. This has been fun.
Thanks for tuning in to Revenue Boost: A Marketing Podcast. If this episode with Lee Levitt gave you something to think about, share it with your sales or enablement lead today—because the fastest way to fix pipeline issues is better prep, more coaching, and real curiosity.
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