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The secret sauce to your sales success? It’s what happens before the sale. It’s the planning, the strategy, the leadership. And it’s more than demo automation. It’s the thoughtful work that connects people, processes, and performance. If you want strong revenue, high retention, and shorter sales cycles, the pre-work—centered around the human—still makes the dream work. But you already know that.
The Unexpected Lever is your partner in growing revenue by doing what great sales leaders do best. Combining vision with execution. Brought to you by Vivun, this show highlights the people and peers behind the brands who understand what it takes to build and lead high-performing sales teams. You’re not just preparing for the sale—you’re unlocking potential.
Join us as we share stories of sales leaders who make a difference, their challenges, their wins, and the human connections that drive results, one solution at a time.
[00:00:00] Kelly Lewis: Everybody, welcome to V5 or V15, our extended cut, where we spend time getting into some of the hottest topics with the hottest takes in all of B2B SaaS, B2B sales, B2B go-to-market.
[00:00:12] Jarod Greene: It's going to be a fun one because I am joined by a former colleague of mine, somebody I had a lot of respect for, someone that I've worked with. We've been in the trenches together through thick and thin. I'm really excited to talk to her today, and I'm excited for you guys to hear our conversation.
[00:00:27] Jarod Greene: The one and only Kelly Lewis, B2B go-to-market strategy and co-host of the what podcast, Kelly—
[00:00:34] Kelly Lewis: The Revenue Insiders.
[00:00:36] Jarod Greene: Revenue Insiders podcast. Kelly, thank you for joining me today. I really appreciate it.
[00:00:41] Kelly Lewis: Oh my gosh, I am thrilled to be here. Jarod was not lying. We have been through thick and thin. We have been through good times and bad times. I think we can both look back at our career and say we learned what enablement and marketing alignment look like. So this is going to be fun.
[00:00:58] Jarod Greene: You've seen our [00:01:00] V5 episodes—you're on our extended version because you're a friend of the program. So get into it, Kelly.
[00:01:04] Jarod Greene: What is—what's a hot take from you? What—what grinds your gears?
[00:01:08] Kelly Lewis: First hot take: CRO role. I think it's changing. I was VP of Enablement at Highspot. I am now out on my own, talking to startups every day, talking to CEOs, talking to CEOs who are trying to hire CROs, and talking to them about what's working and what's not. And what we're finding quite often is that we're hiring master sales—
[00:01:33] Kelly Lewis: Professionals that can go in and sell anything, and they can build a team, they can inspire a team. But when it comes to scaling that team, when it comes to creating processes that are repeatable, when it comes to adopting AI with their team to make them more efficient, they're really struggling. And we are in a new day and age of the CRO role.
[00:01:57] Kelly Lewis: My prediction is we're gonna [00:02:00] see a lot more CRO educational programs. You're seeing a lot of master's in CRO, which is just crazy and amazing. You're gonna see a lot more communities where there's education for CROs on how to get these other skills. But I don't think organizations can continue to pay a CRO and a VP of Revenue Strategy and a VP of Revenue Operations.
[00:02:23] Kelly Lewis: They're going to really need to figure out how they consolidate a lot of that talent into one individual. And so I just see this prediction of CROs who have been out there for a while, haven't needed that skill set, really grasping and looking for knowledge. And then I think we're going to see some VP of RevOps move into CRO roles—people who haven't carried bags, which is very different than we've ever seen before.
[00:02:48] Jarod Greene: I've heard many interpretations of a CRO. If you had to kind of say, hey, job description of what you see most often: CRO is responsible for... What's the reporting structure?
[00:03:00] What are they held accountable to?
[00:03:01] Jarod Greene: Because it's one of those terms I think we throw out, but there's very loose interpretations of it. So help us—help us figure it out. What's a CRO—
[00:03:07] Jarod Greene: To Kelly?
[00:03:08] Kelly Lewis: Great question. I think there's two ways it should be set up. One is: the CRO is over sales, operations, and enablement, and they are key partners with the Chief Marketing Officer. I personally think that marketing and revenue should be partners versus under the same layer—just my personal thoughts.
[00:03:29] Kelly Lewis: I think in other scenarios, you're going to see a CRO responsible for sales, but then with a really strong partnership with a Head of Revenue Strategy that owns the enablement and operations piece. I think my concern there is: that's a really expensive model. And can organizations, as they're trying to get more efficient—as the market's asking us to get more efficient—afford both of those roles at that really senior level?
[00:03:53] Jarod Greene: So Kelly, given that org structure where revenue strategy and enablement are such a key part of what the CRO does— [00:04:00] where do you think they struggle with enablement?
[00:04:01] Jarod Greene: Because I mean, we saw it at a lot at Highspot—it's like they struggle to understand the strategic value of enablement. And I think on the Rev Strategy side, there's this key piece of analytics. Let's break this down for a minute. Where have they struggled with making enablement a core part of the job?
[00:04:15] Kelly Lewis: Because you and I both agree it is. It's that definition from 10 years ago where enablement was sales training. And training isn't really a thing anymore. You are changing behavior. You are working with sellers to make them better. And yeah, training is a key component of that, but it's actually really small. And I think the reason that CROs and that type of role have struggled with enablement is they're not leveraging it well enough. And I also think that combined network or go-to-market alignment of marketing, ops, enablement, and sales leadership have to be really strong. And if any of those areas are broken down, enablement [00:05:00] definitely gets left out. Because no one's having the conversation of like, how are we actually going to roll this out to the field?
[00:05:06] Jarod Greene: How are we going to make this change and make sure it lasts? That is super tricky. And then talk about the Rev Strategy side. We need operations data. We need data to tell the story. We need data to tell us whether or not the changes landed or whether or not we need to go back to the drawing board.
[00:05:20] Jarod Greene: So where are they falling short with the alignment to Rev Strategy and all the analytics and operations that go with that?
[00:05:26] Kelly Lewis: I think a lot of Ops leaders actually run revenue enablement teams today, and that's the way the hierarchy works. And I think that that works well in a lot of cases. But I do think a lot of Revenue Operations leaders are very focused on how do we make sure we have a process.
[00:05:42] Kelly Lewis: But then again, the idea of actually making that behavior change—and the realistic expectation of how long that is going to take—is often where it breaks down. So, I know I've partnered with so many amazing Heads of Sales Operations, [00:06:00] and it's often a discussion of, great, we're going live with CPQ. We expect it's gonna take people, you know, about a week to learn how to make quotes, and then we should be going pretty well. I'm like, oh, that's—that's really cute.
[00:06:17] Kelly Lewis: But no, like people have to be in a situation, A) where they have to use it. So are they making quotes that week? They're gonna struggle because they're gonna make mistakes, because all people think differently about how they go through a process. And frankly, you have to have realistic expectations, because if you don't, RevOps has moved on to the next project and aren't there to support this longer behavior change that's needed.
[00:06:36] Jarod Greene: What would you say to kind of a Sales VP in the archetype you talked to before? So they are great at just doing the sales thing, being a great sales leader, leading a regional team or segment team, who aspires to be a CRO but wants to avoid the fate you predict, which is like, "Oh, I don’t have the full skill set I need to survive in this new climate."
[00:06:56] Jarod Greene: What advice would you give them today to go fill in [00:07:00] for those skills or start to build the skill set so that doesn’t become a challenge?
[00:07:04] Kelly Lewis: Ask the question, why? It's so simple. I've worked with you, and I think we both do this with each other quite often when we work together—like, why are you making that decision? Why should we do this? So I think if you're at that director, senior director level, looking to go up to that VP of Sales role, looking to go to that CRO role, thinking about, okay, they gave me a new comp plan—not ask the question like, I don't like this number, I don't want to hit this number—but actually like, what math did you use to calculate this and understand the thought process behind it? Or, hey, you just provided us new territories. Why did you provide these new territories? What was the data? What was the math behind it?
[00:07:46] Kelly Lewis: I actually loved being a sales leader. It was wonderful. But you often just get handed things. And you're stuck with it, and you're told to make the best of it. But if you don't ask the why questions, you won't understand how it all works. I think the other thing—there are [00:08:00] great communities out there.
[00:08:01] Kelly Lewis: I just actually joined Pavilion, which is one of them. They have a university for CROs. There are CRO programs. There are sales programs as part of the MBA programs today. And then the other simple thing is, like, get to know your head of Ops and become a partner with them. They are not someone who is sales support.
[00:08:19] Kelly Lewis: They are someone who should be a true partner, and you should consider them a partner. And the more you act in a partnership, the more you're going to learn.
[00:08:29] Jarod Greene: It's fascinating to see what happens when people realize that they want the same goals as you. You find that things that may feel or look adversarial on paper are not at all. Your RevOps person is there to support everybody equally, but wants the same outcome.
[00:08:47] Jarod Greene: Why do you think people don't ask the why as often as they should? Where do you think that stems from?
[00:08:52] Kelly Lewis: I think they've been told no or just not given the reason. As you move up in sales leadership, you get more and more [00:09:00] details, and if early in your career you weren't given those details, you're less likely to ask as you move up the ranks. And so I just think it's almost trained that you don't ask those questions.
[00:09:14] Kelly Lewis: But I do think the great sales leaders—and I've seen so many of them—do.
[00:09:18] Jarod Greene: What do you think the next great crop of CROs are going to come from? So you mentioned, like, some are going to come from RevOps, some are going to come from strategy, some might even come from enablement. Where do you kind of see the mix of it all coming from in the next three to five years?
[00:09:30] Kelly Lewis: I think we're going to see a lot of CROs that have taken a unique path—that have actually taken a stint in an operations or a strategy role and not carried a bag for a little bit. That's kind of my gut reaction. I'm going to also answer another question that you didn't ask, because I think it's really interesting and I do have a hot take on it, which is: where do the next generations of sellers come from? So yeah, you've got people at this middle level that will move to that CRO level, and I think they are getting more curious because of AI. They're [00:10:00] getting more data available to them as a seller, so they're going to be able to move into those leadership roles. But because of AI, we're replacing the need for the quantity.
[00:10:10] Kelly Lewis: I don't think you replace them altogether. I'm not one of those. I think you still need your BDRs and your SDRs.
[00:10:15] Kelly Lewis: But that's typically the entry-level sales role.
[00:10:18] Kelly Lewis: And if we're not hiring as many of them into tech and these other industries, then how do they get their feet wet in sales? How do they learn how to be sellers? What does that career path look like? And I'm actually really nervous about it. Are we hiring sellers that come into non-traditional sales roles and then move into sales?
[00:10:40] Kelly Lewis: University of Washington has a great sales program here, and I was talking to some of them, and they're just seeing people are hiring less interns, less SDRs right out of school. And so they're trying to determine what that path looks like.
[00:10:51] Kelly Lewis: And I think we, as a go-to-market community, need to solve for it pretty quickly. Otherwise, we're going to end up in this world where we don't have enough sellers [00:11:00] with that skill set to go, you know, sell.
[00:11:03] Jarod Greene: I have the BDRs in our org, and it's the same thing. We have benefited because they've come in at entry level or second job, but they've done the role. They have a path to the bag. They say, I'm coming in, and I'm coming in to be a seller.
[00:11:16] Jarod Greene: So it's a great entry-level in, and, you know, there's a lot of value, hopefully a good amount of velocity, and if they stick, they stick and they grow. But you're right. We're also under that same pressure to, again, not eliminate the function, but not hire as many—because, you know, AI is going to do all the outbound, and AI is going to manage all the inbound.
[00:11:32] Jarod Greene: But where do those people come from? I can't point to another part of our organization where I say, hey, where do you take a college graduate or an entry-level worker and say, hey, come join our business with low risk? I don't see a function outside of go-to-market. I think you're spot on. Scary.
[00:11:47] Kelly Lewis: Can I ask you a hot take?
[00:11:48] Kelly Lewis: My question for you, Jarod, is you've got Salesforce hiring all of these SEs—Sales Engineers—into AE roles.
[00:11:56] Jarod Greene: What do you think the success is going to be?
[00:11:59] Kelly Lewis: Basically, [00:12:00] these traditional Sales Engineers—quota carrying, but not to the degree an Account Executive is—moving into now being an AE for AI.
[00:12:10] Jarod Greene: I actually think it works really well in a strange way. One thing I've always appreciated about the SEs—and you know this—is that, like, they blend this technical skill set of, like, I know how the product works (the best ones do), they blend this consultative side of, I'm here to partner with you.
[00:12:25] Jarod Greene: I'm here to help you unlock value. I'm here to understand your pain, and then I'm here to design the solution that maps to it. I think that's what buyers have always wanted from the beginning. And we've kind of done the dance of like, well, here's my AE, and they're going to manage the relationship and the commercials and the paper process.
[00:12:41] Jarod Greene: But I'm the technical guru, and I'm going to help guide you. And we've always wanted that great duo. But I think if you gave a Sales Engineer the bag to pursue, I think they could learn the AE skills faster than the AE could learn the technical SE skills. And I don't think that's a crazy hot take.
[00:12:59] Jarod Greene: [00:13:00] One of my really good friends has done that. He was a great SE that I worked with. He's now very successful at a tech company. And it was from that same ethos of, if I just understand what they need, and I understand the capabilities of what we do and how we do it—and I also have knowledge of how every customer struggled with this challenge from the beginning now to the end—I think I could be dangerous.
[00:13:22] Jarod Greene: Not a sample size of one, but when I look at him, it gives me confidence that that can be done, that it can be scaled, particularly as some of the tech gets a little more intuitive. For what it's worth, I had a conversation earlier this week with someone who reminded me that, like, most of the software is becoming commoditized.
[00:13:40] Jarod Greene: If software eventually starts, you know, writing itself or evolving itself, then it's really less about how good your software is. And it really should solve a business problem for you—otherwise, it doesn’t exist. So the faster you can unlock that, the faster you sell it, the faster it gets sticky, the faster you renew.
[00:13:56] Jarod Greene: So I bet a good amount of money that those [00:14:00] SEs that are going into the sales realm will be more successful than folks going the other way.
[00:14:05] Kelly Lewis: Percent agree.
[00:14:08] Kelly Lewis: Sales Engineers are my favorite people. When I think back to when I was a seller, those are people that I still stay in contact with. I watch their careers. They were people that I trusted more than anyone else in the business.
[00:14:22] Kelly Lewis: So they hold you accountable. I think they're naturally curious—it’s part of that role. And so I think the thing that holds Sales Engineers often back from taking an AE role is just a little bit of that imposter syndrome of, you're up front and center.
[00:14:38] Kelly Lewis: You are the quarterback versus the supporting nature. But if you can get over that, I actually think they're going to be phenomenal. And I’m so excited for it. And maybe that’s where our next generation of sellers come from. Because Sales Engineers typically don't start as Sales Engineers. They typically start in a product or some other role.
[00:14:55] Kelly Lewis: So the career path might just look very different.
[00:14:57] Jarod Greene: Might look different. Yeah, we always ask that question when I [00:15:00] sit—"What was your path? How'd you get here?" And it's usually, "I came from product," or some come from product marketing, some came from engineering. They like to build and do solution design. So they do it, and they find that they just—they like being in front of the customer and a prospect.
[00:15:14] Jarod Greene: They like being in the field. They like mixing it up. They like seeing the instant reaction or the instant gratification of something that was built in the world. Yeah, the product side is just like, they'll deploy a product and then they have to ask 15 people like, "Well, what happened?"
[00:15:27] Jarod Greene: "Did they already use it? Do they like it?" There’s all these systems that tell them that. But the Sales Engineer can see right away, like, "I'm going to show you this capability. I'm going to show you this feature." And if the brow furrows or if the jaw drops—that feels good for them.
[00:15:39] Jarod Greene: So I think a lot of people who are looking for the role might struggle to find it. I'll tell you a funny story—we went to a conference last year, and we did a roundtable on how salespeople can influence the product roadmap. And the bridge was the Sales Engineer, of course, right? But I remember being in a roundtable room of about 20 people—our Sales [00:16:00] Engineer caught it.
[00:16:00] Jarod Greene: He goes, "Jarod, about half of these people aren't in tech. These aren't like traditional tech roles. I think we should start with just baseline—what is a Sales Engineer?" And so I said, brilliant call. And we did that. And they said, "I have no idea what a Sales Engineer is. I have no clue." But when we described it, they remembered—it was a salesperson from a car dealership.
[00:16:23] Jarod Greene: And they said, "So it would be the person who has the most knowledge of the cars and what they do and is really passionate about it, but isn't a salesperson. But is technical—that’s who all the people want to talk to." We said, yes. They go, "That’s Eddie in our business. We didn’t know what to call him. He’s just there, right?"
[00:16:40] Jarod Greene: He’s just—he’s there. He’s ready to rock. He’s ready to roll. But they did not have a title. So it was "Sales Engineer." We said, well, there’s a hundred different names—Solution Consultant, Sales Engineer, Solution Advisor—hundred different names for him. But they do exist. And I think that was one of the epiphanies we had around—
[00:16:57] Jarod Greene: Yeah, well, if you go into industries that aren't tech, [00:17:00] how do you change the language that says, there is a technical overlay. There is an expert. There is someone who can guide the buyer. And it’s not always a sales rep. But they're going to need some—some sales skills.
[00:17:10] Kelly Lewis: Yeah.
[00:17:11] Jarod Greene: Hey, where can people find you? They want to—I mean, I know LinkedIn is a place—but like, people want to say, hey, Kelly’s got a point of view and I want to stay in touch with that.
[00:17:19] Kelly Lewis: Yeah, follow me on LinkedIn, for sure. I do blog posts and I'm pretty active there. Would love a follow on the Revenue Insiders podcast. And then my website is kellylewisllc.com. So, pretty easy.
[00:17:32] Jarod Greene: Awesome. Kelly, thank you for spending a little bit of time with us. Really do appreciate it. The game on how to level up—to borrow an old phrase we're familiar with—as a CRO, I think it's phenomenal. And then the essential question of, hey, where do our next crop of great sellers come from is one I challenge anyone listening to help us solve. And to always start with why—from my friend, Simon Sinek.
[00:17:56] Jarod Greene: So, all right. Thanks, Kelly.
[00:17:58] Jarod Greene: Appreciate your time.
[00:17:59] Jarod Greene: All—