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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.
Clay Killgore (00:00):
What I love about our offering with our AI sales agent is really, it feels like I have a shared brain in the form of that copilot that's sitting in on every engagement. It's helping me stay sharper, more up to speed, and allowing us just to do more quality work altogether in a more efficient manner.
Show ID (00:17):
You're listening to The Unexpected Lever, your partner in growing revenue by doing what you already do best, combining your technical skills with your strategic insights. This episode was taken from a LinkedIn Live series about sales engineering with our CEO Matt Darrow. We hope you enjoy.
Matt Darrow (00:35):
Hey everybody, thanks for joining us again today. I'm Matt Darrow, co-founder, CEO of Vivun. I'm here today with two awesome guests. We've got Clay Killgore, Mike Capitolo. Clay's got a baby. Mike's going to save you in the wood, but how about your professional background? And Mike, let's start with you. Tell the audience a little bit about yourself.
Mike Capitolo (00:52):
Yeah, happy to, and thanks for having me, Matt. Mike Capitolo. I'm a strategic AE here with the team at Vivun. Been with the company for about four years now, and my background is in selling. I started as an SDR, became an AE, worked at a company, focused on B2B subscription commerce, and have been with Vivun like I mentioned for about four years now and seen quite a bit. So...
Matt Darrow (01:13):
How about you, Clay?
Clay Killgore (01:15):
Yeah, Clay Killgore, sales engineer. Been with the company for a little over four years as well. Actually got started in my career with customer support, figured out very fastly that I want to be on the other side of the funnel. And so got into sales engineering at SAP, joined Vivun and have just loved every minute of it since.
Matt Darrow (01:33):
Well, you guys have the perfect background for today's discussion because it's all about talking how sales team members can get real lift from AI, and it's great to have both points of view from the sales engineering side and the account executive side, especially two guys that have sort of grown up the ranks as you might expect. So Mike, coming from an SDR to sales rep to name sales rep and strategic, and then Clay getting into the SE role, like a lot of people do a little bit by happenstance. You come in with professional services or support and you're like, I don't want to do that anymore. And then you find your way into a really, really great role. So if you're in sales and you're trying to keep up with AI's increasing impact on your role, you are in the right place. So let's dive right in. What AI tools do you guys currently use and what value do they bring to the table? And Clay, I'll throw this one over to you. I know that you've experimented with nearly everything under the sun out there.
Clay Killgore (02:25):
Yeah, literally any LLM, any model you can think of, when this hit the scene, it just felt like these things were made for me, myself being super curious, asking a ton of questions. The way I've been using these is simply just to learn enablement and just learning complex topics in ways that fit my learning style. Ever since these things have come out, I honestly have never felt smarter and I'm just loving the way that I have this at my side at any time. And my wife really loves it when I'm able to pull it up and prove it wrong in a conversation too.
Matt Darrow (02:59):
Well, and then how about for you, Mike? What excites you the most about AI as a seller? What's the promise that you see for your role?
Mike Capitolo (03:05):
Yeah, there's a bunch of applicability in my day-to-day life outside of being a seller. But when it comes to doing my job, the thing that excites me the most, Matt, is really the body of work that I think about, I put into a super strategic deal, a multimillion dollar endeavor, and being able to do the level of quality and level of depth in the work that I do in that type of opportunity, but for all of them. So being able to scale that depth, that level of expertise for what's historically been reserved for a subset of deals in the pipeline, and being able to replicate that across the entire pipeline.
Matt Darrow (03:40):
I can imagine that too. I mean, it's hard to close big deals, and when you're juggling multiple at any given time, it's hard to give the same level of depth and effort to them all. I totally hear you, Mike. You get more lift there and then great. When you go deep on those deals, good things happen. Clay, how about you as a sales engineer? What's the most valuable thing AI unlocks for you?
Clay Killgore (03:58):
Yeah, I'd say the role typically as an SE, it's very reactive. You get brought in last second, you're supposed to catch up and turn around an amazing presentation. And with AI, we're able to take all of that context, understand what's happened, who's involved, what has Mike done before he's actually engaged me. And so that's allowed us to skip a lot of those prep syncs, all those internal meetings and just allow me to get up to speed quicker, get on there and actually sell with Mike, where I feel like, more than just being the demo, the presentation technical expert, I'm able to strategize a whole lot more due to these tools being able to really extract in all the context for me.
Matt Darrow (04:36):
Yeah, there's a freedom of you're shedding all this work away that it's really important. But again, we always have this conversation around, well, what's the role of humans in AI moving forward? You guys want to do the work that you love to do, which is what you're describing, and you're like, well, let AI handle all of the rest so you can replicate it at scale and get all that crap off your back so you can do what you guys are phenomenal at, which is the sales side and the sales cycle. So you're talking about a lot of these promises of AI, but all these different surveys are in the market basically seeing that people aren't seeing the benefits yet. Conga, they did this interesting report that said 25% of teens are actively using AI in their GTN process, but that's it. And then even from our own surveys, almost 90% of sellers and SEs who responded to us said they haven't yet experienced a real significant lift using a lot of the tools in the general LLMs that you were talking about at the beginning of the conversation too, Clay. So Mike, I'll throw it over to you. Why can maybe agentic AI start to help change that?
Mike Capitolo (05:34):
I think about all the tools I use, right, Matt, and of course they're for me and I use them to do my job, but ultimately I'm not the person that buys them. And inherently, when people are building solutions, you're building value for your buyer, and the buyer is typically my manager or a leader. So inherently all those tools are really going to be designed for the value that a VP of sales would get or any other type of director within the go-to market. So I think the thing that excites me most about this shift from historical kind of point SaaS solutions to agentic AI is that for the first time ever, it feels like something's actually built for me as the individual user and knowing that the team that is developing and engineering is really focused on, hey, what can Mike the AE actually use? And how is this going to make his life better? That feels like a huge breath of fresh air compared to the history of all the applications that teams have bought, all the things that have been put in front of me and I've been told to use, which have really kind of more felt like they've been designed for a leader versus the individual.
Matt Darrow (06:33):
Yeah, everybody 25 years ago, let's put in Salesforce to make your life better, Mike. You're like, well, that's not what this does. And even some of the more modern SaaS applications, like a Gong or whatever, a lot of that is analytics for the management layer versus productivity for what you guys need done. Clay, what's your take on that? Especially as someone who's supported a bunch of different types of sellers for years?
Clay Killgore (06:55):
Yeah, no, I completely agree with what Mike said, and recently I was listening to a podcast, and I think they said it perfectly, is that in the beginning before CRM, it really was built to help work for you, give you a source of record, help with reporting. But currently now it really feels like we are working for the CRM, everything's about recall, things never make it in there. I know Mike is having to spend so much time in the past just going in, updating fields, and it slows us down because a lot of times I don't have the most up-to-date information. We have a lot of internal meetings, a lot of prep calls when we could be doing this a whole lot faster.
Clay Killgore (07:33):
And so the shift that I'm seeing now is that because we have the technology available, it's really freeing up Mike and myself from that vicious cycle of at the end of a deal, constantly having to go back, put all the pieces of the puzzle together, and these things don't just record what happened, but they actually participate with us and do the work on our behalf. And so it's allowing me to be more proactive, take on more work, as well as just be more strategic with Mike. And what I love about our offering with our AI sales agent is really, it feels like I have a shared brain in the form of that copilot that's sitting in on every engagement. It's helping me stay sharper, more up to speed, and allowing us just to do more quality work altogether in a more efficient manner.
Matt Darrow (08:18):
Yeah, I like your phrase, Clay, if I steal that too, just like it does the work for you and you're no longer working for the CRM. And people are trying to get here in different ways. That's why the Conga study and our own data, people are trying to experiment and they're kind of falling flat or they're saying, well, I'm not getting the lift that I thought. And from what I see is there's a lot of Frankenstein applications out there, people like patching different tools together, bolting things onto existing systems, tying things together that probably shouldn't be tied together. Clay, you, as you mentioned, not only a great team member here at Vivun, but on the side too, you've experimented and you've gone really deep and hands on with nearly everything under the sun on the LLM and the AI side, and you've built a bunch of custom applications, prompt libraries. You've duct taped stuff together to experiment. So what's different now, because you're alluding to an AI sales agent is sort of different than that approach?
Clay Killgore (09:09):
I mean, I'd say you nailed it. The main thing right off the top is I'm saving my computer a lot of hard drive space from not having this massive library of prompts that I'm having to save out there. And even though prompting some of the stuff that you can get back from doing really advanced prompts is amazing, but the way that we're seeing these things shift is we know that not everyone is going to be as curious like myself and go to that level to understand and build these crazy huge system prompts. And what if we could take the technology and just basically have it proactively do that work without me even having to type those things out? And so that's where we say, if you're having to prompt, then we're losing. And that's really kind of the main focus of why we built Ava. It's designed so that you don't have to be a prompt engineer. You don't have to be an AI expert. It simply just works, fits into your workflow, and it allows you just to get all of those insights front and center without you even know how to interact with AI at all. So it's been pretty amazing seeing everything that Mike and I used to work together on now just being created by pulling in all of that context from all the tools that we already use. So it's nice. No more prompting.
Matt Darrow (10:17):
Well, even I think these Frankenstein LLM-based applications too, even like 10, 15 years ago when cloud was the new thing on the block. I mean, maybe this is even 20 years ago now. And I think people custom built a lot of stuff because they were really, really excited. They're like, oh, great. It's super easy to spin up a database in a GUI and I could put workflows together. And then all of a sudden people stop doing that because to your point, Clay, there's just a much better way, which is your system shows up, it knows the job that needs to be done. It's an expert at doing that and doing it unprompted. When I was on this CRO panel this week, that's what we described. We're like, what is the definition of an agent? Well, the definition of an agent is a domain expert who does work unprompted. So all of these tools that are sort of Rube Goldberg, jerry-rigging things together, you might get to a similar output eventually, but your users are never going to get the benefit from it because they're not experts.
Matt Darrow (11:06):
So Mike, over to you. Sales is a high pressure game. How does all this translate to the sort of real-time pressure of selling, forecast calls, deal reviews, value cases, exec reviews, what do you feel there?
Mike Capitolo (11:18):
Absolutely. So for all of those more like internal-type scenarios, your forecast call, your deal review, those are always high-pressure scenarios. For lack of a better term, you don't want to look like an idiot. You don't want to get caught flatfooted. So information recall, super important, but that level of depth and quality is also super important to know your deals inside and out. And Matt, to your point, I always think about reverse engineering. What are the questions that I'm going to get asked on a forecast call? What are the questions I'm going to get asked in a deal review? So that requires preparation, right? So I'm going to go talk about deal X. I know that my CEO and my VP are all going to ask me these types of questions, so therefore I'm going to be really meticulous about how I prepare. And the promise of agentic AI and the solutions that can do all this unprompted work is you can just guide them and tell them, hey, when I do a deal review, these are the things that I need to know about this given deal. So being able to go find that information, then surface it in a way that's really easy for me to digest and then present, it's a huge win.
Matt Darrow (12:17):
How about maybe on the external side too, Mike? Because you're right, I think people are tired of spending 10, 15 hours per week during deal reviews and deal inspection both on the rep side and the leader level because your VP of Sales and CRO and CEO that want to know about a deal, they're exhausted trying to go and hunt down every rep in all the context versus just self-serving that, and especially when a lot of them have probably spent a lot of dollars on training on BANT, SPICED, MEDDPICC, something else like this, and then again, wasted a lot of time for the rep that needs to present things in the right way and know where they're going. And then if you flip that around, well, the high pressure point of you driving your customers forward, maybe talk a little bit about how agentic AI is giving you lift and how do you present value and the value case and the reason for change externally, out to who you're trying to do business with?
Mike Capitolo (13:06):
Yeah, absolutely. And I think about all the key junctures and key milestones in a deal cycle. And at those junctures, at those milestones, more often than not, myself and Clay, as my partner in crime, we're going to be doing the same things over and over and over again. But the nuances of the things that we do, the qualification, the discovery, the demoing, the pursuing of securing the technical win, how that actually comes to fruition is going to look very different deal by deal. But it's always going to take us a ton of time to get to those things. So I'm always going to be creating a stakeholder map, right? That's an internal asset, but that's going to help me do all my preparation and all my selling with my B2B selling team. And I know I'm always going to need a customer-facing work back plan.
Mike Capitolo (13:52):
I'm always going to need a value case with a point of perspective on value pyramid, Three Whys, ROI. So I know I'm going to do those things every single time, and I know it's going to look different every single time depending on the deal. So the whole promise of agentic AI and the thing that's got me most excited is how do I do those things without spending the same level of effort on all the same cycles that I historically have so I can do them faster? And I have got that throughput mat around doing more of them, but the key thing for me is there's no sacrifice in the quality, right? Because the quality is ultimately what I know for Clay and I leads to higher than average win rates, leads to success. So how do I do more of these things without sacrificing the quality without going crazy, right? And spending my higher work week outside of the computer doing that level of depth for every single deal.
Matt Darrow (14:45):
Yep. I mean, sales leaders go crazy because they're like, why are these deals stalled and not going anywhere? And then at the same time, well, on the rep side like, well, you want to do the level of depth because everybody here is motivated by the comp plan. So it wins for both parties. I think that was tying back to what you said at the top two, Mike, which is all these old legacy SaaS and selling applications were built for a manager to get manager insights to hold a team accountable. But it did help you do exactly what you just described, whether or not it was internal or external so you guys could win more. Clay, I'm going to throw something over to you, and even if we zoom out a little bit from some of the details and just looking at sales tech evolution over the last few years, how would you describe the shift? I gave you a little bit of my take, but let's hear from you.
Clay Killgore (15:25):
This could probably take a whole session unto itself, but really when I sat down and thought about it, I think there's really just three key phases, especially over the last two years where obviously all of us are used to the old world, which is CRM, spreadsheet-driven, everything tracked manually, and really there's nothing in it for me as the IC. It's really all these tools were built for leadership just to get good reporting, understand where their resources are spending their time. And then from there, once these LLMs started coming to market with all their APIs, we saw the custom build or as you said, Frankenstack era, where you're seeing sellers try to take those LLMs, plug them into all of their own existing stack, spend a ton of money just developing it and trying to hardcode it into their specific workflows and use cases.
Clay Killgore (16:13):
And now we're seeing that everything is transforming really into what we call the agentic era, where these tools simply are just purpose-built for exactly my role and Mike's role, and they just work without me having to do any fine tuning, any crazy system prompts, assign it a role. It already understands my job, it sits on every engagement alongside with us, and it has all of the context from those tools that all of us use day to day, and they're just doing everything behind the scenes automatically, proactively. And I can just live in one system and have it all brought front and center. And that to me is the biggest difference. And I'm loving where all of this is going. So it's been very exciting.
Matt Darrow (16:53):
I love the breakdown there too, Clay, between where we were to Frankenstack to true agents. Back to you guys, it's kind of interesting here because even for our own sales agent, you guys are describing your own use. It actually impacts you, the individual, in a super material way. And that is a different contrast than what you teed up at the beginning, Mike, around why somebody might've bought Salesforce or Gong or like one of the other legacy SaaS applications. It was great for managers, but individuals didn't get anything out of it. And now with agentic AI, you can sort of flip this on its head because the managers get value from it because of how much incredible benefit impacts the individual. And that's a little bit of a different way to approach selling and securing budget and buying. It is relevant for Vivun, but relevant for anybody watching that's selling agentic AI that has that same dynamic, great for the individual, impacts the leadership level. So how do you make the case to somebody that has budget who maybe isn't the actual end user in the same way an ops leader of CRM would've been?
Mike Capitolo (17:54):
Yeah, Matt, it's a great new world where seeing is believing and actually using products. So the thing that I think about is, like you mentioned, there's this massive shift around how you position your products because ultimately the value is coming from providing the efficiency, providing the throughput without sacrificing the quality for the individual. So when I think about the positioning, it's all about how we can continue to do the things that managers and leaders expect of a solution, the insights, the guidance around what's working, what's not, but very quickly drop stepping into for this future world where information is more on demand and accessible than ever before, right? We have this concept that I've heard from other organizations of the AE of the future, the blending and meshing of the AE and the SE role where that individual is expected to be really dangerous customer facing and have the relationship skills and have the ability to develop meaningful close plans and associate problems to objectives, but also has the technical acumen that you would expect from someone like Clay.
Mike Capitolo (18:57):
So I think the big thing when it comes to positioning for the agentic solution of the future is how can we support the workforce of the future? And that's a big broad overarching statement, but for me, what that actually means is how can you equip your best SE to actually do the things that your best AEs do, and how can you equip your best AEs to do all the things that your best SEs do? So I see this meshing and this melding of those two worlds coming together, and AI really being the conduit to help those individuals, regardless of what side of the fence they're on, become proficient on the other side of the fence.
Matt Darrow (19:36):
I like the sales team, sales rep of the future. It's even some of a tagline for us, which is just giving more power to sales to let them go through that transformation. I'll throw it back to you first, Clay, and then Mike to bring us home. One thing, what's the one thing that the audience should take away from the conversation today? Clay, you go first.
Clay Killgore (19:53):
Yeah. I think it's simply that with the state of technology available today, you simply just cannot settle for the tools that require you to have to spend months on end simply designing it, hard coding workflows, having to be a prompt engineer and constantly babysit and adapt and constantly update it. If you're doing that and spending hours like building out flows or treating it like Workato, it's not going to be a very good experience. No one's going to benefit from it. And we have tools available just like our AI sales agent that already are purpose-built to meet us where we work and already do the work for the things that we do day to day faster and remove a whole lot of friction that you would see in the Frankenstack era.
Matt Darrow (20:35):
I love it. You don't like Frankenstack. I got you.
Clay Killgore (20:38):
No Frankenstack.
Matt Darrow (20:38):
Mike, how about you? One thing, what are we leaving with?
Mike Capitolo (20:41):
I want tools that help me do my job. I don't need tools that tell my manager how I'm doing. I need tools that help me do my job.
Matt Darrow (20:48):
Awesome. That one's...I won't push you for more, because that was short and succinct and sweet, man. Well, hey, thanks Mike and Clay, and for the audience out there, I hope you enjoyed this discussion. If you want to learn more, follow us on LinkedIn, subscribe to Vivun's podcast, The Unexpected Lever. We continue to have these conversations with B2B experts and sales teams as we see this big transformation in B2B selling happen. And thanks for joining us and we'll see you guys next time. Thanks again, guys.
Jarod Greene (21:17):
For additional resources, check out vivun.com and be sure to check out V5, our five-minute soapbox series on YouTube. If there's a V5 you'd like us to talk about longer, let us know by messaging me, Jarod Greene, on LinkedIn.