Michael DeLeonardis joins Warren Kucker to discuss Your Buyer Doesn't Know What to Ask For Yet. Key takeaways include Physical products add hard constraints that discovery must uncover early to confirm solution fit and AI has returned enterprise sales to demand creation, so buyers need use-case education.
Your Buyer Doesn't Know What to Ask For Yet
with Michael DeLeonardis
"We are now in an age where there is a brand new set of technology and nobody knows what the best practice is."
About This Episode
Michael DeLeonardis, chief revenue officer at Verity, explains how selling autonomous warehouse drones differs from selling software, and why AI has pushed enterprise sales back into a demand creation cycle. He and Warren Kucker discuss deep discovery around physical constraints, win-loss analysis from call transcripts, deliverable-based selling that guides the buyer through each decision, a client success role that spans pre-sales and post-sales, and why industry expertise and a LinkedIn presence matter for sellers.
About the Guest
Michael DeLeonardis
Michael DeLeonardis is chief revenue officer at Verity, a Zurich-based company that deploys autonomous drones in warehouses as part of a warehouse intelligence platform. He has about 30 years in enterprise technology across software and professional services, most recently at an intelligent automation company.
Key Takeaways
- ✓ Physical products add hard constraints that discovery must uncover early to confirm solution fit
- ✓ AI has returned enterprise sales to demand creation, so buyers need use-case education
- ✓ Deliverable-based selling ensures continuity and guides the buyer through the sales cycle
- ✓ Win-loss analysis is stronger when CRM reasons are cross-checked against call transcripts
- ✓ Industry expertise and presence on LinkedIn are crucial for sales professionals to build credibility and understand their buyers
- ✓ Enterprise selling fundamentals remain consistent: prove value, prove confidence in the solution, and integrate into the client's environment
Chapters
Show Notes
Physical products put hard limits on solution fit
Michael DeLeonardis is chief revenue officer at Verity, a Zurich-based company that puts autonomous drones in warehouses. He spent about 30 years in enterprise technology, most recently selling intelligent automation such as machine learning, OCR and RPA. Verity sells a warehouse intelligence platform. Drones fly the warehouse and scan the movement of goods so that the digital truth in the warehouse management system matches the physical truth on the floor. He says clients see returns of 10 to 15x, from inventory accuracy, recovering goods that had been written off, and better on-time, in-full order fulfillment.
What changed for him moving from software to hardware is the set of constraints. No two warehouses are identical, so the rep has to find the limits of the physical environment early to confirm the solution fits. Once fit is established, the deal runs like a familiar enterprise motion: map the solution to use cases, map use cases to a value story, then build a business case that justifies the spend.
Cold storage is his example of how deep that discovery has to go. There are 10 or 15 variations, from ambient to just above freezing to extreme cold. In extreme cold the hardware needs a heating element, because a battery takes too long to charge from zero to a hundred percent and frost clogs the sensors.
Just because somebody says they have cold storage doesn't necessarily mean you can support it.
Win-loss analysis needs a second source
Kucker notes that software loss reasons tend to collapse into indecision, competitor or price, while a physical product can have a real fit problem that surfaces only in the third or fifth meeting. DeLeonardis says tightening close-won and close-lost reasons has been one of his main focus areas for the past 12 months. A reason like "product capability" is not enough. The rep has to name the missing capability, because that detail feeds the product roadmap.
His team goes a step further. Seller-reported loss reasons are only the seller's view, so his VP of Revenue Operations built a process to run win-loss analysis on call transcripts. When what prospects said on calls matches what reps entered in the CRM, he has a pattern he trusts, and he uses it to set investment priorities with the chief product officer.
Buyers of new technology need to be taught what to ask for
For mature software, DeLeonardis argues, the buyer arrives knowing the use cases because they have probably bought the category before. Verity has to stop and run a dedicated use-case education stage, because prospects tend to see it as "the guys with drones that count stuff." That stage shows the full range of impact, across warehouse operations and further downstream into on-time, in-full fulfillment and working capital. It also helps with win-loss: if a gap was named early in the cycle, the team can go back after a loss and ask whether that gap was the reason.
He sees this as a return to demand creation after years of demand capture. Once categories like CRM and HR automation became widespread, buyers went back to familiar vendors and sellers mostly managed orders. He dates that shift to private equity buying software companies and running them on unit economics, which signaled the demand already existed and only had to be captured efficiently. AI has reversed that.
We are now in an age where there is a brand new set of technology and nobody knows what the best practice is.
In that setting, the seller has to show they are credible, that they can deliver, and that the buyer will not get fired for choosing them. The use case has to be differentiated too. AI research on target accounts, for example, is useful but not novel; he built it as a Claude skill his team runs before calls. He adds that many companies are underinvested in their data, so AI spending without well-structured data lacks context and returns little.
Repeat buying cycles come from product maturity, not budget
Kucker notes that a closed deal often follows several lost opportunities in the same account over months or years. DeLeonardis says Verity's market is about five years old, so buyers and products are both early. In his two years at the company, prospects have come back for a second and third pass. He rarely loses on budget or on poor vendor-client fit. He loses on product maturity, and expects these repeat cycles with the same companies to continue for three to five years while products across the warehouse intelligence category mature.
Deliverables replace pickup truck selling
On the account executive role, DeLeonardis says what's old is new. A long stretch of demand capture meant many AEs never developed curiosity, an understanding of the client's environment and people and KPIs, the ability to build a value proposition, or a grasp of how the client makes money. Top sellers always did this. The enterprise AE who earned $300,000 or $400,000 a year by taking orders is gone.
The bigger structural change at Verity is in client success, which now covers both pre-sales and post-sales. The same team does sizing, business cases and demos during the deal, then owns adoption and value realization after it closes. There is no separate solution architect. The client can hold one person to the benefit promised in the deal.
That leaves the AE to run the mutual action plan, and DeLeonardis does it through deliverable-based selling.
Every stage has a deliverable that we share with that prospect.
Discovery ends with a one-page executive discovery summary that the champion can share with the buying committee, so the problem, use cases and next steps stay consistent. Value creation produces a value story. The proposal ties it together with the use cases, the outcome, the price, the payback period and the ROI. Each deliverable is a chance to reset and confirm the use cases, value levers and outcomes, or to rethink the solution if a showstopper appears.
He contrasts this with what he calls pickup truck selling.
You drive down the middle of the road, right? The client lobs questions into the back of the pickup truck, you lob answers out, and you get to the end of the road and you expect to win.
No decisions get made along the way, so the seller is relying on hope.
Enterprise buying fundamentals have not changed
Asked how he mapped the buyer's journey in a young category, DeLeonardis says he starts from fixed assumptions: prove value, prove the solution can solve the problem, and prove it can be integrated without heavy disruption. He cites Gartner research showing that buyers' top concerns about physical AI and robotics look like enterprise software buyers' concerns from 20 or 30 years ago. He then adjusts for the industry. At Verity that meant adding the use-case education stage and going deeper than basic MEDDPICC qualification questions. He points to OpenAI hiring a CRO without AI experience and staffing sales from established enterprise software firms.
What has changed is who decides. In mature categories, decisions move down to directors because the risk is low. New technology that puts jobs and budgets at risk pushes the sale back up to VP, SVP and C-level buyers, who have to spend their own money or influence.
He believes every AE, manager and CRO should have a presence on LinkedIn to show buyers they understand their business. He links this to quota attainment: industry-wide it fell to the low 30s percent and is recovering toward 40, but the reps at 120 percent are the same group as always. They lead with outcomes, not features, and know the buyer's industry.
Full Transcript Show Hide
00:10 Warren Kucker: Hey there, and welcome to another episode of Selling AI. Today we're getting into a bit of a different sales process around a physical product, robotics. and what's interesting about this space is buyer still wants to see it to believe it. So we've got Mike De Lonartis on the show today. Mike is the chief revenue officer at Verity, which is a Zurich based company, puts autonomous drones in warehouses. interesting, he came to it about 30 years in the digital enterprise tech space. as well. So we're gonna dive deep into some of the contrasts between the sales process. Here's one of the key hooks. every robotics company sells through a paid pilot in a customer's warehouse. Need to see it work. Mike showed up and decided he was kind of tired of having two different sales processes, one pre-POC and one POC sales process. So did his best to kill it and shorten sales cycles by a
00:58 Michael DeLeonardis: Yeah.
00:58 Warren Kucker: drastic amount. we're gonna dive into why he thinks AI has dragged like AI enterprise buying back a few years. but in a good way, and how the sales process has shifted between IT and the innovation team. So, all right. Let's get into it. Mike, thanks so much for being on the show today.
01:16 Michael DeLeonardis: Warren, appreciate the invite and always enjoy being having the opportunity to just can kind of seremo share my experiences and if folks on the other end can glean any s anything from it and apply it, then you know, there's just additional value.
01:29 Warren Kucker: agreed and I always find this to be almost like a mini consulting session for myself. I always learn something new. So when anyone ever sees me like write something on a new n paper over here, it's because I wanna implement something in my sales process that I heard that was brilliant. So awesome. Well first let's ease in. Give us a bit of your background. what was your sales journey and how did you end up at Verity where you're at now?
01:49 Michael DeLeonardis: Absolutely. So as you'd mentioned, I'm 30 years in enterprise technology, both on the software as a service side as well as professional services. I've been fortunate enough to be a part of a handful of high growth startups, five ac for four acquisitions, one IPO through that journey, and a lot of different spaces from sales performance management to healthcare to big data and analytics, and then mostly recently pre Verity,
02:17 Warren Kucker: Yeah.
02:17 Michael DeLeonardis: I was with a company called Ashling that was in the intelligent automation space. So AI, machine learning, document understanding, OCR technology, RPA type technology. So essentially the backbone of anybody's digital automation strategy. And now I've had the fortunate opportunity to now find the intersection between that digital world and physical world with Verity, where we deliver a warehouse intelligence platform. That warehouse intelligence platform. Delivers high frequency, high fidelity monitoring of all the movements across the warehouse floor that allows you to ensure that your digital truth, which is typically your warehouse management system, matches your physical truth at the warehouse level. Our clients are getting ROIs of 10 to 15x, and they're doing that across a spectrum of value levers, everything from improving just simple inventory accuracy to being able to recover lost goods that have typically been written off. And improve on time and full order fulfillment to ensure they're meeting their customer promises.
03:20 Warren Kucker: That's awesome. And we're gonna dive into some of that value prop as part of this call too, which I think would be really helpful. But first let's compare and contrast. Tell us maybe your most recent role versus Verity, let's say software AI space, machine learning and LLMs compared to what you're doing now, which is kind of the nexus of the physical and the digital there. What's been surprising about the sales process or buyers journey at Verity that maybe you didn't know coming into the role?
03:46 Michael DeLeonardis: I wouldn't say surprising, but you know, starting to recognize and it comfortable with the constraints of the physical world is certainly a transition you have to go through. we have a component we call mobile intelligence. That's the autonomous drone technology. That is an endpoint sensor. Essentially, what that drone technology does is it flies through the warehouse and it's scanning all of those movements, right? it is constrained by the physical world that we're operating in, which is within the four walls of a warehouse and Not every you know, no two warehouses are identical, right? so as you're going through the solution and discovering portion, discovery portion of the sales cycle, you have to recognize those constraints. You have to identify those constraints up front to ensure you have proper solution fit. And then that solution fit then drives a pretty typical enterprise sales motion where you're mapping that solution to use cases, those ki use cases are getting mapped to a value story and then you're building a business case to help support the justification for the investment. But really the main difference is just operating within a physical world that has physical constraints, which is very
04:53 Warren Kucker: Yeah.
04:54 Michael DeLeonardis: new for me.
04:55 Warren Kucker: That's interesting. It's like I guess the contrast to that would be you're selling software and it needs to be implemented with other pieces of software. Right. So like but much more drastic. Have you found that that solutions design stage has been drastically different? A much bigger drag, maybe more black and white. It's a yes or no, compared to like software space where you're trying to fit round peg into an oval hole. What's the what's the difference been there and that's part of the sip buyer process?
05:20 Michael DeLeonardis: So the devil's in the details in the physical world and definitely in the warehouse because there are so many different ways of storing things. And then you take one single, what I call storage modality, there may be 15, 20 different versions. So it requires a lot of deep discovery, not different than the digital world. It's just a different type of discovery. And you do need a good sound foundation and understanding of how the movement of goods kind of flows through a warehouse and how it's stored. For cold storage is a simple example. There's 10 or 15 different ways in which cold storage is applied within a warehouse. Everything from ambient temperature to just above freezing to freezing to below freezing to extreme cold storage and beyond, right? So there's a lot of different variations, and you need to take that in account because your physical technology may not be able to always operate in all those
06:13 Warren Kucker: Yeah.
06:13 Michael DeLeonardis: environments. And cold storage is a perfect example. With extreme cold storage, You need to be able to fit your hardware with some sort of heating element that maintains the temperature for two main reasons. One, charging a battery from zero to a hundred percent in extreme cold is almost impossible, meaning it just takes too long, right? the second is the frost element. the sensors start to get clogged up, right? And if you don't maintain some level of heating element, then you're constantly having to do maintenance on the piece of hardware to make sure those sensors are clean. So that's some of the dynamics you have to be able to address. In a sales cycle, and like I mentioned, the devil is in the details. Just because somebody says they have cold storage doesn't necessarily mean you can support it. You then need to be able to dig deeper into understanding what type of cold storage that is, and then be able to map that back to your capability and go, look, is this going to be an environment I can operate in or an environment I can't operate?
07:06 Warren Kucker: It's interesting. I think there's a couple of questions that might be get from a sales standpoint, so I'll take I try to take them one by one. so like in again, software world, there's two reasons that are recorded in the CRM why you lost a deal. Indecision and competitor, right? There might be six others, but no one ever selects those two, right? or pricing. Pricing would be the third. In this space you actually have like a legitimate reason why you're not a fit, and you may not discover it until meeting three, meeting four, meeting five. Do you find that you do or you should like manage like win rates? differently in that perspective and how you like you're focused on what percentage of deals you're winning and what deals are gonna close. how do you kind of manage measure performance in like your opportunity closing cycle there?
07:49 Michael DeLeonardis: You're leaning into one of my focus areas for the better part of the last 12
07:52 Warren Kucker: Interesting.
07:52 Michael DeLeonardis: months that is good solid rigor around understanding close one, close loss reasons. Because again, the devil's in the details. It's not just I lost because of product capability. I lost because of product capability. What was that missing capability? Because that then
08:07 Warren Kucker: Mm-hmm.
08:08 Michael DeLeonardis: starts to feed a feedback loop back to product as far as what we need to start to invest in. And we take it a step further because yeah, wind loss reasons are fantastic, but that's usually through the lens of the seller, right? We are then also
08:21 Warren Kucker: Uh-huh.
08:23 Michael DeLeonardis: doing wind loss analysis based on call transcripts. Good news for us, and good news, I guess, for the our VP of Revenue Operations and who has put together an amazing process.
08:32 Warren Kucker: Mm-hmm.
08:32 Michael DeLeonardis: They completely match, right? Now you're getting triangulation. I'm getting transcripts directly from the word or the mouth of the word, the mouth of our prospects as far as why we've lost. I'm trying I'm I'm triangulating that, cross-referencing it with the data in my CRM and I'm seeing consistency. Now I can start to prioritize with our chief product officer where do we need to start to invest.
08:54 Warren Kucker: Yeah. In that closed loss discussion that your reps have, do you do some coaching around that more so than maybe you would have in the past? Like you almost also need to get past the surface level, right? So like great, you couldn't support this level of cold storage. We'll go with that line right now. You may be able to, but you're not. But it's also like great, that's an e maybe an easy response. Is there a secondary reason why you may not have chosen us? Do you feel that you're able to your reps are able to peel into some deeper reasoning, or that first reason's great, the feedback works well and you just kinda run with it?
09:25 Michael DeLeonardis: So it's more embedded in my sales process. You know, we're for most mature software products, the use cases are fairly well defined, right? The buyer shows up, they've probably bought it in the past. They understand the world of use cases
09:38 Warren Kucker: Yeah, there's some substitute. Yeah.
09:40 Michael DeLeonardis: that are supported within the solution they're trying to buy. And then they usually guide that conversation with the seller that is, hey, I'm looking to solve for X, Y, and Z, right? and then you then take that and you've let that feed a value conversation. We actually have to stop and we have a stage in our sales cycle where we go through and do use case education with our with our prospects to give them first and foremost the universe of impact that we can have on on their their their operations, primarily because folks usually show up and go, You're the guys with drones that count stuff. Well, that's true, but I actually have an impact all the way across the put the pack process. And then financially, further downstream, when you start to think about on time and full order fulfillment. And working capital optimization. So there's a justification that is value for our prospect and educating them on those use cases, because then it allows them to open their eyes up to opportunities for additional value, right? That is also a way to trace back to our win-loss, right? So we've already kind of done the use case exercise in the sales cycle. And then if we lose, we're just kind of going back to that exercise and clarifying with the client, hey, did we lose because of this gap? Because we did identify the gap at the beginning of the sales process. But my goal is to make my process more buyer-centric or what align calls buying process as a service. We are showing up to deliver the right information at the right time for our prospects so they can make good, sound decisions for their business. And sometimes that decision is not going with us, right? Which is okay. But when you show up in that f in that fashion, now all of a sudden you're delivering value. And we are consistently getting that feedback that we show up highly prepared. highly structured and we're bringing information to them that is of value that helps them make a decision. And they don't feel like they're having to just dramatically extract information from a seller to make good information to get to good decisions. And then as a result, the engagement is very, very narrow.
11:40 Warren Kucker: when you talk about this education, it harkens back to something you've talked about where you think we're in a demand creation cycle again. we're able to do that. Tell
11:49 Michael DeLeonardis: Mm. Loud out.
11:50 Warren Kucker: me a little bit more, what are you saying, what's driving this new cycle of like demand creation and education that maybe we were out of for at least a few years?
11:59 Michael DeLeonardis: I mean, when technology or any product becomes ubiquitous and pervasive, there isn't a whole lot of education that has to happen because most of your buyers have already been through the journey multiple times, right? Whether
12:12 Warren Kucker: Yeah.
12:13 Michael DeLeonardis: you're selling CRM, you're selling web design products, you're you're just selling customer experience capabilities, supply chain capabilities, finance automation, HR automation. This has all been around for 10, 15 years, right? So most of your buyers are highly educated. They have probably bought before.
12:29 Warren Kucker: Yeah.
12:30 Michael DeLeonardis: So as a result, what you're doing is more often than not capturing demand, right? Somebody moves into a new role, they realize they have a gap in their technology stack. They go to the top three vendors and they're most likely going back to the one that they bought from in the past, assuming they've had a positive experience. And really all you're doing is just managing an order process more than anything else because your buyer is highly educated. We are now in an age where there is a brand new set of technology and nobody knows what the best practice is. You know, what is the ideal set of use cases for artificial intelligence? How do I apply that to my organization? How is that going to have an impact across all of the other operations that we already solved integration around 15, 20 years ago with software as a service? Now all of a sudden you have to create demand. You have to create the justification with your buyer that you are credible and you know this technology and you're capable of delivering on it and you're not going to get them fired, right? That you understand the value you can create with your solution. And that you have something that's differentiated because I don't know how many people I talk to that come to me, that have come to me over the last six or eight months and said, I've got this great AI use case. It does market research on your target accounts. I'm like, people have been doing that already for four years with AI, right? That's not that's not novel. That's not highly valuable.
13:46 Warren Kucker: Right. Yeah.
13:49 Michael DeLeonardis: is it highly useful? Yes. And I do that today. My user, I I've built that exact skill within Claude. And whenever somebody shows up to a new call, they can click on that skill and it does all that research for them. But that's not differentiated. So that's why
14:02 Warren Kucker: Right.
14:02 Michael DeLeonardis: we're in this kind of demand creation mode is technology the the AI space is moving extremely quickly. Nobody's totally sure what the right universe of use cases is that's going to drive the highest amount of value. And on top of that, what people are realizing is they're underinvested in their data. So even if they're throwing money at the AI problem, if their data isn't structured in the right way. They're missing context and they're not getting value from it.
14:27 Warren Kucker: Interesting. Yeah. yeah, it's it's interesting. I I don't know if we recognize that we weren't in a demand creation cycle for a little while and that there we it always seems like they're we're in a a territory of new technology driving innovation, but I think this is the I mean this is the first time it's been a little while. I think the l yeah, really.
14:45 Michael DeLeonardis: I think the best signal was private equity. I would say about 15 years ago when private equity started acquiring companies and then they would come in with their management consultant and basically go, here's your unit economics and this is how we're going to run your business. And as soon as things turn to unit economics, that was that trigger that is we are in, you know, we're not in demand creation mode anymore. We are in just demand capture, right? The demand's out there.
15:07 Warren Kucker: Consolidation, almost. Yeah.
15:09 Michael DeLeonardis: We just have to be highly, highly efficient at capturing
15:12 Warren Kucker: Interesting. that's an interesting indicator. and now we're more of an E C whoop. Okay. on the flip here, so let's go one step up the sales process here. I I Ugly truth in sales is that like I think the average number is about 2.7 opportunities opened before a closed one. So most of the time you're closed losing an opportunity, you're opening up another one with another that account, six, twelve, eighteen, twenty-four months later, maybe losing it again. And then four years down the line, they're truly in a buying window and they select you as a vendor. I imagine most of the time in your sales process, you're able to create a a picture of a pretty beefy ROI and are not losing on that, you're losing on it's not the right strategic time to implement something pretty major. How are you finding that that kind of evolution through like multiple opportunities to close an opportun a deal is working in this type of like new market where it's obviously a major strategic decision, not like a minor software decision?
16:11 Michael DeLeonardis: It goes back to that demand creation concept. Part of demand creation for our market is solution fit. And a lot of times we'll go through a sales cycle and at the end of the day, we just don't we can't support the use case, right? We're limited either on the hardware side or the software side and it just requires additional engineering. Our space is only about five years old, right? So we are at the very early stages of buyer maturity and product maturity. And so we've already seen this happen just within the two years I've been here where You know, folks have come back to us that, you know, went through a cycle with us a year ago and two years ago. So they're on their third pass. There is clear demand there. It's just the market hasn't caught up from a product capability standpoint to be able to support it. So it's less about the fact that we've l I very rarely ever lose because of budget. I very rarely ever lose because of, you know, poor kind of fit between vendor and client fit. Where we typically lose is just product maturity. and that's where
17:12 Warren Kucker: Yeah, right.
17:12 Michael DeLeonardis: that's just a function of the maturity of where we're going, where the market's at today, and the wide set of use cases that we can get applied against within a warehouse. so we're gonna see kind of these kind of repeat buying cycles with the same companies, I would imagine, for the next three to five years as all of our products
17:32 Warren Kucker: Great.
17:33 Michael DeLeonardis: mature across our space, our warehouse intelligence space.
17:37 Warren Kucker: Cool. Given this type of sale, this heavy solutions, design sale, where are you how are you dividing the line between where an account executive ends and a solution consultant begins? And based on this, do you feel like there's an evolution in the skill set of account executives? at least in your market, but maybe more broadly, over the next few years and how an a count executive should be positioning themselves, how they should be developing their own skills. Has there been a change or is it like everything is old is new kind of scenario?
18:10 Michael DeLeonardis: I think with account executives, it's old as new. I mean, the concepts are still the same. I think again, because of the fact that we've been in primarily a demand capture world, a lot of AEs didn't have to mature those core fundamental skill sets. The cure the pure fundamental skill set of curiosity, understanding the environment they're in, the people that are in involved, the KPIs that are impacted. And then being able to turn that into a good strong value proposition. That has been lacking because again, more often than not, people were taking orders, right? What also has been lacking is truly understanding the financials behind your clients. How do your clients make money, right? And then being able to ensure you can translate your solution and your outcomes into how they make money, right? But that is again, that's old. What's old is new now. Right. Because that has been around for years. Those have been the fundamentals of good sound enterprise selling. And the folks that have been able to consistently make near seven figures or seven figures consistently always applied it. The problem was there was a huge opportunity for folks to consistently make $300,000, $400,000 a year just order taking. It just that doesn't exist anymore, right? The $300,000,
19:20 Warren Kucker: Yeah. Right, right.
19:22 Michael DeLeonardis: $400,000 a year AE that just takes orders in the enterprise doesn't exist, right?
19:28 Warren Kucker: Yeah, inter interesting shift.
19:28 Michael DeLeonardis: so where am I seeing really the fundamental change? The evolution of client success. And we have applied this specifically here. We have completely defined a new structure and new role for client success. It is both pre-sales and post sales. It
19:43 Warren Kucker: Okay.
19:43 Michael DeLeonardis: is the continuity point for our buyers. So the commitments that we're making in the buying cycle, client success then carries that through post sales to ensure there's value realization. So they're doing
19:55 Warren Kucker: Okay.
19:55 Michael DeLeonardis: our sizing. They're doing our business cases. They're doing our demonstrations from a pre-sales standpoint. And then post sales, they're working with the client on adoption and most importantly, value realization. So now you have a continuity point that is, look, Joe, you were involved in the sales cycle. You told us we were we were going to get that benefit. How are you helping us achieve that benefit? And no more can the client success rep basically say, look, I can't speak to what happened in your sales cycle. I can only tell you what I can achieve now.
20:23 Warren Kucker: I'm sure.
20:24 Michael DeLeonardis: So now you have
20:24 Warren Kucker: Yeah.
20:25 Michael DeLeonardis: a completely different level of accountability from our perspective that we can make to our clients. And now you've got an improved client experience.
20:34 Warren Kucker: Do you feel like So then you have let's say your account executive and it's not this dark but we'll pretend it is for a moment. Your account executives really in charge of demand creation, right? Like in that early stamp, identifying the
20:41 Michael DeLeonardis: I've got to do anywhere.
20:44 Warren Kucker: problem and the solution set there. Then there's a solution design process that that's handled by an expert that knows how everything works from a let's say a physical technology standpoint as well. that's probably
20:55 Michael DeLeonardis: Nice.
20:56 Warren Kucker: a little outside of the AE's purview. And then you have client success to talk about real results and what the project will look like and what implementation will look like and what the like what you would expect to achieve over what'll be a three to ten year journey with you at a minimum as a customer. Do you feel that AE role tails off pretty significantly throughout? What's the through line on the back end for the AE? How are they staying ear to the grindstone on what's happening in an opportunity?
21:22 Michael DeLeonardis: So the one that solution design component to it isn't a separate role. That is that client success role. So it's basically client success and an AE, essentially in my world. There isn't a specific
21:27 Warren Kucker: That's the same role, Katra. interesting. Yeah.
21:32 Michael DeLeonardis: technical pre-sales or technical solution architect function that is embedded within my client success function. So
21:39 Warren Kucker: Gotcha.
21:40 Michael DeLeonardis: again, that continuity point that is what I demoed is what I'm delivering to you. What I built my business case around is what I'm delivering to you. And the quality that I promised you in the sales cycle is what I'm delivering to you.
21:52 Warren Kucker: Yeah.
21:52 Michael DeLeonardis: Right. So the key component for the account executive is essentially managing the mutual action plan with the prospect, right? Ensuring
22:00 Warren Kucker: Mm-hmm.
22:01 Michael DeLeonardis: that we are staying on track through that sales process. The way I do that is deliverable-based selling. Every stage has a deliverable that we share with that prospect. That deliverable is kind of core to buying process of service because now I'm giving you something that you can leverage to then make a good decision and you can socialize internally. For example, at the end of discovery, we have an executive discovery summary, right? It's just a one pager that then we can share
22:28 Warren Kucker: Yeah.
22:29 Michael DeLeonardis: with our champion that then they can use to share across the entire buying committee. Now you're not losing continuity in what the problem is. You're not losing continuity in the use cases, you're not losing continuity in the next steps. We then move into value creation. We then have a deliverable that is our value story. value story gets shared with the prospect. So essentially it's the AE's responsibility to manage the process and ensure we are delivering those outputs or those deliverables to the buying committee and supporting that process all the way along the journey until they make a decision.
23:05 Warren Kucker: Yeah, I think that's a perfect segue. I think you actually posted this on LinkedIn maybe yesterday or today about sellers losing sight on the fact that you're trying to usher someone through making the next decision they have to make to get you down to the final decision that they need to make. And it's not just showing up meeting to meeting and like, it's what decision has to happen and how do you get them to that decision as best you can. How have you give me a little bit more about that framework, and how do you kind of like instill that mindset in your in your team?
23:39 Michael DeLeonardis: So I used to call this and I still do, I call it pickup truck selling, right? You drive down the middle of the road, right? The client lobs questions into the back of the pickup truck, you lob answers out, and you get to the end of the road and you expect to win. You've made no decisions. You haven't gone right, you haven't gone left. All you've done is answer questions. And more often than not, you don't win because you haven't delivered any value. You haven't guided the cross through the buying process. So really what I've done is I've designed a process. geared around deliverables that allows people to make decisions throughout their sales cycle and guide the buyer and let the buyer guide us on what the right path looks like, right? And that all comes down to those deliverables I was talking about. We've got our discovery executive summary. We've got our value story. We've got a proposal that wraps the whole thing together into a summary that includes here's been our journey together. Here are the use cases that we've identified. Here's the outcome we're going to deliver for you. And here's what everyone wants, here's the price that's gonna support it, and your payback period and your ROI. So all of these deliverables are all connected into kind of that endpoint that is here's a proposal. Now you know, now you're in a good position to be able to make a good sound decision. But if you're not making decisions throughout the sales cycle, you're doing pickup truck selling. And that's hope, right? You're hoping that by answering all of these questions and you get to the end of the road, they're gonna pick you rather than you're controlling. by giving them the right information and partnering with your buyer through their buyer journey.
25:09 Warren Kucker: Interesting. that's a good framework. and I think it's it's definitely easy for a seller to lose sight of what a buyer's journey actually is, right? basically gathering consensus. Yeah, right.
25:21 Michael DeLeonardis: Especially if you're not producing outcomes. Especially if you're not producing deliverables. Because every deliverable is kind of a reset opportunity, right? Let's sit
25:29 Warren Kucker: Yeah, right.
25:29 Michael DeLeonardis: down, let's review this deliverable. And again, they build on each other. Do we have the right use cases? Do we have the right value levers? Right? Do you believe in the outcomes that we can that we can deliver? And will you sell these outcomes, you know, via,
25:43 Warren Kucker: Yeah.
25:43 Michael DeLeonardis: you know, our champion, right? All of these things build on each other and those deliverables allow you to kind of reset and recalibrate. buying cycle as you're going through it. Because as you go through each stage, the buyer's learning something new. And maybe at some point they go, well, this is a showstopper now. No, this is not something that we can achieve in some way, shape, or form. There's a reason why we can't, you know, get to X, Y, Z goal within our operations. Okay, we need to
26:08 Warren Kucker: Mm-hmm.
26:09 Michael DeLeonardis: rethink the solution now, right? Or we need to rethink how we look at the business case. But if you're not holding yourself accountable to deliverables, it's very easy to fall into that pickup truck type selling that is What do you mean I've lost? I answered all your questions for you.
26:22 Warren Kucker: Yeah, right. Right, right, right. I'll make an assumption that may be wrong in one of my last questions here. So I assume when you came in your sales cycle was still on the immi immature side, right? Like you hadn't done this for again, it's a new company, you hadn't done this for ten years. So you didn't have tons of evidence of what the buyer's journey truly is. what I've always found that was challenging, this mapping the buyer's journey is the holy grail. most of the time is done by sitting in a room and talking about it. and it's hard to the I always find the baseline is kind of like a guess on my part. Where I literally listen, I've seen sales cycles in the past, I've seen decision journeys, I have an idea as what's happening in this product. Let me see if I could figure out what the six decisions that need to be made would be along the way and then they become Salesforce Gates and we don't have to worry about the actual like mechanism here. How did you find like that ha mapping that journey? Did you do it any way more robust than that? And how have you evolved it over time?
27:19 Michael DeLeonardis: So I think that what you end up finding is enterprise sales cycles and buying processes are not that different, even once you start could do you cross the chasm from digital to physical, right? And Gartner just put out some research on it on, you know, what are the top concerns of buyers buying physical AI, buying robotics, and they don't look that different than buyers number one concerns
27:43 Warren Kucker: Really?
27:44 Michael DeLeonardis: of enterprise software 20, 30 years ago. It's confidence in the solution to be able to solve their problems. confidence that they can adopt the solution and integrate it into their processes and having a good sound ROI. Well, I mean, that's been the foundation of enterprise selling for the better part of the last 30 years, at least since I've been
28:00 Warren Kucker: Yeah. Right.
28:01 Michael DeLeonardis: doing it, right? So what I always do is I start with just a set of foundation of assumptions that are, look, enterprise selling is enterprise selling. I've got to prove value. I have to prove confidence my solution can solve the problem. And I have to prove that I can integrate this into the client's environment without being highly disruptive, right? And you build the process around that. And then you just take information, you adapt, right? Until you get
28:23 Warren Kucker: Yeah.
28:24 Michael DeLeonardis: to, you know, something that is a fit for the very specific industry that you're in. For example, one of the things I had to adapt to in this environment was the heavy use case education. One for you know for two reasons. One is most folks showed up and you're the guys with count with drones that count stuff, right? And I
28:39 Warren Kucker: Yeah.
28:40 Michael DeLeonardis: needed to be able to change that perspective because we're more than that. But the second thing I needed to be able to show them is. We have the use cases to be able to solve their problems, right? So that was an area where I had to go a little bit deeper with how we design the sales
28:53 Warren Kucker: Yeah.
28:54 Michael DeLeonardis: cycle than I've maybe done in the past where I could get away with just basic kind of med pick discovery questions to be able to qualify, right?
29:02 Warren Kucker: Right. yeah, that's interesting. It's funny that the Gartner analysis there is funny, right? again it's the same scenario, it's it's what's old is new, right? And then you find specific decision points that start to come up more frequently that are industry specific that you wouldn't have known. but you pick them up along the way and you implement them when you can. So I really like this framework, I'm gonna end up cripping it. yeah. Yeah.
29:20 Michael DeLeonardis: I mean look at open look at open AI, right? And there was just a post that came out that, you know, the new CRO they just hired has absolutely zero AI experience, right?
29:30 Warren Kucker: Okay.
29:30 Michael DeLeonardis: and then you look at the concentration of where their sellers are and who they're hiring, and it's a who's who of enterprise stars from a s the software world over the last 20 years. They're hiring from,
29:40 Warren Kucker: Yeah, right.
29:40 Michael DeLeonardis: you know, Salesforce and S X SAP, ex Microsoft and stuff like that. So to use your words, what's old is new, right? Because at the end of the day, enterprise selling hasn't fundamentally changed, right? It may be a different technology. You may have to apply different approaches to be successful with that technology. But the core of how enterprises make decisions hasn't fundamentally changed. And that's why you you've got an a leader in a brand new space at like open AI that is going to a tried and true kind of approach to selling with a tried and true set of team members from You know, the SAPs, the sales forces of the world, the Googles of the World, et cetera.
30:21 Warren Kucker: Yeah. It's fun yeah, Sam Altman just came out and said that AI adoption hasn't happened as quickly as he thought it was when he was at GPT four in twenty twenty three in the enterprise, and he said it's just chalked up to the same old problem is that people change slowly. He said it was a good thing, which I I think he actually meant. A good thing for society, maybe not as a good thing for his IPO off the rip. But like it's still the same enterprise buying journey, right? You're asking someone to use their professional capital to make a decision to choose the right platform. There'll be people that disagree with you with the org and are upset about the choice and was it the right decision or not, can they validate it afterwards, right? So it's the same problem, right? Why should I use OpenAI versus COD? for any perspective. Yeah.
31:00 Michael DeLeonardis: And it's dis and it's changed the layer of decisions, right? Again, highly adopted, highly mature technologies, the budgets, the decisions start getting pushed further down in the org because the risk is lower. The technology is
31:12 Warren Kucker: Right.
31:13 Michael DeLeonardis: proven, the people buying it have bought it a couple a couple of times. So it's like, yeah, I'm gonna trust my director level to make these decisions, right? You start to introduce a new technology that puts people's jobs at risk, puts job puts budgets at risk. All of a sudden you got to work your way back up. And all of a sudden you're consistently selling
31:30 Warren Kucker: Yeah, it's interesting.
31:31 Michael DeLeonardis: at the C level, the SVP level or the VP level, because it's a new technology. And to your point, they've got to use some of their own internal capital to get something done like that, right? Whether that's actual
31:41 Warren Kucker: Right.
31:42 Michael DeLeonardis: capital in the form of dollars or that's capital in the form of relationships, right? And influence.
31:46 Warren Kucker: Yeah. Agreed. excellent. I mean maybe the last question I had for you is you do a lot of posting on LinkedIn. people will be surprised. I think s sales folks from what I've noticed, it's about s thirty to thirty five percent of people are active on LinkedIn in sales. I actually think this is a big drag on an account executive's day. I think an account executive, especially now, has to really position themselves as an industry expert. They have to look like they're from industry or be from industry and like show that they are, right?
32:12 Michael DeLeonardis: That's the RB on the trade.
32:15 Warren Kucker: But let's stick a talk about the CRO role. You you obviously this isn't a space you've been in before. How do you view your role as positioning your team as industry experts? Sorry, you obviously know a lot about the space and a lot about the topic. Do you feel it's a CRO's job to be out in front and like being that let's say flag holder for like we understand your industry really well and being out there, or do you feel like that's more important at the seller level to kind of understand what's happening on the ground?
32:43 Michael DeLeonardis: So I think the answer is yes, you know, across the board. Whether you're a seller, you're a sales manager, you're an AVP, you're a CRO, you should be active and you should have a perspective out in the marketplace because that gains one credibility, but two, more importantly, is it shows your buyers you know them and you understand them, right? Now the type of posting really depends on the maturity of the market, the maturity of your organization, right? Am I talking about how, you know, my solutions are going to help you change your earnings per share? Well, that's a very different conversation than, you know, teaching you how to improve inventory accuracy, but that's really just a function of the maturity of the market you're in, the maturity of the organization you're you're coming from.
33:28 Warren Kucker: Yeah.
33:29 Michael DeLeonardis: But to me, every CRO, every VP of sales, every R VP, every AE should have a presence. Because if you don't have a presence, you're not showing your buyer you know them and then you understand their business. you understand their challenges and then that that you can credibly tell them that that you have a solution to the problem.
33:49 Warren Kucker: Yeah. that's great feedback. I I often talk about like on almost every call there's something that's interesting that could is public, non-like private information that could be discussed on LinkedIn. This is what I learned in the industry that's happening right now. non proprietary, so like there's a line there, but easy to easy to judge that like kind of shows as a rep that like you understand problems, you understand when novel problems come up, you understand what might be useful to other prospective buyers, so that you have a presence in the industry, which I just think is gonna be absolutely key over the next couple years. You're both your company and as a rep. I think it's gonna be harder than ever for reps to switch out of industry. You had a foothold, things are going well, you're making quota, great. Maybe you're not at the company you want to be at, but you stay tangential to where you are so your buyers are the same. There's a huge value lever to being present with your buyers. And I think LinkedIn's
34:32 Michael DeLeonardis: Okay.
34:35 Warren Kucker: the good a good point for that.
34:37 Michael DeLeonardis: And it's and it's coming through just loud and clear in quota attainment in our industry, right? Quota attainment
34:43 Warren Kucker: Interstate, really.
34:44 Michael DeLeonardis: has gone through the floor, right? It is starting to recover because it was almost down to below 30%, low 30s. I want to say a couple of years ago. It's getting towards 40 or so, 40%, nowhere near where it used to be. Call it 70, 80%, right? But
34:58 Warren Kucker: Yeah, right?
35:01 Michael DeLeonardis: the top tier still the same, right? The people that are 120% of quota, it's still that same group. And it's that same group that was always applying these perspectives. They always came from a position of, I know your business, I understand your industry, and I can solve problems for you with my technology. They are outcome focused before they are feature focused or capability focused, right? But it's that but that that that
35:23 Warren Kucker: Yeah, right.
35:25 Michael DeLeonardis: tier that was kind of relying on the tier that was, you know, consistently doing $300,000 or $400,000 as an enterprise rep that is now just barely getting by on their base salary because they're at 40%. that never applied those sorts of things. So, you know,
35:38 Warren Kucker: Yeah.
35:39 Michael DeLeonardis: again, what's old is new. And, you know, I think it's coming through in industry quota attainment because the ones that are killing the numbers are still the same folks that we've been killing it for the last 15 years. And they're just applying what we've been talking about. They're just consistently doing it just in a new world
35:52 Warren Kucker: Great.
35:52 Michael DeLeonardis: now that's an AI world.
35:54 Warren Kucker: Yeah, there's like a a four, five, six, seven year span where being a generalist was worked fine. Right. So like understanding sales process
36:01 Michael DeLeonardis: Okay. Yeah.
36:02 Warren Kucker: got you through the door and you made some money off it. I I I would five years ago as a dumb founder, I would struggle to hire someone who told me they were a relationship seller. Like if you didn't understand how
36:12 Michael DeLeonardis: No.
36:13 Warren Kucker: buyers think and buy then I wasn't a like it wasn't a fit for my org. I'm I wouldn't that's not a disqualifier for me any longer. It's a qualifier overall, right? so I I couldn't agree more. Great. Well Michael, this has been a great conversation. Where could our listeners find you? Where are you posting? I was saying I mentioned LinkedIn. Anywhere else that they can find you, any conferences you go to regularly?
36:33 Michael DeLeonardis: LinkedIn is the best place to find me for sure. And anybody's welcome to reach out to me. I am active on LinkedIn. I do respond as folks kinda if folks want to send me direct messages. So LinkedIn is the best way to get me. We are always at Pro Mat, Manifest, Logimat is kind of the core supply chain type events. And then we're going kind of broader over the next twelve to eighteen months, just expanding our demand gen strategy. So we'll be a lot more events. But the core big ones that are in our industry, you will definitely find me and find Verity at
37:04 Warren Kucker: Awesome. Michael, it's been a pleasure.
37:08 Michael DeLeonardis: Warren, I appreciate the invite. Thank you very much. It was a pleasure chatting with you this afternoon.
About the Host
Selling AI is hosted by Warren Kucker, founder of Topiq. Each week he sits down with revenue leaders, founders, and operators to unpack the strategies, tools, and stories behind selling AI products and using AI to sell smarter.
Warren Kucker
A revenue leader and entrepreneur who founded Basiq.work, focusing on conversational AI for sales teams. Previously served as VP of Sales and CRO at Series B companies, scaling revenue to $2M+ quarterly bookings. His exits include Shelly.ai (ML email automation) and Boxton (digital freight platform). Started his career at Apple managing a $100M shipping efficiency program.
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