Dan Morgenstern joins Warren Kucker to discuss How Enterprise Views Buying AI Products. Key takeaways include Managing multiple stakeholders in enterprise sales and Transitioning from restaurant franchise to sales career.
How Enterprise Views Buying AI Products
with Dan Morgenstern
"Cutting off a prospect mid-sentence cost him the deal — giving buyers space to tell their story matters."
About This Episode
Dan Morgenstern discusses managing complex 12-18 month enterprise deals selling customer feedback software to major retailers. The episode explores stakeholder management across multiple departments, the balance between storytelling and data-driven pitches, and the importance of letting prospects speak.
About the Guest
Dan Morgenstern
Co-founder of a restaurant franchise who transitioned to enterprise sales leadership at TrueRating, where he manages complex B2B software sales to major retailers.
Key Takeaways
- ✓ Managing multiple stakeholders in enterprise sales
- ✓ Transitioning from restaurant franchise to sales career
- ✓ Storytelling vs. data in sales pitches
- ✓ Stakeholder alignment and management in complex deals
Chapters
Show Notes
Enterprise retail deals are slow because the product touches every customer
Dan Morgenstern is an account executive at True Rating, which sells customer feedback and insight software to operations and CX leaders at large retailers. The product asks single-question surveys on the pin pad at checkout and ties the answers back to spend, so a retailer can see whether customers who say the store was clean spend more or return more often. Morgenstern calls it the anti-Yelp. He came to it after co-founding a fast casual restaurant with his dad and brother, where a day spent pleasing 99% of customers could end with one two-star review from someone who waited five extra minutes.
His sales career started when the restaurant's rep from the News and Observer, a McClatchy paper, suggested he try selling. He sold digital ad campaigns such as geofencing and Google AdWords to small businesses and rose to VP of sales over five managers and 35 to 40 reps. Those deals were a cold call, a needs assessment and a pitch, done in weeks, and 90% were closed directly with the owner. Kucker notes that small businesses are roughly two thirds of US GDP, a useful check on how much of "modern sales" is a SaaS bubble.
At True Rating, deals with large retailers can run a year to two years. The product sits on the payment device, which Morgenstern calls the single most important device in a store, and it changes checkout for every customer. Inventory software is invisible to shoppers; this is not. It also falls between camps: traditional surveys belong to customer experience teams, while True Rating's value is closer to retail operations, so a lot of early work is finding out who owns the problem.
One produce question built the ROI case
The clearest example came from a grocer. A standing question on product quality showed scores falling in the evenings, along with basket size. The team suspected produce, added a question about it, and the heat map lit up. When they asked the operations team why, the answer was uncomfortable: managers had been incentivized to cut waste and spoilage by keeping produce on the shelves longer. Customers noticed, spent less per basket and came in less often. Morgenstern describes how the decision framed itself:
Then it just becomes a simple math problem of, is the lost revenue worth the saved costs of not throwing away the rotten fruit?
The answer was an immediate no. The grocer used the heat maps to rework replenishment schedules and put staff on the floor at the weak times of day.
Surface objections early, and lead with a story before the data
Morgenstern likes to get objections out as early as possible. The common ones are whether surveys slow down checkout lines, which True Rating handles by throttling how often questions are asked; whether customers answer honestly in front of a cashier; and, from IT, that nobody touches the payments device. On honesty, he says score drops keep lining up with real operational stories like the grocer's, and what matters is the spread between top and bottom performers. On IT, nobody wants to be the person who bought the tool that stopped a store taking payments.
Kucker asks whether he answers objections with data or treats them as emotional reactions. Morgenstern says people will usually tell you when they want data and when an anecdote is enough.
Nobody wants to have their nose rubbed in an assumption that they're wrong about.
His default is a story first: another customer felt the same way, and here is what they saw. Data follows if needed. He has also learned he does not have to answer everything on the spot, and that asking for a day to check with his team is fine. Kucker connects this to his own habit of over-extending to close a deal, arguing there is a balance between trust and process that sellers should not push past.
Tie every stakeholder to the same company initiative
With IT, CX and operations involved, Morgenstern's first move is to find a common thread, usually a company initiative. He looks at what leadership says on earnings calls and where the company is investing, then attaches the deal to something bigger than any one group, like a horse race where every group has to finish at the same time. That does not mean being everything to everybody; it means picking one theme that matters to all of them. Kucker links this to Skip Miller's ProActive Selling, where executive priorities are trains leaving the station and the seller's job is to get on several of them.
This research is standard prep for Morgenstern. For public companies, he asks ChatGPT to summarize the latest earnings call and explain how it applies to the CX or operations team he is about to meet. He calls it table stakes, because the last thing a seller needs is to walk into a first discovery call unaware of massive layoffs or a major expansion.
Deals are won at the margin by letting the prospect finish
Asked what separates winning from losing, Morgenstern describes a prospect who went silent for three months after a call he felt good enough about to nearly commit a pilot to his boss. He rewatched the recording. The prospect had been hard to draw out, and when he finally opened up, Morgenstern heard what sounded like a perfect transition to his next slide.
I basically cut the guy off mid-sentence, but right before I think he was about to give me something that would have been really useful and meaningful.
His lesson is to lay the foundation but leave prospects room to share their point of view, rather than racing through 11 slides to secure the next call. Kucker agrees that the skill is giving buyers enough context without steering the conversation. He admits he says he hates demoing his own product and then demos for 20 minutes anyway, and frames the whole problem as holding buyer attention.
Buyers can tell real AI from AI fluff
True Rating is launching a natural language queryable version of its data, so a user can ask what three things to focus on at a given store. At NRF, the National Retail Federation show in New York, Morgenstern heard prospects say they were tired of vendors claiming AI they did not actually use, or passing off 2015-era machine learning as AI.
AI adjacent is not AI.
He still cannot ignore AI, because public companies are expected to invest in it and some retailers have budgets that can only be spent on AI-related tools. Kucker has stopped mentioning AI in his own sales process. Only the end result matters, a better product or service at lower cost, and shoppers never care whether the produce improved because of AI. He compares it to a shipping company still pitching its website to him in 2014 and expects leading with AI to look just as dated within six to 18 months.
Full Transcript Show Hide
00:00 Warren Kucker: Hey there and welcome to another episode of Selling AI. Today we're diving into one of the toughest part of enterprise sales, managing multiple stakeholders across complex deals. I have Dan Morgenstern,
00:11 Dan Morgenstern: videos.
00:14 Warren Kucker: I have Dan Morgenstern, I have Dan
00:15 Dan Morgenstern: Morgan's turn.
00:18 Warren Kucker: Morgenstern on the show today and Dan is an account executive at TrueRating where he's selling customer feedback and insight software to operations and CX leaders at major retail enterprises. Dan's got one of those eclectic backgrounds, gives him a unique lens on sales. He co-founded a restaurant franchise with a regional ad sales at McClatchy, worked at an early stage FinTech startup, and now he's navigating complex deals at TrueRating. In today's episode, Dan and I talk about what it actually looks like to manage five, six, seven stakeholders in a single deal. how we can be using AI to help keep track of those interactions and leverage them better, and specifically what it's like selling True Rating's new AI-powered platform to retailers. We'll also get into lessons from his past, shape how he sells today, and from there, we'll dive in. Hey, Dan, thanks so much for being here today, talk about selling AI into some retailers. Welcome to the show.
01:13 Dan Morgenstern: Yeah, Warren. Thanks for having me. Excited.
01:15 Warren Kucker: Awesome. So first off, give us a little background. How did you get into sales? You owned a restaurant franchise at one point. Let's talk about how that kind of defines some of your careers and what you're focused on now at True Rating.
01:25 Dan Morgenstern: Yeah, happy to. guess we'll start there with the big gamble that I took about a decade ago with my dad and my brother. Yeah, to try to build out a fast casual restaurant concept, the goal was to really become the next Five Guys. Long story short, never quite got to a place where we were. So we never got to a point of profitability where we felt like we could actually go franchise it. So we built a few locations out, had a heck of a time doing it. Good news is we all still get along, but ultimately never quite panned out. had to wind operations down. And so I think like most people, I from there kind of stumbled my way into sales. feel like a lot of sales careers start in a similar fashion. But yeah, and essentially we had done a lot of advertising with the local paper and the sales rep for the News and Observer, which is one of McClatchy's properties, came to me when he found out we were shutting down operations and he said, hey, have you considered sales? And I think I had a pretty... immediate allergic reaction to that question, both on the sales side, but also like, I don't know if I want to go work for a newspaper. And then he walked me through. So the class has about 30 different markets when I've got papers, but they also have really awesome digital advertising agency, so to speak, that sits along each of those papers. And it seemed really interesting to me. So I thought, you know what, I'll give it a shot. And so started selling ad campaigns to SMBs and was really fortunate, had some had some success there and was really fortunate to have some leadership that took a gamble on me and allowed me to kind of move up fairly quickly. I ultimately led a sales team and then where I landed at the end of round with McClatchy was a VP of sales where I had five sales managers reporting up to me. Each of them had a handful of reps under them. So was team of about 35 to 40 reps. so, yeah, got to see a huge, huge variety of, how everybody got into the sales and then just generally like a lot of different approaches, which was awesome for a guy getting into sales. But unfortunately, back in 2020, we had a little bit of a double whammy where in February we declared bankruptcy. And then a month later was the COVID shutdown, which was a really, yeah, an interesting time.
03:38 Warren Kucker: Yeah, right.
03:38 Dan Morgenstern: And so it became a little bit more, a little more unpleasant routine layoffs, restructuring kind of thing. And I decided I didn't really want to be a 28 year old executioner. And so
03:47 Warren Kucker: Okay, right, yep.
03:49 Dan Morgenstern: hit a little bit of a pause and said, know what, I need to figure out something, something where I feel like I can, can grow. so a couple more, a couple more kind of peaks around what else is out there. And it ultimately landed in enterprise SaaS, which is where I am today. And just absolutely loving that.
04:05 Warren Kucker: That's awesome. Let's dive into just a couple of those pieces. So the restaurant piece, let's say three, four locations, it's always a hard launch from that four location to a franchise model. I'll ask two questions there. Is there something you learned in your work that is helpful now from your sales perspective? Did the Java 2 rating, is that completely coincidental? I know you deal with POS and customer ratings. Is your experience played into that at all, or is that just a coincidental or happy circumstance?
04:31 Dan Morgenstern: Yeah, no, so it's not coincidental.
04:34 Warren Kucker: I gotcha.
04:34 Dan Morgenstern: One of the things that really excited me about tru-rating is I consider us really the anti-yelp. And I guess for helpful background, the quick one-liner on tru-rating is that we've got a software where we ask single question surveys on the pin pad as customers go to check out. And so then we tie that back to spend so we can see, you know, if somebody says, yes, the store was clean versus no, it's not. What does that influence on how much they spend or how often they come back? So really cool. kind of a retail analytics. I consider it like the death of the receipt survey. And then we a customer-facing proposition as well that is like a Yelp page but actually gets the majority of your customers as opposed to the noisy few. And I just remember this was a brutal thing that we had to deal with in the restaurant world where we could have just an awesome day. You you knock it out of the park with 99 % of your customers. You go home that night and you're like feeling pretty good and then you get that one guy to give you a two-star on Yelp because you had to wait five extra minutes and it was just
05:26 Warren Kucker: yeah. Right,
05:29 Dan Morgenstern: brutal. so when I heard the vision of True Rating of Hey, get the real picture. Don't just hear from that noisy few. Yeah, that's really what excited me about the concept there. Definitely an inspiration for why I'm here today.
05:43 Warren Kucker: Yeah, that's awesome. How about ad tech first, like SaaS sales? What are the pros and cons to both processes?
05:50 Dan Morgenstern: Yeah, for sure. think there was a little less complexity and a little faster timeline on the ad sales side. So
05:57 Warren Kucker: Okay.
05:58 Dan Morgenstern: part of that was a function of my, my role was really more SMBs. so it was, know, smaller ad campaigns and, kind of helping, helping local businesses just get their name out there, do some, doing things like geo-fencing and Google AdWords and whatnot. And that's a, a cold call, a needs assessment at a pitch and you're pretty much done. might take. a couple weeks up to maybe a couple of months to start to finish there. now in this world, we sell to fairly large retail enterprises and it can be a year, 18 months, two years long, lots of different groups getting involved, trying to navigate with IT roadmaps and whatnot alongside of your business stakeholders. And so there's just a heck of a lot more complexity. Frankly, I enjoy it. It's fun. It's sport. It's like a giant game of chess, but it also... Yeah, it can be a lot more taxing on your patients to see these deals go a couple years long.
06:53 Warren Kucker: That's awesome. Beyond speed, is there something on the ad-style side that's more fun than typical SaaS tech?
07:01 Dan Morgenstern: Something on the ad sales side you said?
07:03 Warren Kucker: Yeah.
07:04 Dan Morgenstern: Yeah, you know, think there was really what we were doing was bringing the ability to be more, I guess more technically forward than some of these small businesses would otherwise have access to. So things like, you know, if I'm a local wine shop and there's a convention nearby, we would run things like geofencing campaigns where we'd say, hey, we can go grab every phone that walks into this, into that convention center while they're there. and then go serve them ads while they're in their hotel to pop by and go grab a bottle of wine for their stay there and things like that. it's just stuff that sounds really complex if you're like a local wine shop owner and we were able to basically take things that normally would be reserved for much larger budgets and much larger businesses and bring those assets back down to the small business world. So I just really enjoyed it as a small business owner myself prior to that. just
07:54 Warren Kucker: Yeah, I'm right.
07:55 Dan Morgenstern: really loved the idea also of just being able to help that group out.
08:00 Warren Kucker: No, it's awesome. It may be just a bubble I live in, I don't think so. When it comes to like modern sales, think like SaaS tech sales is what like gets put up as what modern sales processes are like. And I think we forget like as I dip in, dipped in a couple of different areas here that one, I think in the US small businesses is something like two thirds of the GDP. Two, a lot of that is still like. Mom and like mom and pop newspaper radio. They're dipping into like Google ads. They're
08:29 Dan Morgenstern: Right.
08:29 Warren Kucker: trying to figure out SEO and we're over here thinking that like LLMs are going to disrupt like 80 % of the economy and it's like no like most people are still not on the cloud. Most people are still are trying to figure out SEO at scale and they're advertising local right like the real the real world is a lot different than selling a piece of enterprise tech and trying to convince the CFO that the software will have an ROI and you'll be able to implement, right? It's actually not the real world, right? It's kind
08:52 Dan Morgenstern: Yeah.
08:55 Warren Kucker: of like this bubble that we've made for ourselves along the way. It's kind of fascinating.
08:59 Dan Morgenstern: Absolutely. 90 % of the deals I got done were directly with the business owner just basically saying, this sounds good. Let's give it a shot.
09:05 Warren Kucker: Right, exactly right. They have like cash to spend. They either go to spend it or you're like, hey, listen, I do have 10 grand and I think you might be able to help, right? Like, there's
09:12 Dan Morgenstern: Right.
09:12 Warren Kucker: like a, then the business owner's like, hey, I gave you 10 grand, got nothing out of it, right? Like it's a direct conversation, right? Like next time you call. So
09:16 Dan Morgenstern: I'm sorry.
09:18 Warren Kucker: it's fascinating. Cool. All right, sounds good. Tell me a little bit about true rating. You're, again, you said 12 to 18 months sales cycle. I think anything longer than 60 days is considered a long sales cycle. 12 to 18 months can be long. What's the sales process like and where does the rubber meet the road? That's why the sales cycle becomes so stretched.
09:40 Dan Morgenstern: Yeah, I mean, I first and foremost, when you consider where we live in the payment stack, we are touching what I think most in the retail world would argue is the most the single most important device in their stores. And if they can't take payments, they can't they can't make money. And so there's a lot, first of all, of attention on touching anything that has to do with payments. It's also a pretty fundamental shift to how customers are, you know. It's a pretty fundamental shift to the experience of checking out. And so we try to be as painless as possible. It's one question, one button per customer, and it is a quick interaction. But at end of the day, it's something that is going to touch every single customer. And there's not a lot of technology out there that you're selling that does in fact touch every single customer. If you're selling something like inventory management, customer never notices it. We have something that customers notice. It touches something that's really critical. And then also we tend to live in this blend where there's really kind of an old school or traditional view of these types of surveys that really live in the customer experience world. And our offering is really much more geared towards retail operations. And so a lot of it, honestly, we're
10:50 Warren Kucker: Interesting.
10:51 Dan Morgenstern: just trying to figure out, hey, who owns this? And, we don't necessarily always attach ourselves to the those who own the long form receipt surveys. We're more a matter of that you need to understand what's a key priority, what's happening in your stores down to the store, down to the shift, and that's really more of an operations lens. And so we just tend to touch a lot of different camps, including that customer experience, which generally speaking, there's gonna be a lot more scrutiny on anything that is that far reaching.
11:21 Warren Kucker: Yeah, it's always interesting to hear about products that are finding ways to leverage areas of the customer experience that you didn't think about before, right? So
11:31 Dan Morgenstern: Yeah.
11:32 Warren Kucker: like, without being in the industry, be blunt. I would think in, let's say, the retail industry, the interactions that you're having primarily with your customers are when they're talking to your employees, either at the checkout line or when they're in an aisle and they're asking questions, right? But like, I wouldn't think about the fact that like, The only thing that they touch in a store that has any sort of electronic transmission is when they're checking out. I'm
11:54 Dan Morgenstern: Right.
11:56 Warren Kucker: just picking up products off the shelf. It's analog. It's how we've always done it. On the way out the door, that piece is the only electronic information gathering area that I have. When you are in a sale, is that a new way of thinking that you have to approach the team? Or because they've managed this receipt survey thing, it's an easy leap for them?
12:19 Dan Morgenstern: No, it's certainly new. Yeah, I don't think that most, like I said, most technology in the retail world is not necessarily something customers touch. And so there's there is, yeah, there's absolutely a learning curve there of how you're interacting. And I think the other thing, too, is you think of like, you know, if you bring up the receipt survey example, that's very much an opt in. If I'm a customer who wants to give feedback, I will go seek that out. But frankly, we believe that's the fundamental problem today is there. That means naturally you're only gonna get the person who had a horrible experience and wants their pound of flesh, or you're gonna get the guy that was like, you know, wow, that cashier was incredible, I better go give her a five star, you review and fill it out. But that doesn't actually tell you what's happening in your stores. And so, yeah, there's a shift from just a general philosophy of how they should approach customer feedback. But then, yeah, to your point, there's absolutely a learning curve there of you are doing something that impacts each and every customer.
13:16 Warren Kucker: Yeah, I think before we dive fully into sales process, you were telling me a story and we don't have to be descriptive as to who, but like one of the ROI pitches you had made was a similar like kind of retail location was using true rating. They found out that there was a dip in sales right around a time that there was a increase in focus on reducing food spoilage.
13:39 Dan Morgenstern: Yes.
13:39 Warren Kucker: Can you dive into that story a bit and like how you pitched ROI and how that conversation went?
13:44 Dan Morgenstern: Yeah, super interesting. we had just one of the questions that we ask that's just always in rotation is around product quality. And one of our grocers noticed that, hey, that product quality score is dropping in the evenings. And by the way, so is our basket size. We're selling less in the evenings than we are at other times of day. And so again, it was a grocer. And so we thought, OK, well, the only thing that's probably variable. is fruit and veg and produce. And so we introduced a new question that was, hey, what do you think of the produce today, as opposed to just general products? And the heat map got so much more intense along the produce. so we thought, okay, we nailed it. And we went back and asked the operations team, said, hey, we've introduced this new question around produce. We're seeing that there's this huge decline end of day. Why do you think that is? you think maybe you're just leaving things on the shelves too long and you can feel the air go out of the room when they realized, hey, we've actually been incentivizing our managers to minimize waste and spoilage and keep produce on the shelves longer. And so it was just an incredible use case for us to say, well, look, you tell us what you think you're saving on that because we can tell you that you're missing X dollars per basket and people are coming in less frequently because of it. And so, yeah, your customers, they certainly noticed that that incentive that you gave your managers in a really bad way. And Then it just becomes a simple math problem of, is the lost revenue worth the saved costs of not throwing away the rotten fruit? And it was an immediate answer of, absolutely not. We need to fundamentally change this. And they ended up using our heat maps to say, here's the clear times of day where the produce is struggling. Let's rework our replenishment schedules and have somebody walking at those times. it's really awesome prescriptive. data that comes out when you actually hear from the majority and not just a couple of noisy, noisy grumpy guests.
15:37 Warren Kucker: Awesome, yeah. So I really like what you saw for it. It's just like the friction and the data capture, right? So like you could have, if everyone took the survey, showed on a receipt every single time, then true rating may not have had to been a thing, right? So like, but like the way you end up is oftentimes these types of review settings, you end up with that like kind of selection bias of who says what, So let ask like, it sounds like a slam dunk, like who, what are the objections to using? true rating during the sales process, who are having those objections and how do you like run towards those?
16:08 Dan Morgenstern: Yeah, for sure. that's, yeah, I like that final point of running towards it is there's no reason to hide what the objections are. I'm a big fan of getting the objections out early, you know, as early as possible. And I think, you know, one of the main ones that pop- that pops up is just, are you slowing down my lines? Especially in a place like a grocery store that, you know, the people will abandon their basket and that kind of thing. And so we do have the ability to do things like throttle up and down how frequently questions are asked and whatnot. And so I think it's, you have the speed of checkout. There's a little bit of angst sometimes around, hey, will people give honest feedback if they know that they're giving it right in front of the cashier? I hear that one a lot, which is of course an interesting, you know, second. lesson in psychology of, will I give an eight when I really think it was a four because I'm worried that the person can see me. And
16:59 Warren Kucker: someone's staring at you, right? Yeah.
17:01 Dan Morgenstern: you might think that that's the case, except what we have dug into time and time again is the, guess the fidelity of the data proves out that when you see scores drop, it is so commonly tied to a story like that grocer that had the replenishment schedule or that it just becomes really obvious that no, actually. Customers are answering honestly. And so even if there's some subset of customers that do skew a little bit nicer, it's really more a different, more a matter of what's the spread between the top and bottom performers and the data becomes really clear and obvious at that point. those are probably some of the key objections that we get. And then the, I think the final piece, and this is where some of the length can come in, is just IT guys like to say, nobody's touching my payments device.
17:49 Warren Kucker: Yeah, yeah.
17:49 Dan Morgenstern: Yeah, that's where the complexity comes in for sure.
17:52 Warren Kucker: And the IT folks are worried about the device going down primarily or is there another?
17:56 Dan Morgenstern: Yeah, that's certainly a concern. Now we've got all kinds of controls around it. have, if they'll hear us out, then there really is no risk of it the way that our software functions. But yes, that is certainly first and foremost, the fear among everybody in IT. Nobody wants to be the guy that bought the solution that shut down the stores ability to collect payment for any amount of time.
18:20 Warren Kucker: So Simon, again, we'll talk about the sales part of this. We talked a lot about data, and it seems like it's a big data-driven play, which is excellent. You're in data gathering mechanism, and you're trying to gain insights from it. That's all you're trying to do, right? Hopefully, you hit the bottom line. When you have an objection like, will someone give honest feedback in front of, say, the cashier or an employee right there, do you hit them with data to say, no, actually, in self-checkout, we see similar scores on these types of questions, where there's no one staring at them? Or do you... Like just try, do you realize it's an emotional response to a question? They're just trying to find an objection and you actually try not to sledgehammer them with like data. What's the play? What's working?
19:00 Dan Morgenstern: Yeah, I think there's a happy medium. I there's the I have found that people will frequently tell you when they want an answer backed up by data and when they feel like your anecdotal response is good enough.
19:11 Warren Kucker: Interesting.
19:12 Dan Morgenstern: And I don't like nobody wants to have their their nose rubbed in like an assumption that they're wrong about. So I think if you answered every single question with like, good objection, but here's the data that says why you're wrong. It's not a great feeling on the other side. So
19:24 Warren Kucker: Right, that's a good call. Yeah, right. Yeah.
19:27 Dan Morgenstern: yeah, I think I mean, my preference tends to be go with storytelling first and say like, hey,
19:33 Warren Kucker: Okay.
19:34 Dan Morgenstern: great, great thought. We had somebody else who had felt the same. Here's what we saw and speak to it anecdotally. And if you have to back it up with the data, then pull in the data. And I think the thing that I've tried to learn for myself too is you don't have to answer every single question on the spot either. And so it's perfectly fine to say, you know what, if that's a hangup for you or your peers, give me a day. And I'll go. hunt this down with my team and I'll see if we've ever investigated this and I can bring data your way. think, yeah, you tend to find out what needs data and where somebody's comfortable with just storytelling.
20:09 Warren Kucker: That's interesting, yeah. It's something I struggle with as well. Not answering every question on the spot or not having to say yes to everything in order to get a sale over the line is a happy medium. It always seems like, great, nine out 10 things that they asked about, it was kind of dumb for us. And that one thing we don't do, but then I worked around it, right? And it's like, no, if you don't work around it, then you're like, oh man, that's the thing. That's gonna kill this deal, we don't have this feature, right? You extend yourself in a way that just like... There's a balance between just like trust and process, right? So like it's like you don't want to extend past that trust barrier. that's really interesting. On top of it, you're a data play. So like it's good for you to, if you were like, hey, great, self-checkout, same thing. You're actually showing them your dogfooding, like your own data and your own process, right? Like, well, actually we thought about this, right?
20:55 Dan Morgenstern: Yeah, absolutely. Right.
20:58 Warren Kucker: Like oftentimes 92 % of the questions are not about interactions with people. So people have no problem. saying the fruit's bad to the cashier, right? So there's
21:06 Dan Morgenstern: exactly.
21:07 Warren Kucker: something there. So obviously we're over indexing on this grocery item, but there's a lot of different
21:10 Dan Morgenstern: I'm sorry.
21:11 Warren Kucker: plays. Cool, great. How are you handling stakeholder management? So 12 to 18 months, IT, CX, operations, it's a good call out. Most of this would have lived with the CX team before, but you're trying to drive
21:24 Dan Morgenstern: Going to change that.
21:25 Warren Kucker: improvement for the operations team. So they're the ones with the personal stake. The CX team maybe doesn't explain it maybe, but like the... Value proposition doesn't drive a result for them compared to what they do now the same way it for operations. How are you managing stakeholders in a deal like that?
21:40 Dan Morgenstern: Yeah, I think first and foremost, you've got to figure out what is a common thread that they all care about. And generally speaking, that ties to some sort of company initiative. so, yeah, just trying to figure out exactly what is leadership from the very top saying on earnings calls, where are they investing, those kinds of things to try to figure out. All right, if I can tie this and attach this to something that is bigger than any one group, then I can get them marching to the, yeah. Sorry for the cliche, to the beat of the same drum. But yeah, I think that's really the first thing that comes to my mind is figuring out what do they all care about that can tie them together so that you don't just have this giant, well, hey, operations team, cool solution, but I've got this priority over here and the two are disjointed. And so I really think that's a lot of what a seller's job is, is figuring out, hey, if there's multiple groups. and you're running this horse race and they all have to finish at the same time, then how do you get them all focused on your solution to solve each of their problems at once? yeah, I don't mean to, what I don't mean is try to be everything to everybody. What I do mean is pick a common theme that you know matters to you.
22:54 Warren Kucker: Yeah, no, I'm skipping the Lord talks about this and proactive selling, right? Like in order on complex deals, each executive, what he called was trains leaving the station, right? They have a problem A, B and C they need to solve for. And your job as a seller is to generally try to reach out to the people that you know have problem A the most for you and your scenario, right? Like the operations teams, right? They need to drive EBITDA or top line revenue and there's a new way to do it, But then getting on a CX train, getting on an IT train, like in a way that makes sense. You get alignment, you start to build this through line up so that you don't, when you have an objection, there's a what's in it for them for multiple functions and it becomes harder to manage. You mentioned like, again, understanding the top line. Let say this, I think, I don't know that most sellers are actually spending time reading 10Ks and trying to figure out outside of
23:42 Dan Morgenstern: Thank
23:43 Warren Kucker: discovery calls, what the top priorities of executives are. Do you find that you're able to do that on 30, 40, 50 % of deals and leverage good information walking in or do you find you're getting most of that? Intel from your conversations with the team.
23:56 Dan Morgenstern: So that's part of my standard prep at this point. I mean, assuming they're publicly traded, first of all, it's a little hard when they're private and you're hunting through press releases and whatnot. But I will also say this is where I tend to leverage AI in a big way. And I'm just really trained. It's probably boring, but I'm a huge chat, chat to be the user. That's really my go-to when it, when it comes to AI solutions. But yeah, letting, you know, kind of running through and saying, Hey, I've got an upcoming call with such and such groups within this organization. tell me what was seven of the most recent earnings call from executive leadership and tell me how you think that applies to the CX team or what the operations team might care about. So that tends to be where I lean is, yeah, you've got to know what's important to the broader organization before you're walking in. I think that's kind of table stakes to be honest, before you show up to that first discovery call. The last thing you need to do be blindsided and. you find out that you missed that there were massive layoffs or that there's this massive expansion that because you didn't take the five minutes to go do some of that research, you don't even realize it when you're walking into the...
25:02 Warren Kucker: That's awesome. What we'll do is on the podcast episode, if you don't mind, we'll snag that prompt that you use on a recent customer, right? Let's say, let's figure
25:11 Dan Morgenstern: Yeah, go.
25:11 Warren Kucker: out the app that it is, right? Because most of the time it's a simple prompt. Sometimes there's a couple of nuances to it, but leave the listeners back with a little bit of to do. Cool. That takes me to my perfect next question. You talked about how basically there's a fine line between winning and losing a deal. There's really some margins between success and failure. Is there anything in particular, let's say other than that type of research that you feel like doesn't get done enough during the sales process, but is like, I lost a deal, I didn't do this, and you know what? Like I should have done this. Like what's the, in sales, what's potentially something that could be on that margin?
25:45 Dan Morgenstern: Yeah, I think I go back to... So you just asked the question around how are you getting most of your information and so what I don't want to come across is that I'm discounting getting that information from those calls and so I think what can be the difference between winning and losing sometimes is just giving your champion or your prospect or anybody within that prospect company a chance to tell you what's important to them and I will say I think this is something that I struggled with for a while and I think there's a... there's a difference, or there's a needle you have to thread between, I've got to get my story across. I need them to know that there's certain things that are, you know, fundamental about the solution. And I feel like I've really got to get through that. But also I need to give that prospect the space to tell their story and to see where their brain is and where they see it fitting in. And so guess I'll give you a quick, quick example. I was really ghosted by a call by a prospect, maybe two years ago that I felt like it was great. Like I had had this most recent call and I was like, my gosh, this is awesome. I was like borderline committing a pilot deal to my boss. And, and then of course the guy goes like three months and I haven't heard from him. And I'm sitting there thinking, okay, like that call felt great. Why did that not go well? And so I went back in and I watched the recording. I was like, there's gotta be something in here I can use to get him to come loose. And I'm hearing him open up and he was one these guys that, you really had to pull to get to share anything. And so when he finally started to share the, I must have heard something that I thought was just this awesome transition point into my next slide. And I basically cut the guy off mid-sentence, but right before I think he was about to give me something that would have been really useful and meaningful. And I went right back to my own narrative. And literally as I was watching this recording, I was like yelling it. the recorded version of myself, like shut up Dan. That was what we
27:34 Warren Kucker: All all right, all
27:34 Dan Morgenstern: needed. The end of that sentence is what we needed. And so I think, yeah, that margin of not overshadowing where your prospect's head is and allowing them that space to tell, to say their point of view is just huge. And if you're just so focused on, well, here's my 11 slides that I need to get through and I've got to make sure that I get through them on time because I know if I don't get to them, then I'm less likely to get that follow-up call. Forget some of that. Get your foundation out there, but also make sure that you give your team, your prospects the space to share what's important to them and their point of view.
28:11 Warren Kucker: That's a call out. think even in that particular example, something I struggle with, I actually don't even think it's as black and white as I'm just trying to get through, like, let's say my 11 slides, right? Like, let's say, I actually feel like, I think the art and sales is the balance between giving them enough to understand like what you're trying to talk to them about, but not so much that you're guiding the conversation, right? So like, I would love, I really prefer, I hate demoing my own product. I hate talking about my own product. Honestly, I'm on the other side of this. I want to hear about you, and then I want to give you a hypothesis I have about a problem that I'm solving, and then if that solves the problem, great, and if not, let's move. But you have to them, I feel like especially early stage, you're not known as much in the industry, don't know, there's a lot of like, you have to figure out what you're doing and why you're having the conversation. There's a weird balance to strike there, and you could really easily get off kilter, right? Where it's like I give it. I want to give you a nugget and then have you tell me about what you're doing. And then like that nugget can turn into too long. Right. And then
29:14 Dan Morgenstern: Okay.
29:14 Warren Kucker: some people just want a demo and you're trying to figure it out. But I often say, listen, happy to I'll go through a 10 minute demo. I say I hate them on my own tech. It's almost like my self deprecation. I much rather hear about you. But then I do it anyway and launch into 20 minutes of a demo. So you're absolutely right. There's a fine line. I think it's all about to me. It's all about buyer attention. Right. Like how do you have a limited attention span at work when I'm evaluating a piece of like outside service or software, I have a limited amount of context that I can spend brain power on this really easy to lose attention. And so how do you maintain attention throughout the process that to me is like a big area where like, that's where deals are one on loss, right? That's the margins. Cool, man. Awesome. All right, let's maybe two
29:52 Dan Morgenstern: obviously.
29:54 Warren Kucker: final questions. So you moved in from Banyan, which was let's say around financial transaction data. Now you're true rating, which is again, customer interaction data, I'm sure I'm oversimplifying. So it's kind of like a similar space. Do you feel like LLMs change this type of interaction three to five years from now? Where's the advancement of the technology in this space?
30:15 Dan Morgenstern: Yeah, I think in our space in particular, we're actually launching a product as we speak at True Rating that is essentially a natural language queryable version of our data where somebody can go in and say, what are the three things I should be focusing on most for this particular store and whatnot? And so
30:32 Warren Kucker: OK.
30:33 Dan Morgenstern: I think there's a lot of, you've got to meet people where they are. And right now, I like the vast majority of us, the vast majority of the public is generally familiar now with LLMs and using LLMs. And so I think there's kind of this divide, this, yeah, I think too, sorry, let me start that sentence over. I think there's kind of this trade-off where you need to make sure that you are meeting them where they are, but also continuing to find ways to innovate. And so, you I just got back from a big retail show called NRF in New York, National Retail Federation. And what I heard there from a number of, Yes, of our prospects and just people kind of walking by is they were kind of tired of hearing companies talk about AI when they didn't actually use AI. It was like, like AI adjacent is not AI. Like if you're you're saying that you are developing and growing on AI, you actually you better have something that really is AI and not just like 2015 machine learning. And so
31:33 Warren Kucker: Yeah. Okay.
31:36 Dan Morgenstern: what's interesting is I think the the average buyer now is just becoming more perceptive to what is. AI fluff and what is actually AI. so, yeah,
31:44 Warren Kucker: interesting. Yeah.
31:46 Dan Morgenstern: my two cents is I think there's, you know, got to be able to continue to innovate. You don't want to just be lagging and just doing what everybody else does. But you also need to be able to have products that meet people where they are as you have this evolution of.
31:59 Warren Kucker: Yeah. It's interesting. I've actually found that I actually don't talk about AI during the sales process at all anymore. I've actually like dragged myself into it's the same who cares how the sausage is made, right? Like it's just like this is a new problem that I'm solving that obviously we couldn't solve before with machine learning or traditional like computing mechanisms. We have a new way to compute and I have a new way to solve a problem. Who cares? don't call anything like nothing set as AI or separate anymore, right? Do you feel that like, at NRF, people were like, kind of like clamoring for AI solutions for like, not clamp, like probably over emphasis there, but like, there's that discussion, I want an AI solution, or is it more like, let's stop talking about AI? Let's just like, tell me what you're fixing, which which side of the coin might that be?
32:47 Dan Morgenstern: Yeah, a little of both. I vendors are certainly clamoring over telling you where they're at with AI.
32:50 Warren Kucker: Yes, of course, yeah.
32:52 Dan Morgenstern: So, yeah, I mean, think to the one point I just made of people are getting tired of some of the AI fluff. It's like get me to the nitty gritty, me to what's actually real here and don't just call AI and think that's good enough. But I will say, especially if you look at like publicly traded companies right now, there's an expectation that they are innovating and that they're investing in AI powered solutions. And so I don't think you can completely ignore it, at least in my world. don't think I can.
33:22 Warren Kucker: Yeah. Right. Yeah, right.
33:25 Dan Morgenstern: There are retailers I've spoken with where they have entire budgets carved out that are, hey, I have this pocket of money that I can invest as long as it is AI related.
33:35 Warren Kucker: Right, okay now.
33:37 Dan Morgenstern: There's some of that of feeling out how innovative is this company or at least how innovative do they want to be on paper and are they?
33:44 Warren Kucker: Yeah.
33:45 Dan Morgenstern: you know, required to go invest in AI. So I think there's a balance, I completely agree with you, just calling something AI, but not actually getting to like what the problem that it solves is useless. It's, it's, yeah, just describing a tool, but without the actual results.
33:59 Warren Kucker: Yeah, and that's part of the reason I think there's a tail wagging the dog scenario here where like, the reason that every company is telling you they have an AI solution and some of them don't is not everyone has an AI solution and everyone wants to hear where your AI solution is, right? So like, it's like a, and there's also a scenario where you're absolutely right, like boards are budgeting for AI. So then like part of the sale is that you have an AI initiative to talk about, right? But that's a rather ridiculous way to operate, right? So it's like, cool, like, When you're looking at innovation, innovation in itself is all that matters, right? Like, it's like providing a better product or service to my customers at a lower cost is all I care about at any point, right? How it gets done doesn't matter. And like, if someone's doing something with LLMs that is extremely innovative compared to somebody who's doing not using LLMs and is not innovative in terms of that final proposition, which is a better product or service for my customers
34:46 Dan Morgenstern: Yeah, it's not right here.
34:49 Warren Kucker: at lower cost, like then that speaks for itself, right? But like it doesn't. the function doesn't matter, right? really good example is like, your retailer's customers don't really care that they're using AI. No one's like, you know what, it's awesome. That true rating asked me the right question, right? Like, they
35:06 Dan Morgenstern: Exactly.
35:08 Warren Kucker: just answered a question, they had an experience at a store. If the experience gets better, if the produce is better and they're happier, that happened, honestly, because of like, true coaching, right? So like, you've had this open platform along the
35:18 Dan Morgenstern: Bye.
35:20 Warren Kucker: way to help it. They don't know and they don't care. No one's in that store is like, hey, you know what? This produce is brought to you by AI, right? That's not happening. So
35:25 Dan Morgenstern: Thank you.
35:28 Warren Kucker: I'm just like, let's talk about the problems. I have access to your conversations the way you never had access before. And
35:32 Dan Morgenstern: Yeah.
35:32 Warren Kucker: this is the end result. But there's a there's a middle ground. I think we're like six to 18 months away from like, it'll be silly that we were talking about AI as much. People be like, stop saying this is rather absurd. This is
35:43 Dan Morgenstern: Yeah, 10 degrees.
35:45 Warren Kucker: just like no one talks about like. Great, like we're digitized now. Like we used to be on paper, now we're digital, right? Like we have this
35:52 Dan Morgenstern: Yeah.
35:52 Warren Kucker: digital solution. That would be silly. Like, no, it's just a thing, right? So, exactly right.
35:55 Dan Morgenstern: Kind of ended up at www.
35:59 Warren Kucker: You should come to our, I still have a shipping company pitching their website to me in 2014. We have this website.
36:03 Dan Morgenstern: Yeah
36:04 Warren Kucker: Who cares, right? Like stop telling me about your website. This is a great example. I hadn't thought about this in a long time. So anyway. Dan, this is really insightful, really appreciate it. I want to
36:13 Dan Morgenstern: Good.
36:14 Warren Kucker: this, you have any conferences coming up or someone wanted to connect with you, where should they find you?
36:18 Dan Morgenstern: Yeah, I'm on LinkedIn, happy to connect there. I don't think I'm anywhere necessarily in person quite yet, but based in Charlotte, I tend to hop around the country. So by all means, connect with me on LinkedIn and say hey.
36:29 Warren Kucker: Awesome. Sounds good. Dan, really appreciate you the time. Thanks for being on.
36:32 Dan Morgenstern: Absolutely. Thanks, Warren.
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.
Related Episodes
Your Buyer Doesn't Know What to Ask For Yet
with Michael DeLeonardis
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.
Great Marketing Should Reduce Your Sales Calls
with Jen Chaney
This episode explores how AI influences demand generation strategies, examining contemporary approaches to buyer research and the transition from pursuing lead volume toward accelerating pipeline velocity. The discussion covers AI's contributions to content creation, individualized outreach sequences, and the integration of marketing and sales functions for revenue growth.
A Champion Isn't a Person — It's a Behavior That Shows Up When There's Good Friction
with David Weiss
David Weiss challenges conventional sales approaches by distinguishing deal management as a separate discipline from sales methodologies. He reframes champions as behavioral patterns rather than individual contributors and examines how behavioral shifts manifest across sales cycles.