Vicki Cantrell and Dave Finnegan on what retailers and retail tech vendors get wrong about each other.
Nobody has "champion" in their title. So how do retail tech vendors find the person who will push a project through?
Recorded live at RetailClub AI Festival in Huntington Beach, Ricardo Belmar and Casey Golden talk with Vicki Cantrell, CEO and co-founder of Vendors in Partnership, and Dave Finnegan, Operating Partner and Chief Connection Officer at BlackFinn Partners. The two hosted VIP Connect, a three-hour session held right before RetailClub kicked off, where retailers and solution providers sat at the same table to learn how the other side makes decisions.
Retailers think they know how retail tech vendors operate. Vendors think they know what selling to retailers takes. This conversation shows how much both sides have been guessing.
with.
In This Episode, You'll Learn
- Why "we do AI" stopped working as an opener for retail tech vendors, and what great marketers lead with.
- What's happening behind a vendor rep's pitch, and why the budget question keeps coming up.
- The ROI question that retailers say makes selling to retailers a real conversation.
- How to find the champion inside a retail organization when nobody's title says it.
- The one question a former CIO says changes the whole discovery meeting.
- Why retailers want vendors to challenge their roadmap.
If this episode changes how you think about how retail tech vendors sell to retailers, leave us a five-star rating and review on Apple Podcasts, Spotify, or Goodpods.
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This is the first of eight episodes we recorded live at RetailClub, rolling out across all four shows on the Retail Razor Podcast Network. Subscribe so you catch every one!
Featured guests
Vicki Cantrell, https://www.linkedin.com/in/vickicantrell/
CEO & Co-founder, Vendors in Partnership - https://vendorsinpartnership.com
Vicki is a retail strategist and community builder, recognized for relationship building and accelerated growth. She founded Vendors in Partnership and the Vendors in Partnership (VIP) Awards, celebrating partnerships between retailers and solution providers and creating a joint community of these industry experts to advance retail innovation and partnerships.
Her career includes Retail Transformation Officer for Aptos, NRF’s SVP Communities and Shop.org, COO of Tory Burch, CIO of Giorgio Armani and Gucci Group. Cantrell is a Vice President for the Retail Orphan Initiative (RetailROI), a non-executive director of Tandy Leather Company, and on the Executive Leadership Committee of the Retail AI Council.
Dave Finnegan. https://www.linkedin.com/in/davefinnegan/
Operating Partner - Chief Connection Officer, BlackFinn Partners. https://www.linkedin.com/company/blackfinn-partners/
Dave Finnegan is an award winning retail innovator, brand anthropologist, and storyteller with over 25 years of experience leading customer experience, tech and digital transformation. He helped launch Build-A-Bear Workshop (CIO) and later served as Chief Experience Officer at Orvis, driving the brand’s most successful era. Dave now advises brands and investors through roles at BlackFinn, the NRF, and NewRoad Capital Partners.
As a brand anthropologist and a member of the Explorers Club, in 2022 Dave dedicated a year to studying human experience. He traveled to every continent—interviewing indigenous leaders from the Amazon to Africa, scientists from Antarctica to the Galápagos, and some of the most interesting people in the world, including the librarian of the world’s oldest library at the Monastery of St. Catherine. He is currently pursuing a master’s in Anthropology at Harvard which is helping him to continue his journey to better understand human experience.
Chapters
00:00 Teaser
00:52 Show Intro
03:46 VIP Connect Recap: Inside the Room Where Retail Deals Get Made
04:18 What Is VIP Connect? The Event Bringing Retailers and Vendors Together
05:37 Everyone Says They Do AI — Here's Why That's a Problem
06:48 How AI Has Completely Changed the Sales Conversation
08:38 What's Really Happening Behind the Vendor's Pitch
11:40 The Decades-Old Disconnect Between Business and Tech
13:03 Forget Titles — Find the Real Champion
15:36 People Buy From People: The Power of Just Asking Questions
18:16 Stop Asking "What's Your Problem" — Ask This Instead
21:56 Show Close
Meet your hosts
Helping you cut through the clutter in retail & retail tech:
Ricardo Belmar is an NRF Top Retail Voice for 2025 and a RETHINK Retail Top Retail Expert from 2021 – 2026 and a Top AI Leader for 2027. Thinkers 360 has named him a Top 10 Thought Leader in Retail and eCommerce, a Top 25 Thought Leader inCareers, a Top 50 Thought Leader in Agentic AI, AGI and Management, and a Top 100 Thought Leader in AI Ethics, Marketing, Digital Transformation and Transformation. Thinkers 360 also awarded him an Elite Expert Certification in Retail, a Master Expert Certification in Management, and named him a Certified Expert in AI, Marketing, and Digital Transformation. Thinkers 360 also named him a Top Digital Voice for 2024, 2025 and 2026. He is an advisory council member at the Retail Cloud Alliance. He was most recently the partner marketing leader for retail & consumer goods in the Americas at Microsoft.
Casey Golden, is the North America Leader for Retail & Consumer Goods at CI&T, and CEO of Luxlock. She is a RETHINK Retail Top Retail Expert from 2023 - 2026, and Retail Cloud Alliance advisory council member. After a career on the fashion and supply chain technology side of the business, Casey is obsessed with the customer relationship between the brand and the consumer and is slaying franken-stacks and building retail tech!
Episode Music
Includes music provided by imunobeats.com, featuring Overclocked, and E-Motive from the album Beat Hype, written by Heston Mimms, published by Imuno.
[00:00:01] Retailers think they know how tech vendors operate. Vendors think they know how retailers buy. Look at my roadmap and say, I get that, but if you thought of this, challenge me. At VIP Connect, both sides found out how much they'd been guessing. Vicki Cantrell and Dave Finnegan join us live from Retail Club in Huntington Beach. If you're a retailer and wanted to know why tech vendors say the things they do and why they act the way they do that makes you scratch your head.
[00:00:30] Or if you're a tech vendor and you've always wondered why retailers react and respond the way they do when you call on them. This is the episode for you because no one has championed in their title and understanding how each other's business really works is the key to real partnership that solves your business challenges. Stay with us and get all the answers. You're listening to The Retail Razor Show, where your expert hosts and their guests
[00:00:59] cuts through the classroom retail and retail tech. Welcome back to season six of The Retail Razor Show, the top ranked indie business management and marketing podcast on good pods, and the original show in the number one indie podcast network for retail. I'm Ricardo Belmar. I'm Casey Golden. Welcome back, Retail Razor fans, to Retail's favorite podcast where we cut through the clutter to give you sharp insights on what's happening in retail today, tomorrow,
[00:01:28] and where we get real about what's driving the future of commerce. And we're just getting back from an incredible time at Retail Club AI Festival in Huntington Beach, California. We were recording live and in person. So rare, so rare, but it was amazing by itself. I can't remember the last time we had the opportunity to do this together. Yeah, 100%. And this is the first in a series of great interviews we captured at Retail Club.
[00:01:56] Eight amazing episodes in all that are going to be coming to you guys across the Retail Razor Podcast Network, not just on this show. So be sure and subscribe to all of them. So let's jump into this first episode, again, live and in person from Retail Club. Actually, this one is technically from right before Retail Club kicked off in a sense. Vendors in partnership held their VIP Connect event, three hours of retailers and solution providers on a lawn overlooking the Pacific,
[00:02:24] talking about how each side runs its business. It was my first time attending one of these. What a horrible venue. Yeah, right? You'd be in the grass, right? I missed it. So you're catching me up here. Retailers and tech vendors both think they know how the other makes decisions. Put them at the same table and they learn what matters to each other and why. Yeah, why vendor sales rep keeps asking about budget.
[00:02:53] Why what ROI do you need is the better question. And why nobody has champion in their title. Our guest ran the event, Vicki Cantrell, CEO of Vendors & Partnership, known across the industry as the very godmother of retail. That's right. And Dave Finnegan, operating partner and chief connection officer at Blackfin Partners and a former CIO and CMO. I mean, I think two of the most loved. Oh, absolutely. No question about it.
[00:03:23] It's so nice that you can usually find them together and get both at the same time. That's so true. What luck was that, right? Only at Retail Club. Well, the sunscreen's on. So let's get to it. Here's our conversation with Vicki and Dave.
[00:03:46] I'm here with Vicki Cantrell and Dave Finnegan, who hosted the VIP Connect this morning from 11 to 2, bringing businesses together to talk about business. I missed it. But Ricardo was there. You missed it. I was there. And your first time at the VIP Connect. Yeah. So what was the big takeaway? Oh, well, I want to hear from Dave and Vicki first. And then I'll give you mine after. How about that?
[00:04:14] Maybe you start with just what is VIP Connect? What was the event? Yeah, let's do that. So our audience knows what we're all talking about. So we're all in on the deal. Okay. Give us the rundown on what is VIP Connect. Yes. What VIP Connect is, is a group of solution providers and retailers. And we come to the table equally. We come into the room, although into the beautiful lawn today. Very nice. Very nice. Vista lawn.
[00:04:44] Outdoor looking at the ocean. That's not a bad deal. Every conference room should be in outdoor room. Yes. So we come into the room as industry experts because all of us, regardless on which side you're on, has been in the industry for years. For too long. So we put all those labels aside and we come in. And the premise behind VIP Connect, what we really have achieved, is that we are teaching each other about the way the different organizations run.
[00:05:12] Not about what their product is that they sell, both on the retailer side and the solution provider side. It's not about what they're selling or what kind of SI they are or anything like that. And on the retailer, it's not about their brand and what they do. It's how they make decisions and do business. And so it's a lot of aha moments and teaching each other because we're trying to get to business done better. Yeah.
[00:05:37] And the overall thesis was, you know, everyone talks about AI, obviously. Right. And we're standing on a beach at a retail club AI festival. And there's a huge opportunity to unlock the power of AI through partnerships, the right partnerships. Yeah. Because everyone in the industry is saying, hey, we do AI. Right.
[00:06:03] It's almost impossible these days for retailers and for partners to break out of that echo chamber where everybody is saying that they do it. So what we wanted to talk about today was the existing go-to-market motion. What does that look like? It's clearly broken. Yeah. Everybody is saying that they do AI. And when everybody says that they do AI, how do you make a great choice for what you're going to do? And how have the questions changed?
[00:06:32] We really heard a lot today about how, what the normal things that happen in a meeting cycle and a sales cycle and how you get to those real conversations that are going to potentially lead to a partnership. Wow. The questions have completely changed. It has changed.
[00:06:49] And I think that it's an effective AI itself and both not just in AI that tech vendors selling to retail, but just in how retailers use AI natively as it is or before they even get to selecting an AI solution of any kind for anything else because we're all using it. Everyone's using it in that meeting for their own purpose. And I think that, I agree, that is one of the things I noticed that the questions that are getting asked in those early discovery meetings. I think every reader is probably used to hearing, do you have budget for this?
[00:07:18] Do you have, is there a project assigned for this? What's your timeline for deployment? All these kinds of standard things. Those never change in a project. But I think how you get there is changing because of the AI questions. So that was to me the big thing that, and at least I thought it was great that from all the vendors, I think, recognize that in a way, right, they get it. They can't lead first by saying it's AI. Yeah.
[00:07:42] Because every retailer assumes that they wouldn't even be talking to you if you weren't doing, if AI wasn't some aspect of what you're doing. But to me, the big thing for the vendors there is understanding you got to lead with what you're solving. Yeah. All right, don't tell me that you have this amazing solution. Tell me what problem you're going to solve for me. Yeah. So one of the examples actually to this point that someone used was that someone said, hey, can we meet with you? Yada, yada, yada. They clicked through their website. It was all about AI.
[00:08:11] It was zero about the problem that they were trying to solve. Yeah. And they walked away saying, I don't even know what this company actually provides. Right. Right. So we talked a lot about really great marketers. They market the problem. Right. They don't market the solution. They market the problem. And so as we go into this as retailers and vendors, marketing the problem and getting super clear on the problem clearly was an important part of the conversation today. Yeah. Yes. I agree.
[00:08:38] And one of the things that you and I talked about, Vicky, that I thought was a big takeaway. So that to me is kind of like on the vendor side, what do you need to be aware of? But what I thought was interesting on the retailer side to be aware of what's the process happening behind the scenes at the vendor and how they're positioning to you, how they're pitching you and understanding why it's coming across that way. Because there actually is meaning behind it on the vendor. A lot of it has to do with how the sales team, how the marketers are being measured in their own business. Right.
[00:09:06] Because much like retailers trying to hit a sales number, right, and how much product, how much merchandise are they selling? Well, the vendor's got the same thing. They're trying to meet a number every quarter of how much technology are they selling and they're all being measured on it. So every person you interact with from that vendor, somewhere behind them is someone asking them, what's the status on this opportunity? Right. Do they have budget? They're getting asked the same questions that they're asking you and that's why you're getting them.
[00:09:29] It's not because they're trying to waste your time or, you know, find the super secret in to get in there and sell their solutions. So as much as it is, someone's going to ask them the question and they're likely to get told. I think this is the part that gets left out. If the answer is, well, I don't know yet, we haven't gotten to that part of discussion. There's going to be a sales manager behind him that says, we'll move on to the next account. You don't have time for that. Yes. And that's not really what I think gets anyone to their end goal of solving problems.
[00:09:55] I think that how that got reframed, that was a really good way to explain that, how that got reframed was really helpful. So the retailer realizes now that there is someone behind them that is saying, if we don't, if you can't identify who your champion is, where your budget is, et cetera, then we need to move on because they're hitting, needing to hit quarterly numbers.
[00:10:21] And what really the retailer helped to reframe is that's not the question. Budget is not that they have budget, but that's not the question. The question is, what do you, what ROI do you need to show? What is on the roadmap that, that you're struggling with as far as what is going to have to, because you don't have extra budget lying around, what do you have to do?
[00:10:46] So the retailers helped reframe when they understood there was somebody behind asking those questions. They then said, let's reframe this. I'm happy to tell you these five things. And honestly, the big takeaway from that is we all understand and agree that behavior has to change and organization structure on both sides.
[00:11:11] It's really, we have to start digging into that because we know what happens inside the vendor and the marketing manager and all of that. Right. And who's going to turn that over? We know what happens on the retail side, who's making procurement, et cetera. And so we did end up saying, everybody go and take fresh eyes on your organization and figure out how we can educate each other inside our organizations, even just to burn education. Yeah.
[00:11:40] I mean, that's, they're just not having the same conversation. We've had this problem for decades with the business side and the tech side, like not really being able to communicate, not being able to find business models that are aligned with each other, that support each other. And that, that hurts the projects going live and helps keeps us from going live. That sounds like the voice of experience. Yeah. Like you've been in therapy for that. Not yet.
[00:12:10] Not yet. But it is this, we have to be speaking the same language when we're in meetings, when we're in the same rooms and we can't do that with badge turners. Yes. We need everybody to show up and participate. Right. Because vendors are, they're quite nice. If you spend some time with them, they're fun and they'll pick up the bill. Look, they're, they are coming from the right place. Yeah.
[00:12:37] They're being asked certain things and it's translating rather than understanding. And the other thing I loved about that we covered was how to think about discovery. Um, you know, there's some, some things in the industry about who's your champion, who owns budget, et cetera. Uh, but we really kind of dug into how do you educate about your organization?
[00:13:03] Who can in fact be, who can help you understand the culture of the company to know who to talk to instead of going after titles? Should I, this is a struggle for vendors right now. Who do I talk to? Right. Right. And it's even getting worse because of AI. Yeah.
[00:13:21] And so when we started to talk about what the retailers need to educate them on from the standpoint of not titles, that was a big unlock, a big aha moment. It goes from titles to champions. Yeah. Right. Right. Because I've, we've worked with directors and VPs and CIOs and CMOs, all of which could be a champion. Right. Right.
[00:13:46] And so sometimes we get very, very focused on one of the, you know, one of the people who have a seat in front of their title. But realizing that what you're really looking for from a partner perspective is who's the champion inside the organization. Right. And nobody has champion in their title. Yeah. So it makes it tough. Which was one of the comments someone made that I thought was one of the ones I'm going to remember. That was a good. No one has champion in their title. You have to find that person. Right. Right.
[00:14:11] But like the follow on question was being really transparent and say, who's the champion and asking CIOs who's the champion of this. Yeah. As a CIO myself, former CIO, I would have a zero problem answering that question. Yeah. This is the person who I've kind of set aside to do this kind of thing. Yeah. So I think it's all about asking the question, doing a little legwork.
[00:14:34] In fact, we talked a lot about one of the worst pet peeves for retailers is the lack of research going into a conversation. Right. And that's never changed. And by making, by taking a few extra steps, including who's the champion, that makes a huge difference. Yeah. And then changing the question from do you have budget to what kind of ROI do you need. Exactly. Right. Yes. Makes a big difference. Makes a whole different thing.
[00:14:59] And to the champion thing, the other thing that we uncovered that we thought was really interesting was who, who in your organization, they don't have to be your champion yet. Who in the organization can help you understand how to navigate the organization? Right. Like just have somebody explain their company culture. Yeah. And if you go here, this one's going to get upset, but here's a person.
[00:15:24] And we thought that was goal too, that just have somebody, it won't take long to help them understand how to work in the company instead of just beating their head against the wall. Yeah. It's great. I kind of thought that one of the things, and it was said a few times, but I think this is a recurring thing that we've heard for years, you know, people buy from people. Yes. And, but I think the phrase itself isn't the important thing is what does that really mean to everyone when you say it?
[00:15:49] And I think what I heard from all the different things everyone said is that part of it is it's okay to ask questions. Yes. I think a lot of people on the vendor side are afraid to ask the retailer too many questions. Yes. Every salesperson on the vendor side has been trained to use questions to uncover as part of their discovery process, but they try to be sometimes a little too cautious in the questions.
[00:16:12] And so they're not asking things like who's going to have the most interest in this, you know, to get that to the core problem you're trying to solve so that asking more questions can be better. Yes. And then it's okay to ask questions like switch from asking about budget to asking about ROI. Right. Yeah. Which I think comes back to at the end of the day, you're trying to solve a problem. Yeah. Right. So as long as if you're coming at it from the vendor side, you're not just trying to sell something. Right. And move on.
[00:16:38] You're trying to solve someone's problem with whatever the technology or solution is that you have to offer. And the retailer's goal is to just understand, can it do that? Yes. Because, and I think this maybe is something a lot of vendors miss too, is when they go into that meeting, they have a little bit of an assumption that the retailer already knows something about what they're coming to tell them. Yes. And the fact is the retailer might not know because part of why they accepted the meeting is because they want to find out. Exactly. Can what you have solve my challenge and my problem?
[00:17:05] And that's really the thing that both of you are trying to communicate to each other. You're trying to get to that same answer of does it solve the problem or not. So something that Casey and I were talking about off camera before this is, look, if you come to me as a CIO or a CMO when I was in seat and said, what is the problem that you have? That's different than saying, what are you most excited about in the next 12 months that you're going to invest in? Yeah. There are problems and opportunities. Most of the stuff I was doing wasn't problem solving.
[00:17:36] It was opportunity seeking. Yeah. Right. Yeah. I was trying to innovate. I was trying to get out there. Especially now. Also, yeah. So I think right now changing the what's your problem to what is the thing? I learned this from my brother when he sits down with people. He's an investor. So what are you most excited for in the next 12 months? And they start explaining things that they're excited about. And guess what? It'll plug into stuff that you do or people that you can introduce them to.
[00:18:05] Right. And so I think switching it from a problem base that you and I were talking about to a what are you excited about? Changes the dialogue in a really meaningful way. And I think we can all agree that like AI is going to be part of the solution. Sure. At some level, yeah. At some level, yeah. We don't need to talk about it immediately because the brands also have access to AI. Right.
[00:18:28] Just like every single solution that a vendor is putting out right now and being able to go direct to these players. And work directly through partners. So I think we can just make the assumption AI is going to be involved. It doesn't need to be the number one narrative. Mm-hmm. It's assumed now. It's assumed now, yeah. We need to take the language to it. And maybe some of the solution. Nine months ago was different, but we're not there now anymore. Some of the solution will be driven with AI. Some of the solution won't be. Yeah.
[00:18:56] Some things will be solved in other ways because it doesn't need it. Yeah. So it starts with the right business opportunity or problem solve or opportunity and assume that it's going to be AI enabled. Yeah. But right now, a lot of people are starting with the AI story and then not telling the other part of the story. Yeah. One other thing that we learned today that I thought was also interesting and a big aha moment for the vendors, the retailers, because they can't keep up with everything that's out there.
[00:19:26] And because they are now in the point where they're coming to events, talking to their peers in the industry, that has skyrocketed. Mm-hmm. Because everybody's trying something different and they've got to sit across and say, what'd you do? What'd you do? I tried this. Okay. So knowing that that has skyrocketed, what the solution providers don't capitalize on is how much information that they have across their customer base of what people are doing. Yeah.
[00:19:52] And I've heard this at three things in the last two weeks that I've been at where the retailers were saying, I would love it if the vendor would look at my roadmap because they're developing stuff so fast. Mm-hmm. Look at my roadmap and say, I get that, but if you thought of this, challenge me, challenge me. Right. Because I can't keep up with their enhancements and innovations. No, we need to do that. Okay? Yeah.
[00:20:18] And they're so used to being pushed aside or pushed at arm's length, they don't realize how much the retailers would love the expertise they have of the vision across the customers they have. Mm-hmm. And they're too worried about giving away someone's name that didn't get approval. That's not what it's about. Right. It's about speaking about the business problems that have been solved, what's working. Yeah. And that- It's about learning from others, right? Yeah. Who've already done it. Yeah. It really needs to change. They need to capitalize on- That's a great takeaway.
[00:20:47] Great knowledge that they have. Yeah. Yeah. From an anthropology perspective, we're going through a massive change, like a cultural change. And when we experience cultural change at this scale, comparing notes to others with others is the quickest cheat code to navigation of change. Yeah. Is comparing others' notes.
[00:21:10] So, vendors who understand that they're going to be talking to my customers and I want to put them in contact and I want to be in those trusted networks. Yeah. I want to be in the right rooms. Yeah. I think are the ones that are going to win. Yeah. Yeah. That makes sense. Yeah. I agree. That's a great takeaway. Did you have a good time? I did, yeah. I'm hoping I get to go again. Yeah. To another VIP connect. You and Casey are invited. All right. We'll be there. We will be there.
[00:21:34] Well, Dave, Vicki, thank you so much for stopping by and talking with us about VIP Connect. Yeah. It was great. And we're excited to see everything that happens. Definitely. I think something that everybody stands to gain for us. Yeah. Great. Thanks for the invite. Thanks, guys. Always good to see you guys. Bye. Put your sunscreen on. Enjoy. Yes, for sure. This episode is a wrap. Okay. Admit it. You love this episode. I know you did.
[00:22:04] Hit subscribe and drop us a five-star rating and review on Apple Podcasts, Spotify, or GoodPods. And if you're watching us on YouTube, like and subscribe and drop a comment before you go. I'm Casey Golden. Follow us on LinkedIn, Blue Sky, Threads, and Instagram. And subscribe to our Substack newsletter for highlights and bonus content. For transcripts and guest info, visit us at RetailRazor.com. I'm Ricardo Belmar. Thanks for joining us on The Retail Razor Show, part of the Retail Razor Podcast Network.
[00:22:34] Until next time, stay sharp, stay human, and stay ahead. This is The Retail Razor Show.



