Episode #262:
Sagi Reuven, Chief Revenue Officer at Deepdub, explains how ABM must evolve in an AI-driven market. He explains why trust and market knowledge set demos apart from production outcomes. He explains that sellers must communicate the roadmap and execution, not just the product. He closes with a lens for enterprise ABM that starts with the size of the customer problem.
“Successful ABM is about building something really unique and doing something new with your clients. Is this a $100 million problem I can help my client solve? If the answer is yes and you understand that, then you probably have a play that will lead to an enterprise deal.” – Sagi Reuven
This conversation breaks down how ABM changes in an AI-driven market, where buyers judge vendors by production outcomes, not demos. Sagi shares how trust is built through honest guidance, clear roadmaps, and real execution support. He also explains how to qualify opportunities based on the size of the customer problem to secure enterprise-level deals.
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[Transcript]
[00:00:05] Steve MacDonald: Welcome everyone to the C-Suite Sales and Marketing Perspectives Podcast. I’m Steve MacDonald, your host, and today we’ve got a really interesting conversation with Sagi Reuven. Now, Sagi, you are a Chief Revenue Officer, and your specialty, I would say, is helping your clients navigate the constant change we face.
[00:00:26] Steve MacDonald: And we already had a lot of change, which is we always know our ICP, the markets, the trends are always changing. You throw AI on top of that, and we’re in a constant state of evolution. In fact, do you have a definition or a thought on how ABM should evolve from a CRO’s point of view? I want to ensure we spend significant time discussing that today.
[00:00:52] Steve MacDonald: But if you don’t mind spending just a minute or two more on your background so we get a little bit more of an understanding of who you are before we dive in.
[00:01:03] Sagi Reuven: Great. Thank you, Steve. Great to be here. Hi everyone, my name is Sagi. I’ve been leading AI initiatives and bringing them to production for the last 11 years.
[00:01:15] Sagi Reuven: Married, plus two boys. I live here in Tel Aviv, like swimming, and I’m a music geek. I like to collect new music constantly. Big techno fan. It’s been an interesting ride with AI, as this technology is a significant transformation, both in how people think and in how they perceive value.
[00:01:36] Sagi Reuven: I think what led me to this role is doing that in several different industries and helping them capture and understand. I have been an advocate for bringing AI into real-world use cases for many years.
[00:01:52] Steve MacDonald: This is a great place to start out, right? Like great sales leadership has evolved and changed with AI in fundamental ways as well, and I’d love to just kind of start us out with your point of view on how that change has evolved and where we are today.
[00:02:11] Sagi Reuven: Yeah, so I’ll start with an interesting anecdote to answer your question. I had lunch with one of my clients the other day, and he told me that they just delivered a great project.
[00:02:21] Sagi Reuven: Obviously, again, it’s an AI company, and they just delivered a great project for a very large enterprise client. And someone called them and asked if they can help them with another AI project. Now, at first they were like, it’s outside of our scope. And you know, now they are considered the AI experts for everything because they made AI work.
[00:02:43] Sagi Reuven: So you see how this is becoming more consolidative when people actually perceive a vendor. Now you are the expert for everything AI, and I need your help with other things as well. So it goes in the direction of, people can quickly get access to software or build something, but there is a huge gap between selling a dream or a shiny demo and bringing it to production.
[00:03:11] Steve MacDonald: So, depending on where you get the source, 85 to 90% of AI implementations fail. So I can clearly understand if a big AI implementation works really well, the company’s going to say, “Hey, can you help us over here? Can you help us over here?” Like, in your mind, what’s the difference between failed AI implementations, which is the majority, and those that don’t?
[00:03:37] Sagi Reuven: I think it has to do with a couple of things that you need to be minded to. First of all, you have to know the market by heart. Like you really need to know what’s going on. And the second thing is that you have to be consensual and honest with your client at the level, even sometimes saying there may be a better way to do that.
[00:03:58] Sagi Reuven: Even if that component is from another company, you have to be trustworthy. They will consider you when they’re building something unique. You know, like if they have a really unique project and they’re expecting you to guide them on how to do that. And in terms of value efficiency,
[00:04:20] Sagi Reuven: it is not strong enough. You know, because you have a backlash from people saying, “Okay, so you’re automating a few things.” It may be conceived as automation 2.0, but in fact it’s not the case. If you do it right, you can take it in a completely different direction. It can be about scale or personalization. I think this is where it gets interesting. This is where your added value as a seller comes into play.
[00:04:49] Steve MacDonald: Okay. I have to unpack a lot of that because you just laid a lot on us here. So, one, I love that you answered the question between what’s a successful and what’s a non-successful AI implementation. You focused on trust almost right away.
[00:05:04] Steve MacDonald: I was just on a webinar with Forrester, and they talked about their number one prediction for the new year was: trust means everything. It’s the difference between success and failure. So I love that you, from a practical perspective, brought that up. The second part, though, that I want to ask a little bit more about is, the quick win on AI, which makes us more efficient.
[00:05:29] Steve MacDonald: Right. Then we can move on to the proactive items on our to-do list that we can never get to, right? Yeah. So AI and efficiency is a huge win. What I’m taking away from what you’re saying is if that’s all we’re requiring of AI, we’re leaving a huge amount of opportunity on the table. And is that a good takeaway? Or how would you reframe that or explain that?
[00:05:56] Sagi Reuven: I’ll give you an example from a developer standpoint, right. There’s one way to look at it. We can deliver the same amount of features, but with AI, instead of having five developers, we can keep one developer, whereas somebody else would say, with AI now I can keep my five developers, and if I train them to use AI properly, I will deliver much more features.
[00:06:22] Sagi Reuven: I can be a team of 25. So that’s the question: where do you want to take it? If this is all about optimizing something, it may well be that some existing automation solutions would work for you, or some cost-saving by procuring stuff or whatever. There could be other ways to optimize for efficiency.
[00:06:42] Sagi Reuven: That’s where also you can evaluate value. If you are only looking for the buck, then there is no transformation here. It’s just a cost-saving process.
[00:06:53] Steve MacDonald: So value. Huge word, overused all the time, but from our previous conversation, what I took away was that yes, we can gain efficiencies, right?
[00:07:05] Steve MacDonald: We can do a lot more than what we used to do before, but how is AI helping us to do things we were never able to do before? There’s so much potential in AI beyond increased efficiency and productivity, and I know that’s a huge part of value. And you talked in our previous conversation about how we need to recreate value on a continual basis to the point where your new business prospects that are coming in, they’re wanting shorter and shorter-term contracts because they don’t want to be locked in, right? They want to see how value is evolving in the marketplace. So what does that mean to us as single organizations, right? There’s only one contract with us, right? How do we rethink how we’re delivering value?
[00:07:57] Sagi Reuven: I think eventually sellers are becoming more and more—I don’t say multidimensional in a sense—but in many cases, I feel like although I’m coming in with a CRO hat or the seller hat, I have to wear the product hat for a moment. You know, like listen, or the other way around—it goes back to trust, and it’s a combination, right?
[00:08:19] Sagi Reuven: You also have to reflect: what is your roadmap? What is your risk team going to do? Things that, again, would give more trust to your clients in your ability to keep providing value to them. So they’re looking for a longer-term partner because they know that things are evolving very, very fast.
[00:08:37] Sagi Reuven: If our model is really good today, but my clients don’t trust me that it’ll also be the best in six months, then it brings us to this conversation about shorter terms. Right? Someone might say, “Okay, I’ll use it until somebody else comes in.” Whereas they are looking for someone they do want to stay with for the longer term as a strategy, but they need that trust—they need to know that they can stay with you. They want to choose a company that can serve them for a longer period of time. It’s not like a one-off. Things are moving very fast, right? Like on a weekly basis. So they need to know that they chose the right horse.
[00:09:20] Steve MacDonald: Oh, that’s really interesting because typically we’ve sold on an existing product and what it does. What you’re saying is we’ve got to know that product,
[00:09:31] Steve MacDonald: but we’ve got to sell the fact that we are the people who are going to come up with the next set of features and the next value equation, right? That we’re the smart ones that are ahead of the game, not only with what we have today, but we’re going to be the ones bringing the innovations on a regular basis. How do you sell that? That is a very different sell, right?
[00:09:55] Sagi Reuven: You have to communicate—communicate everything that you do with your clients constantly, all the time.
[00:10:00] Steve MacDonald: Is that also another reason why you started out the conversation in a various different way, saying you have to know your market better than anyone else?
[00:10:07] Steve MacDonald: Right? You have to know your customer better than anyone else because being somebody who’s going to continually innovate and provide value, you can’t be seen just as a technology company. You have to be seen as a consultant, right? You have to be seen as a peer, as a colleague, as somebody that gets it better than anyone else, because only that kind of company is going to innovate.
[00:10:31] Steve MacDonald: Right?
[00:10:32] Sagi Reuven: Exactly.
[00:10:33] Steve MacDonald: So how do you train your sales team? Like you are the leader of this organization—how do you practically do that?
[00:10:40] Sagi Reuven: It’s a trick that I learned from my previous boss. He was the CRO at Theater Array, and he taught me to always qualify by either a goal, a problem, or a need, and not to go to the usual blunt kind of approach.
[00:10:55] Sagi Reuven: His mindset was that when you want to do something big with a client, you want to build something, you want to support your client when they’re serving their clients. Then you need to search for either a goal, a problem, or a need, because then you can propose something that goes beyond just a product offering.
[00:11:15] Sagi Reuven: Then you can change the discussion into “Will your budget fit the solution?” to “Let’s see how we are going to solve the problem,” or “Let’s see how we are going to build together what you are aiming for.” I can give an example from existing situations that we have almost on a daily basis, because some of our clients, they serve voice agents, you know, so it’s a critical thing, right?
[00:11:40] Sagi Reuven: Because they do customer support on the phone. So our clients demand from us to be there constantly, all the time, and help them. And if they need to fine-tune the model for a new project, they expect us to do it quickly. So it’s not typical, just being a vendor. Again, the conversation about trust—they trust us because it’s their business and they provide services to large enterprises and they don’t want to be at risk.
[00:12:13] Sagi Reuven: So they have to know the people. It’s not even a company—they need to trust me at a very high level of assurance that I will be there for them and help them creatively figure out a solution.
[00:12:30] Steve MacDonald: So what you just described is very different than the typical process, which I always liken to, in an ABM model,
[00:12:38] Steve MacDonald: it’s like a baton race. Marketing creates leads. They hand it over to sales. The baton has now been passed. Sales closes a deal. Customer success takes over. The baton has been passed again. What you’re talking about, though—tweaking the model, always there—you’re talking about an elevated service component that hasn’t been there in the past. And that changes things. Clients don’t want to change teams all the time either, right? They build relationships. ABM is a relationship-based business.
[00:13:09] Sagi Reuven: Absolutely.
[00:13:09] Steve MacDonald: Right? So the last thing they want to do is talk and build the relationship with you and somebody in your team just to be handed off, especially when they know they’re going to need an elevated level of service—like tweaking the model. Right? That’s not a small thing. But tweaking the model not only helps you if you look at it that way, right? I have clients all the time that come in and are tweaking what we’re trying to do, and the first thing you think is kinda like, “Dang, I kind of had this down, right?”
[00:13:38] Steve MacDonald: But that continual feedback helps us evolve, right? We should really accept that. We should welcome that kind of feedback. We should want that kind of feedback. That is market feedback, tuning our service so we can sell it and do better and better as time goes on. But how do you—whether it’s a compensation question or whatever—keep it from being a baton pass and keep that level of service high?
[00:14:08] Sagi Reuven: My approach is to get a few people from the company involved earlier in the process. So I can say that I have a few subject matter experts on the project from the company. For example, if someone from the customer success team is talking to the client, they’re briefed on the client’s motivation—what they’re trying to achieve, why they chose one way or the other. This is a level of information that you may not always transfer, because it usually happens before the contract is signed.
[00:14:45] Steve MacDonald: Yeah.
[00:14:46] Sagi Reuven: So it’s mostly about that.
[00:14:48] Steve MacDonald: Here’s what’s interesting about this, right? I’ve told this story a couple of times on the podcast. I was talking to a Chief Customer Officer who recalled a conversation he had with his client, a Chief Information Security Officer—a CISO. This CISO had just gone through a buying process for a portion of their tech stack. They sent out an RFP—14 different companies responded. Every single company said, “I can check every box in your RFP.” And the CISO told the Chief Customer Officer, “The only thing I really wanted to know is what it’s going to be like to work with you after I hire you.”
[00:15:31] Steve MacDonald: Right.
[00:15:32] Sagi Reuven: Yeah. That’s when all the fun begins.
[00:15:34] Steve MacDonald: Absolutely. And what you’re doing is you’re taking some of that experience—what it’s like to work with us after you hire us—and you’re bringing it into the sales process. Is that a good way to articulate it?
[00:15:47] Sagi Reuven: Absolutely.
[00:15:48] Steve MacDonald: How important is that? Like, tell me on a scale of one to ten. It’s not brand new—it’s not something we’ve never heard of—but it’s not well executed. How important is it to do that?
[00:16:03] Sagi Reuven: I think it also depends on the market situation right now. There are conversations about where SaaS companies are going, because now everyone can build stuff on their own.
[00:16:15] Sagi Reuven: That changes a little bit about what you’re selling, because the product may be shifting away as the main IP of the company. People are starting to build internally because it’s relatively easy. But what you see in AI initiatives is that sometimes companies are missing how to bring it to life in the most proper way.
[00:16:42] Sagi Reuven: I think the shift in the selling process is also related to what you see in the business model. Maybe before, execution wasn’t that important. You could buy software, get trained, start using it, and it was okay.
[00:17:04] Sagi Reuven: You get a few training sessions, work with the tool for two or three years, and you’re happy. You didn’t need constant customer support. But now, this is all new. Even clients are doing something new, discovering things you didn’t think of. That wouldn’t happen as much in a typical SaaS play—it’s usually stable.
[00:17:37] Steve MacDonald: Although, it’s really hard to go to any SaaS company these days without them touting their new AI component. Everybody has a SaaS angle on selling their product. It’s almost like if they don’t, people ask, “Well, what are you guys doing?”
[00:18:00] Steve MacDonald: For all SaaS companies, a major lesson here is that inclusion of AI means we need an elevated customer service orientation. That wasn’t unimportant before, but now the customer experience—CX—is the most important thing we’re selling. Literally two years ago, McKinsey did a study and determined that CX was the number one differentiator in the marketplace. And if they updated it now, considering what you’re saying, it’s only more important.
[00:18:41] Sagi Reuven: Yes. I would even go further and say the importance extends into customer education. It’s really about teaching the client how to get the most out of the solution.
[00:18:52] Steve MacDonald: So how does this change things? Not only as a CRO, but fundamentally—how we hire people, how we train people?
[00:19:08] Steve MacDonald: If CX is the driver, everybody is in CX. Even down to invoicing, billing, procurement—everyone impacts the customer experience. How does this evolve the go-to-market strategy?
[00:19:30] Sagi Reuven: It changes how I operate with resources from the company participating in the process. I might bring someone from the creative team or the product team—people you wouldn’t normally bring into the sales process. Usually, you have your sales engineer or pre-sales engineer, the account executive—the usual squad. But here, I pick the person most relevant to the business case, not by title.
[00:20:11] Sagi Reuven: Sometimes I even bring someone from the research team if it’s relevant to what the client is trying to do. The goal is to bring the right person into the room and give the client exactly the information they need.
[00:20:26] Steve MacDonald: The ideas are popping into my head as we talk. I’m classically trained on the marketing side. Part of what you’re saying here is that there’s always a big disconnect between marketing and sales in the industry. Even what marketing says versus what sales says.
[00:20:46] Steve MacDonald: A big takeaway is that marketing should be talking much more about that first conversation they’re trying to broker with a company—and what that conversation really is. Right?
[00:21:02] Sagi Reuven: Yeah.
[00:21:02] Steve MacDonald: Because what you just described isn’t the typical sales conversation a B2B buyer would expect—where they think, “I’m going to be sold to.” What you just described is really a consulting session with the company.
[00:21:15] Sagi Reuven: Yeah. It looks more like a consulting session.
[00:21:17] Steve MacDonald: Yep.
[00:21:18] Sagi Reuven: I agree. Yeah.
[00:21:19] Steve MacDonald: And marketing typically doesn’t communicate that, right? They’re trying to coordinate that first conversation, and the expectation is, “Oh, this is a sales conversation. Let me hear the pitch.”
[00:21:33] Sagi Reuven: Yeah.
[00:21:33] Steve MacDonald: What you just described is not a pitch. That’s not a pitch session.
[00:21:37] Sagi Reuven: No. No. It’s very tailored to what people are trying to build or achieve.
[00:21:43] Steve MacDonald: So what’s your recommendation for CMOs listening, or CEOs thinking, “Hey, this is a good idea”?
[00:21:51] Steve MacDonald: What’s your recommendation for them in this new world—where it’s less about pitching, more about consulting, more about innovating on value over time?
[00:22:03] Sagi Reuven: I think you really have to advocate for best practices—how to maximize the output someone can get from the solution. This also ties into what we discussed about the competition.
[00:22:16] Sagi Reuven: Things are popping up all the time; new competitors are saying things. If you don’t help your client get the best value they can, when they compare you to the competition, they’ll be at a disadvantage. So for CMOs and CEOs, I’d say get more client feedback on usability.
[00:22:38] Sagi Reuven: That’s the real point. Going back to what you said—everyone has AI in their tools now. Look at studies where companies bought, I don’t know, a thousand Copilot licenses, and only four developers used it. Adoption isn’t there.
[00:23:00] Sagi Reuven: I have an anecdote about adoption. In one of my roles, I participated in a deal sold at the management level. It was a three-year software deal, a massive multi-million-dollar contract.
[00:23:17] Sagi Reuven: They instructed all branches to use the software. After nine months, it didn’t work. People pushed back—they didn’t get it, didn’t want to adopt it. Nothing good came out of it, even though the client had already made the decision.
[00:23:36] Sagi Reuven: They paid for the software, did the three-year contract, did all the training—but failure was in the adoption layer: getting people to actually start using it. When you add an AI feature, what do I do with it?
[00:23:50] Sagi Reuven: Remember when ChatGPT first came out? People were saying, “Try this prompt, try that prompt.” Then more content came out with all the “try this” instructions. You have to be there to guide people.
[00:24:08] Sagi Reuven: Maybe a new function for marketing is someone focused on prompt engineering, education, and posting micro-guides—“Here’s what you can do with your tool.” Otherwise, people won’t get it, won’t get the value from the AI feature.
[00:24:26] Sagi Reuven: Then it just sits there as a buzzword—it won’t help you stand out.
[00:24:34] Steve MacDonald: It’s interesting—you’re talking about marketing and prompt engineering. Nobody’s talked about that. Right before the holidays, I interviewed Intel’s CMO.
[00:24:46] Sagi Reuven: Wow.
[00:24:47] Steve MacDonald: One thing he did—he outsourced a majority of his marketing department to Accenture. On the team, he recreated the mix—developers and prompt engineers are part of the marketing team. That’s part of success these days. We need to rethink how we go to market, develop teams, and build expertise.
[00:25:16] Steve MacDonald: He said, “I don’t need leadership skills to oversee prompt engineers and developers, but I need them on my team.”
[00:25:23] Sagi Reuven: Wow. Amazing. That’s a great move. It shows the evolution—people were saying AI would take jobs away.
[00:25:37] Sagi Reuven: But what you just said is that AI created a lot of new jobs for Intel’s marketing team.
[00:25:44] Steve MacDonald: Yeah.
[00:25:44] Sagi Reuven: Right?
[00:25:45] Steve MacDonald: Yes. And it created new jobs for customer success, for sales, for every department.
[00:26:00] Steve MacDonald: I wish we had another couple of hours. Maybe we’ll have you back on. We’ve covered so much territory.
[00:26:01] Steve MacDonald: If there was one thing you wanted C-suite peers to take away today, what would it be?
[00:26:11] Sagi Reuven: The key to successful ABM and doing great things with clients—building something unique, doing something new—is really getting into their business case. Lead yourself by the size of the problem they have, not by product value or ROI.
[00:26:22] Sagi Reuven: Ask yourself: Is this a $100 million problem I can help my client solve? If yes, and you understand that, you probably have a play that can lead to an enterprise deal. That’s my take.
[00:26:50] Steve MacDonald: I’m very excited—you’ve permanently expanded how I think about many things. That’s the goal of this podcast: bring different perspectives, insights, and experiences together. What’s working, how we need to evolve.
[00:27:07] Steve MacDonald: From all different C-suite angles, that’s a rising tide that lifts all boats. Thank you so much for being part of that rising tide today.
[00:27:20] Sagi Reuven: Thank you very much. Thank you for having me.