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Selling Enterprise AI with Context, Adoption, and Measurable ROI with Daniel Simon

61m 30s

Selling Enterprise AI with Context, Adoption, and Measurable ROI with Daniel Simon

Dan Simon, strategic account executive at Glean, shares his career journey from legacy EMC/Dell (selling storage) to Lacework (cloud security) and now enterprise AI. He emphasizes the shift from "speeds and feeds" to selling business outcomes—tying solutions to revenue, cost savings, or risk reduction. At Lacework, he learned to quantify value and use MedPIC for qualification. Today at Glean, he applies these same fundamentals: identifying champions, multi-threading across stakeholders (IT, DevOps, CRO), and leveraging proof points to build trust quickly. Dan notes that AI has changed how sellers work—he uses call recordings and AI agents to automatically score deals within MedPIC and recommend actions. However, core principles remain: no pain, no champion, no deal; and hyper-specific, value-first outreach. He advises sellers to be diligent with qualification, even more so with powerful solutions like Glean. The company’s context engine addresses the inefficiency of multiple LLMs (ChatGPT, Co-pilot, Claude) by providing accurate answers, security, and governance. Dan stresses that adding value at scale—whether through insights or helping customers get promoted—builds trust and drives success, regardless of the technology era.

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You have the ability to build that context in, which is role-specific. And then when I kind of really looked at the industry, I'm like, "No, that's a big deal." It is. It's a huge deal. Where I'm starting to see the main traction is you come back to somebody. Like I said before, no pain, no deal. There wasn't a lot of pain because they're like, "Oh, are AI initiatives? Co-pilot." And they're like, "Well, Co-pilot only works really well in Microsoft. So let's like buy Chattu Bt. Chattu Bt says they plug in more into that. And now we're seeing a big pivot to Claude. So now all of a sudden, these companies have three different licenses and maybe they've got some point products for like call center, like legal. But they don't have a platform. Like you really need to have the context to have your AI be effective in the enterprise. Otherwise, you're going to have a bunch of different AI products that don't talk to each other. Welcome to the Revenue Builders podcast, a weekly show featuring B2B's sales leaders and executives, hosted by five-time CEO John McMahon and force management co-founder John Kaplan. The show takes guests in the barrel behind the scenes with the people who've been there, done that, and seen the results. Revenue Builders covers best practices for scaling and growing your business while sharing the pitfalls to avoid. Today, John McMahon and John Kaplan sit down with Dan Simon, strategic account executive at Gleene. They have a timely conversation on what it really takes to sell complex enterprise technology in the age of AI. Dan walks through his path from legacy EMC and Dell EMC where he started selling storage to lacework, where he then became one of the first sales reps on the East Coast and learned to move beyond speeds and feeds into business outcomes, metrics and executive level value. Today at Gleene, Dan is applying those same fundamentals to the fast-moving world of enterprise AI. In this episode, Dan shares how elite sellers can use AI to sharpen qualification, expose deal gaps, personalize outreach and move faster without losing the human skills that actually win deals. The conversation covers MedPig, Champions, Proof Points, Multithreading, Executive Relevance and why AI will likely make lazy sellers worse, but great sellers even better. Here we go. So, Dan, you're currently strategic account executive at Gleene. For the audience, just walk us through your career path at like a high level going from Dell, then lacework and Gleene and talk a little bit about why you moved from selling storage at Dell to do an enterprise software sales. Yeah, so I started at actually legacy EMC and we were part of the acquisition of Dell. So, I was still in storage boxes like VNXE, Extreme Myos, and then I was able to make my way from the SDR incubator program to inside sales, was covering the DC territory for a couple of years and moved my way down to DC to cover in the field sales. And then while I was at in the field at Dell EMC, I got a call from Chad Peats if you guys are familiar with him. One of the group is at Dell at the time, and obviously in the space, he hit me up and one of the things I'd always heard from my customers, they were moving to the cloud. So, that was the new movement and a wave that I heard happening and I heard that everybody's scared of security in the cloud. So, really me trying to look ahead in my career. I saw obviously a pay bump was important to me, so I saw a bigger W2 at the new role, but also trying to get to where the puck is going to be. I saw everybody moving to the cloud and I wanted to make sure that I was part of that movement and security was going to be very important there. So, I spent some probably about five and a half years there, I was one of the first sales reps on the East Coast, worked under Andy Byron, Mike Hoss, W2, and my really strong mentors, love working for those guys and they were the ones that really helped me adopt the force management and command of the message process. That was something that we really stuck to diligently there. Frankly, we had trainings come in and yeah, that was a huge part of the investment in my career and that led me to getting this job here at Gleene as being the first strategic sales rep in Southeast. So, yeah, good for you. And then talk a little bit about how you have the change or your skills had to change, your knowledge had to change as you went from selling storage to selling security and now selling AI enterprise software. Yeah, so when I was selling storage, a lot of it was just around refreshes. So, I'd be selling you a newer faster box per se when I got to lace work. I'm selling, it felt like I made a pivot to selling more outcomes. So, everybody's moving to the cloud. There's a reason behind that movement, whether it's they're trying to save cost or generate more revenue. So, I had to find a way to have Gleene have lace work tie to that revenue driver for them and maybe, you know, obviously we all hear about driving revenue, reducing risk, reducing costs. Like, those were the real outcomes that I had to focus on and that was a new muscle for me. It took me probably a year to get going and probably lost a bunch of deals just talking about speeds and feeds and then once I started to learn more about the business and talk about outcomes, that's really, I really saw a big transition how I sold it and obviously affected my W2, made more money at lace work than I had ever made in my career. But that's what like my biggest learning is if you're not talking about the business outcomes and the thing that the CEO, the CFO care about, you're really going to be doing small deals. And the moment that you start talking about really strong outcomes that tie to revenue or reducing cost, that's where I felt a huge transition and obviously using a lot of the force management methodology practices as a part of that med pick and I'm really just diving into metrics. How do we quantify that business case? I have a finance background coming from Brian. So I got really interested in being able to quantify that business value and dive into the metrics and what does that actually mean from a cost savings perspective? So that's the muscle that I started to develop really strong. And Adele, you knew, like you did refresh, you knew who the buyer was and then you step into a lace work and you go to an account and you're like, wow, I got to find out who the potential buyer could be here and who could be my champion and who could be the coach. And there's a whole bunch of things that you had to learn or skills that you had to pursue that, right? I think even like multi-threading was part of that. Like that was something that I realized was much more important as I got into these more complex software sales is storage. You go into the director of IT. Like maybe the CIO is the decision maker, but the one who really cares about that is the director of IT. Then when I'm at lace work, I'm starting to talk to security people because obviously they own security. But the person that has to implement that is on the IT, the IT or the DevOps or CloudOps team. And then we also have products that would weave into the software development life cycle. So then I'm going to talk to like the director of DevOps and the VP of engineering. And the more I can create a ground swell across multiple selling avenues, right? Like that translates to the more business value helps me sell a higher premium or higher deal size and ultimately moves my deal much faster than just going single-threaded into the account. Yeah, so those multiple stakeholders you've talked a little bit about knowledge. And then what about qualifying? Like where am I in this deal right now? I've been calling on this account for three or four weeks. Where am I? How did you learn how to qualify where you were in the deal? I would always lean onto some of our principles we learned in force management like MedPick, right? Like what is the decision process? Who's the buyer and use that as kind of my gauge to really identify my holes? And I think what makes that a little bit easier today for me is using some things like AI to help me with that, right? Like it took a lot of think of how it works at lace work. I probably hop on a call with my area director and maybe my VP Mike and we would talk about the deal. I would maybe take me an hour of a discussion and then we'd leave that with outcomes where today I have a lot of my calls on call recordings. So I can up and even use Glean the company I work for today for that. And I have my call recordings on my notes. So I can say, "Hey, in my John McMahon agent that I've built that actually inherited a lot of the principles in your book that we have embedded that into an agent." And I think what's really cool is I can just say where are we at in Opportunity X? Give me a score worth where we're at within the MedPick. What are two or three actions that we could take in the next 48 hours to try and close some of these gaps? So before like I am trying to identify that on calls and putting a team together with my SE and multiple sales leaders. And now I think what's cool is you can use AI to automate a lot of them, which has been really fun. You're thinking of royalty for that? The John McMahon agent? I'll talk to Glean about that. Yeah, for sure. Hey, Dan, you've progressed. You were lucky, I think, to have rigor around qualification that the first companies that you work for and all the companies you've worked for have been really methodical about rigor, about bringing skills and knowledge to the sellers. What advice do you have for sales people out there today that says, "Yeah, I understand MedPick, I understand command of the message. I've been through that before." I'll just ask you a question. Do you believe it's more important now to really live and breathe those principles? Or if you've been through it 10 years ago, it's still the same as it relates to qualification inside of an account. So if you just thought about that, how much? And then And by the way, if you're going to automate, you're going to use Gleen to maybe automate, create a John McMahon agent. What does your previous knowledge help you to do with your future performance? And how have you found that? What's the cumulative effect? - So what I've found is I need to be, I guess, hyper-specific with the agents that I'm building, first and foremost. So when I'm saying like a John McMahon agent, I've embedded like what is a champion into that, right? So I think the first thing is like without a champion, you have no deal. That's always like no pain, no champion, no deal. That principle does not change. Even a, like we're obviously going, Gleen is a pretty big company at this point. We're going against some of the biggest players in the space right now. We've got myself with Copilot, you got ChatGBT, and Thoroppyc is the new baby that everybody's starting to adopt you now. I think that we need to be more diligent with how we're qualifying these deals and really getting to the business outcomes quicker and really helping the customer understand that much faster. So I'll put this into, I guess, a little bit of Gleen terms and how I'm selling today. So when I go head to head to somebody like a ChatGBT or a Cloud, for example, I need to come in with a perspective on how I can help that company in the first meeting and really kind of open their eyes to different outcomes that they might not have been able to solve today. So Copilot's great in Microsoft. ChatGBT is great as like a general knowledge management when you start to bring things into your internal company knowledge, it really starts to fail. So that's where when I'm selling, I try to talk to, like Sam calling on the CRO, like what are three to five use cases that you can implement today that would drive a very, very different outcome for your business? Like those are some of the things that I like to be hyper-specific. As it relates to like forced management, that stuff doesn't change. Like we still got another decision process. We got to know the metrics that that impacts across all the different business units. What is the buyer care about? If it's a CRO, they probably go up to like a COO. Most of the time it's reducing the amount of time it takes for them to sell or improving the amount of revenue that they could sell per deal conversion rates. So those are some of the different language and terminology that I'm using, but I have to change that depending on the person I'm talking to. So I love that. I think that what I heard you say is multi-threading. Like that's a non-negotiable today. If you're gonna be successful in sales and you know, I don't care what you're selling. If you're not multi-threading, you're gonna be in jeopardy. So what I kind of hear you saying is, instead of thinking about what I've learned and how it's kind of like a check in the box, like I have a champion, that ain't cut me anymore. So you tell me you have one champion selling Glean, you ain't gonna make it, right? Because the good news is the massive opportunity on the problems that Glean solves. So I would just encourage people and to listen to this and what you said is like all those principles that you have, the better your solution, the more impactful your solution, the more diligent you're going to need to be with your communication, with your execution, with your qualification. And if you just learned how to do med pick a check in the box, like I have a champion or I don't have a champion and you don't know how to get multiple champions at this stage of a career. - You're a lot of trouble. A lot of trouble. That's why I love your book, Johnny. I think one of the, I told Johnny in the Qualified Sales Leader, one of the favorite parts that I think John did, which was so unique is that he told the story. Like he took the principles of qualification and messaging and all the things that a rep has to do from an execution standpoint. It's almost like you took like a pre-AI version of it and you got it into the workflow of what a CEO and a CRO and a sales VP and a seller actually go through. And I think you just did a great job of talking about like what's real. And not doing like MedPick is this. You know, it's this check in the box and say you gave real live examples with real live scenarios. And that's what's selling is now. Real live examples, real live scenarios that are going to question how you qualify, who you qualify with, what you say to them, not just the need to qualify. - So sure. - I'm glad to have you. - Good question to the board, Johnny. - I'd say I'm fortunate here at Gleene too. Like we do have a lot of successful customers and part of the mantra is proof points. So if I can share a relevant proof point with somebody and actually talk about the outcome that somebody has had, it's only gonna add more cloud to my pitch, right? I'm a salesperson. Like everybody has the seller deficit disorder. They don't understand, I don't understand their business. And like their eyes are already glazing over a little bit by the time they're talking to a salesperson. But if I come in with a perspective, I'm hyper specific. I have a business outcome that I can affect with that person. It's really gonna open their eyes. And I always, I think trust is a huge part of every single sales cycle, right? We're gonna have to build that trust fast in the way that they trust you as you bring value to them very quickly. And you come hyper researched. You're very specific to how you can help that person. One of my favorite books is called The Go Giver. And the principle of it is how much value can you add to somebody at scale? And ultimately that's gonna come back to you and return whether it's financial return, which is I'm a coin operated guy as a salesperson, right? So I'm always trying to add value to people as fast as possible in at scale. So if I can add that to one person, well how can I add that to multiple people in the business? - I love that. - You know what I'm saying? - I still have as we're gonna help people grow their careers too. Like a lot of the people that I've sold to have gotten promoted. Like that's something that I take a lot of pride in as well. - I love that example. For years, we used to talk about how to add value to a customer even without a conversation. And you know in the old days it was sending them points of view. Like now it's an expectation. And I think we're actually evaluated by our customers by what value, if I'm gonna spend some time with somebody who's just not just gonna give me information about their product, but who's actually gonna tell me something or ask me a question that I haven't thought of. What I love about what you just said, Dan, is I encourage all sellers. Like every time you interact with a customer, doesn't have to be zoomed, doesn't have to be face to face. You send them something, it has value, not just filling up their inbox. It's almost as if you had a face to face conversation. So if you sent three or four things with a highly relevant point of view, that's highly relevant to their problems or challenges or what have you. In the way the human brain works, it's like they know they get to know you better every time. It's like three flights, not taking away being in person, but I think people really underestimate that. They don't figure out how to sell in their absence. And I think it's a powerful thing you just said. So go give her a good read for that. - I agree, yeah. It's not even, you wouldn't even say it's sales specific, but it's a great read about adding value to people. - Love it. - It's the audience, 'cause we mentioned clean a number of times and most of the audience might know what they do, but at a high level just explain to the audience what Bluene does, dude. - Yeah, so we were found and it was an enterprise search company. So when I started, that's actually what we were selling it as, is you can search for anything across your company and find it really fast. And now what we're seeing is the lines are starting to blur across that as somebody like ChatGPT, like Claude can plug into your company data. So what we're seeing is the real pivot of how we're selling the value of Bluene right now is our context engine. So what context mean is how you work as an individual in the organization. There's a lot of different application hops that you have. So I'm a fisherman, so I'll kinda do an analogy for you. So you can cast the net out, right? And maybe you're going to enough fishing, but you cast the net out on the back of your boat and you're just trying to catch everything. Like you might catch some other fish, you might maybe catch some trash floating to the ocean. And the ocean, what Gleene does really well is think of as having a fish finder, we have a setup already with a lure that knows how to catch that tuna and we're gonna go find that fish immediately for you. And the way that kind of translates the business value right now is we're seeing massive token consumption across all of the main LLMs. And it's the way that they're calling out to the different applications is very inefficient. It leads to poor accuracy, more token is being used. And ultimately you're trying to get your users to use this. So if they're not having accurate answers and they're spending a lot of money for that, they're not gonna ultimately see the value. So we're selling our context engine as a service right now. And that's where I'm seeing a ton of traction as people have said, "Hey, I'm trying to build an AI platform for my teams. Obviously I have chat GPT, I have co-pilot, but what we're lacking is like the accuracy, the security and governance layer in the context." And that's-- - Which nobody is talking about Johnny. - Well, we have people on. We're always kind of, oh, by the way, what are the concerns about security and permissions and that kind of stuff? Can I add to your analogy a little bit? 'Cause like I came and spoke at your day before you guys probably got there. I was with all of your sales leaders and was with Brad and his tail. And my stomach was hurting a little bit for you guys. Like what I was, 'cause I've been following you guys. guys, I really, really think you guys got something great going on. And I'm looking at where all the other companies are going. And when I started to think about like this analogy, you just said, your fishermen. Well, I think one of the unique advantages that you guys have right now, at least, and that's just saying, "Hey, I right now, right?" But like, I can get the context as a fisherman. I can get the context as the boat captain. I can get the context as I want to get the context up. I want to go and I want to rent that boat. And I want to be the person that's fishing on that boat. So you have the ability to build that context in, which is role-specific and permission-specific. And when I first read it, I was like, "Yeah, of course." And then when I kind of really looked at the industry, I'm like, "No, that's a big deal." And my right or wrong, is that a big deal? It is. It's a huge deal. And I think that's like, but I was feeling in South Florida. It's a great territory, of course. But I'd say a laggard compared to some of the folks like Silicon Valley, like Boston, like New York. There are some more tech-forward companies out there, areas out there, where I'm starting to see the main traction is you come back to somebody. Like, like I said before, no pain, no deal. There wasn't a lot of pain because they're like, "Oh, are AI in this? Is this co-pilot?" And they're like, "Well, co-pilot only works really well in Microsoft. So let's like buy ChattuBT. ChattuBT says they plug in more into that. So now all of a sudden, these companies have three different licenses, and maybe they've got some point products for like call center, like legal. So that's really what I'm seeing is going to be a big shift in the industry over the next, I don't know, year or two, but even gardeners writing around it about it now is the context is really can't. Like, you really need to have the context to have your AI be effective in the enterprise. Think about the slop that we get. You know, I think you guys call it the slop problem or the AI slop. And like Johnny does, like I do, like every other consumer out there is trying to figure out. We all have licenses of the same stuff. Yep. Well, I have three main licenses, at least three main licenses. And what I've noticed is, okay, if I have my personal situation and I have a Gmail account and I have, you know, like that workspace environment, that could be interesting if I have, you know, if I want inference, if I want speed, that's one that could be very interesting. If I want, you know, so they're starting to kind of morph out a little bit. And at the end of the day, I see that people still lean for one reason or another to a specific technology because they come to the realization that that's what helps me do my job better. So I think that the AI winners are the ones that get close to the work of the individuals. And they make that individual massively more productive. I think that's the only thing it's going to win. Yeah. And that will happen over time where there'll be different specialties for each domain. But right now, that's exactly. And I think what Dan is talking about and what I've seen is, if I'm very familiar with the domain, it doesn't give me the right answer. Right. When I'm not familiar with the domain, all of a sudden, I think, well, that sounds right. And I'm really familiar with the domain. And I ask you the question, you know, it's hallucinating. It's giving me an answer. And I look at it and go, that's not right because it doesn't have to deep domain knowledge that it has. I think that's what Dan's talking about when you're talking about accuracy with clean, right? Yeah. And what's good about us, you don't have to do a lot of pre-prompting. So you can probably get a good outcome with a cloud with a chat GBT. But there's a lot of upfront work that you would have to do with Glean, we're inheriting how we position ourselves, right? Is it merges together content, activity, and people data? So we know who you are in the organization, we know how you're working. And then we look at all the content. So it understands how you work and builds an enterprise graph. But then it also knows how Dan's Simon works and that I'm going into Salesforce every day that I use Google that I go into Slack that I have calls recordings and gone and how often I'm using those. So when I ask a natural language question, it just pops up. It just makes it so much easier with like I'm not I'm decently technical, but I'm not like an engineer, right? Like I can't create a hyper custom workflow. I just want to use the AI assistant or maybe use natural language to build an agent. And it just works. A lot of these tools like you try to do then. And it hallucinates like John was saying that you just hit it for me. I think it's the context of the user and those that have the ability to figure that out the quickest. It's the permissions and the security of a company and what somebody's going to be allowed to do. It's the proficiency of the I don't call it code code or no code or low code or whatever, but that you know creating agents and people's appetite to do that. That's where it's kind of leveling out for me. That's exactly going to that thought process is how I wound up with the tools that I have. Tell me a little bit about the one that's a sneaky one for me is like slack kind of a sneaky one. Like everybody's you know so many people are using slack. They're I hated it. And in fact, that's not that I hate. I want to be careful. I don't you know, but you know my company uses it and everybody says, low, it's it. I sent you a message and slack or whatever. Well, I'm one of those dudes. It's like, okay, well tune slack to when something gets sent to me gets sent to my email because that's my normal swerp flow. However, that is agent himself now. Go ahead. You're doing good job. Well, I hey, I still do it. I get it, you know, I'm not in slack every day, but I don't miss anything because they wrote it so I could get an email. However, for me, like like slack AI, just talk to me a little bit. Like I can imagine you guys are out there every day and they're like, you know, it's it's these companies, these big companies that are adding AI tools specific for that application that are that are probably not interesting, but you guys have your eye on. So talk to me a little bit about that. Why would I just, you know, just you we're all using slack. Why wouldn't we just use their slack AI? I know you may have a great answer for this, but give us some context. So slack AI is going to be great in slack, just like code Microsoft, co-pilot's great in Microsoft, but when you start to go out of their ecosystem, like Salesforce and Slack don't want to build a context aware connection for all of the different applications out there. So you could ask a natural language question and slack and be like, where are my most recent slack conversations? But I'm like, hey, where are we at on the deal with company X? Like I have had communications in Slack as part of that, but I also have gong recordings. I also have emails that through Gmail that have went out, and I just need it to pull in all of those different sources and give me a like we call on an account 360 agent that we built. I just need to type in a natural language question. It needs to pull all of the most relevant information for me. Sock doesn't do that. Or at least it doesn't do it well. They might claim that they do, but it's not it's not doing it well. That's why Gleens frankly been getting a ton of traction and like the enterprise wide casting a much wider net, but pulling back the most accurate answer for you. You said something at the beginning of this that I I just want to highlight, you know, you said there's a difference between being in Johnny set like a domain expertise in an application versus the ability to connect hundreds of applications and get that 360 view. And that is I think that's extremely interesting for customers right now. I do. For sure. Where have we sold deals like this before? Right. Like what are some roadblocks that I could face? Like maybe that's not in Slack. And there's even like you're pulling stuff from the public domain too. Like hey, help me do some research on this company. What are the different business units that I'm going to sell to? What are the different outcomes that these individual personas would then focus on? And I can craft my very tailored messaging to each of those people that's not just going to live in Slack. So you really do need something that's much broader. And of course there are great like there's legal tools out there. There's call center tools out there and they're going to do things that Glyn cannot do. But you're always like the first thing that everybody does in a company. And I'm sure we've all had an experience with like Google driver SharePoint like their search quality is terrible. And what a lot of the MCP MCP is the connectors that a lot of our competitors use. And MCP is inheriting that terrible search quality. So if you don't rebuild the context engine, you're going to have a really tough time finding the most accurate answer. Which again is going to go to how the user uses you know at the executive levels. Talk to me a little bit about like I think selling in your environment is not just selling at the executive level. It's like if I was selling your product, I would be selling to Dan almost as much as I would be selling to the CEO or CFO of a company. Because at the end of the day, how they are going to look at a success of any AI strategy is if I turn it off, we'll Dan screen. We'll Dan have a problem. That's my right now. That's my ultimate measure right now. You take away any of these tools. Will the wrap? Will the user use the will the end user screen? For sure. I think it goes back to multi-threading because I want multiple people to screen when that turns off. So I'll talk about a recent deal. I sold it a really large e-commerce company. So the way I landed at the CTO, he then passed me down to a couple of different personas. There's somebody who leads the AI program for the organization. She has a plug into the product managers, the engineers, the finance team, and then also legal with another domain. We build a use case for all of them. There is something that we can solve for each of those personas. So I like to sit down with each of them. They're one of the biggest differentiators that I learned early at EMC too with a very crowded competitive space is getting person. And person is going to differentiate you very quickly. And with all the noise out there in AI, I think there's also something to be said of, like, go build a real relationship. You're going to get a lot of outreach that looks very similar. Go build a relationship. You do that better in person. So my engineer and I flow up, flow up to this customer. And we met with each of these people for about an hour. I identified what their current state is. What are some of the different metrics that we had on some of these use cases? So maybe it's like, I'm drafting a PRD product review documentation. An HR use case around onboarding new employees, like drafting open racks, for example. There was like a variance analysis agent that we had to build for the finance team. We quantify each of those use cases. How long would it take you to do that today? In some cases, like it took, took maybe 10 hours, 14 hours. And part of that would be like, oh, well, now I have to go wait on an update from this person that sits over in a Mia. Right? We're on a different time zones. I'm waiting and waiting. Like that's stalling business. It's stalling revenue. So we have all of these little quotes as well and betted into this with the metrics, which I think really amplified the business case when we went back up to the CTO, who had already brought in chat GPT mind you. So we showed him a business case of like, yeah, you have chat GPT, but you're spending 10 hours on this task, seven hours on this test. This is how many different people that this is affecting the business. It was like a seven to 10 million dollar loss for them to not buy going. We were a fraction of that, of course, but our ROI of something ridiculous, like 50, 100X, right? Because we've been able to multi-thread. But if I only landed with like a single team, I wouldn't have had as compelling of a story. Now, do you think if they hadn't taken in chat GPT and you showed up that you could have gotten the deal because they might have said, well, let's use chat GPT first because we hear the deck could do it. So is it almost better that for salespeople that are selling a real good AI tool that they've already used one of the large LLM models to try to achieve what they're business outcome and you come in afterwards because they're more educated? I mean, I'm confident in my abilities that we could have got a deal down there, but I think you're right. I'm on that there is no pain. There's no deal. Like there probably wasn't a lot of pain yet. And that's what I've heard in my first year of selling is like, oh, co-pilot's our strategy. Oh, chat GPT's our strategy. I'm kind of feeling today like it was back at my UMC days. Like nobody gets fired for buying Cisco, buying UMC. Like people, yeah, we're not going to get fired for buying co-pilot or chat GPT. Like everybody knows about it. They're the biggest company out there right now. And I'm starting to feel that a little bit with Anthropic too, but they all have the same challenges. It's token consumption, accuracy. Like they're just not there. And now that they have the pain, my message has become much more compelling. And it's also helped us sell into a lot of Fortune 500 accounts now who have tried to build this themselves. They have two or three different products that are still not working. And it makes our story that much more compelling. They're not worried about security. That doesn't come up where you take in all your internal data. And it's getting consumed by these models and even customer data, our central data. They're not concerned that much about security and compliance. I mean, I'm sure they've got some good sales reps telling the story and then on the other side, like they're six to 12 months into that implementation. Like, hey, this isn't really what we're expecting yet. So, yeah, I think what's cool about Glean too is we actually do have a security product embedded into our platform. It's called Glean Protect. So it actually will scan for sensitive content. So you have credit card information or any type of PII that you don't want in there. So you can create a bunch of rules embedded into that or you can create your own rules to remove that from your index. So it also like some of my strongest champions have become CSOS. Like I was looking at some data, data security protection tools and like I'm a little scared of chat GPT them making sure that they get this right. And you're telling me Glean not only could help me alleviate the need to buy a separate, a separate product, but they feel much more comfortable rolling out Glean with the way it's not is permissions as part of that. And harr it the permissions of that source application, but also making sure that their users can't search for something that's overexposed and share point like there was an instance in a pilot that we were running, which frankly helped us sell the deal. They had the salary information of all the executives and it was publicly accessible. So somebody like me a seller, I could if I knew where to look for that and share point, there was probably hidden in a bunch of folders. But if you're in a chat GPT and a copilot like I'm not so sure that they would have been able to catch that and that's something that Glean can find. And who have you found in these deals, where's the power base does I mean you have the technical buyers like the CIOs you talked about a CTO you get the chief digital officers. And you have the business buyers you got sales you got up she got CS. Where do you like to go first second and why? First I'm always calling in the tech organization because I do believe that they are the ones that are going to roll this out and a lot of them have tried to build their own platforms. There's also a lot of opportunities I've had around the data teams. So people that are working with some of the warehouses out there like a data bricks like a snowflake they tell a very compelling message to they actually both use our product for their own internal use. And what they do really well for structured data Glean does really well for the unstructured data so they're a customer and a partner of ours. We can integrate with their platforms to tell them much better. Better together story but instead of having data scientists have to kind of create their own Glean. We can actually automate a lot of that for them. So I'd say tech organization is a great fit for us like engineering data teams. And then go to market is also a great one if we can drive revenue faster help with better conversion rates help win rates against your competitors. What I mean I'm it's QBR season right now so I'm actually using Glean to build my QBR deck and they're urging us to do that. And it's not even a deck anymore we actually have interactive HTML pages where I can say, hey, what's my forecast? What are the white spaces in my accounts? It's like a presentation but in a website format I can just type that all out into Glean and we'll create an HTML website for me which is really awesome. Wow. You got to start somewhere and for you to be able to do something like you just said these have to be like massive implementations. It's like the sucking in of content and like explain to us like how hard that is to implement Glean. Yeah, I mean the connect the good news is you can connect to you know 100 agents the bad news is you got to connect to 100 agents. Yeah, the connection is the simple. The part that takes longer is getting the people to actually want to build their own agents like Glean does have some agents out of the box. But until somebody understands the value that it can bring to them like that's why it takes a lot of handholding and I there's a big movement around like forward deployed engineers to try and use these agents forward people. Yeah, to deploy Glean. It could take a week or two. We index we understand like that's not the long part the part that takes longer is talking to somebody in finance and identifying the use case that we can help them with and then working with them to build that agent. Most of the time to build that agent is like an hour or two. But you really got to help find a task that they're doing multiple times over and over again like that's where I like how often are you doing this task is kind of step one because if it's only you're doing this once a year like it's not going to be that impactful. Like is there something you're doing every day or once a week walk us through that step by step process and that's where we'll we have a team ourselves and AI outcome manager that will help them actually build that agent out. But it takes some time you got to sit down with each individual person they're all doing different roles within the organization. Delta and I mentioned at the beginning you have to be hyper specific and really understand the person you're speaking to what is their day in the life look like so I can prescribe them the right agent or the right outcome. I think that what you talked about on like business outcomes. Why this is so critical today you can go in like these forward deployed engineers that's going to cost the company money whether they're going to pay for it or not you know that's a whole not the conversation where they have resources to do what customer success looks like the best advice I give to go to market teams today is find out the biggest business issue facing that customer and work backwards all the way down to the workflows. At the critical exchanges of information it's like what we used to whiteboard 20 years ago when we would say what are you trying to accomplish walk me through your process where the biggest bottlenecks and so it's like you can't sell this you talked about multi threaded earlier you have to sell this at all you have to sell it at the executive the business the line of business level. You have to sell it at the technical level. You have to sell it at the user level and you're going to have your crap together Like you can't be missing any of those like I tried to sell Glean at the CEO level of a company CEO is going to say this is an unbelievable concept. I Couldn't imagine why my company wouldn't want to do this But I'm certainly not going to tell them which AI strategy to go now. I'll ask them why the hell didn't you use Glean? But and that's you know, you can't shortcut these things anymore You're the mouth. They thread absolutely and start with the business issue I think the advice I have starting with the biggest business issue work your way backwards So you work your way backwards to the process flows the you know the technologies the User workflows and it's I don't think it's that hard, but you got to keep them connected You can't do it for a thousand different ones if you pick the biggest business issue and work your way backwards You're going to hit home run For sure. I mean I love starting high right a lot of the executives are getting like you've seen some of the reports around Just mentioning AI just jacks up the stock price, right? So they're all getting a push to roll out AI So if I can land high have a nice message around why Glean can be an enterprise wide solution Get there buy-in to actually send me to these different personas like that's where I've seen my biggest deals Happen versus if you are landing low you might be able to solve one problem, but It might it might be a little bit harder for you to go around the organization Right if somebody in engineering might not talk to somebody in HR that often So I'm always trying to get as high as I can and then work down the chain if I do land low of course Ask your champion to introduce you to other people right that's gonna benefit them. It's gonna be benefit the sales process, but The fastest ones that I've seen especially recently at our company you're landing yet Sometimes it is the CEO and smaller accounts, but for strategic it's CIO CTO And even the CFO because they probably already spent on Another LLM provider without all these tools if there is a way for us to justify that and Glean right now We're coming out with these really cool enhancements. We have a new LLM ourselves. It's called Waldo Waldo if you use that as the pre-processing engine We can actually reduce the amount of token consumption by about 30% So if I do a math problem and I've done this for a customer just today I was like hey if you roll this out to 20,000 of your employees that could be like a six or seven million dollar cost savings Just in the token consumption alone that isn't even me quantifying the Use cases of the outcomes for each of those business units that's strictly in token consumption and then that gets them like the CFO Holy crap, this can solve a really big problem for me and now I will sponsor you to go to the different business units to Identify where specifically you can help Are you selling this seat wiser consumption? We had been selling seat and I actually think this is where I see a big movement to this whole model is consumption Based moving forward is you're going to see I think a lot of the different AI providers Charging for consumption green now has a consumption model ourselves very recently So I think and benefits both sides is they're gonna be using our product more the more value that they're getting the more they're going to consume and it's our job as sellers and Post-sale resources to to make that customer hyper successful so we are Oh, it's come back into play here In consumption they do for sure But that's also the out they're getting more if they're using more tokens that means they're probably getting more value out of the tool Well, Dan when you go into these accounts as anyone talk to you about like they're worry about agents braw Like every sales rep is building agents Dales is building agents CS is building agents. They got agent, you know initiatives up top You know with the chief digital officer chief tech officer do they ever talk about my gosh Just seems like this agents braw and then that worried about that. Yeah, I hear that a lot I see it ourselves like lean like people are building their own agents And there are some great ones out there that sometimes I don't even know exists like there is I think there needs to be a management layer on top of all of those agents to better identify Like what are the best agents to use and we do kind of gamify this a little bit within the glean platform You can you can break it down By like sales agents how often are these ones being used? For example, you can ask our assistant like is there an agent for call coaching or is there an agent for me to do account research And glean will actually pop that up But I do think that's a big opportunity in the market right now to help with that problem for sure And when you're mapping an account we talked about multi-threading the account when you're mapping an account Walk us through like your methodology or or how you how you frame that When you're walking through these stakeholders these pains these use cases here's how I'm going to go after them Yeah, what's your methodology to do that? I lean on glean very heavily for that now What it looked like in my past life is I mean I still go into LinkedIn sales navigator I'll create a map of all the different personas. I'll look at their website And then I'll say hey to glean. I'll just ask Do research across their 10k financials find everything you possibly can across the internet about this company Then break out the different business units within this business whether it's like supply chain HR Legal etc Provide me a value statement across each of those and then provide me a proof point where I could Position this to somebody and then when I have that all I have in like a nice excel spreadsheet where it's all organized I like as they cool now today's my day to go after HR Give me maybe a five step sequence that I could send over the next couple of weeks to this persona and Provide a proof point there use some actual metrics a similar customer to them So I am leveraging AI for a ton of that right now and it saves me a lot of time because getting hyper specific is what you need to do to break into these accounts and cut through the noise I think the biggest Challenge is a lot of these emails are gonna sound the same because all are using the same AI tools The number one way to get meetings still to this day Is cold call for me People are leveraging their AI tools and I think people are getting stuck of like oh, I'm gonna write the perfect email I'm gonna write the perfect LinkedIn message well Your competitions also doing that but a lot of people are still lazy just to pick up the damn phone and make a cold call And we've actually been able to get a lot of meetings that way. I think it's still Just as valuable as it was when I started my career as a BDR and you got to believe that customers are starting to build or get You know some sort of spam type filters on the front of it front end of their emails where they just set sort of through knowing that some of this stuff is Just they've seen it for time and time again, and they're just rejecting. No, so they'll do Getting through for sure. Is it really is on the phones too? There's call screeners all over the place I got them on my own so it's it's definitely getting harder for sellers out there for sure. Would you even say that the Is it I wouldn't even call it co-calling anymore? I mean, I know maybe we emotionally connected that like the the good old days up but like AI There's no reason to co-call You could make every single call that you like what you just described And you've seen this and you're in your murray young guy You've seen this like if you had this back at the eat when you started at EMC You say okay today I'm going after this sector. I'm going after these your productivity level and your effectiveness is just off the charts And so anybody picking up the phone right now That isn't or or excuse me that's listening to this and thinking about you know How do you build a really good solid prospecting day like PG days like they're still companies I talked to today They're like oh, yeah, we don't do that anymore. I'm like what? Like I didn't say you do it the same way Right you did it 20 years ago, but like I mean that's so exciting You I mean what have you seen and just your ability to do walk me through like to do prospecting when you first started to do prospecting now just give us a high level overview of what that looks like for you I think the the biggest time saver has been my research and you're right It's not it's a warm call nowadays because I know exactly how I can help that person I've got a proof point of use AI to find that it is much more tailored. It's not hey I'm calling from EMC You know would love to talk more about your storage. It's like hey I know that you guys are building an AI platform. I read all about it on XYZ blog or I saw a YouTube video of you presenting and that's probably pulled from AI Here's how Gleen can specifically help and here's how we saved this customer millions of dollars and help them accelerate their AI And issues by using Gleen like would love to just get a couple minutes of your time to share more Yeah, the earlier's coming in with a point of view a business outcome And proof points and he's hyper specific about it and that's what's differentiating that I love it. You know what I hate right now. I'm getting so many reach outs from these from these people It's like they're taking a half swing. You know Johnny sometimes and you tell me like I just kind of I didn't I didn't follow through on the swing And they'll say hey, I listened to your revenue builders podcast with Dr. Jive And I'm like, okay, I lean in and then that's it I have this tool that allow you to do what the hell there's no connection between you listen to a podcast that Johnny and I did And I leaned in a little bit and then you freaking did a half swing like it's almost insulting but they still went to the play and struck out so clearly. - Only one three to play. - To play. - Every now and then, if I have a little time, I mean, I'm not a bad guy. But every now and then, I'll just say like, really? You listen to a podcast and then set me a spreadsheet of, you know, what, if it's just like there's no eat, there's no even connection. - Still get, I still get offers for sales rep jobs. - Oh, I know, I know me too. Me too. - I'm like, really? You did, John Mark? - Yeah. - Hey, Dan, talk a little bit about the tech stack that you're using right now. What do you, you said Gung, you probably use in Zoom. What else do you have in that tech stack over there? You have Salesforce.com? - That's right. So clearly, my favorite tool, of course. - No, it's literally my favorite product I've ever used. Gling is, like, I use it probably 15 or 20 times a day. So we have that plugged in, at least for me. We have a bunch of other applications, but I'll talk about us as a seller. So Gung for call recordings. We have Zoom and actually Google meet, our founders are from Google. So we've got a relationship. Actually with both, we use GDrive, Gmail, Slack for messaging. And I think there's a content management system that I actually never go into 'cause I have Gling, just suck the content out for me with the question. So we use all of those, but like, that's what, why I use Gling so many times a day is, that's my entry point. And I'm asking a natural language question. And I'm like, I need to compete with co-pilot on one of my calls and how do I position them? Like that might suck it out of the content management that we have for our sales team, but I'm rarely going actually in there. Or then it will pull some of the like call transcripts from other calls with other reps that we may have talked to about a very similar competitive situation. But I don't really need to go into that source that app anymore. It's just pulling that out for me. - Now does it learn, Danny? If I go in, I say, give me this 'cause I'll go into co-pilot. I'll say, give me this and it won't give me the right thing. And I'll refine the search. And I'm hoping that it learns from my first question to my third question to my third prompt. And then obviously, I go by learn from how I'm prompting. But will Gling learn when you ask like, maybe a two generic of a prompt for Gling and it gave you back something that was not exactly what you needed. And then you ask it again, does it learn from that? - It does. That's part of our memory layer with Gling. So it understands how you like to interact with the solution over time. There's also a new feature that a lot of the LLMs are coming out with and Gling has it as well, skills. So when I, it's a skill for outreach. Like what is the way that I like to do outreach? What is the way that I like to prep for a call? You can create a skill for that. So every single time it knows that Dan Simon would like to get this, maybe it's a bullet point format or executive summary of the company. What are three to five questions that I can ask this customer in a call? What's a proof point? Give me a targeted next step. Like that's a skill that you can pre-frame within Gling. So it absolutely does learn over time. So you don't do as much prompting. - Dan, when you guys are forecasting, or you have to update the systems, how often do you have to update these tools to feet with your forecasts? So once a week, if it Thursday, they expect our forecast to be updated before our call on Friday. We have agents, of course, within Gling that I could say auto update this for me. So it'll push our latest update. Maybe I had a call with my customer the day before or that day, it'll understand that. It'll see the emails that went out. And then I can say, hey, what was the next step that we had talked about with company X? Push that into Salesforce, or you could actually take the call recording, upload it to our Salesforce update agent that we have. It'll understand everything on the call. And then you can just click about and it'll push it out to Salesforce for us. - I think you're managers still asking you for updates, like verbal updates on where the deals are throughout the week. - Thank God. (laughing) It's like a blessing that we don't have to do that. Even I talked a little bit about call coaching. Like there used to be, you know, a big deal review calls with your managers, right? Like that's something that I can self-service as a rep now. And that's why I said like the qualified sales leader agent, like just help me understand where I'm at and the deal. Like if I need help, sure I can go to a leader to get a different perspective. But I think that it just helps expose my gaps, gives me some actions that I can take today. Like a lot of this is now able to be self-service as a rep. - The agents could, they could hallucinate as you could say, here's the three reasons I think John Kaplan is my champion. And the thing will come back and say, yeah, John Kaplan is your champion. And then you could say, well, you know, John Kaplan did this and then it could come back and say, yeah, John Kaplan is definitely not your champion. - Yeah. - I think that relies, you have to go back into the agent and I think Chatsy B.T., for example, to greet, I think everybody says, like agrees with everything that you. - Right. - You can also prompt the agent. - You can go in with you, ask that, right? - That's right. - And Kaplan is my champion, it answers that. Yes. And he said Kaplan's not my champion, it answers Kaplan's. - It's a pleaser. It's an AI pleaser. - There's ways to tune that within Glean. So you can say, be a hypercritical of my deal, right? Like expose the gaps, don't be in agreement with everything I say, like the way that you prompt it and ask it to respond, it will follow that instruction. So the qualified sales leader agent is actually very critical of your deals. It's not gonna make you feel good, but it's gonna tell you where all of the gaps are in your deal and it actually give you a color, it'll give you a red, yellow or green where you're at in that opportunity. So I think the way that you prompt it is gonna be very important. 'Cause if you just go to the LLM, you're right, it's gonna say everything's great and fine, but you really have to refine that in the agent. You can do that for sure. - Can I get a royalty on that one? (laughing) You got to make man agent, the QSL agent, all right. All right. - Yeah. It's probably pretty accessible knowledge, I guess. You gotta buy the book and then you got access to it. - Got it. - I've heard it many times with people who've copied a lot of that stuff and actually tried to put it into LLM and put it into their own system that they're building. - Oh, that's a problem for you, John? - Yeah, probably shouldn't have wrote the book. - Yeah. Try to be a force management. That was you giving, right? The go-giver you're giving. You're giving back to the sales community. - That was the whole intent. I mean, you don't really make any money on a book. - That's right. - So do I. - I don't think you ever. - That's why you're interviewing me on the podcast that I'm not interviewing you now. You know all the value that you brought. - So it's just such a giver. - I ain't like that. - I appreciate it. Unless you're playing golf with them, forget it. - Yeah. - Forget it. Hey, one last point I'd like to make and get you guys coming on. All this AI that we're talking about, it gets me fired up because I think it's gonna make the lazy sellers worse and the great sellers better. And we just kind of alluded to it. Put my job, McMahon agent, you know, activating that. It's gonna tell me why John McMahon would tell me that I don't have a champion. But knowing how to get a champion and knowing how to, you gotta keep these skills sharp. You know, telling you you need to be multi-threaded versus multi-threading. You need that human factor. And as much as you learn about productivity and learning these AI agents, or what have you, do not stop learning about the human behavior of sales. Because, you know, the, I don't know what the software company was, but the last week or two weeks ago that we're AI, I don't know if it was clawed, I think it might have been clawed. We're at deleted the source code. It's like deleted the product of the company. And what I first thing I thought about was the human factor of you and I, before we push that delete button, our finger would be shaking a little bit. And they couldn't teach it to AI. The AI just said, "Don't have this, we don't need it." And deleted the whole freaking program. I can't, it was in the Wall Street Journal, I can't remember what it was. But that finger shaking, that bubble in your stomach, that, you know, use these tools to take your skills to the next level. Don't be lazy. You know, what's my opening pitch that I should use for this customer? You know, practice it, try it on. Just don't be lazy and just, you know, first of all, like you guys have talked about, you could be getting some slop or some hallucination. But at the end of the day, you're responsible for what comes out of your mouth or, you know, what gets sent. - Well, I love what Dan is doing. He's separating himself by being hyper-vigilant on what he talks about. And more importantly, he's showing up face to face that you can't. - Love that. - I think a lot of these AI tools, people are hiding behind the AI tools and not going face to face with the customers. And then I'm just not sensitive, hyper-vigilant about what they're talking about. So you can really separate, you can use these tools to cap-spoint, to make yourself a whole lot better and really separate yourself. Or you could just be lazy and use the tools and you're never really going to gain any new skills or anything showing up in person though. I haven't we felt like that was like a real strength because you can read the room, you can feel, you can use your intuition and when you just over email or over the phone or even over, you know, video, it's really difficult when there's other people in the room to have that type of sensitivity to your intuition. - For sure. - Can't read about the language over the phone, right? I think like, you can understand very quickly if you got a real deal or not, just by looking at the way that the person reacts. You can ask them more direct questions by being in person. They're gonna trust you more. They're gonna appreciate that you flew out to their HQ to meet with people for a couple of hours. Like that absolutely differentiates you. - Yeah. - So Johnny Gleens gonna be on one hand, they should pay us some royalties, bro. They're gonna be really happy at how Dan represented the opportunity, the company, the, and they're gonna be a little nervous on Dan represented himself because I can't imagine your phone's not gonna ring off the hook dude for the skill sets that you displayed today. Well done. - Yeah. - Great job, Simon. - Thank you. I'm grateful that I got to chat speak with you guys. Thanks for having me on. - Thanks for coming. - Thank you Dan Simon. Thank you John Kaplan. Thanks to everyone for listening to another episode of the Revenue Builders Podcast. - Thanks for listening to today's episode. If you enjoy the content, please subscribe. Ray and review the show to help us reach more people. This show is brought to you by Force Management, where we help companies improve sales performance, executing the growth strategy at the point of sale. Check out ForceManagement.com for more information. (upbeat music)

Podcast Summary

Key Points:

  1. Dan Simon sold storage at Dell/EMC, then security at Lacework (one of first East Coast reps), and now enterprise AI at Glean, moving from "speeds and feeds" to business outcomes.
  2. Selling enterprise AI requires multi-threading
  3. Qualification remains critical; principles like MedPIC, champion identification, and proof points are non-negotiable, but AI can now automate gap analysis and suggest next steps.
  4. AI tools (like Glean) help sellers sharpen qualification, personalize outreach, and move faster, but human skills (trust, adding value) are still essential.
  5. The key differentiator for Glean is its "context engine," which improves accuracy, reduces token consumption, and provides security/governance across LLMs like ChatGPT and Claude.

Summary:

Dan Simon, strategic account executive at Glean, shares his career journey from legacy EMC/Dell (selling storage) to Lacework (cloud security) and now enterprise AI. He emphasizes the shift from "speeds and feeds" to selling business outcomes—tying solutions to revenue, cost savings, or risk reduction. At Lacework, he learned to quantify value and use MedPIC for qualification. Today at Glean, he applies these same fundamentals: identifying champions, multi-threading across stakeholders (IT, DevOps, CRO), and leveraging proof points to build trust quickly.

Dan notes that AI has changed how sellers work—he uses call recordings and AI agents to automatically score deals within MedPIC and recommend actions. However, core principles remain: no pain, no champion, no deal; and hyper-specific, value-first outreach. He advises sellers to be diligent with qualification, even more so with powerful solutions like Glean. The company’s context engine addresses the inefficiency of multiple LLMs (ChatGPT, Co-pilot, Claude) by providing accurate answers, security, and governance. Dan stresses that adding value at scale—whether through insights or helping customers get promoted—builds trust and drives success, regardless of the technology era.

FAQs

Gleene started as an enterprise search company and now sells a context engine as a service. It helps organizations improve AI accuracy, security, and governance by providing context across different applications.

Dan moved from selling storage refreshes at Dell EMC to selling security outcomes at Lacework, then to AI at Gleene. He learned to focus on business outcomes like revenue and cost reduction rather than just product features.

Multi-threading is crucial because it involves engaging multiple stakeholders across different departments, which accelerates deals and increases deal size. It prevents relying on a single champion and builds broader support.

AI can automate qualification by analyzing call recordings and notes to score deals against frameworks like MedPick. It can identify gaps and suggest actions to take within 48 hours, saving time and improving accuracy.

This principle means that without a clear customer pain point and a champion who advocates for your solution, a deal is unlikely to succeed. It remains essential even with AI tools.

Gleene’s context engine provides a fish-finder-like approach, targeting specific information efficiently. This reduces token consumption, improves accuracy, and lowers costs compared to general LLMs.

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