The Discipline Behind Nine-Figure Deals with Stuart Gwynn

Summary

Revenue Builders Podcast – Episode Summary
Episode Title: The Discipline Behind Nine-Figure Deals with Stuart Gwynn
Date: May 28, 2026
Hosts: John McMahon and John Kaplan (Force Management)
Guest: Stuart Gwynn, Top Enterprise Seller at MongoDB

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Episode Overview

In this episode, hosts John McMahon and John Kaplan engage in a deep-dive conversation with Stuart Gwynn, one of MongoDB’s top-performing enterprise sellers and architect behind their first and only nine-figure deal. The discussion focuses on the discipline, mindset, and tactical rigor required to pursue and close massive enterprise sales, unpacking best practices from rigorous discovery through champion identification, scaling a sales team, and the proper use of process and frameworks—the so-called “science and art” of high-stakes B2B selling.

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Key Discussion Points & Insights

1. The Most Crucial Stage in Enterprise Sales: Discovery

• Discovery as Foundation: Stuart emphasizes that discovery is the most critical phase of the sales process. It’s where you deeply uncover pain, implications, and true positive business outcomes.
  • "You have to listen with intellectual curiosity...if you're able to fix it, what's the benefit to the customer? How is it going to make or save the bank money?" (04:17)
• Intentional & Personable Approach: Discovery isn't just a checkbox—it's an exercise in situational empathy, probing with authenticity and the “so what?” question to get beyond surface-level pain.
  • "The good reps really sit in it and really listen and ask the second or third level discovery questions to understand the implication. So if you do nothing, so what?" (04:17)

2. Building Trust and Champion Development

• Earned Trust: Customers will only open up and share true pain and quantification once they trust the seller understands their world.
  • "You need to earn trust and credibility...this is not the Spanish Inquisition. You can't go into any discovery meeting and ask 30 questions in a row. At some point, the client will shut down." (09:52)
  • Leverage stories from prior successes to build relevance and credibility.
• The Role of Champions: Real champion development goes hand-in-hand with business case building. Champions are tested by their willingness and ability to drive the deal internally.
  • "If you don’t have a champion, no deal is absolutely true...Are they willing to represent your product in the same way with or without you in the room?” (11:55; 13:55)
• Signals of a Real Champion: Incentive alignment, willingness to act, capability to influence, and the ability (and desire) to get others involved.

3. Going Deep: The Discipline of “Sitting in the Pain”

• Patience and Understanding: Don’t rush to solutioning. Let the customer articulate the full impact and implications of their problems.
  • "Pipeline builds courage...If you have enough pipeline...you're qualifying out as much as qualifying in. Our time is the most valuable asset." (16:14)
• Team Preparation: Internal pre-briefs and role assignments allow the team to probe with curiosity and authority, staying on point even with product or technical folks in the room.
  • "A prep call is industry standard, but making sure there’s a document. Usually, I have a readout...here’s the line of questioning we may want to go down." (18:58)

4. Scaling the Sales Team and Account Coverage

• Win the Ecosystem: Moving from “hero ball” (doing it alone) to coordinated, role-based selling across a POD structure.
  • "Winning the ecosystem means bricklaying versus cathedral building. If you view your role as just laying bricks, you’ll get bored...but if you see you’re building a cathedral, now your team's motivated." (38:00)
• Internal Enablement: Teach, trust, and empower your inside team – 70% done by others is better than 0% if you wouldn’t get there alone.
• Scaling for Large Deals: Laying the groundwork, building demand plans, and aligning multiple champions and stakeholders is a months- or years-long team sport, not a solo sprint.

5. Large & Strategic Deals: From Signs of Success to Execution

• The “Three Why’s” for Deal Confidence: Why anything? Why now? Why us (MongoDB)?
  • “If I was trying to take a step back...it boils down to the simple three whys. Why anything? Why now? Why Mongo [us]?” (23:11)
• Champion Testing and Prep: Have champions "recap the value framework back to you"—when the customer can pitch the solution themselves, conviction is high.
  • "If they can recite that back to you—holy cow, that’s a rock-solid customer." (24:35)
• Role Play as Essential Prep: Prepping champions for their internal objections and meetings is non-negotiable, especially in multi-million or nine-figure deals.

6. Enterprise vs. Mid-Market Selling: Scaling Depth and Breadth

• Org Chart Selling: Enterprise deals require understanding the web of EBs, influencers, and stakeholders—each line of business can be as big as a whole mid-market client.
  • “An account plan isn’t just a QBR. You really have to understand who owns what… Color-coding relationships and continually mapping stakeholders is critical.” (42:03)

7. The Role of Process, Frameworks, and “Art”

• Science + Art: Repeatable value frameworks (like Force Management’s) are married with situational, human nuance.
  • "The big difference is you got to marry the science of the value framework and command the message...But you can’t be the McMahon robot...” (37:12)
• Qualification Discipline: Maniacal qualification is essential, especially in a world (like open source) where many will use but few will pay.

8. Personal Career Choices: IC vs. Manager Track

• Staying as an Individual Contributor: Stuart discusses why he’s continued to choose IC over sales management, emphasizing the joy of the craft, mentoring others, and tackling new challenges.
  • "You don’t do nine-figure deals without leading. But for now, I love being an IC...I want to be your best rep.” (46:56–48:24)

9. The Evolving Role of AI in Selling

• AI as Prep and Acceleration Tool: AI enhances research, meeting preparation, and automates tasks, but top sellers must still master the human aspects—trust, curiosity, active listening.
  • "AI is changing the buyer...there's a decreasing tolerance for sellers who don't know the product...AI lets me automate prep and research." (51:18)
• Remaining Human: Deep discovery, coaching champions, and relationship building “can’t be replaced by AI.”
  • "It's called being a human. And I think AI is going to struggle with that." (33:58)

10. Leadership Best Practices for Managing Top Talent

• Give Time Back, Not Just Less Meetings: Remove unnecessary process, treat top talent as peers, and tailor support – not everyone needs the same touch or reviews.
  • "A lot of first time managers, they'll manage a 7-year, 10-year rep the same as the new rep, and they don't have to...Let's not spend time going through the operating rhythm type questions..." (56:24)

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Notable Quotes & Memorable Moments

“If you do nothing, so what? If you’re able to achieve this outcome, so what? ...You almost say, follow the money.”
— Stuart Gwynn (04:17)

"No champion, no deal is absolutely true."
— Stuart Gwynn (11:55)

“Pipeline builds courage…our time is the most valuable asset. If you can sit in that moment with the client…you’re qualifying out as much as qualifying in.”
— Stuart Gwynn (16:14)

"It's called being a human. And I think AI is going to struggle with that."
— John McMahon (33:58)

"Winning the ecosystem means bricklaying versus cathedral building…if you see that you’re building this cathedral…now your team's motivated."
— Stuart Gwynn (38:00)

“It’s absolutely okay to pursue the IC track as long as you want, but make sure you’re investing in the next generation.”
— Stuart Gwynn (48:24)

“AI is changing the buyer...There’s a decreasing tolerance for sellers who don’t know the product. AI allows us to be more technical…prep faster…that’s table stakes now.”
— Stuart Gwynn (51:18, 53:29)

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Timestamps for Key Segments

• [02:41] Discovery as Foundation
• [04:17] Personable, Intentful Discovery; Role of “So what?” questions
• [09:52] Building Trust & Avoiding “The Spanish Inquisition”
• [11:55] Champion Building and its Synonymity with Pain Quantification
• [13:55] Signs of a Real Champion
• [16:14] Sitting in the Pain, Patience, and Qualifying Out
• [18:58] Preparing Your Team for Deep Discovery
• [23:11] The “Three Why’s” for Deal Qualification
• [24:35] Recapping the Value Framework Back to You—the Champion Test
• [37:12] Marrying Value Framework (“Science”) and Human Nuance (“Art”)
• [38:00] Winning the Ecosystem; Leadership for Scale
• [42:03] Transitioning from Commercial/Mid-Market to Enterprise Selling
• [46:56–48:24] Staying as an Individual Contributor vs. Manager
• [51:18] AI in the Sales Process
• [56:24] Best Practices for Managing Top Talent

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Takeaways for Listeners

• Mastering large, complex sales requires not just process discipline, but genuine curiosity, patience, and tailoring your approach to both the customer and your own team.
• Rigorous discovery and champion development are foundational—not optional.
• Process frameworks are critical enablers, but never a substitute for situational human judgment.
• Individual contributors can and should lead from their seat, especially by mentoring and scaling their impact across a team.
• Embrace the evolving impact of AI on both buyer expectations and your own preparation—but know that the human element remains central.
• Leaders should customize their management style, reduce unnecessary complexity for top talent, and involve them as peers to drive retention and results.

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For listeners aiming to scale their impact in B2B sales, this episode is a roadmap to the discipline and mindset needed to unlock enterprise-scale revenue—grounded in best-practices, war stories, and memorable, actionable insights from the field.

Transcript

[Stuart Gwynn]

The big difference and the big magic secret that's hard is like you got to marry the science of the value framework and command the message because that's absolutely the only way that you can have repeatable process scale. I'm convinced when I came to Mongo I never sold an open source product. Granted we open source the community version, but we own the ip. But it's an open source product. Meaning for the listeners out there that don't know what that means, because I didn't. Someone can use Mongo, a customer can use Mongol, deploy it, run their entirety of their business on it, and never pay us a dollar, right? In my past life when I worked at Pure Storage, if you had a Pure Storage box with the orange glowing bezel, you paid us for that at some point. And so you have to be diligent with your time and discovery and qualification because otherwise you'll be spending time and resources investing in the next application that's going live on Mongo and they could choose to open source it and they never pay us a dollar and you just wasted your whole quarter chasing a deal that's a $0. So the value framework, you. You have to be maniacal about qualification.

[Podcast Host (Force Management Representative)]

Welcome to the Revenue Builders Podcast, a weekly show featuring B2B sales leaders and executives. Hosted by five time CRO 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.

[John Kaplan]

Let's talk to a top enterprise sales rep today and learn more about the current enterprise sales environment. Today's guest is Stuart Gwynn, who's currently at MongoDB. Stuart started as a BDR of Pure Storage in 2012. He was employee number eight and he was SDR number three. He spent seven years at Pure Storage growing his way from SDR to inside closing rep to white space field rep to commercial named account rep. Stuart was number four out of 99 reps the year he left Pure Storage for MongoDB. Since joining MongoDB in 2019, Stewart has been over goal every year and Stewart closed the first and and the only nine figure deal in MongoDB history. Let's welcome Stuart Gwynn. So Stuart, good to see you. So you beat your number at MongoDB. At the last five years you've closed the largest deal in MongoDB history. Talk a little bit about what you think is the most important stage in the Sales process. Let's go deep right away.

[Stuart Gwynn]

You bet. And thanks for having me. I listen a lot to this episode. So as a revenue builder, so, you know, at Mongo, I've been fortunate to learn from a lot of people have been on your episodes. And to answer your question, I think the most important stage in sales process is discovery. And the reason for that is because if you want to have an educated opinion, if you want to really understand how you can identify pain, attach to that and what are the pbos positive business outcomes you can attach to or ebs are going to reassign money and actually spend to solve this problem. You have to do that in discovery. You have to listen with intellectual curiosity and in a personable way. And you have to do that in a way that I would say you can really understand the pain. And if you can solve their problem and if we can do that successfully, then you're going to be able to go speak with an executive and have an opinion that's relevant to them and they're going to actually listen to you and partner with you to solve that problem together.

[John Kaplan]

Do you think that there's something that because a lot of people get it wrong, right, they can't get in there in discovery, ask the right questions, connect with a potential champion to. To even get to the next stage to kind of quantify the pain, you know, in the. In what you might call the scoping stage. So is there something that you do that's special in discovery that really helps you, that you think is a possibility that a lot of other reps don't do?

[Stuart Gwynn]

I think I'm very intentional and personable in discovery. So at the end of the day, we're talking to people, and these people are going to have personal problems. They're going to have professional problems. In college, I was an econ major, and one of the things that stuck with me was intent to drive behavior. So I really try to listen and understand what this person cares about, what motivates them, because different people are motivated by different challenges or different things. And so in discovery, it's no different. We may be talking to an engineer, we may be talking to an app owner, we may be talking to the VP of modernization. But all of them have a job to do. They want to be successful, and there's some implication if they don't do that job right? And so in discovery, just really sitting it. And I think the biggest two words I like to say is so what I'll say that probably more than most, but we may be you know, searching for answers to fill out our discovery capture. She as we call it, Mongo. But the good reps really sit in it and really listen and ask the second or third level discovery questions to understand the implication. So if you do nothing, so what if you're able to achieve this outcome? So what if we modernize and we move from legacy relational to MongoDB, so what, what implication does that have to the business? And I almost say follow the money. So I covered a large bank for a long time here at Mongo, and I like to coach my team and the inside reps who joined the team specifically to really look through the lens of intellectual curiosity. Look through the lens of if you're a client of a bank, everyone is, how is this going to impact you? How am I going to touch the process? What's wrong with it? And if you're able to fix it, what's the benefit to the customers? How is it going to make or save the bank money?

[John Kaplan]

Yeah, but what I really hear you doing, because you're, you're sitting in there, like you said, with intellectual curiosity and you're trying to understand the pain that the customer's in and you're trying to say, okay, so what? Big deal. You're not really thinking ever and you haven't said it. Thinking about, presenting, talking about your solution. What you're doing in the beginning is just sitting in the customer's pain with them.

[Stuart Gwynn]

That's the goal. And it's hard to do. I mean, let's, I won't lie. When I joined MongoDB, you know, I joined for a lot of the reasons of what Force Management was built to teach. And so Mongo has this BDR to CRO program which we can talk about later. But it's really, you know, they teach the value framework, they teach command and the message the way that I think it should be taught and the way that helps sellers build a repeatable process from top of the funnel PG to deal execution. But the challenge is it's hard at times. I always, I call it with my friends, I was a McMahon robot. That's a term we use sometimes, John. But you know, we're in there just trying to fill out capture sheets and get on a dashboard of how many NBMs or how many meetings we've had. And it's easy to tense up in the moment and just go through the motions. But if you can really take a step back and as a sports person, like the game slows down and once you go through with enough repetition Enough preparation, the game will slow down and you can sit there with the client and customer and live it with them and really understand the pain they're in and what they're trying to accomplish and why. And once you do that, then you can have the opportunity to present a solution. But otherwise you're just throwing spaghetti at a wall and seeing what sticks.

[John Kaplan]

So when you're going through discovery and you do and some scoping and doing, identification of pain, quantification of pain, you talked about implication of pain, how can you tell whether or not you are with the right customer or the wrong customer that's going to be able to give you that type of information? What's your clue? What do you hear, what do you don't or what don't you hear?

[Stuart Gwynn]

You often get delegated to those you sound like. And so first I think it's the types of questions you're asking. And then very soon, if they can't ask your questions, the types of value questions that you may be asking in the right moment, then you're not high enough. In that example, if you're looking for technical pain. And a lot of times I don't have to hear my voice in the room. One thing I think I do a little bit differently than others perhaps is in a discovery call, it'll be one on one. I'll make cold calls till this day. But if you're in a meeting and you want to, if you have a certain set of goals to go get, it may be prompting a different person in that room to ask that question. Even if I feel like I'm perfectly capable, maybe it's the essay, maybe it's the csm, but having the right plan and prompting a team member to ask that right question, it may get the contact to open up a bit more too. But specifically what you asked me is, you know, if you don't hear the answers that you're, that you're looking to get, either you're asking it the wrong way or you're asking the wrong person because they're not at power or they don't have the full purview to give you the answer that you're looking for.

[John Kaplan]

Well, can it also be, you know, a lot of times if you haven't built trust as a sales rep, then and they don't feel comfortable with you, that you truly understand the domain and that you might have a solution and you've seen the problem at other companies, you haven't built that trust, then a lot of customers are sitting there saying, why should I tell this guy how much that really costs us in the quantification and what the implication of the, of the, the pain is or negative consequences of not solving that pain. So talk to me a little bit about how you build trust so that the customer wants to give you that type of information.

[Stuart Gwynn]

And you're absolutely right. I think there's two things. One, it's what I started about.

[John Kaplan]

I'm.

[Stuart Gwynn]

I like to try to be very intentional and personable. Like these are people buying from people, and I don't think AI will replace that. So making sure that you are hearing them and acknowledging your active listening and that you tie that to where you solved it before. I mean, this is not the Spanish Inquisition. You don't go in and yes, you're not present, presenting a solution, but you are selectively giving and taking throughout a discussion. And you can't go into any discovery meeting, as we call it, and ask 30 questions in a row. At some point the client's going to shut down. So you're absolutely need to earn trust and credibility throughout the dialogue. And that may be. Here's where I've done it before, and here's a similar challenge or here, here's a similar challenge that you're facing, and here's how MongoDB has solved this challenge before. And here's the outcome that this person was able to achieve or this organization was able to achieve. Does that sound relevant to what you just described to me? And the answer is yes. And so as you're doing this give and take and this dialogue, this dance, if you will, they're going to start opening up if you're presenting them with relevant, credible information that leads them to a desired target state that's better off than where they're currently sitting.

[John Kaplan]

Yeah, you're telling them, look, you could feel comfortable with me because I understand the pain that you and you're in. I've seen this pain at other customer sites and here's. They've used my product before and here are some of the positive results that they had from using the product. So you're making them feel a lot more comfortable that you truly understand the problem. They're not the. Because a lot of customers think they're the only ones in the world that have that same problem. So they're a little reluctant to give out that information unless they understand that you understand their problem and have fixed the same problem at other customers. Talk to us a little bit about the quantification of the pain, because when I talk to a lot of sales Reps this, they can discover the pain, they can implicate the pain, but they have a really difficult time quantifying the pain.

[Stuart Gwynn]

I think a lot of that has to do with, it's synonymous almost with champion building. Because if you, if you don't have a champion, you know the saying no champion, no deal is absolutely true. And so to quantify pain, you really have to have someone on the client side who is in the boat with you and who's willing to go get information, collaborate with you on information, and almost build that business case, as we would call it. So throughout the journey of identifying the pain and the implication, but then the so what, that's where the so what comes in. And so I'll talk to the champion target champion often at this point and we say, okay, so what? And if they, if, if they can't answer that question, then you're going to have to help lead them to, well, at some point you're going to have to reassign dollars to this or at some point you're going to have to take this up for approval. And if you can't document, if we can't doc together how this is going to solve a problem for your organization that leads to either money saved or money earned or revenue accelerated time to market, then why are, why are we even going to do anything? We're both wasting our time and in that line of questioning and really asking the question, so what, you're really testing that champion. Are they really a champion or are they a coach? If they're a coach, they're either not going to have the answer or they're not willing to go get that answer. And if they're a champion, they're willing to do it. If they don't have it, they're willing to introduce you to the EB and maybe it's, hey, let's go have a, a meeting with my boss because they have that answer and together we can document this. And so I think really quantifying the pain is you got to partner with your target champion or champion to get that done right.

[John Kaplan]

Maybe you almost gave, gave the answer away already, but what are some of the clues or signs or actions that tell you, okay, this person can actually be a champ before they are identified as champion. What are some of the things that you look for and signals that tell you, I think this guy could actually be a champion?

[Stuart Gwynn]

I think first you, you're going to want to understand their incentives like I mentioned and, and you're going to want to build a relationship and Then you're going to want to test them. And so, I mean, not to repeat what I said, but I think it's a flavor of that and it's really making sure that are they willing to. To represent your product in the same way with you in the room as if you're not in the room? And to do that, they have to have some type of personal, professional motivation because there's no way that they're going to, I mean, the extreme examples put their job on the line. I know that this is going to be such a, you know, hellacious situation if we don't solve this problem. I'm not willing to work here. And I know that I'm so convinced that in this scenario, MongoDB can solve that problem that I'm willing to say, without this, this isn't going to work. That's an extreme example. But in everyday life, there's ways that these, our customers lives will be better with our technologies because we've proven them, we've done it elsewhere, and they're willing to stand up for that budget or for that prioritization of the project to ensure it gets done so that them and their team get their time back and they can, you know, continue to work on other areas of modernizing the business.

[John McMahon]

You talk about Stuart, sitting in the moment, it's so hard for sellers to do. It's great advice. Probably one of the best advice I've ever heard is, you know, teach yourself to be patient. Thinking about the, you know, that, that famous scene in, in the movies where the, you know, where the person saying, hold, hold, and you just, you know, you want to jump in and say how MongoDB can solve something. What are some of the ways. And you talked about your personality being, you know, you're personable, probably empathetic. How do you get somebody to sit in their own moment of pain without it feeling like you're badgering them? How do you do that? Like, first of all, do you agree with that? Is it hard to hold and stay in a point and just go, customer says, yeah, we got a problem with that. Okay, I got a problem. Got a check in the box. You know, we'll move on to the next problem. How do you go deep with a customer and earn the right to do that?

[Stuart Gwynn]

To answer your question is definitely hard. And it's also hard to make sure the team does it. Like, sometimes there's scenarios where you have your essay or your CSM or your inside rep with you and someone wants to jump in and. Or even product Person, Right. We may go in with our product team. We're disguising this as a Trojan horse. Here's the product person. We got to do some discovery up front. And we hear something, the product person goes, our product can do that. Here's how we do it. It's on the roadmap. So holding the line is definitely challenging, especially for sales reps, too, because we're supposed to be the face the relationship we are. And I think there's a few ways that you can do it. I mean, one, the most important thing, and it's almost obvious and cliche, but pipeline builds courage, right? And so when you. When you're desperate for a deal, you're going to attach to everything, you're going to move too quickly. If you have enough pipeline, you have the experience, but you have the courage behind. Okay, I don't need every deal, but let's really make sure this is the right fit. And we're qualifying out almost as much as we're qualifying in. That's really like, our time is the most valuable asset. And so if you can sit in that moment with the client and make sure you're slowing down, you're holding the line, and you're asking them the series of questions in a way that doesn't feel like the inquisition. So, like marrying the science of the framework with the art of being personal and intentional and curious, you can get to a point where we say, drag them through the glass, right? They have to participate in their own rescue to some degree. And to do that, they have to understand exactly the current state that they're in and maybe perhaps more pain than they think they are.

[John McMahon]

Don't. You have to be prepared with a potential. Like when you're sitting there, you have to have a high confidence that this problem probably exists with or without you sitting here having this conversation that gives you confidence. And then you also have to prepare. It's especially important, I think, in the implication of the problem where we know and we understand the implications because we see the problem every day. But getting a person to stand in that moment of the implication is, oh, and by the way, I don't think that's ever going to be replaced by AI is that moment where somebody gives me an answer, but I need to go deeper and understand the implication of that problem financially, emotionally, all the different implications of it outside of my department, attached to a bigger business issue. And then what you just brought up, that's just for yourself. How do you prepare the team? Hey, man, we want to go deep here. So let the customer talk. How do you do that?

[Stuart Gwynn]

So to answer your question, reverse, you know, a prep call is I think probably industry standard, but making sure that there's a document, right. Usually I have a readout and I'll send it to the team that's going to be in the meeting with me and say, look, here's the one or two goals of what we're trying to accomplish. Here's the line of questioning that we may want to go down depending on, you know, be audible ready. But here's specific people that I think in this situation would be relevant. And then we get on a call, we talk it through, hey, if it goes this direction, here's where I think, you know, you, you can take this cap versus if it goes y direction, then I think it'd be better if, you know, Johnny over here takes the, takes the question or prompts this note when you prep in that way and you also bring it through the lens of we're curious, we care, but also we've seen it before. So a lot of times the internal proof points as powerful as the external proof point. And it's. We've worked with your org, we've seen this more than you. We work with your org who solve modernization issues day in and day out. And they've run into these challenges just over there in, you know, the other line of business, neighbors of yours. And here's what they found is that sound relevant? And so when you ask questions like that, and it's almost like the herd theory you're leading them to, oh, if all my peers are doing this, then maybe that's something I should care about. And also they're the experts. We're the ones selling every day. You have to remember, we probably know more about their business from a technology stack standpoint and what their peers are using within the same org than they do. Then there's the level of confidence that comes in with, no, let's hold the line, let's ask that extra question. It's not going to offend them because we're giving them credible, relevant information that they actually probably do want to know. And you can tell when you're asking a question. You know, I still prefer on site to zoom. You can read body language and you'll be able to tell very quickly if, if this is resonating with the right audience.

[John McMahon]

That's a really good answer. And I, I love what you just said because it kind of went full circle, is that that's how you get people to trust you. You listen to their problem, you show up and you have the ability to demonstrate that you know their business. And in. In the kinds of accounts that you're calling on, they have an expectation that you probably know more about what's going on as it relates to the problems you're solving. And if you are getting resistance, you probably haven't. There's a number of things that you could read off that they probably don't know the answers to. The challenges that you're highlighting in their organization, big red flag. And. Or they have somebody else that they are relying on to solve that problem, like one of your competitors. So it's. And when you have the ability to sit back and just analyze what they're saying and why they're saying it and what their body language is, I think you just did a. You did a really good job of explaining that, Stuart. And I think that was just really well done. Where most people don't take the time to do that, they're moving through an agenda.

[Stuart Gwynn]

Yeah. Thank you. And one last thing. One other outcome would be it's not a big enough problem we're solving. There's people that want to play around with toys and POCs all the time, especially in AI era just to say they did a little AI POC, hey, yeah, I want to do this vector search POC, build an agentic chatbot. But when you're asking those questions, you're either losing to a competitor because they got a champion in the room that you don't, or they're not understanding the value of bringing to the table, or the three is like, it's just not a problem we're solving. That's okay, too. I tell my team all the time, like, let's qualify out just as quickly as we qualify in. And let's spend our time to attach to big problems, because big problems get big dollars assigned to them to fix. And so let's get out.

[John McMahon]

Let's get your certificate from Force Management. You need to get a certificate, bro.

[Stuart Gwynn]

If you. If you've worked at Mongo for as long as I have, you got a couple of those things. They redo the training, you get the refresher.

[John McMahon]

Well done.

[John Kaplan]

So, Stuart, tell me you're in a deal. When's the moment where you say, I know I'm going to get this deal. It may be two more months, it may be six more months, it may be six weeks, but I know I'm going to get this deal. What's. What do you see? What do you hear? What do you feel? Where you Say, I just know I'm going to get this deal. Some of it and some of it may be very tangible.

[Stuart Gwynn]

It depends what type of deal we're talking. So I've been fortunate at Mongo, right? I've, I've, there's been years where I've done, you know, 50 plus transactions positive and then there's, there's years where we've had one P.O. and that P.O. is you know, a nine figure P.O. which is, you know, it's an awesome opportunity to have. And they're similar from how you build them from the bottom, but then they answer your questions a little bit different as the transaction size gets larger and you're, you're selling across an org and multiple stakeholders from multiple lines of business and the CEO signing off of it versus just a transaction. So if we went in a transaction, let's start there. The smaller ones, right, they're equally important. They build the demand. There has to be a demand plan to justify, you know, we call it the bfd, the big effing deal. So you got to have a demand plan to build the, the big effing deal. And then in the demand plan you're closing individual transactions. And in that moment, if I look at, if I was trying to take a step back, first of all, you're always emotional. You're attached to your own deals. You should review it with someone who's not as emotionally invested. That could be your manager. They're still a little invested. Could be a peer. A lot of times deal review with a peer is great. Just, hey, how would you look at this? Because they're not emotionally attached. They don't know the names. But it's boils down the simple three whys. So do you have answers to the three whys? Why anything? Why now? Why Mongo in our sense? And then do you have a champion? And then test, do you have a champion?

[John McMahon]

Right?

[Stuart Gwynn]

So like why is that person a champion? Why is Rachel a champion? What has she done to prove that she's a champion? Is she willing to represent this product for us when we get kicked out of the room? And they have to answer basically the same three questions, the three wise to their leadership and they're not trained to do it. So I think in a, in a transactional deal or, you know, six figure deal, that's how you know you're getting a deal is when you're like, holy smokes, I just recapped the value framework with my damn customer and they pitched me on it. And this person has done deals Before. Right. So have they gotten this size of deal transacted through the comp. Through this company before? I'm not, I'm talking about your customer. I'm not talking about have they done a Mongo deal before, but have they done a software deal that's six figures before? And do they know the buying process and can they walk you through all that? It's almost like the same things that my leadership asked me, but now we do it with the customer and if they can recite that back to you, holy cow, that's rock solid customer.

[John Kaplan]

You know, the customer is going to go into this meeting without you and you're role playing with the customer and you're actually giving some advice probably to the customer saying, how are you going to handle this? Objection. How are you going to handle that objection? Because it's going to come because I've sold this product for five years and I know everyone asks these questions and

[Stuart Gwynn]

even better, they ask you, literally it's happened. They'll ask you, they'll say, Stuart, you've done this before at this bank. Help me understand like what I'm going to run into. And they want to role play.

[John Kaplan]

Very good.

[Stuart Gwynn]

And, and that's, that's the magic moment where you're like you're doing something right. That's what feels good is because you know, they care enough about this problem, it's worth solving that. They're asking you because they realize that you've done these type of transactions before and you have more expertise than them in this specific domain and they want your help.

[John Kaplan]

Yeah, there's a lot of times where reps don't prepare a potential champion and the champion takes off on their own and then they get shot down. And somebody that could have been a potential champion if they would have role played with them and told them what they're going to run into, could have been a real champion, but got shot down and never will try, you know, to push the product again.

[John McMahon]

See, I've seen before what's the reality of the types of selling that you've done, that you're doing now for Mongo. DB what's the reality of having one champion on a deal, A nine figure deal?

[Stuart Gwynn]

I mean that's, it's a softball. I know you're teeing me up like that, but you can't just have one champion on a deal that size. There's going to be multiple stakeholders. And to. When I talked about the demand plan, what I mean by that is, you know, imagine the global head technology sees hey, I'm going to sign off on a nine figure deal commitment to one vendor. Okay, who's using this? Why do we need it? Why can't we use anything else? What value is it providing me? Those questions got asked. Those are the questions. Get asked behind closed doors. And you have to have prepped the line of business heads, each of them, and make sure they're aware because again, we truly do know more about where they're using, what database platform they're using to solve what modernization challenges and what business initiatives than the head of a line of business would at this bank. And so in that moment, we had to prep them kind of bottom up and say, look, let's do a portfolio review or let's demonstrate here. These your top three initiatives? Yes, they are. We've heard that. Great. How you solve them, why are they important? Do you realize that we're actually attached to these five? And here's what we're doing for. And here's the value and here's the app owner and here's why. No, I didn't know. That's great. What else can you do on enablement? How can we make sure that we're scaling this? This is wonderful.

[John Kaplan]

Okay.

[Stuart Gwynn]

That type of work doesn't happen in one call. That happens over, you know, months, quarters, years. And you get to the point where in that last week when we need the po, well, okay, now this global head of technology, they're going to the CEO of the big bank to sign off. They better be damn sure that this is providing value to the bank. And they go ask their delegates, what are we using Mongo for? Why? What value is it providing? And do we need this much of it? And when the answer is yes, yes, yes, yes, then you know you're getting the deal done. But that's a multiple stakeholder, multiple champion

[John McMahon]

in those types of deals. Is it? Talk to me about the champion. By the definition. They follow the definition so well. They have power and influence, they're actively selling on our behalf and they have a vested interest in our success and they follow that so well that they're actually hesitant to bring other champions in. Have you ever experienced that where you have like a really powerful champion and they want to go alone, not without you, but you walk us through, because I hear that a lot today. Give the audience some advice on how do you take that lone wolf and tell them it's time to collaborate with others? How do you do it?

[Stuart Gwynn]

Yes, it's happened. And when it happens, it's a red flag because that person is probably for, for whatever reason, you got to get to the bottom of it. You know, there's either a selfish interest, a self promotion interest, or they really feel they can get this done and someone else will, you know, detract from the goal. And so understanding their incentives once again and really getting to the root of will help us understand why you want to go this alone. Why don't you want to bring John McMahon with us along the way? Because he's done this before too and he can help you. And if this problem's really worth solving, don't you want the whole calvary with you? And I think in that moment, one of two things happens. Either that person's going to realize they haven't done this before, you're going to show them that you've done it. And that in this scenario it's going to be helpful to have their, their peers and colleagues here, because this is exactly how it went three years ago. And here's the type of questions that were asked and we need to make sure that we have these answers and only this other person that you bring to the table will have those answers. Maybe they convince you they can get it done and there's a reason why there's something you're unaware of in the political environment that account that you shouldn't bring, you know, the suggested executive with you. But more than likely you're going to get to the point where they realize that this is in their best interest if they really do care about solving the problem. And you're going to prove that like this is going to only benefit their career, their brand within the organization instead of detract from it. So there's usually some hidden agenda that you're seeing.

[John McMahon]

Isn't the answer also in the, the more you tell me I'm not the champion or I need other champions, the more I'm going to resist you. And so we really have to be prepared to ask questions that makes that person answer it themselves, that says, you know what, we probably need to bring some other cavalry with us. Do you have advice on that? Like, do you have advice on that kind of situation? Because I think a lot of people will go, hey, Mr. And Mrs. Customer, you're not following our process. And if you don't follow our process, I can't forecast this or I can't get the resources that we, blah, blah,

[John Kaplan]

blah, and we usually comes down to a personal win and that. And, and the, the guy that maybe wants control over things, doesn't want to, you know, let go of that person?

[John McMahon]

Yeah, a lot.

[John Kaplan]

Usually. Yeah, down to that.

[Stuart Gwynn]

I think that's what I was getting at. You know, there's a hidden again agenda, there's some type of personal win they're holding on to. But really, I mean, cap, you have to speak in the customer's language. I mean, you guys taught that to us. I, I mean, I learned that a long time ago. It can't be about our process. You can't say, hey, I can't go to the next meeting because I didn't cross my NBM gate. No, you speak in their language, you tie it to what they care about. And if you're aligning your behaviors and the act suggested actions to what they care about, what they want to solve for, then you're going to get them in the right direction. And if that means bring in, you know, Mr. Customer Executive and their boss. But a lot of times it happens when you're going above them, especially like, hey, no, I want to do it. And if you're trying to get to their boss, no, I'm capable. Don't worry, I'm in charge here. That happens all too often. And you have to.

[John McMahon]

What do you say? What do you say? Just because there's, I guarantee there's sellers leaning in right now going, okay, I get it. What do I say?

[Stuart Gwynn]

Yeah, in those moments, what I'll typically do is I'll help them understand a lot of what we recited before. To get this type of deal done, it's going to have to go to XYZ person or it's going to have to have this approval chain. And have you had a discussion with those people before and you're going to ask them a question that leads to, you know, you're leading the water, they're going to say no and say, okay, well, in that moment, this other person has unlocked us for us. Have you talked to them about it? No. Well, don't you think it makes sense that we should have that dialogue together? And maybe you're, you can still bring this down the process for us and champion it for us. But there's, you know, you're, you're at a large bureaucratic organization and they often understand that. And to get things done, you're going to have to go through the process that your team has outlined. And right now, if you haven't done that before, there's some risk in us accomplishing that goal. So is it a worthwhile discussion to get there?

[John McMahon]

Well done, Stuart. I like that. And I also like, for the listeners out there, don't freaking overcomplicate it. If you're sensing that there's a hesitation to get others involved, just ask. We've asked a couple of questions here. We've talked about some others that could probably help us. You and me, Mr. Mrs. Champion, you know, get this thing in a perfect scenario. I'm sensing a hesitation to bring those others involved. What's causing you pause? And just like there's people out there reading books and they're like, it's called being a human. And I think AI is going to struggle with that. Right. So we can talk about that later. But it's that sense of there's hesitation. All the scenario we're talking about should prompt this person to do X. They're not doing it. I need to find out why and I need to do it with humility, with vulnerability. And I just think people over complicate it. It doesn't matter how many zeros the deal has on the side of it. Make sense?

[Stuart Gwynn]

Yes.

[John McMahon]

Well done, Stuart.

[John Kaplan]

When in a deal do you think I'm gonna going to forecast this deal? Maybe you don't want your CRO to be hearing this,

[Stuart Gwynn]

but I think it's

[John Kaplan]

really important for a guy that has so much experience at. At overperforming to share with the audience is to when does it make sense for you to actually commit to a deal into. In the forecast? Yeah.

[Stuart Gwynn]

And I think the answer is when you have your answers to your three why's you've identified a champion. Maybe you haven't tested them, but we have gates in the sales process and we have a gate that leads us from unqualified to qualified. And really the difference between those two are the answers I just described. Like you've gone in, you've identified pain and you've validated that the target state and the after scenario drives a positive business outcome that is worth assigning budget to. There's a person that cares about it, that has power and influence and we know that our solution is differentiated and how we can solve that for them. And so I forecast a deal once. I feel like I have a good grasp on those three whys. But not just me, but there's someone on the other side of the fence that's going to fight for it alongside me in their organization and navigate the internal politics and process to get it done with us.

[John Kaplan]

That makes sense. Plus how much time you have left in the quarter and what the paper process is.

[John McMahon]

Right.

[Stuart Gwynn]

If I need to keep my job. Yeah.

[John Kaplan]

Three weeks to go and you don't

[Stuart Gwynn]

know the paper Exactly.

[John Kaplan]

So you've been really consistent over time. Mean you 6 years over performance and then, you know, you do the largest deal at MongoDB. Do you have, have you developed a certain personal system or certain methods that you use that have helped you be consistent over time?

[Stuart Gwynn]

Absolutely. And as, as I was prepping for this episode, I tried to think about, you know what, how have I evolved as a salesperson in the last seven years and even before that, you know what, what did I used to do differently when I was a commercial rep, 10 plus years ago versus now? And I think the big difference and the big magic secret that's hard is like you got to marry the science of the value framework and command the message because that's absolutely the only way that you can have repeatable process to scale. I'm convinced when I came to Mongo, I never sold an open source product. Granted we open source the community version, but we own the ip. But it's an open source product. Meaning for the listeners out there that don't know what that means, because I didn't. Someone can use Mongo, a customer can use Mongo, deploy it, run their entirety of their business on it, and never pay us a dollar.

[John Kaplan]

Right.

[Stuart Gwynn]

In my past life when I worked at Pure Storage, if you had a pure storage box with the orange glowing bezel, you paid us for that at some point. And so you have to be diligent with your time and discovery and qualification because otherwise you'll be spending time and resources investing in the next application that's going live on Mongo. And they could choose to open source it and they never pay us a dollar and you just wasted your whole quarter chasing a deal that's a $0. So the value framework, you have to be maniacal about qualification. At the same time, you can't be the McMahon robot I described earlier. And then you have to drive scale in the business. And what do I mean by scale? So we, we have something at Mongo called the POD program. Think of it just as like a strategic account program where there's dedicated resources, where they only work on one account. So I lead one of the pods and on our team, you know, we have four inside sales reps, we have three SAs, we have two CSMs, we have a post sales team, we have a TAM, we have all the typical, you know, acronyms that you have covering a strategic account. How do you get everyone to roll in the same direction? And I think you know one thing that's helped me be very successful, I've talked a lot About? I've talked a lot about incentives that drive behavior, but that's the same for internal. So you have to win the ecosystem. I say so. Winning the ecosystem means bricklaying versus cathedral building. And perhaps I've heard this story on a podcast. Maybe I'll butcher it. But at the core basics is everyone's doing a job, we all have a role, even me. And if you view your role as you're just laying bricks, then eventually you're gonna get pretty bored and you're not going to be motivated and you're not going to see the vision. But if you're doing that same role, you're laying bricks. But you see that you're building this cathedral and everyone has a specific role. You may be building the outside of it and caps building the inside of it. Well, now your team's motivated. They want to achieve the big picture. You understand, you're all rolling in the same direction. There's a destination and when you get there, you know what's in it for you. And so winning the ecosystem, making sure that the team's inspired, making sure that we're getting scale in the business. A lot of reps try to hero ball it in basketball, I call it. I'm a big basketball player. So you can't run hero ball. You can't do everything yourself. Because if you're going to manage an account at this scale and if you're going to try to pursue a nine figure transaction, there's no way you can be in every discussion, nor should you be. You really have to empower, teach, and then trust the team. And they're going to make mistakes, man. Shoot. I made mistakes When I was in the field for the first time, my first field meeting, I was so excited. I was outside. I was outside of inside sales. I go on site, I schedule a 12 to 1 meeting, I don't bring lunch and I don't bring business cards right now, how dumb do I look in front of this customer? And so people are going to make mistakes, but if you're investing time in teaching them, your inside team, for example, and then you're trusting them when you get to the other side, a quarter, two, three, down the road and you're at this scale. Well, now everyone's running. Jack's running 10 meetings a week and Sam's running 10 meetings a week, and Preston's running 10 meetings a week. And everyone is running at a scale that no way I can do 30 meetings a week by myself. And so what if at first they're doing it 70% as well as you would have done it yourself. 70% is a lot better than 0% if I didn't have time to get there. And so I think the long winded answer to your question really is if you win the ecosystem and you invest in the team for scale, you're going to get to a point where there's this force multiplier effect in an account and there's no way you could have done that by yourself. And I think that's the long term recipe for success in enterprise selling that takes multiple years to accomplish a goal of this size.

[John Kaplan]

Yeah. And you, let's go back, you were a commercial rep and then you made the move to, you know, selling, you know, bigger deals and then the, and then the largest deals. It gives some advice or, or maybe a better question is what were the top two or three things you had to learn to move from mid market or commercial up to the enterprise when you were selling?

[Stuart Gwynn]

Yeah, I did that across two companies. So I spent seven years at Pure Storage, then I came over to Mongo and I was born into our enterprise POD program. And then I still had a ton to learn at Mongo and that was the first time I was introduced to, you know, force management. And the answer to your question is like one is how do you org chart sell? What I mean by org chart sell is you're no longer in a mid market account where there's one EV and you got to get to that EB and if they sign off, you're good. There's different EBs for different types of transactions for different initiatives. And you have to make sure that you understand, you know, an account plan isn't just like a once a QBR every quarter thing and you get back to the slides and quarter later. You really have to understand who owns, you know, who's the EB in this line of business. Who are the influencers? Who are the potential champions? Who are the champions? And then as you progress through a quarter, who have you gotten to? What information did you learn and what did you have wrong? Maybe? And now who are the key stakeholders that you need to get in front of? And over the course of a year you work towards, you know, color coding. This from what I used to have is like yellow and blue as a target. Yellow is warm and green is. Okay, we met with them, I got their cell phone number. I can text them any moment. How do we get this thing green? And once you get that thing green, then you can start running some plays with it. Okay, we're working on a nine figure deal, who can I call to gain into society? Who can I call to try to go influence the EB or just to understand the lay of the land. And so I think the biggest difference between mid market and enterprise selling is really just the scale and the breadth of how wide and deep you have to go into an account because each line of business is bigger than probably that mid market account that you covered yourself. There's no one or two people that make the decisions. It's very political and there's a lot of business relationships that happen even if you have a technical win.

[John Kaplan]

Yeah, but what I also heard you say earlier was how much you prepared for these, these meetings, which you probably didn't do as much. I'm assuming you didn't do as much prep when you were in mid market as you did when you were in a big strategic account.

[Stuart Gwynn]

Absolutely. Prep is key. And I almost, I had less meetings like the more senior I got in selling to these enterprise customers, like empowering the team for scale to have them run the discovery meetings and inform me of the output and then align myself to the execs, the C level folks in the account. Now for those types of meetings, you're doing a ton of research, you're doing a ton of role plays. Before every meeting with an exec, I would build the sheet I described to you, what are the two to three goals or the lines of questions I want. I'd go role play it with whoever's in that meeting or my boss or my SA and say, hey, look, let's see where this goes. And so that way when you're in the moment, you're audible ready, as we say, and you can take the conversation in any direction that the customer takes it. But you have to be ready. You have to understand, you know, what you can find on LinkedIn, what you can find it. A lot of people speak on podcasts like this, and that's part of what allows you to be personable in those moments too is you can relate to something they really care about and they're passionate about that they're posting on a platform, perhaps in the social world, social media world, that you can attach to and that gets them to open up and trust you and build credibility and then you're also bringing them information. Hey, I heard your teams are working on these things. My team's engaged with yours on XYZ initiative. And here's the outcome we're driving. Here's the people we're working with and all of a sudden when you go work with that executive, you open that meeting. That way it's. Stu and his team are operating a scale I wasn't aware of. I should probably listen a little bit.

[John Kaplan]

Yeah, but the role playing is big and I think you. I keep hearing that consistent theme throughout this podcast that you do a lot of role playing and I don't think enough reps role play, you know, with their manager or with somebody else, you know, in the company before they get into these meetings and then they get, you know, typically you're going to get hit with something you're not ready for. The more you can role play, the better prepared you are in because you can have all the knowledge in the world. But it's a skill and skills are what really happens in the role play.

[John McMahon]

Stu, how do you pick with your capabilities? You've obviously made a decision to stay in a lane to be an individual contributor. That's not a bad thing. That's to take this. Well, I'll just call it the seller track versus the manager track. I just want to hear other people are listening. They're like, Stu's killing it as leading sales, leading sales and sales teams. From an individual contributor standpoint, can you just give some advice to the, to the listeners? Have you ever led before? Have you? Leading is not the right word. Have you ever been in a management role, Sales management role?

[Stuart Gwynn]

I have not. And it is certainly, I will say it's rare. Like Mongo's adr, the BDR program is really prefaced on like, hey, do well in the job and go become a first line manager, second line manager. That opportunity certainly presented itself to me. I've chosen not to take it. I'm happy to describe why, but you're right, I've chosen good observation and astute observation. I've chosen the IC track. Fricking love it. And that doesn't mean I don't want to be a manager at some point. But I also don't feel that means I haven't, haven't led, folks. And I think one of the things that I love most is really the mentorship and seeing the inside sales rep rise up and become my peers. And four years later at the same company, that's really neat to me because I know a lot of people invested in me, a lot of mentors helped me get to the point where I'm at, especially when I was inside sales rep. And I make it a point to make sure I'm investing that much, if not more, and pay it forward to the next generation. And Crap coming up among you're leading for sure.

[John McMahon]

Yeah. Or you don't do nine figure deals without leading. How do you deal with some of the pressure that you know, it always comes to great players where people come to them and say we want you to have, we want you to take over a team or we want you to just give some advice to the, to the listeners on when is the time? Is it okay never to be the time to take the management track like share your experience.

[Stuart Gwynn]

Personally, I love being IC and like you said the you know, others, others and, and I've been given the opportunity. Do we want to be a first line manager? I passed it up at Mongo for now. It's just so happened that I've always felt like the challenge of I'm hyper competitive. I think a lot of salespeople are but I hate losing in anything. It could be tic tac toe, it could be whatever. I don't like losing. On top of that, I'm a learner. I love really understanding like okay, how can we get to the unattainable the nine figure deal? That's never been done and what would it take to accomplish that? And now that it's done, I have changed accounts. I don't cover that account anymore. I cover one of the AI Frontier Lab native now. And that's like a whole new challenge in itself. It's a completely different world if you imagine a Frontier Lab versus a legacy bank. Completely different. And so is it okay to stay as an individual contributor? Mongo has allowed it to be okay, which is why I'm still here. I mean they've certainly pushed me to be a manager but they've respected hey, right now I want to, I want to be your best rep. I want to be the number one guy and I'm not the number one rep every year. I wasn't last year from you know, total achievement quota attainment and I didn't deserve that number. But we did close the largest deal. We made plenty of money and we're having fun doing it. And I think when you can have fun doing the job and you can seek and attack the new challenges and you're learning every day. I think that's why I'm still doing what I'm doing. Can there be too much pressure? I'll tell you when there's too much pressure. When I was a STR at Pure Storage I wanna, I was the number one STR one the incentive trip and it was at pebble beach and so Ronnie Lott and Harris Barton were early investors in our company, and I was supposed to golf with them. I said, hey, guys, I'm not good at golf. They said, everyone says they get out here. So we went out there. That was the first round of 18 I ever played in my whole life. I never golfed before. When I say I suck at golf, I didn't golf. I realized very soon thereafter I should take some lessons. And I'm addicted to the game now. But that was too much pressure. But we were talking about selling. I mean, shoot, man, we have a hell of an opportunity, and I'm grateful for it, but there's not, you know, we're not. There's professions where there's a lot more at stake. So, yeah, pressure is here, but I embrace it as a competitive person. And I think it's absolutely okay to answer your question to, you know, pursue the IC track as long as you want, but make sure you're investing in the next generation. And if you're an IC rep and I see for this long, you're going to have the opportunity to lead, people have a direct impact. And I probably spend more time with them than their manager does. In fact, I know that I do. And I think that's what's rewarding to me, is really seeing the development through that type of mentorship. Am I level?

[John McMahon]

Great answer, Stu.

[John Kaplan]

Do it. What about AI? How. How is that affecting your business? How is it helping you in your business? Can you talk a little bit about that? And then we can. We can always go a little deeper.

[John McMahon]

Sure.

[Stuart Gwynn]

I mean, I'm learning AI. Sometimes I feel like my dad, like I'm a boomer. I, I sometimes I don't know what I can accomplish with AI until some of these kids show me. But AI is changing the buyer. I think it's accelerating what we already knew. They've researched more about you and your product and your competitors before you walk in the room. A lot of times, like SaaS started that SaaS, you could use the product before the trial version before you talk to us. Atlas is our managed data service. You can start a free cluster and play around with it before you talk to me. AIs only continue to accelerate that. And so I think one thing that I heard, actually two recent guests, Sahir Mongo's old CPO and Brian McCarthy on your recent episodes, say, is, you know, there's this decreasing tolerance for sellers who don't know the product. And I think that's absolutely true. We have to be more technical. AI allows us to be more technical because I can ask questions to it. It helps me prep more quickly, helps me automate the prep. And you know, there's tools that will allow us to certainly research accounts better, but also just grab the information that's in our systems and present it to me in a way that if I'm writing a memo. I spoke to our CEO for a prep call earlier today. That used to take me hours to write that memo and now it's taken me minutes because I have an easier starting point. And do I ever just take that and run with it? No, I augment it. But I think from the customer side, they're better research, they move more quickly. I mean, some of these frontier labs, you see what they're releasing, whether it's OpenAI or anthropic, they're releasing things. And product cycles are weeks now, not months or quarters. So you gotta be on your toes. You gotta expect to know more about your product than you do. And then you have to be prepared. And I can help automate and allow you to prepare in less time than it used to as well. So that's how I answer that question. John.

[John Kaplan]

So I hear that you're doing more. You actually called it auto prep for meetings, I'm assuming, right? Then you do in research before you go into an account, you're doing research just like the customer is doing on you. And then that meeting prep note that you put out to everyone and all your internal stakeholders, you were also using AI to help you generate that. Those are the three big things I heard you say.

[Stuart Gwynn]

Yes. And quite frankly, I think that's table stakes and I think I'm behind the curve on that. Like one of my big challenges for myself here is how do I lean in to AI? How can I make it do more for me? I mean, if companies are releasing products that are coded by agents and maybe not even developers anymore, then I got to be doing more than that. So that's absolutely how it's helping me today. But I feel like if I'm going to keep up and maintain this, if I, if I want to continue to be a top tier rep in enterprise selling, I have to learn how to embrace AI and use it as a force multiplier to allow myself to scale the way I previously described the team allowed me to scale. Otherwise there's no doubt I'll fall behind.

[John Kaplan]

Why haven't you so far? I'm. I don't want to put you on the defensive, but what, why you like try to adopted or has someone that's around you in your office have they done a better job of picking up AI? And you can, you can.

[Stuart Gwynn]

2 Answers yes, there are certainly people who have invested more time and are more intellectually curious than I do. So I need to challenge myself to do that. And the other is like what does the organization allow? And you know, as you're rolling these things out, there's security, there's governance, there's compliance. And as a public company we have to make sure that, you know, you don't just go install cloud cowork and allow it to take over full write access to your laptop. So there's a balance between what your organization is going to allow versus, you know, just experimenting in personal time with personal data and seeing what the tools are capable of and marrying the two. And I think I'm on that journey, everyone's personal journey down that path. And right now it's half of it has to be here's how Mongo wants you to embrace AI. Here's the tools here, what they use for. But the other half is the same as everything else that's made as successful as what's the intellectual curiosity and go out on your own and determine what interests you, how this can help you and you know, have a hypothesis and start trying testing some things out. And I think that's been something that has been a, a priority for me and we continue to work through.

[John Kaplan]

Awesome.

[John McMahon]

I got a question, I got a question for Stu on we've talked about, I think the sellers. This is really, really going to resonate for our sellers. It's really, really going to resonate for companies that think about how to feed people like you. It's going to help companies think about their customers. I want to throw in a little bit of something for the leaders that are listening to this podcast right now. What is some advice that you could give on managing top talent in a company? What are some things they should do more of and what are some things they should do less of? When they think about like the stews of the world, what adds a lot of value to you and what doesn't add so much value to you?

[Stuart Gwynn]

What adds a lot of value to me is if you can give me time back. And I'm not saying cancel meetings. There's I want to be a steward of the culture. I do. And there's members who are joining Mongol for the first time and they deserve to sit in the same team meeting as me and hear how I'm doing things similar to how I'm describing this podcast. So what I'm not suggesting is get me out of the team meetings. Because when I was new, I remember the senior reps investing time. Hey, let me. Stuart, you want to sit on this call? You want to go on this, this meeting with me? That was invaluable. What I do think, I mean is there's, you know, we're becoming a bigger company and everyone hits this to different scale. But when I started we had 600 employees at Mongo or at 6,000. Now there's just inevitable process that comes with that and the more that managers can help remove some of that process, the better. I think the other thing is, you know, a lot of first time managers, sometimes they'll manage, you know, seven year, 10 year rep, the same as the new rep and they don't have to. Right. There's different things in different areas that I need help and guidance versus someone else. A big area where I like spending time with my leadership is, hey, here's a crucial conversation I need to have with someone on my team. You've gone through formal leaving leadership training with Mongo. I've gone through half of it. Help me understand, like let's talk through that. We don't need to pull up M4S metrics for success and go through how many discovery meetings I have. You want to ask me about my business, let's go. I'm ready. Any point, anytime. I just did with our CEO. I absolutely can do that. But let's not spend time going through, you know, the operating rhythm type questions that you may go through with a first year rep. Let's instead spend time where you can actually add the most value and drive the most impact. And I think that's a dialogue you can have with your top reps. You can treat them like peers. Even though by title we're not a lot of the first line leaders. In fact, most of the first line leaders I was ICs with when I first started. And so we maintain that relationship and through that dialogue it really helps us progress and it's a big reason why I'm still here. Leadership treats me as a peer in most scenarios and in the scenarios they shouldn't, they don't. And I still need to be held accountable the same way as every other rep. And I still want to be a steward of the culture. So I think that would be how I'd answer your question. I don't know if there's any part you want me to double click on, but that's, that's what's helped me stay here.

[John McMahon]

Well said. But the, the main point I love to hear you say is you don't manage everybody the same way. You hold them to the same outcomes, but you don't. You meet them wherever they are. And I think that was really powerful how you described that. Well done today, Stu.

[Stuart Gwynn]

Yeah, thank you. I think that the. The key, whether you're an RD in the situation you just described and how do you manage your top talent, or if you're a rep like me, it's something Cedric said. It's just like when the map and the terrain don't show the same thing. Make sure you trust the terrain, trust your instincts. Right. The process is here as a guide, but you never have to just follow that map, no matter what it says. You got to put a little bit of instinct in there and you got to trust your gut because your gut's what got you here. We're all sales professionals. We've all had success in our careers. And that's why they hired you at this company, at Mongo. And we have to trust ourselves. We can't just run the same playbook over and over and over without any, you know, any deviations or subjectivity to it.

[John Kaplan]

Excellent, Stewart.

[John McMahon]

Excellent.

[John Kaplan]

Stuart Quinn. Thank you. Johnny Kaplan, Once again, thank you. And thanks to everyone for listening to another episode of the Revenue Builders podcast.

[Podcast Host (Force Management Representative)]

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