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#607 - How to Turn Every Sales Pilot Into a Closed Deal | Shaun Crimmins

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#607 - How to Turn Every Sales Pilot Into a Closed Deal | Shaun Crimmins

The approach to sales pilots has evolved from showcasing technology to delivering tangible, measurable value within a four-week timeframe. Instead of abstract demonstrations, pilots now start with clear, customer-defined success metrics—like ticket resolution time or deflection rates—established early through baseline measurements and real-time tracking. Progress is visibly demonstrated, creating a compelling narrative of improvement. A critical strategy is identifying two champions: a business leader responsible for outcomes and a technical expert (e.g., IT director) who sees daily operational gains. This dual alignment ensures both leadership and technical teams are engaged, reducing resistance and building trust. The value is also mapped step-by-step through the pilot—starting with an upstream, actionable metric and linking it to downstream business impact—such as cost reduction or revenue growth. This method turns the pilot into a high-velocity, evidence-based journey where outcomes are concrete and measurable. Crucially, success criteria are defined upfront and embedded in contracts, eliminating wasted time on trials with no intent to buy. The pilot becomes a co-creation experience, where technical teams are embedded and actively involved, reinforcing value through real-world results. This shift addresses the "build vs. buy" objection by showing that customers co-develop solutions, not just purchase off-the-shelf tech—leading to stronger adoption and long-term success.

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And I think that is one of the differences that I've noticed in pilots over the last five years. Is that it used to be very much so, show you how the tech works, demonstrate what is possible versus, I can move a metric over a two week, four week period that ties to the case that I really want to make. And that is sort of the reverse engineering of the value case. It becomes a natural next step because I've already shown how I can influence some metrics over a four week period. Great, now if you extrapolate that out, here's what that actually equates to. So it's a different type of sort of environment, like a proof of value, but exactly how we think about it. (upbeat music) - Already, Sean, you literally win 100% of the pilots, trials and POCs that you kick off. And today you were gonna be teaching us, step by step, how you do that. Where the heck should we start? - Okay, so first thing, we call it the baseline bet. So the customer has about two or three metrics that they already are reporting on, right? These are things that matter to them, not necessarily me. They actually write down a guess of where they stand today in week one, the actual number. And then we understand after the first week what it is, and they compare it to what their guess was. But the concept here is that we are getting success criteria and their baseline metrics up front. So by the end of week one, two, three, four, I am showing tangible progress against those numbers. And that's where we're mapping our sort of value asks to. - Sean, I feel like I've had reps try to do this for years and people come back and like, I just don't know the numbers. And we're like, just guess, and they're like, I don't want to guess. How are you getting them to actually give you numbers? - A lot of times it's through stories we're telling, right? So we will talk about, for example, we did this with ASOS. And we'll say when we met with ASOS, they really didn't understand the concept of even knowledge coverage. So for us, that is an important concept that we explained to the customer and say, look, knowledge coverage, we would define as there's an incoming question, do you have an answer documented somewhere? And a lot of times people would actually tell you, okay, well, probably 50% of the time I think we would. And we read back to them and say, you're actually like five to 15%. And by the way, we just made a bunch of updates in 48 hours. Now you're at 90%. So I think defining that for them can help draw it out. But a lot of it is, here's what we've seen. Here's all the companies we worked with and how they've defined it and what they've seen before the pilot and where their metrics actually work. - So let's like get serious specific example. Like when I was out outreach, sometimes we would say, okay, what's your reply rate? People would have no clue. And then we'd be like, well, we can't tell you, we can increase your reply rate, X%, if we don't know what the baseline is. In your world, what's like a common metric that you anchor on? And then how do you talk to somebody to give you that actual number, that they believe, 'cause they all know what you're going to do, man. They all know that you're going to say, we're going to double this number and you should pay us all this money. So they're already kind of like hedging their bets a little bit, like how you get them to give you a real number. - I think the first thing is for us, at least it's knowledge coverage, is how we would like it, that's a metric that matters. But nobody really has that. So we will start with whatever metrics that they actually are reporting on right now. Sometimes that is tickets that are incoming, like if we're selling an IT case where, okay, here's our ticket resolution time, here's our deflection rate or how many times we don't need to actually answer a ticket. And it is never where they really want it to be. The way that we actually get that number from the customer, though, is to say, look, throughout this four week pilot, we plan to actually show you live in production, improvements to those numbers. So by the end of this pilot, not only are we going to show you, here's what we project. We've actually done that work over the four week period. And they can now say not only has this pilot shown, what this overarching could look like over the next call it year of engagement, but we've already moved to the metric they care about and introduced new insights for us, that's knowledge coverage, which no organization has anything documented or written down. So when we explain that concept and then show them where they are today, baseline and the improvement, they lean in. But I think the key thing is like, what are the things that you're already reporting on? And we feel comforted enough that we will say, great, we're going to move that metric in the next four weeks. Never mind a value case that's going to show you how we do it. We actually, can you just quickly rattle like the list of the top five, six, seven, eight most common metrics that you are using as the upfront success criteria? Mark, I'd also be curious to hear what you have done at either their table or outreach. Just so folks can get a sense of like, what you're anchoring to upfront. Yeah, okay, so it's very use case dependent. For us, it's a lot of IT service management use cases or customer support. So for us, that is ticket resolution time, that is the deflection rate, that is how many tickets are being resolved in any given day, it's the volume of tickets, the amount of time it takes to actually triage something, ticket resolution time is a big anchor for us. Great, Mark, how about yourself? Yeah, I think at outreach, you know, since we have like a GTM oriented audience, that would be the most appropriate thing to share. It's like, we would look at how many people are you actually touching in a day per rep? That's a big leading metric that we could control. We might go after something like the number of sales activities somebody could do a day, but what we always try to do was stay something that we could impact versus saying like, reply rates or meetings booked, because there's so many variables between what we would do and what the rep would do, like if they picked a bunch of bad companies, a bunch of bad people, we could do everything perfectly and they still wouldn't book meetings and they're blaming us instead of the rep. And so that was always the key to us is like, what metrics can we absolutely control or impact like John's talking about? John, so one of the things I heard that sounded interesting to me was you said basically, we kind of start the beginning of the pilot with the metric that they're interested in and we measure that and then we measure that same metric at the end of the pilot and then show the delta. Is that right? - 100%. - That's the key to me, man. Like, you don't know your number? Tell you what, we're gonna show you your number and then we're gonna show you that number go up over the next four weeks in this pilot. That seems like some secret sauce. - Absolutely and it sort of leads to one of the other things that we will usually do, which is map each value touch throughout the pilot. So for example, knowledge-based coverage or is there a document and answer to an incoming question, whether it's IT or customer support, is a metric that we effectively educate the customer on. So we say, great, you may not know what this is. Most people don't. We measured it for you and here's what that number actually is. And then after the first week of the pilot when we get access to their data, we improve that metric usually by threefold. So for example, we worked with a customer that came to us their knowledge-based coverage to start the pilot at week zero or day one was 30%. Seven days later, we said here's what that number actually was. By the way, it is now 90%. And you're going to keep this knowledge-based at the end of the pilot no matter what. So we just went through and documented a reverse engineer their old business process and now I'm handing that to them after one week. Now I have some asks of them driven by insights where I will say, okay, great, because now I'm thinking about my week two value touch. I am saying, look, based on the data as well, there's different tools that if we connected to, we could actually start to auto-resolve these tickets or draft responses for people. That's my week two value. So I allude to it. And then I'm also touching on another metric for them, which is usually deflection or auto-resolution. But I have mapped out, before I get into the pilot, exactly when I'm delivering these value touches and what my ask is going to be pre-planned. - Sean, as an experienced sales leader, selling past the clothes is like always this thing that sellers are willing to do. You're taking it to product or ticket resolution time, but I think a lot of over eager reps might say, well, I need to tie it to revenue or risk or time. But I don't know if necessarily you can show how there's time savings or something around something around like ticket revolution time. It just happens faster, it doesn't. So I mean, maybe that's not the great example 'cause it has time in the name. But like how far do you tell a rep to take that metric or do you just take the metric at face value and be like they know how important this is? They'll make the connection to time risk or revenue. - It depends on who your persona is, but we know that all the metrics I'm going in and looking for, I can tie back to revenue and cost. Because that's what my business champion cares about. That's the person to give me access to the pilot. But I will usually go in and whoever is working with us during the pilot may be more of a subject matter expert, more of a technical person, they have a deep understanding of the operational metrics which are going to lead to business impact metrics. But if I go into the oil and I kick it off and I say great, the point of this four week pilot is to show you how we can decrease your costs, won't land. But let me pick one metric that I know I can move that the buyer cares about, we start there. And again, I give them some other insights to metrics, they didn't actually know that they had with analysis. But I pick a metric that they care about that I know ties back to broader business impact that I can now basically go and do the science experiment over the four weeks, move the metric, bring it back to the business champion and say, this is the thing that's going to help you reduce costs. Look what we did in four weeks, imagine what we can do in a year and here's how it ties to dollars and sets. - Today's show is brought to you by ambition, the coaching and performance platform helping sales leaders turn metrics into action. To understand any metric, you need two things, context and trend. If your team booked 40 meetings this week, there's no way to tell if that number is good or bad. Because if the goal was 80, you're in trouble. If it's 20, you're crushing. That's why you need context. But trend can change things. If you averaged 80 meetings a week for the last quarter and then you only hit 40 this week, something went wrong. Now we built a guide with ambition on how to actually use data to coach your team without becoming a dashboard manager. It's free in the show notes. - Today's show was brought to you by Outreach, the agentic AI platform for driving execution across every stage of your deal. Great sellers drive velocity at every stage of their sale and one thing that's worked well for me is assigning red line deadlines to my prospects when we kick off vendor review. Even artificial micro deadlines for things like first cut of red lines and security review helps my prospects get there internal team moving. We built a guide on how to help you drive six and seven figure deals with our friends at outreach. Get it free in the show notes. The worst discovery advice is just be curious and ask lots of questions. Look, our prospects are not showing up to sales calls to answer our questions. They're showing up to get their questions answered and to figure out how we can solve their problem. And this is what Pipetripe does. If you want to get clear, complete sales visibility, you can use Pipetripes easy to use and customizable CRM that is designed to be simple from day one and stay easy to use as your team grows. We actually put together an entire resource hub with Pipetripe to help you get to Presidents Club and you can get them for free in the 30 MPC Pipetripe Closers hub. The link is in the show notes. That's really interesting. So Mark, your your question was in your right, like when I thought about when I was a rap, I was like I got to get to business impact. I got to get to business impact. That would be the equivalent of a rap doing an outreach trial and saying we're going to show the increase in your total pipeline gen across your entire mid market segment. We're going to increase piped gen by 30%. Well, that might be how you justify the business case and what they're ultimately trying to do. But in four weeks, you actually need to do the sort of less, less sexy, less business impact impact impact the metric, which is just can we increase the number of accounts that you touch by 30%. So you're not overly concerned is what I'm hearing with getting to the true sea level metric. You're looking at the thing upstream of that because you can impact that quickly. Am I understanding this right? 100% think about it this way. There's a customer that we worked with and this is a sort of a story of somebody that we that we won where they were paying an outsourcer. It's called like five million dollars a year and they were paying per ticket. All right. And I knew they wanted to decrease that cost by what's called 30%. Now I can't sell that in a four week pilot. But what we did was then we found the metrics that are sort of downstream of that. One of it would be if we could auto resolve some of these tickets using our system, we could clearly show that less tickets will flow to the outsourcer. Therefore, they would pay less. And that's how we justified it. We said, look, over a four week period, we're plugging into your systems where auto resolving 30% of these tickets. Here's what that looks like on an annual basis. Here's how you get to the metric you care about. But that's not something where I was totally focused on cost reduction during the pilot. It was a downstream metric of that, which like and show the value in a smaller period. I think when you have a product that can have a direct tie to risk time or revenue, pilots become a little simpler to figure out. But there's still always this assumption and it's the leading lagging metric assumption. If I make more phone calls, I'll book more meetings, leading and lagging. If I do better discovery and stage one conversion, I'll have a better ARR gross leading and lagging metric. And I think what I'm hearing Sean is you have this kind of pilot is impacting a leading. But then you help them connect the dot to the lagging. But you don't necessarily accomplish the lagging. Is that right? Exactly. And I think that is one of the differences that I've noticed in pilots over the, let's call it the last five years is that it used to be very much so show you how the tech works, demonstrate what is possible versus I can move a metric now over a two week four week period that ties to the case that I really want to make. It becomes a natural next step because I've already shown how I can influence the metrics over a four week period. Great. Now if you extrapolate that out, here's what that actually equates to. You guys are both sort of alluded to it. Most pilots, like they kind of suck, they kind of tank. So what are you doing? You called us the two champion rule. You've got two things you're doing here that you are, you are using to make sure that it is impossible for the pilot to fail. If you're a seller, you've probably heard like, oh, we could probably just build this ourselves. By versus build is a conversation that needs to happen in every single sales process right now. And I think the way through that is to build two champions. Your business champion was responsible for the outcome. They're trying to improve a process or have their sort of neck on the line for whatever the metric actually is. And then you have technical champions that you also need to build who live in this day and day out. That's the team where I find more often pilots die in that room. Your technical person is saying, you know what, we can probably set this up ourselves. I don't understand the value. This is really going truly bring. And I'm really not sold on this. So you need to walk into the pilot knowing exactly who both of those people are. You probably know your business champion because again, you've probably had the discovery demo gone to this point. The technical champion is the next step. You need to know exactly how that person is, how they're doing their work today, what metrics they care about as well, and how you can show tangible value to them in a short period of time. Because you can improve their life and you can also demonstrate differentiators that your product brings. They're not going to walk into that room and someone's going to ask them the question of, do we need this and they're going to walk out and say, no, we can build this ourselves because they understand the impact it's going to have on their day to day or at least the thought that's gone into exactly what the experience is that you're delivering them in this pilot. Again, that ties back to the value map because if you can also deliver value to a technical champion, make their lives easier. They are less apt to say, oh, we could probably just build this ourselves. Now they're receiving value from it. Can you give us like two or three examples of titles of technical champion and business champion? Okay, so for us, there's usually three levels to an opportunity of your executive sponsor. That's for us to CIO, CTO, chief AI officer, right? Sometimes CEO, lesso. Then we have our, what I call like our business leads. That's my VP of IT, my VP of customer experience, or someone who oversees AI initiatives, right? We're working with them. This more embedded technical person could be the director of the IT support desk. It could be the director of customer context to overseas the technical writers team, right? But these are folks that are living and breathing in the sort of challenge as it works today, feeling the pain probably most acutely. And those are some examples of titles, but usually it's the managers and directors. They're in this day in and day out. And my goal to build them into a technical champion is to really turn them into somebody who says, this will make my life exponentially easier. And I'm not going to embark on a journey to build this. There's usually some engineers that could be a part of that conversation as well. Maybe it's because we most often work with IT departments, but we usually see them show up to understand what is this technology actually doing? Which is something we need to get them bought into. Could a VP of IT be a technical champion or a business champion for us business champion? They're responsible for the outcomes that for us, maybe the help desk or service desk is actually delivering, but they are not in that day in day out, sort of figuring out the workflow, looking at ticket volumes, they're responsible for the outcome of what's actually being delivered. So, and then like the director of IT services would be your technical champion? Yeah, or their team, it could be depending on the structure and size of the org. Oftentimes, we see with the enterprise organizations that that person is still heavily involved in the day-to-day in the weeks, so we can make their life a lot easier. And the other thing that's a part of this is the politics behind it. Yeah, what do they have to gain? What do they have to lose by you coming into the organization? Always something to consider, but making sure you've identified those champions is key. Can we talk about how to win over the technical person, the engineer, because I feel like that's probably, that's where my head is going, which is like, okay, sure, I know how to build a relationship with and win over a business champion. I'm pointing to the metrics we're impacting. I'm going, we're working with their team, but I feel like winning over the engineer, there's probably harder. So, what do you do to win that? How do you get access to that person and then how do you win them over? So, it depends on what your product is touching, whether or not they may be involved. This could also be if you're selling more of a GTM product. Maybe it's your Revops counterpart, right, where they're deeply embedded in the technology. They're doing some of the building, you're responsible for orchestration, for us sometimes that is engineers, IT engineers, specifically. One thing I would say is that, my CEO says this all the time, engineers respect other engineers. Why? Because they're doing the work. And I think this is one of the hidden values of the forward deployed engineer motion, because if you're talking to another engineer who understands your environment, because I've armed them with, hey, here's what we're trying to accomplish, here's what matters to them. Great. They go in and uncover what that engineer is doing on a day today. What's their world like? What are the challenges they encounter? And then actually building things, in this case, to make their lives easier. So, that immediately displays value. And the engineer can also technically appreciate what the forward deployed engineer is doing, because they're also an engineer. But it's hard to go into a salesperson talking to an engineer and be like, this is going to make your life easier. Just trust me versus a forward deployed engineer saying, help me understand your workflow. What do you guys do in today? Great. I'm going to come back to you in a week and show you something that I think is actually going to be impactful that I've built. All of a sudden, the engineer is sitting across the table from another engineer, and they understand the technical components of this. But I think the FTE model helps unlock these technical champions because they are embedded. They're of the same functional area, and they speak the same language. Do you sell mostly to a extremely technical buyer? I don't know if I see IT support people being overly technical. Yeah, I would say we are not always the end users of our product. They're subject matter experts. But we are selling to someone who understands the AI landscape from a technical lens. We're effectively infrastructure that plugs in to empower AI agents. So we are selling to folks who understand that landscape under technical in that lens. But the end, like for example, our business champion may not be overly technical. Even our technical champion, the person is running the 90 support task, may not be overly technical, but they understand and their subject matter experts within this. But more often than not, we are encountering someone because we're touching data. Who is more technical and apt to think along those lines? I feel like one of the shifts that's happening in addition to this promise versus proof is this idea that while a salesperson can help me figure out value, they're not building it, they're not in the weeds. They have to bring in other people to understand the technical parts of the product. And I am somebody that needs to understand and also relate to the person that's giving me that. And so now when you throw in these FDEs, which they have now as they're working with a peer that does their job that speaks the same language versus a salesperson is never going to speak the same language as an engineer or overly technical person just by the nature of their job, right? 100%. Like we are very lucky. Like the team that works on all of our pilots are extremely talented. They're incredibly good at what they do. And they, you know, a lot of this team was part of the forward deployed engineering creation motion. That is exactly what they are doing is they're with the customer. They are building and shipping to improve the customer's life. That's what builds technical champions. So when that's happening in a four week period, it's very easy for me to say, look what we've built. Look at the metrics we've touched. I go back to the business champion, and I've got a case that is very built out that can start to touch on some of the things they care about. But I think one of the benefits of the forward deployed engineering motion is exactly that. They're embedded with the customer. They're building and shipping to make their lives easier, improve a business metric. And when I can work alongside them, the pilot goes so much smoother and really actually delivers outcomes. And this is what PypeDrike does. If you want to get clear, complete sales visibility, you can use PypeDrives easy to use and customizable CRM that is designed to be simple from day one, and stay easy to use as your team grows. We actually put together an entire resource hub with PypeDrives to help you get to Presidents Club, and you can get them for free in the 30 MPC PypeDrive Closers hub. Today's show is brought to you by 11X. You're all in one digital GTM team handling, creating, qualifying and converting Pype Blend across every channel. If you are still using stale triggers like congrats on the funding, you're getting blended in with everybody else. The best use unique signals, exact LinkedIn posts, negative product reviews, podcast appearances, and use those as their trigger. And we built a growth playbook with our friends at 11X breaking this stuff down. You can get it for free at 11X.ai/30MPC, or grab it in the show notes. Today's show was brought to you by Outreach, the agentic AI platform for driving execution across every stage of your deal. Great sellers drive velocity at every stage of their sale, and one thing that's worked well for me is assigning red line deadlines to my prospects when we kick off vendor review. Even artificial micro deadlines for things like first cut of red lines and security review helps my prospects get their internal team moving. We built a guide on how to help you drive six and seven figure deals with our friends at Outreach get it free in the show notes. Yeah, I don't know, man. If right now the difference between SAS and AI is the difference in the technology. As you're saying this, what I'm starting to think is the difference is in the build versus buy mentality, meaning when I buy SAS, I don't get to build it. I just get to buy it. But when I buy AI and I have an FDE, they build it for me, which feels like me building it, because I get to inform it and they're embedded with me, but I'm not actually ones with the fingers on the keyboard. So it's actually easier for that to happen. And when I look at the cost, and you know, I'm sure you have things like if you have three internal engineers work on this for six months in a row, and they're not really subject matter experts, it cost you this much money. We'll have it deployed in three months. And with the value you get in the cost savings, like it's overall like an economic win for you. This is like a very interesting thing. And I wonder like for people listening, when you're, you might not be in a business like Sean's, but the lesson is if you don't move to or towards a business like Sean's or emotion like Sean's, where the buyer feels like they're co-building so that the build versus buy never becomes an issue. They're building it with you, but they just aren't buying a SaaS off the shelf. That might be like one of the biggest takeaways I've had in an episode in a long time. The other thing to think about there, I think you're absolutely right, is that even everybody that's going into a SaaS buying conversation or buying cycle right now, and this is somebody who I've spent with 12 years in SaaS. This is an AI native company that has a different motion, but it rhymes in a lot of ways. And one of those that I've seen over the last two years is that every buyer, even when they're looking at a SaaS product is asking, should we build this ourselves? Because the cost to build technology has just come down. Now, what they're not thinking about is the enterprise great security that they need to put on top monitoring that they need to do. Everybody's asking that question, but if you can preempt that, and you can still get access to data to give insights, analysis, and actually educate them on what has gone into the product that has been built already that they're getting access to, and still figure out a way that you can showcase outcomes throughout the pilot, then you're still going to accomplish the same goal, because you may not be building product or shipping things during the pilot itself. But if you can at least attach to those downstream metrics and show how they would be influenced and educate the buyer on here is why our SaaS product has been built the way it is. Because we've gone through all those failure modes that you're probably thinking about as you consider a buyer versus build, it's still worth addressing in some way, but I completely agree with you Mark that that has shifted. So, and there's something that you're doing in your contracts, your paper, which is you are building in conversion from POC free to paid. Can you explain two things? One, the language, the mechanism that you are putting in the contract, and then two, how you voice that over with the customer, because I imagine that is a place that if I'm listening to this, I might be like, yeah, there might be some friction there. I mean, it's a way to have the hard conversation up front. So, the way I think about this is, if there are agreed-on success metrics, which you've done at the beginning of the pilot, these are the things that we want to see, these are the metrics that actually matter to us, that we want to move, and now comes that we're effectively moving towards. Now I understand, okay, here's what we need to showcase during the pilot period. But I will also put in there, if we can achieve these, why wouldn't there be a reason for us to move forward? Oftentimes, I'll do that right at the week zero kickoff, so that at least now I understand, there's other things I need to do, there's other things that we need to talk about during this pilot period. But more often than not, it is, if that is what this pilot can showcase, then yes, we will sign on and move forward. And that heart conversation has had. And all of a sudden, you're not going through a tire-kicking evaluative pilot, you're going through this period of time that we've agreed on, is going to hit these metrics. And if we do, you're going to move forward. Do we have a line? Because if the metrics that we're talking about actually matter, and if the business outcome that you're moving towards actually matters, there's no world where that answer would be known. It wouldn't make sense. Or if it is no, there's a conversation that I need to have to understand what's blocking that. What are the other things? Who are the other people that would need to be involved? Are there other areas of the business that potentially have different outcomes that they're moving towards that would get in the way of this? Is it politics? Is it another motion? I don't know. But if the answer to that question is no, usually indicates the metrics don't matter. This is not truly a priority. Or I'm not talking to the right folks because there's other areas of the business that just are moving at a different clip. This is like one of those tactical questions that helps people so much if he asked me, but are you rolling the cost of the pilot into the first contract? That's like one of these little details people don't think about. We charge for the pilots. So it's $10,000 for weeks. Now, again, at the end of that, there's a reason that we're charging $10,000 and that's you get a fully updated knowledge base. You can do with that what you will. You can feed that to an AI agent. Now, the continual learning infrastructure is one actually is the ongoing value. But if you want an updated knowledge base, no problem. We'll do that for $10,000. But my question to them is more so outside of that, if we can show x, y and z metric improvement over the four weeks, what would be the reason that you wouldn't move forward? And more often than not, the question is like, no, I mean, if we can accomplish those things that are great, we would do it. And all of a sudden, we're negotiating live agreement in parallel with the pilot actually. If you can align the buying cycle and the sales cycle, the pilot is where those two meet. And with knowledge, I'm sure you can show like some kind of degradation, like, hey, four weeks ago, like 17% of your information is already out of date and been replaced. Like if you don't go through with the pilot and buy it in four weeks, what this knowledge base is going to be 17% inaccurate, you're going to be headed back to where you were. Yeah. Exactly. Right. That's the whole sort of thesis. But absolutely. Sean, one other question, you talk about the concept of embedding a pilot deployment team. I think I understand how you as the AE or leader might be engaged with the customer. I think I have a sense of like how your engineers are pairing up with their engineers. But could you give me a sense of the roles on your side that you are involving in the pilot, who you are pairing them up with on the customer side, and then one or two sentences about the task or the charge that you give each of those people. Okay, absolutely. So here is how I simplify this explanation because again, roles, responsibility is going to look different across every organization. Our pilots are effectively staffed with a couple of roles, one of which is the Go-to-Mar to resource. So they are the person who's responsible for, in my lens, building the technical champion. and the making sure that the pilot narrative connects to the outcome that that business champion cares about and the business cares about. Then you have more of a, let's call it an engineer type of persona. Could be a forward deployed engineer, could be a sales engineer. There are more technical persona. My mission for that person is we need to find and flip a technical champion that says this product will deliver X metric improvements either in my life or within the business. And that effectively ties to the business case that we are building. Simple terms, those are the ways to think about it. The go-to-market resource is kind of a translator of technical to the business outcome. And my engineer is deep with their team embedded and actually building these technical champions day in, day out as they're using the product as they're seeing value. They are communicating that back. So it is one cohesive narrative, right? But it's an engineering resource and it's a go-to-market resource. It's effectively like a translator and the technical person. Great. Last question I have for you, Sean. Top three mistakes that you see people making with pilots. - Hmm, good question. One, it is not aligning on success criteria upfront. Even if it's qualitative, right? You need to have an understanding of what's gonna make this a win. And if you're doing a pilot or a trial without actually defining success criteria in depth, if somebody says to you, well, we just wanna get a look and feel. No, that's, it's not gonna work. You're gonna leave that sort of week or two weeks with a lot of feelings and actually no tangible value. But success criteria number one. Number two would be not actually building technical champions. I've seen this in prior roles as well. When I think about going, it was our Revops persona. If they're not bought into how this helps orchestrate larger plays or builds into their data infrastructure, then you're not gonna win the deal. No matter how much the sales leader says, yes, this is gonna make my forecast better. If the Revops person doesn't understand how this fits into a broader ecosystem, you're not gonna get that person over the line. The last one I would say is not actually mapping out and thinking about the value you're gonna deliver. And I think AI has changed that to make it easier to showcase value. But if you're not thinking, what is this person, this customer going to see at the end of the pilot that they did not have before yet? It forces you to think differently about how you show up in that pilot, right? We are doing it through knowledge updates and becoming that infrastructure layer. At Gong, we were doing it by actually showing them insights on their sales conversations. But they need to leave the pilot with something of value, it's tangible that they did not have before. And if you can map that out throughout the path of the pilot, you're gonna win. But I think everybody considers a pilot as, all right, they're gonna go test it out. I'm gonna have a couple calls in my sales engineers, maybe run some trainings, that's not enough. They need to walk out of that pilot period, having learned something or having been given something new that's valuable to their organization. - All right, Mark. It is time for our two by two recap. What were your top two takeaways from that episode? Number one, I love the two champions. You always want to build out a good buying committee and have different people. I don't know why. I'd never thought of every deal needs to have two champions. Two heads are better than one, two champions are better than one. So, and I liked how he designated what type of champions. We don't need repeat champions, individual technical and business champions that that was pre-dote. And then the second thing is like, I don't know if this is like a tactical takeaway, Nick. In that episode, I literally thought the way that my team can combat build versus buy is to create more of a build experience in the sales cycle versus just a we're convincing you and showing you why you should buy experience. I think a seller can control that. I think a seller can orchestrate that if they're intentional about it, even if their company isn't necessarily a building type of AI infrastructure company like Sean's. - Yes, all right, my takeaways were number one, a line on what success looks like up front and literally right into the contract, the conversion to paid. And so the reason you do this is it is a waste of your time, 99% of the time to do a trial with somebody that has zero intent to buy. And so if you don't know what good looks like, if you don't know what a win looks like and it's not written in the paper, you're just messing around with the contract, with a trial that like is a waste of your time, go focus on people that are going to buy because that is how you get paid as a sales person. Now I'm sure there are edge cases someone's gonna let me know about in the comments. That's an edge case. Number two, Mark, you actually brought my mind to this, which was there's this obsession in sales about gotta get to business impact all the time. In a four week POC, you're probably not going to get to the downstream level of business impact that your sales manager spin selling told you you needed to get to. Pick something upstream that you can point to impacts that downstream out trick and impact that quickly. So those are my two takeaways. And Mark, this is where people can figure out how they can help us out. I'm gonna help you out today. Sounds like you're interested in that build versus buy objection. And we actually just did a deep dive episode with Jen Allen Knuth, who literally, she's got 15 plus years as an enterprise seller and she works with hundreds of different enterprise sales teams. She broke down the step-by-step framework to overcome build versus buy. If you can't actually build with the customer. So that episode is going to come out on our YouTube channel. It might have already come out actually by the time this episode goes live. So find it on this YouTube channel and make sure you never miss another 30 MPC drop by subscribing to our channel. It would warm my heart and we will see you all next week on the show. Today's show is brought to you by Mutiny, the AI agent that helps you personalize your buyer's experience and beat the competition. The best sellers connect the dots between what they learn and discovery and everything else they share with their prospect. Every demo you show and every piece of content you share, you need to explicitly tie back to. I'm presenting this to you because you said X. Now this applies to business cases, proposals, and more and we partner with Mutiny on the three magic sales templates to help you move your deals without needing your marketing teams help. Grab it in the show notes. And this is what PipeDrive does. If you want to get clear, complete sales visibility, you can use PipeDrive's easy to use and customizable CRM that is designed to be simple from day one and stay easy to use as your team grows. We actually put together an entire resource hub with PipeDrive to help you get to president's club and you can get them for free and the 30 MPC PipeDrive Closers hub. Great sellers drive velocity at every stage of their sale. And one thing that's worked well for me is assigning red line deadlines to my prospects when we kick off vendor review. We built a guide on how to help you drive six and seven figure deals with our friends at outreach, Get it free in the show notes.

Podcast Summary

Key Points:

  1. Pilots now focus on tangible, measurable metric improvements over a four-week period rather than demonstrating technology capabilities, creating a "proof of value" that directly ties to business outcomes.
  2. Success is anchored in pre-defined, customer-relevant metrics—such as ticket resolution time or deflection rate—established through baseline guesses and real-time tracking, with clear progress shown by week four.
  3. A dual-champion model (business and technical champions) ensures alignment and buy-in: the business champion drives outcomes, while the technical champion (e.g., IT director) sees operational improvements, making the pilot more credible and reducing resistance to adoption.

Summary:

The approach to sales pilots has evolved from showcasing technology to delivering tangible, measurable value within a four-week timeframe. Instead of abstract demonstrations, pilots now start with clear, customer-defined success metrics—like ticket resolution time or deflection rates—established early through baseline measurements and real-time tracking. Progress is visibly demonstrated, creating a compelling narrative of improvement.

, IT director) who sees daily operational gains. This dual alignment ensures both leadership and technical teams are engaged, reducing resistance and building trust. The value is also mapped step-by-step through the pilot—starting with an upstream, actionable metric and linking it to downstream business impact—such as cost reduction or revenue growth.

This method turns the pilot into a high-velocity, evidence-based journey where outcomes are concrete and measurable. Crucially, success criteria are defined upfront and embedded in contracts, eliminating wasted time on trials with no intent to buy. The pilot becomes a co-creation experience, where technical teams are embedded and actively involved, reinforcing value through real-world results.

This shift addresses the "build vs. buy" objection by showing that customers co-develop solutions, not just purchase off-the-shelf tech—leading to stronger adoption and long-term success.

FAQs

Success criteria start with metrics the customer already reports, like ticket resolution time or deflection rate. These are defined upfront, with a baseline guess and actual measurement after the first week, providing clear, tangible progress over the four-week pilot.

Sales teams initiate conversations by explaining key concepts like knowledge coverage and asking customers to estimate baseline numbers. When the actual data shows a significant improvement (e.g., from 30% to 90%), it validates the metric and builds credibility, encouraging customers to engage in real number discussions.

The 'two champions' approach includes a business champion (responsible for outcomes) and a technical champion (deeply involved in daily operations). Having both ensures alignment, builds trust, and makes it harder for the customer to say they could build the solution themselves.

Pilots start with an upstream, measurable metric (like ticket volume or knowledge coverage) that can be improved quickly. The improvement is then linked to downstream business outcomes—such as cost reduction or increased efficiency—showing clear value without overpromising on long-term results.

Forward-deployed engineers embed with the customer’s team, build real value in a short time, and demonstrate immediate improvements. This builds trust with technical champions and shows tangible, day-to-day benefits, making it easier to win buy-in.

Mapping value touches ensures each week of the pilot delivers a clear, incremental benefit—like improved knowledge coverage or auto-resolved tickets—so the customer walks away with new insights, actionable changes, and a stronger case for adoption.

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