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  3. #607 - How to Turn Every Sales Pilot Into a Closed Deal
30 Minutes to President's Club | No-Nonsense Sales

10 Sep 2026 · 36m · 12 chapters

Episode artwork

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

In short

How to run sales pilots/POCs that reliably convert to closed deals by defining baseline success metrics, proving measurable progress within 4 weeks, and building “two champions” (business + technical) so build-vs-buy objections don’t kill the deal.

Guest

Shaun Crimmins (sales leader; runs pilots for an AI/infrastructure product that plugs into empower AI agents; uses forward-deployed engineering during pilots). Co-host Mark (asks questions; shares examples from Outreach and Gong).

Key claims

Start with the customer’s existing reported metrics (baseline bet) and measure the same metrics at pilot end to show the delta. Educate customers on metrics they don’t track (e.g., knowledge coverage) and improve them quickly (example: 30% to 90% in one week). Use upstream “leading” metrics in the pilot (e.g., ticket resolution time, deflection rate, accounts touched) and tie them back to downstream business impact. Build two champions: business champion (e.g., CIO/VP IT/VP customer experience) and technical champion (e.g., director of IT services/support desk). Embed technical teams via forward-deployed engineers.

Notable examples

ASOS knowledge coverage; Outreach reply-rate uncertainty; IT service management metrics (ticket resolution time, deflection rate); customer paying $5M/year per ticket where 30% auto-resolved tickets justified cost reduction.

Written by AI. May contain mistakes.

Chapters

0:00

Understanding Pilot Success Metrics

Learn how to effectively measure pilot success through metrics.

“And that is sort of the reverse engineering of the value case.”
0:42

Establishing Baseline Metrics

Discover the importance of establishing baseline metrics for pilot success.

“Okay, so first thing, we call it the baseline bet.”
1:20

Storytelling to Extract Numbers

Explore how storytelling helps in getting accurate metrics from customers.

“back and like, I just don't know the numbers.”
2:14

Common Metrics in Sales Pilots

Identify common metrics used to anchor sales pilot success.

“So let's get serious, a specific example.”
3:08

Connecting Metrics to Business Impact

Learn how to connect pilot metrics to broader business impacts.

“And it is never where they really want it to be.”
10:30

Building Champions for Pilot Success

Understand the importance of having both business and technical champions.

“So, Mark, your question was, and you're right.”
14:00

Identifying Business and Technical Champions

Learn how to recognize and engage business and technical champions in sales.

“Your business champion who's 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.”
23:09

Navigating Build vs. Buy Decisions

Explore how the build vs. buy mentality impacts sales strategies and customer relationships.

“Yeah, I don't know, man, if right now the difference between SaaS and AI is the difference in the technology.”
28:00

Value of Knowledge in Sales Pilots

Learn how to leverage an updated knowledge base for successful sales pilots.

“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.”
28:58

Roles in Pilot Deployment

Understand the key roles and responsibilities in a successful pilot deployment.

“You talk about the concept of embedding a pilot deployment team.”
Show all 12 chapters
30:37

Common Mistakes in Pilots

Identify the top three mistakes made during sales pilots and how to avoid them.

“Top three mistakes that you see people making with pilots.”
32:31

Key Takeaways from the Episode

Explore essential insights and takeaways about navigating sales pilots effectively.

“What were your top two takeaways from that episode?”
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Transcript

Automatic transcript. May contain errors.

0:00Shaun Crimmins: 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 eclates to. So it's a different type of sort of environment, like a proof of value, but exactly how we think about it.

0:33All righty, Sean, you literally win 100 % of the pilots, trials, and POCs that you kick off. And today you are going to be teaching us step-by-step how you do that. Where the heck should we start?

0:47Shaun Crimmins: 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 at where they stand today. in week one, the actual number. And then we understand after the first week what it is, and then compare it to what their guess was. But the concept here is that we are getting success criteria and their baseline metrics upfront. So that 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 too.

1:18Sean, 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?

1:30Shaun Crimmins: 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 explain 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 at like 5 % to 15%.

1:57Shaun Crimmins: 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 other companies we've worked with and how they've defined it and what they've seen before the pilot and where their metrics actually were. So let's get serious, a specific example. When I was at 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 ply rate x percent 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 get you give you that actual number that they believe because they all know what you're going to do man they all know 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 are you getting 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, that's a metric that matters, but nobody really has that.

2:54Shaun Crimmins: 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 that by the end of this pilot, not only are we going to show you, here's what we project.

3:24Shaun Crimmins: 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 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 confident enough that we will say, great, we're going to move that metric in the next four weeks.

3:58Shaun Crimmins: Nevermind a value case that's going to show you how we do it. We actually move that. 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 DeTabo 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.

4:34Shaun Crimmins: 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, since we have a GTM-oriented audience, that would be the most appropriate thing to share. 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 reply rates or meetings booked.

5:10because 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? Sean, 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.

5:43Is that right? 100%. That's the key to me, man. Like, you don't know your number? Tell you what, we're going to show you your number. And then we're going to show you that number go up over the next four weeks in this pilot. That seems like some secret sauce.

5:57Shaun Crimmins: 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 documented 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%.

6:34Seven days later, we said, here's what that number actually was.

6:38Shaun Crimmins: By the way, it is now 90%. And you're going to keep this knowledge base at the end of the pilot, no matter what. So we just went through and documented and reverse engineered their whole 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'm saying, look, based on the data as well, there's different tools that if we connected to, we can actually start to auto-resolve these tickets or draft responses for people. That's my week two value. So I allude to it.

7:07Shaun Crimmins: 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 close is like always this thing that sellers are willing to do. You're taking it the product or a 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.

7:46It just happens faster. It doesn't. So, I mean, maybe that's not the great example because 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.

8:04Shaun Crimmins: It depends on who your persona is. But we know that all of 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, maybe 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 pilot 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.

8:36Shaun Crimmins: 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 cents.

9:05Today's show is brought to you by Proposify, the proposal management software designed to make every deal a closed deal. When you send a proposal to a prospect, include a video of yourself walking through the proposal because it's going to be shared with stakeholders beyond just your champion. You want to make it easy for those other people to digest and you want to be able to control the narrative with your presentation. And bonus, Proposify data shows that when buyers watch the video, it increases your chances of winning by over 3x. So do not let your proposals become a disappointing plot twist.

9:31Get our proposal success guide free in the show notes. Today's show is brought to you by ConsenSys, which helps your demo keep selling even when you're not in the room. Before I show a demo, I set it up like it might have to work without me. I include these three slides before I drop in. Number one, the biggest problems I learn and discovery. Number two, how we solve those problems. And number three, a what does success look like today slide. You can steal that exact 30 MPC demo deck template powered by consensus. Go check it out in the show notes. Today's show is brought to you by Full & Rich, which compiles 20 plus premium data vendors in one place to dramatically improve your call connect rate.

10:07When you're cold calling, you have to make sure you're not showing up as spam likely on your prospect's end. And one way to do this is to stop calling bad numbers over and over again. Mark your disconnected or fax lines or wrong numbers so you know not to dial them again. Or even better, make sure your data provider only gives you verified numbers to start with. We partnered with Full & Rich on a guide of nine ways to improve your call connect rate. Get it for free in the show notes. That's really interesting. So, Mark, your question was, and you're right. Like, when I thought about when I was a rep, I was like, I got to get to business impact.

10:37I got to get to business impact. That would be the equivalent of a rep 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 pipe 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 sexy, less business impact-y 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 C-level metric.

11:18You're looking at the thing upstream of that because you can impact that quickly. Am I understanding this right?

11:24Shaun Crimmins: 100%. Think about it this way. Okay. There's a customer that we worked with, and this is a sort of a story of somebody that we won, where they were paying an outsourcer, let's call it like$5 million a year, and they were paying per ticket. And I knew they wanted to decrease that cost by, let's call it 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.

11:56Shaun Crimmins: And that's how we justified it. We said, look, over a four-week period, we're plugged into your systems, we're 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 I can 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.

12:31If 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 growth, 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?

12:56Shaun Crimmins: 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. 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.

13:33You guys have both sort of alluded to it. Most pilots, like they kind of suck. They kind of tank. So what are you doing? You call this the two champion rule. You've got two things you're doing here that you are using to make sure that it is impossible for the pilot to fail?

13:47Shaun Crimmins: If you're a seller, you've probably heard, like, oh, we could probably just build this ourselves. Buy 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 who's 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 in, day out. That's the team where I find more often pilots die in that room. Your technical person is saying, you know what?

14:20Shaun Crimmins: We can probably set this up ourselves. I don't understand the value this is really going to truly bring. And I'm really not sold on this. So you need to walk into every pilot knowing exactly who both those people are. You probably know your business champion because again, you've probably had the discovery demo gotten 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.

14:54Shaun Crimmins: 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.

15:19Can you give us like two or three examples of titles of technical champion and business champion?

15:27Shaun Crimmins: Okay. So for us, there's usually three levels to an opportunity of your executive sponsor. That's for us, it's a CIO, CTO, chief AI officer, right? Sometimes CEO, less so. 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 who oversees 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.

16:04Shaun Crimmins: 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. Would a VP of IT be a technical champion or a business champion?

16:40Shaun Crimmins: 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 the director of IT services would be your technical champion. Yep. 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 and the weeds, so we can make their life a lot easier.

17:13Shaun Crimmins: 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, it's probably harder.

17:51So what do you do to win that? How do you get access to that person? And then how do you win them over?

17:56Shaun Crimmins: 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. They'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.

18:30Shaun Crimmins: Here's what matters to them. Great. They go in and uncover what that engineer is doing on a day to day. 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.

19:01Shaun Crimmins: What are you guys doing 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.

19:37Shaun Crimmins: 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 and are technical in that lens. But the end, like for example, our business champion may not be overly technical. Even our technical champion, the person who's running the IT support desk, may not be overly technical, but they understand and they're 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.

20:12I 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, what they have now is 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?

20:54Shaun Crimmins: 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.

21:29Shaun Crimmins: 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. Today's show is brought to you by Proposify, the proposal management software designed to make every deal a closed deal. When you send a proposal to a prospect, include a video of yourself walking through the proposal. Because it's going to be shared with stakeholders beyond just your champion, you want to make it easy for those other people to digest, and you want to be able to control the narrative with your presentation.

22:03And bonus, Proposify data shows that when buyers watch the video, it increases your chances of winning by over 3x. So do not let your proposals become a disappointing plot twist. Get our proposal success guide free in the show notes. Today's show is brought to you by ConsenSys, which helps your demo keep selling even when you're not in the room. Before I show a demo, I set it up like it might have to work without me. I include these three slides before I drop in. Number one, the biggest problems I learned in Discovery. Number two, how we solve those problems. And number three, a what does success look like today slide.

22:34You can steal that exact 30 MPC demo deck template powered by ConsenSys. Go check it out in the show notes. Today's show is brought to you by Full & Rich, which compiles 20-plus premium data vendors in one place to dramatically improve your call connect rate. When you're cold calling, you have to make sure you're not showing up as spam-likely on your prospect's end. And one way to do this is to stop calling bad numbers over and over again. Mark your disconnected or fax lines or wrong numbers so you know not to dial them again. Or even better, make sure your data provider only gives you verified numbers to start with.

23:04We partnered with Full & Rich on a guide of nine ways to improve your call connect rate. Get it for free in the show notes. Yeah, I don't know, man, if right now the difference between SaaS 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 SaaS, 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 the ones with the fingers on the keyboard.

23:42So it's actually easier for that to happen. And when I look at the cost, and 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 costs you this much money, we'll have it deployed in three months. and what the value you get and the cost savings, like it's overall like an economic win for you. Like 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, is if you don't move to or towards a business like Sean's or a motion 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.

24:25That might be like one of the biggest takeaways I've had in an episode in a long time.

24:30Shaun Crimmins: 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 12 years in SaaS. This is an AI native company that is 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-grade security that they need to put on top of, monitoring that they need to do.

25:02Shaun Crimmins: 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.

25:37Shaun Crimmins: Because we've gone through all those failure modes that you're probably thinking about as you consider a buy versus build. It's still worth addressing in some way. But I completely agree with you, Mark, that that has shifted. Sean, 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.

26:13Shaun Crimmins: 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 the outcomes 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.

26:44Shaun Crimmins: There's other things that we would 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 hard conversation is happening. 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 alignment? 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 no.

27:15It wouldn't

27:16Shaun Crimmins: 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 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 you ask me, but are you rolling the cost of the pilot into the first contract?

27:53That's like one of these little details people don't think about.

27:56Shaun Crimmins: We charge for the pilots. So it's$10 ,000, four 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 what 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'd be great.

28:28Shaun Crimmins: We would do it. And all of a sudden we're negotiating live agreement in parallel with the pilot actually running. If you can align the buying cycle and the sales cycle, the pilot is where those two meet. Yeah. 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, um, absolutely.

28:58Sean, 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's side, and then one or two sentences about the task or the charge that you give each of those people?

29:28Shaun Crimmins: Okay, absolutely. So here is how I simplify this explanation because again, roles, responsibilities 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-market resource. So they are the person who's responsible for, in my lens, building the technical champion and 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.

29:56Shaun Crimmins: They're a 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.

30:31Shaun Crimmins: So it is one cohesive narrative. But it's an engineering resource and it's a go-to-market resource. It's effectively like a translator and a technical person. Great. Last question I have for you, Sean. Top three mistakes that you see people making with pilots. Good question. One, it is not aligning on success criteria up front. Even if it's qualitative, right, you need to have an understanding of what's going to 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 want to get a look and feel, no, it's not going to work.

31:07Shaun Crimmins: You're going to 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 Gong, 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 going to win the deal. No matter how much the sales leader says, yes, this is going to make my forecast better. If the RevOps person doesn't understand how this fits into a broader ecosystem, you're not going to get that person over the line.

31:39Shaun Crimmins: The last one I would say is not actually mapping out and thinking about the value you're going to 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 beforehand? 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 that's tangible that they did not have before.

32:13Shaun Crimmins: And if you can map that out throughout the path of the pilot, you're going to win. But I think everybody considers a pilot as, all right, they're going to go test it out. I'm going to have a couple of calls with 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 righty, 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 know, you always want to build out a good buying committee and have different people.

32:42I 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. I thought was pretty dope. 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.

33:16I 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, align on what success looks like up front and literally write 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 a trial that is a waste of your time.

34:00Go focus on people that are going to buy because that is how you get paid as a salesperson. Now, I'm sure there are edge cases someone's going to 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 got to 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 metric and impact that quickly.

34:34So those are my two takeaways. And Mark, this is where people can figure out how they can help us out. I'm going to 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.

35:11So 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 Proposify, the proposal management software designed to make every deal a closed deal. When you send a proposal to a prospect, include a video of yourself walking through the proposal because it's going to be shared with stakeholders beyond just your champion. You want to make it easy for those other people to digest, and you want to be able to control the narrative with your presentation.

35:38And bonus, Proposify data shows that when buyers watch the video, it increases your chances of winning by over 3x. So do not let your proposals become a disappointing plot twist. Get our proposal success guide free in the show notes. Today's show is brought to you by ConsenSys, which helps your demo keep selling even when you're not in the room. Before I show a demo, I set it up like it might have to work without me. I include these three slides before I drop in. Number one, the biggest problems I learned in discovery. Number two, how we solve those problems. And number three, a what does success look like today slide.

36:09You can steal that exact 30 MPC demo deck template powered by ConsenSys. Go check it out in the show notes. Today's show is brought to you by Full & Rich, which compiles 20 plus premium data vendors in one place to dramatically improve your call connect rate. When you're cold calling, you have to make sure you're not showing up as spam likely on your prospect's end. And one way to do this is to stop calling bad numbers over and over again. mark your disconnected or fax lines or wrong numbers so you know not to dial them again or even better make sure your data provider only gives you verified numbers to start with we partnered with full and rich on a guide of nine ways to improve your call connect rate get it for free in the show notes

From the publisher

Our new Social Selling course with Sam McKenna is live! Save $50 during launch week, through October 25. Order here →

Shaun Crimmins breaks down how to run pilots and POCs that prove measurable value and actually convert into paid contracts. Learn how to define success upfront, build the right champions, and engineer value throughout the entire pilot.

📈 Pick metrics you can move: Start with measurable upstream metrics you can impact during the pilot, then connect them to larger business outcomes.

🤝 Build two champions: Win over both the business champion responsible for the outcome and the technical champion living in the workflow every day.

🎯 Agree on the conversion upfront: Define success criteria before the pilot starts and establish that hitting those outcomes should lead to a paid agreement.

You're one step closer to President's Club!

📝 Build vs Buy w/ Jen Allen-Knuth

🏋 30MPC Training

🛠 Weekly Tactical Breakdowns

📚 Things you can steal and use today

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