#218 Katie Swick - The Sales Strategy Behind Stripe’s Growth

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In this episode, we have a special guest, Katie Swick, the Global Sales Enablement Lead at Stripe and an accomplished sales executive.We dive deep into the intricate world of sales enablement and strategies for success. We explore how Katie Swick has contributed to driving sales growth at Stripe and learn from her extensive experience.

Key Highlights:

  1. Sales Enablement Innovations with Katie Swick

We uncover the innovative 'teach back' model at Stripe, a unique approach to sales enablement. Katie Swick shares insights on how Account Executives can cultivate a culture of continuous learning and growth, providing you with practical strategies to implement in your own sales team.

  1. Vendor Selection and Psychology of Buying Decisions

We delve into the complexities of vendor selection and unravel the psychological intricacies that sway buying decisions. Katie sheds light on the critical role of adaptability in challenging circumstances and its impact on future biases. Gain a deeper understanding of how these factors can shape your sales approach.

  1. Sales Transformation and Predictable Revenue

We explore the significance of sales transformation and the steps to achieve predictable revenue and an efficient sales pipeline. Katie shares valuable insights into the importance of decoding your customer's buying process and how this knowledge can pave the way for sustainable success in sales.

Be sure to watch till the end as Katie shares her remarkable journey and leaves you with actionable tips to excel in the sales domain. 

Tune in now to elevate your sales journey and unlock the secrets of sales success.

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Katie Swick: 0:00

Sales enablement is often called in to be the voice of the salesperson, which I think is really important to any time that you're in either the driver's seat or an influential seat in some of these buying decisions. So I think it just depends on you know what service you're looking at. Sales enablement is a consumption-based model. Just because we bought the licences doesn't mean that the salespeople are going to use it. So I have to make sure that I'm going to purchase something that, ultimately, is going to be worth every seller's time. They're not going to get up and walk out of the room because if they do, I failed.

Luigi Prestinenzi: 0:32

Welcome to another episode of the How to Sell podcast. I am your co-host. I actually don't like saying that, dave, because I'm not my own. He says I'm your host, luigi Preston-Indy, but unfortunately I have a co-host who is a Chelsea fan. We haven't spoken about that.

Dave Fastuca: 0:51

You're a Chelsea fan Dave, Big Chelsea fan Even my daughter's name, Chelsea, which gives a glimpse into the craziness in this house.

Luigi Prestinenzi: 1:01

Yeah Well, Chelsea's doing great things at the moment, you know, winning against Lottentown 1-0 for those football fans out there. But this is not a podcast to talk about football, even though we always start the episode talking about football. But yes, we've got a great episode this week David again jumping into the trenches talking to another incredible person from the enablement space. But what was your key takeaway from the last session with Regan?

Dave Fastuca: 1:31

I think it's just leveraging the power of buying and letting, bringing in the team members, seeing where else the vendor can help other parts of the business without just focusing and being one-dimensional. That's how that provided a lost deal in that case.

Luigi Prestinenzi: 1:49

That's pretty interesting, isn't it? Well, we'll jump into this week's episode. We're pretty fortunate and privileged to have somebody from an absolutely enormous brand where a lot of people probably use the platform in some capacity if they're buying online and they might not even know it. But just want to say welcome to the how to Sell podcast, Katie.

Katie Swick: 2:11

Thanks for making me Happy to be here.

Luigi Prestinenzi: 2:13

Yeah, we're pretty excited and obviously I heard you recently on one of our good friends podcasts, Donald C Kelly, the sales evangelist, and you dropped some.

Katie Swick: 2:21

Yeah, that was a lot of fun.

Luigi Prestinenzi: 2:22

Yeah, awesome. But before we jump into today's session, we'd love to get your. You know just a bit of background and how you got into enablement. Obviously, you've worked with some huge brands such as Google, but yeah, why enablement?

Katie Swick: 2:38

Yeah, good question. So probably like many of the folks that are listening, and you guys as well, I started with carrying a bag, so I actually started in sales to put myself through college. I sold large travel packages and then I was supposed to get my degrees in criminology. I thought I wanted to be a parole officer actually, but I found that I could make more money in sales than I could as a parole officer, and so I did sales for a long time everywhere, from inside sales, sdr work all the way up to enterprise sales. And then I was that person that would get up in the middle of our training and I would leave right Because I didn't think it was worth my time. And so at the time, google said to me like, hey, you either need to go to the training or you need to figure out something better. And I was like, well, give it to me, I'll figure out something better. So that's how I got my start in enablement. Before enablement was really a thing of getting up and leaving training that I didn't think was worth my time.

Luigi Prestinenzi: 3:37

And it's funny because I remember when we started working together oh, over a year ago what do mean over a year ago now? I remember you telling me that story and saying, yeah, I got up out of training one day and I'm like, oh my God, I'm going to be training you and your team. You get up and walk out.

Katie Swick: 3:56

Sayonara.

Luigi Prestinenzi: 3:58

Yeah, but that's really interesting, right, Because obviously I feel you. I feel that pain because as a sales professional, my whole life I've been thrown into sales training sessions and you kind of sit there and switch off in some cases. So actually we'd love, just before we obviously jump into our topic of you know how to sell. But there's one thing that you do very differently from an enablement perspective, that not a lot of companies actually execute, which I think more companies should do, which is to teach back. Can you maybe just talk us through the teach back model that you've incorporated the practicums in your business?

Katie Swick: 4:37

Yeah. So to me it's pretty intuitive, right. So it doesn't feel like something unique that we're doing. It just feels like something that everyone should be doing, to be honest with you. But so a lot of the programs that we do, the managers are actually the professors or the sellers are the professors, right? Because they're really the ones that are doing it day in and day out. And so you know, if I'm not going to lead a training on how to create the best proposal, I'm going to go out and get the last three AEs assigned big deals and have them come in and talk about their proposal process, what worked, what didn't work, and so we've actually found that to be pretty successful. At Stripe, you know, everyone is kind of in a give get relationship where the AEs want to show off what they've done, like they worked really hard at it. So we want to give them an opportunity to show off what they've done, and then the SDRs and other folks are really eager to learn. So it seems to be a nice flywheel effect. If you will, that's working for us at the moment. That's great, yeah.

Luigi Prestinenzi: 5:46

I've loved it and I've obviously had the privilege and the pleasure of seeing it live. And it's awesome, you know, because it's a different level of respect as well, right, when you've got an SDR or an AE hearing from somebody that has been there or is still doing it, they just say it from a different perspective.

Katie Swick: 6:06

Yeah, I think I mean, Luigi, you were doing a training for us a while back and during the training you're like I don't know, let's give it a whirl. And you picked up the phone and made a cold call, right, and that was really powerful in the room. And now all of the managers do that as professors for a very similar enablement session that we do where they're like okay, everyone, we did the, you know the programmatic research, we did this, we did that, like let's pick up the phone. And they pick up the phone in the room and they make a cool call.

Luigi Prestinenzi: 6:37

So yeah, pretty powerful, wasn't it?

Katie Swick: 6:41

Yeah, it was good. It was a good one.

Luigi Prestinenzi: 6:43

I must admit, my stomach does drop every time. I do that because I'm always worried. What's going to be the outcome of this? Yeah well, obviously, the framework of our show here is about we really want to help sellers understand how they can, how they can position themselves when they're engaging with buyers. And obviously, Katie, even though you're in a position where you're building the enablement roadmap, you're also buying, and you're buying software and you're buying services all the time. So we'd love to really understand, from an enablement perspective, where do you like, are you the influencer or are you the ultimate decision maker when it comes to buying products?

Katie Swick: 7:30

Yeah, good question. So, like in all things, I think it depends, right. So if I'm going out and buying a sales enablement platform like a, a high spot or something like that, then obviously I'm in the driver seat. Yeah, because that's kind of my realm of, kind of my domain expertise. However, there have been situations where I'm an influencer and my level of influence that really depends on you know not only what position I'm in now, but what I've done in the past, right, like I've stood up, CRM’s and past roles, and so anytime that we're looking to do a CRM integration or a plug-in or something like that, people often come my ways. And I find this to be the same for a lot of my kind of colleagues in the sales enablement world, where Sales enablement is often called in to be the voice of the salesperson, which I think is really important to any time that you're in either the driver seat or an influential seat and some of these buying decisions. So I think it just depends on you know what service you're looking at.

Dave Fastuca: 8:34

That's an interesting one there, Katie, and Can you walk us through where you were brought into a decision buying process in a good way and On the flip side, in a bad way? We sort of put you, put your back up. You know potentially where you may have been in the last minutes or, you know, do you have a situation on both sides?

Katie Swick: 8:56

Yeah for sure. So I think in Situations where it's worked well is Obviously it all goes back to the pain point, right, like what problem are you going to solve for the salespeople? And so in those situations, obviously there's a lot of momentum and a lot of energy that comes. I can just speak for myself, for me and try to help solve that problem, right. So Conversation, intelligence tools, right, something like that, where I think there's a lot of value that could be added to a salesperson's motions Times when it hasn't worked as well. Usually for me it's and this is a bias on my side where I feel like you're going to increase the operational burden to a salesperson. So if another team needs better reporting or you know they need a better tool to do XYZ, I think if they don't bring sales enablement or in early, like, sales enablement is often going to be the blocker Because we have to be the sales. You know the voice of the salesperson.

Dave Fastuca: 10:05

That's really interesting, and have you found yourself having to influence Someone to implement a solution where you know that your team needs this particular coaching service product, but you don't have the buying power? How, how have you influenced that decision maker within the business?

Katie Swick: 10:26

Yeah, I think you have to create FOMO right, like people at their core don't want to miss out on something. So I think it's really important, like when I've Been successful at influencing budget, especially right now when budget is hard to come by, right, it's like what is the cost of not doing something? Or where are they going to lose if they don't put this into play?

Luigi Prestinenzi: 10:52

Nice, nice. Yeah, I love that because, to be an action right, and I'd like to know, like in is there a recent purchase that you've made when the selling organisation helped you define that cost of inaction? And how did they do it? Because I always love to hear those stories like how does a selling organisation actually share With the buyer? Hey, this is the cost of not doing anything.

Katie Swick: 11:23

So I think ultimately, like in my role, I become the salesperson, you know, in those situations, right? So if I'm a really good salesperson in those situations and maybe this is just because I've carried a bag in the past but I need to create that FOMO for my sales people so that ultimately they're the ones that are pushing it through and I'm just kind of behind the scenes Making sure that their voices are heard, right? So what are they unable to do without this? Where are they missing revenue because they don't have this? How are they, you know, less productive because they don't have something again? It's like this whole fear of missing out because there's gains, for sure. You can sell on gains, but it's easier to sell on FOMO, in my opinion.

Luigi Prestinenzi: 12:11

Because that's the emotion right.

Katie Swick: 12:15

For sure and no one likes to be left behind right, especially like I work in the tech space. No one wants to be, kind of you know, left behind in the tech space.

Dave Fastuca: 12:24

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Luigi Prestinenzi: 12:49

Yeah, it is actually. It's really interesting because that's a very different perspective. The perspective that you're bringing is that you're becoming the salesperson internally and that's the way you're influencing others, not just the buying committee, but also the people that need to use the product right, Because there's nothing worth buying something, and the people that you meant to serve with that product or service. If they don't come on board, then it becomes a purchase that doesn't deliver the right ROI.

Katie Swick: 13:21

Well, and then it's not worth any of our time, right? Yeah, Like, why do I want to spend time? Because all of these purchases take a lot of time and a lot of effort, not only to just get the you know signed and get the budget, but to implement and onboard and all of those things. I get the big time investment to actually purchase something.

Dave Fastuca: 13:40

It's like two cycles, right. Like you mentioned there, it's the initial cycle of getting the product in the business and then the cycle two of adoption of insurance that they went in. It's similar to like in any tech business, where you know you made the sale and now they need to implement the product. Otherwise, stripe doesn't make any money unless it's implemented.

Katie Swick: 13:59

I mean sales enablement is a consumption based model, right? Like we, just because we bought the licences doesn't mean that the salespeople are going to use it. So I have to make sure that, to your point that I'm going to purchase something that, ultimately, is going to be worth every seller's time, they're not going to get up and walk out of the room because if they do, I failed.

Luigi Prestinenzi: 14:20

Yeah, and do you mind me asking, has that happened to you in the last couple of years? Oh for sure, yeah, for sure, for sure.

Katie Swick: 14:32

I like to think about it. I think about the time where, you know, sales leadership was saying and they rightfully so we're saying like, hey, we need to go back to the fundamentals. We need to go back to the fundamentals, bring in folks, have them train all of our salespeople. We did it, we spent a lot of money doing that, but the salespeople themselves, like the AEs especially experienced AEs back in that situation, didn't want to be there. They didn't feel like they really needed the fundamentals and I hadn't created an attractive economy where, you know, they saw the value. So I mean, in that situation, I would say that I failed because I didn't call out the disconnect between what I was seeing from senior leadership and the real needs of the business when I made that purchase.

Dave Fastuca: 15:21

That's really interesting.

Luigi Prestinenzi: 15:23

Yeah, so on that point, right, you know you've mentioned that you failed, but from the selling organisation. So the organisation that engages with you to bring those fundamentals in place, right, because I'm assuming that was an external company. I mean, would you expect, like, looking back now, would you expect that? Or, upon reflection, wouldn't they have done an analysis to define that this could be a problem that your sellers might not want to hear the fundamentals, and this is maybe a strategy that we need to use first.

Katie Swick: 16:08

So probably right, but I think that goes into how I obviously didn't sign a renewal with that company. Yeah, you know so. So I think you know, just looking back on that particular situation, like we trained thousands of people or attempted to train thousands of people globally using this vendor and it didn't work. I would have loved for them to say like, okay, time out, something's not working, let's pivot. So, I think it was on them to keep on going and, frankly, again, on me to keep the sessions going, but ultimately they sold us what we thought we wanted and needed at the time. So I think if there's any quote unquote blame to be put on them, it's that they didn't pivot halfway through.

Luigi Prestinenzi: 16:52

Yeah.

Katie Swick: 16:53

And that's what I would expect from vendors. Nowadays, if something's not working. They need to be looking at this like I am, like a consumption based business, and if people aren't consuming, then like time out, let's. Let's rethink this purchase.

Luigi Prestinenzi: 17:07

Yeah, because I think what you're describing, that's. That's what creates future biases, like people then start to when they're looking at other solutions because of past experiences. It creates some concerns and fears, and this is a topic that we've discussed not just with others, but it's a topic that I'm constantly talking to sellers about. It's needed to understand the past, because that will help you determine the business case and if that's something that's happened previously, then you can at least say you know, in that business case you can build out what is the strategy if this occurs right, and how are we going to work through that? Because that could become the ultimate blocker, right. That could happen in your case. If you're selecting another vendor for training, you might say, well, I haven't got the confidence in you because we haven't addressed something that actually occurred previously.

Katie Swick: 18:07

Yeah, and I think what you're calling out is you know you need to meet your buyers where they're at right, like in this situation. I was the buyer and what I needed at the moment was flexibility. I needed a vendor or someone selling to me that could be agile, right. So I think it's about again meeting folks where they're at and really conveying that you can do things like that, because some vendors aren't flexible, right. If I go out and buy 50 licences and then I hire 400 people, like, I need someone that can scale with me right. So those are other things that you have to think about when you're buying. If I latch myself to this vendor, because that's what you're doing is you're latching yourself or creating a relationship with this vendor? Are they able to go with me over the course of time?

Dave Fastuca: 18:58

That's a great point. And what does it feel like when you're working with a vendor, katie? And what does a business case look like? How is it presented to you, and then what's the process internally to get that signed off within a business of stripe size?

Katie Swick: 19:17

Yeah, I mean it's a good question. I don't know that my experience has been any different than what I've heard. Like typical sales training right, I always say that for me moving to an internal role. Sometimes I find myself working harder on my sales skills than I did when I was carrying it back right. So, because I need to, you know, going back to the FOMO, I need to show why now, why the solution, what people are missing out on. I have to build my champions. Like all of those things that you would do in a normal sales cycle, if I was selling to customers externally, I have to do it internally and at the end of the day, I have to stand behind my decision because these are also the people that are doing my performance review right. So I have to make sure that the sale really goes well.

Dave Fastuca: 20:09

And it's added pressure, if anything.

Katie Swick: 20:12

Yeah, For sure. For sure, right, like I need this one to stick. It's not a sale that I can say like oh good to go, like move on to the next go. I have to put my political capital behind this one.

Luigi Prestinenzi: 20:27

Because your reputation is at stake as well. Right, this is the thing that for sure. If you're endorsing something and it doesn't work, then it could negatively impact your brand within their business. Right.

Katie Swick: 20:41

For sure. I mean, everyone loves to say that, like you, learn from your failures, and you absolutely do. But like you don't. You don't want to get known for your failures, right? So you have to make sure that you might fail once in a while. But you have to have more wins and losses at the end of the day, and every time you make a purchase it is a win or a loss.

Luigi Prestinenzi: 21:02

Yeah, and is that sometimes like in the back of your head when you're looking at a large purchase or a purchase of some form and you're kind of going, you know, if this doesn't work, how is this going to impact the way my peers view me or the way my bosses view me?

Katie Swick: 21:20

100%. Yeah 100% Like I am spending the company's money right or I am taking up sellers time, which, in my opinion, is probably the most valuable resource that the company has, and so it's not me to be really diligent about that.

Dave Fastuca: 21:37

Yeah, and it's great psychology getting into the seller's mind here when selling to enablers all the things that they need to be really aware of, right, some of the team reputation of the buyer, all these key factors here that a lot of people just miss in that buying journey.

Luigi Prestinenzi: 21:56

Yeah, Because sometimes it doesn't get addressed. Hmm, right, and we heard that.

Katie Swick: 22:01

Well, and I think sales enablement also sits within a really interesting spot or at least it has for me because ultimately you're kind of in this triangle, if you will, of like. You have stakeholders that are salespeople when you're making a technology decision. You also have stakeholders that are systems and tools and processes people. Usually, sales enablement flows up to some sort of revenue, operations leader, right, so you have them. And then you also usually have HR or L and D, yeah, so those are all of you know. When I think about my buying committee and who I need to influence to make a purchase, I need to influence all of those folks.

Luigi Prestinenzi: 22:43

You've also got marketing right Because marketing is doing the top of the funnel that's feeding your SDR sort of unit. That's quite a lot. It's interesting. And it's really interesting because we spoke with Gale, who's the founder of Aligned and they build digital sales rooms, and he shared some really interesting stats on what they've seen that if you're in a small medium enterprise or small medium deal, if you think there's three stakeholders, there's usually six. If you're in a mid to large, if you think there's six stakeholders, there's usually 12, right, so the actual buying committee is bigger than what we first think about.

Katie Swick: 23:21

So it's interesting that you shared that because you just kind of mapped out what that looked like- yeah, I mean, there's different decision making, like frameworks if you will, whether you want to use rapid or raci or you name it. But I think whenever you're selling to someone, you need to understand not only who the decision maker is, but who needs to agree, who needs to influence or consult to. Understanding that whole framework is really important.

Luigi Prestinenzi: 23:49

Yeah, this is so good and could you maybe just tell us like a really good experience you've had buying something and what did the salesperson do that really made that experience memorable for you?

Katie Swick: 24:04

So I think, if I think back to, kind of, I'll take you through a technology sale. So I made a purchase of a CRM a few years ago at a previous company and I think what the salesperson did at the time was just be brutally honest, right, like just brutal honesty. I would also say at the time I didn't recognize it, but she was definitely more of a consultative sales approach and she didn't necessarily care about the licences. So I really, kind of going back to this idea that you have to sell on a consumption based model, she took that to heart because it was like look, I'm actually going to undersell you on licences and I'm going to put you on a managed services contract and then we'll increase it as we go, right, but it's on me to make what people want to use the CRM, which I thought was no, I've never found a seller that says I love my CRM, right, so like that was a tough position for her to put herself in. So I think just she put herself in a position where she had a stake in the game and responsibility to make it work and I think that made it an easier or less of a risky buy for me.

Dave Fastuca: 25:20

I like that. It's like she's put her, like you said, skin in the game. She understands the CRMs and massive, massive purchase for any business and adoption is the killer of CRMs. So that's where she's put her neck on the line to ensure that it works and you have her support. I like that. Do you have a great product but are struggling to reach more customers? Are you spending hours on sales activities that aren't generating results, leaving you feeling frustrated and discouraged? The SalesOS program is a step by step operating system that will help you slash your selling hours in half while rapidly growing your revenue. In under just two weeks, you can be well on your way to creating predictable revenue. In SalesOS, we'll show you how to build predictable sales pipeline, build lasting relationships with your customers and sell more in less time. The art of negotiation and motivating and leading a successful sales team. If this sounds like something that you need in your business, visit a growth forum for slash sales and apply to see if you have the right mindset to achieve predictable revenue. The SalesOS program is your ticket to predictable revenue. Don't want any longer. Apply today.

Katie Swick: 26:36

It's not like when you buy a house, right? No, you want properties or something. It's like, okay, you bought your house. Adios, amigo. Hope you like it. You know it was the exact opposite of that.

Luigi Prestinenzi: 26:50

And it's an interesting model, right? And also she obviously sold it, but I'm assuming, because you hadn't bought heaps of licences at the start, that the salesperson continued to engage with you through that process.

Katie Swick: 27:07

For sure. We had bi-weekly calls. How's it going? She would send me the results. Here's how many active users you have. Here's how many contacts have been uploaded. Here's how many people have pulled reports. So again, kind of just going into this, she had a stake in the game.

Luigi Prestinenzi: 27:25

Yeah, that's intense, that's awesome, so it's very different to the modern day model right when it's whole. I sell handballs off to the next person. I might just say adios and then all of a sudden that relationship is kind of potentially lost right, which I'm a big advocate for, that relationship funnel as a salesperson, your bank, your equity is in the relationships that you build because no matter where you go, potentially you can actually bring those relationships with you. Oh, 100%.

Katie Swick: 28:01

I mean I would like to think that her comp was on like total revenue, right, and not activated revenue. But I mean, either way, she made me feel like I was really important and, like I said, that she had skin in the game.

Dave Fastuca: 28:14

So good, so good. That's a good point. What Katie mentioned is right, it comes down to the compensation model for that seller. You know how they are incentivized? If it's the go along the journey retention, then it's a smart move that she did. But if it's just on net new sales, then it's sold. Katie bangs onto the next one. So it's in the brain into the model.

Katie Swick: 28:39

Yeah, and I think that's important. You know if you're a sales leader or building a company or your charge of compensation. I think early in my career I underestimated how compensation plays a role and what people sell, what people buy. All of those things matter.

Dave Fastuca: 28:58

Yeah, and let's. Let's flip the funnel a little bit here. Let's go back to the top of the funnel when dealing with salespeople. What triggers you to take a meeting if someone's reaching out to you?

Katie Swick: 29:12

Yeah, they, you know this is tried and true. And actually, Luigi, you preach us to your blue in the face, which is like they know me right, or they've attempted to know me. They're not trying to sell me something. That's kind of either off the shelf or I could be interested, things like that. It's the exact opposite of folks that call me and they're like hey, you know, they give me kind of their spiel and I say what company do you think I work for? And usually they're telling me about a company I worked for two years ago or three years ago. So I think personalization and just understanding where I might be in my buying cycle is really important.

Luigi Prestinenzi: 29:51

Yeah, it is, it's important, right, and I actually got one. I've forgotten a couple of times actually saying, hey, we can help you scale your restaurant business. I'm like that's fantastic. I don't know where my restaurant business is, but if you don't cook, you can ask my kids. Hey, this has been awesome. Okay, I actually like I've got notes of my takeaways and I could. We could probably turn this into like four different episodes because there's so much quality content that you've shared with us, but we are almost at the time to wrap up. But for our listeners and for our audience that would love to engage and learn more about what you do, where is the best place and we'll obviously put that in the show notes, but where is the best place for them to find and engage with you?

Katie Swick: 30:47

Great question, LinkedIn. So I'm US based, so LinkedIn is kind of king or queen here. So just hit me up there and we can take the conversation forward.

Luigi Prestinenzi: 30:58

Yeah, awesome. Well, this has been fantastic. Katie, just want to say thank you very much for being a guest but also for, like I said, you had a really big impact on me when I was able to see those practicums live. It really did change my perspective on what's possible from an enablement perspective, and I believe that is a concept Every enablement person should be able to. It should be seen live, because it's fantastic. When you flip it right, when you flip it from, you're not the facilitator, you're actually empowering the people that you're serving to become the facilitators, and it's such a great concept. So thank you very much for the impact that you've had on me.

Katie Swick: 31:41

Well, thank you guys for doing this. I've listened to quite a few of your podcasts and they're great, so thanks for having me on.

Luigi Prestinenzi: 31:49

Thank you, katie. Hey, Dave, what an awesome, awesome session.

Dave Fastuca: 31:54

Yeah, that was great. There were so many takeaways there from Katie. I guess, like one of the big things you know if I talk about, my biggest takeaway from that was you know the risk of her role when she's selling internally yeah, she's selling, she's. You know, she's using the company's money. Like she said, she needs to make sure her boss is on board and then she needs to make sure her team is on board, make sure that they adopt the sales training, the tools, whatever it is that she's buying. It's it's. That is a really tough role.

Luigi Prestinenzi: 32:27

Yeah, and you know, also, I think something that I probably didn't consider was what if it doesn't work? Yeah, yeah, the brand impact. And you know we sometimes look at, oh, if it doesn't work? You know that they're spending money that might not deliver an ROI, but that emotional aspect probably has more of an impact because that personal brand internally could be tarnished if something doesn't work well. So for me that was a pretty big, pretty big takeaway.

Dave Fastuca: 33:02

Yeah, like she used the term like politician, right? Yeah, I've got to use my political capital and we know, like any politician, you're only as good as your last decision that you've made. So you make it. You know you could make five great ones, make a really bad one and you're almost one foot out the door. Yeah, people start to turn against you. You know there's someone better that can take your role, someone better they can move the company forward. So it's, you know, I never thought about it in that way. Where you're, it's like a little campaign, political campaign internally to buy something and then to sell it internally, like that cycle. So I think, from a seller, if we flip the hat. You know, it's great to understand these things because then, as soon as you're aware of them, it's how can you help Katie in her role, knowing what you know now and the challenges that she has? How do you help Katie overcome those? Because that will make you stand out as the supplier of choice versus someone who doesn't.

Luigi Prestinenzi: 34:03

Yeah, absolutely. So let's jump in. So how would we sell to Katie, like with you know another enablement folk, different perspective, very different. You know a little bit different social style in comparison to Regan, right, and obviously we've got other incredible enablement folks coming up as well. So we'll dive into this. But I think the first thing, obviously in any initial conversation that you'd have, if I was selling to Katie for the first time and in fact I've had the pleasure, I was that person carrying the bag and winning that account with Stripe Katie was my key stakeholder In understanding her need, like she said, that FOMO she spoke about, you know, the cost of doing nothing, etc. That example that she shared of saying, hey, I used a previous vendor, we did all this training, it didn't fundamentally work. I actually did pull that out early in the conversation with her. How did you do that? Because I asked pass based questions. Right, I asked questions around. You know, talk to me, talk me through the last initiative that you did from using an external vendor. What worked well, what would you do differently? Right, I asked those questions and Katie shared the answers. Katie said, hey, this is what I like, but this didn't work. Right, this was the impact. So, in understanding the impact and the issue that she had experienced previously, I was unable to bring that into the proposal. I was able to bring that into our conversation and we spoke about it and that's where I positioned a few options to allow her to have that consumption based model.

Dave Fastuca: 35:46

Have you ever had a time where you could sense that they had a bad experience in the past but they're not being open and sharing that and it's critical, you know, for you to put the, you know to have that information, to put a proposal together. Have you worked around that?

Luigi Prestinenzi: 36:03

That's you know. That's why I use what worked well, and I don't ask questions like, hey, what didn't work well? I say, if you could go back and do it again, what would you do differently? Because it's not a negative. It's not a negative question, yeah, and you're not asking them to say, well, because sometimes, especially if they chose the previous provider, they don't want to say, hey, you know, this is what, this was a disaster, this didn't work, and blah, blah, blah. So say, what would you do differently? Yeah, it's kind of a coaching based question. Right, think about it. A coach would ask, hey, this is great, this is what I saw you do. Well, what did you do? Well, what would you do differently If you could go back and do it again? So it's a, it's a, it's a coaching question, but you're using it in the sales process, and so that then allows them in a safe space because it's not a negative question. They don't have to go on the defensive. Yes, tension doesn't rise up. Think about that relationship tension. It's still reduced. So they say, well, this is what I would have done differently and say, great, okay. So do you mind me sharing that? Do you mind me asking if that's what you'd done differently, what was the impact of X, right? What could have been the outcome if you did this? And all of a sudden, you're getting a bit of a picture into what occurred, right, and then, as a salesperson, I would then craft exactly like I did in that scenario. I would then craft what the desired state needs to look like in the business case for change, yeah, yeah and create a couple of scenarios around that, because that's the other key is options are pretty important to a person like Katie. Yeah, providing a few options so that, internally, Katie can then go around that buying committee and see which is the best option that's going to get the best adoption Right, because that was something that's important she mentioned. Adoption is key. Yeah, she's not working with a team of 10 sellers, she's working with a team of hundreds and hundreds and hundreds of people all over the world. You know, in the thousands.

Dave Fastuca: 38:14

Yeah, the impact will be shown if something's not adopted or if something's not working.

Luigi Prestinenzi: 38:20

Absolutely Right. So that's a couple of things that I would probably advocate to any seller. Anyone listening to this, anyone watching this. It's diving into the past is an amazing opportunity to help you scope what the future state needs to look like, and if you're not doing it, just start. Start by doing when you did X, what worked well, and if you could go back and do it again, what would you do differently? Just start with those questions and you'll be amazed at the intel that you'll gather and how you can then start to think about what that future state needs to look like and embed that into your proposal.

Dave Fastuca: 39:06

Yeah, I think that's a perfect note to end this episode on Louis.

Luigi Prestinenzi: 39:10

Yeah, awesome. So for all of our folks out there, all of our community members we have, we're going to continue down this path. So we've got another episode that's going to be dropping and that's with Jacob Dave, is that correct?

Dave Fastuca: 39:27

Correct yeah.

Luigi Prestinenzi: 39:31

And that is. He's a CFO, so a very different take. He's going to look at things from a different lens, which is important, right, obviously, then we've got other episodes dropping, continued with enablement, continued with CFOs. So this is critical, right, because we are. In order for us to sell during any economic climate, we need to sell the way our buyers buy. So these conversations will help you get a different understanding and change your perspective on how you can sell to the way your buyers buy.