Go Big or Go Home with Sam Mckenna

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Oh, my gosh, my ego is through the roof. Thanks for that amazing introduction. I'm so stoked to get to talk to you and to talk about enterprise sales and everything under the sun, sales related. So thank you so much for having me.

I'm very, very excited to have this. And what people love about this show is we get right into the good stuff, right in the tactics. So we're going to kick this off. What does enterprise sales mean to you as someone who's lived it? Like, what does it mean? I think people get twisted ideas around it sometimes.

Yeah. You know what I think that this is? Everybody looks at enterprise sales as the holy grail, right? They want to get there, they want to do it, they want to deal with the big boys. I think even startups think like, okay, we're going to get into enterprise sales even if the product isn't ready for it, right? Want to make sure we're ready for me. Enterprise sales, one, it is tough. It's tough, right? So let's just admit that first and foremost. The other thing is it's really complex, right? So you've got to go into enterprise sales thinking about the idea of how do I multi thread as much as I possibly can? How do I really understand the challenges of the business, not only of this line of business, but of the business as a whole? How do I really get into the nitty gritty of what the business is, Right? Are you reading their annual report? Are you reading their earnings reports? Are you staying on top of what's going on with the business? Do you understand how to monetize the pain from multiple lines of business and solve that pain through what you do? It is a lot of work, right? But the reward, holy moly, the reward in bringing in those logos for your company and the reward of the deal size and the commission check can be monumental.

Hell yes. Hell yes. So actually I'm going to take even one step back here for people that are listening, because I have a whole. Like the people that listen to this show are from SDRs to sales leaders. You said a few terms in there that they may not even understand. So let's hit on multi threading. What does it mean and why is it important?

Multi threading. Okay, let's think about even this year. So multi threading, one of the things that a lot of reps do is they find one champion and then that's the only person that they're talking to for the entire. Right? Let's think about this year. What if your champion gets furloughed? What if your champion gets laid off? What if your champion changes jobs like everybody's bound to do in January? Most popular time to change jobs. Who do you have then? Who are you talking to next? So multi threading is the idea of getting away from single threading, just having one person that you're involved with, but now moving it into who else you can talk to in the organization. Who are their peers, who are their bosses, who are their cross functional partners, who are the influencers in the deal. All of that is multi threading, right? Getting in there. But I'll give you a little curveball too. Multi threading works both ways. So who in their organization knows people on your side of the table? So have your bosses been involved? Have your cross functional partners been involved? Who are you having involved in the conversation? Because if it's one on one, you're going to lose. If it's one on many, that's a great step forward. But let's make it many on many. So we have all kinds of conversations going on for your deals.

I love that because so often as salespeople we can say like, this is my deal so I'm going to try to bring this home and it's like yo, like involve anyone and everyone you can to bring that deal home.

Well, and let's even touch on that real quick before we go into our rest of our vocabulary. I just posted about this, I think on Monday. Are you a lone wolf, right? Do you think of that? Is this my deal and I want to bring it in without any help or just as Katie said, are you the person that says like let me bring everybody into the conversation now? Now this is for your larger deals, right? We're not talking about involving your CMO or your CRO for like a $2,000 deal. But as you start to build these deals, right, like get help, get different points of view, see who knows who in your organization. That is how you'll win.

And so I'm going to jump on that one real quick. Why is that important, right? As these deals get bigger, why is it important to pull in some senior leadership as these deals are getting close or even earlier, like why? Why is that so important as the deal size gets bigger?

Yeah. Let me give you three things that I think are really important here. So one, when you bring in your senior leadership Think about the deal size and volume that they have exposure to, not only given the length of their career in their tenure, but what they do all day, every day with other reps. If you are working, I don't know, 10, 15, 20 deals on an annual basis, if you're in enterprise sales, your leader is working that time, six, seven, eight people that report to him or her, right? Same thing with other cross functional leaders. So they have an opportunity to look at your deal through a completely different lens and to also look at it without the emotions that you carry. The second thing you want to think about is that they might also know different things than you know of what's happening in the market, in the space, in competing accounts. Depending on how siloed your organization is, you might be chasing a deal that somebody else is chasing a deal with, with a competitor. We have intel to gain from whoever that leader is that's managing that deal. So get them involved, right? Talk about that in team meetings, et cetera. Final thing I would say, if you are looking to get a promotion, get a raise to move your way up the ladder. Involving people in your deals is one of the easiest ways for them to see how you work, right? Because they're working alongside you, they're cc'd on your emails, they see how you build rapport with your clients, how urgent you are and responding to things, how thorough you are in the sales process. That is the best amount of exposure that you can get to one, them seeing you for who you are. But two, being a champion and a sponsor for you inside your company.

Ooh, that was, that was good. I hope people grabbed that one because that's a tip that I haven't heard yet through this show and a lot of other places of why involving other people benefits you. A lot of salespeople do. They see it as a way like I want to prove my worth or I want to show I can do it without help. But by involving people, that's a phenomenal tip.

That was really good because then everybody knows that you're a great deal bringer, inner. Is that a word?

Absolutely it is.

If you go about it yourself, that's the only thing they know about you, right? But when you start to involve them and they see what you're like, a light clicks on and I'll tell you, one of my mentors who's actually going to be my officiant in my wedding, so that's how much we pulled him in. But one of my mentors, that's exactly what I did with Him, I started to bring him in on deals. He was a great evangelist for my company and as soon as he attended a few meetings with me, he was like, you are, are an exceptional seller. Like, I can't, like, let's work more on these deals together because you and I as a partner can really get some things done. So just by virtue of bringing them in now, I got elevated across the organization in great ways.

Hell yes. I love that. I love it. So let's hit another term that you said. You said champion, right? So there's these. All you have Champion selling, mobilizer selling, influencer selling, like all these different types of selling. At the end of the day, we're selling either with or through someone. So let's talk about Champion selling a little bit. Right? How do you know if it's actually a champion and then how do you work with them to try to bring a deal through on these longer sales cycles?

Yeah. So I think something that's interesting is that as you get into enterprise sales, there are 100,000 different levers that you can pull to make deals happen. And also 100,000 different little clues that you need to pick up on in reading the room and also reading your champion to see, just like Katie said, is this actually a champion? Right. So your champion might have tons of enthusiasm for what you bring to the table, what you can do, but you need to start to understand their organizational place in their company. Right. So are they really junior and they don't have a seat at the table? Are they slightly junior? They do have a seat at the table because they're a top performer. You need to start to understand truly what their role is in the decision making process. I think one of the interesting ways to look at that too is if you change your perception of how you're working a deal and change your perception to say, you and I, champion, are partners in this. Like you and I are trying to get a deal done. It's not us versus you, champion, it's us working together to get my boss probably to agree to a discount and to get your boss to say yes and improve the deal. If you start to look at it that way, see how they react to you wanting to make a partner out of them. See how willing they are to bring other people into the conversation. Katie, you and I talked about one of my taglines, which is double the quantity or double the quality of the people that you have from one call to the next. And so even with this Champion example, right. If you have a great discovery call with A champion. And at the end, you think about it, we're partners. We're gonna get this deal done. And you say, who else can I involve from your side, right? How do we get this deal done as fast as possible if that champion becomes a roadblock and says, like, well, it's just gonna be me for the time being? Signal to you, right? Signal to you that they're not willing to open the gates. Signal to you that they might not have even the authority to really be on this call with you. And they're just kind of getting a lay of the land. Or if they're like, yes, okay, here's what we need to do. Bring in these people, bring in this partner, bring in somebody from it. When you get that feedback, then, you know, if you're really working with a champion and just changing that perception of you guys being partners will significantly enhance your chances of winning the deal.

I love it. Now, just so you know, I have already applied the trademark for the sales double double, because that's how I remember. So the double double, I hope you kind of double the quantity or double the quality. That's technically hers, But I'm trademarking it. Cause that's how it works. I just moved.

I love it. It makes me think of cheeseburgers, but I'll go with that.

Oh, that's exactly what it is. I'm west coast for life, right? So like that in and out, double double, remember it? So now, something you said there, though, that is important. I think a lot of people can struggle with is, okay, you're dealing with a champion. But then they do put that roadblock up, right? They say, okay, let's get your boss involved. And they go, no, no, no, I got this. No, no, no, I'm on it. Well, now what? Like, how do I not ruin the relationship that I do have there? But at the same time, I know this person can't bring this deal in by themselves. So how do we navigate that?

Yeah, so I think a couple of things. One, if you get that roadblock, and again, you need to read the room and read their kind of stance, right? Like, are they being friendly about it or are they being, like, really stone faced? But if they're still being friendly and you feel like there's room to budge, say, oh, that's great, that's amazing. Like, have you purchased a lot of deals on behalf of your company? Like, tell me what that process is like, so everything runs through you. Do you need, like, it involved, et cetera? They'll start to open up by Then because you're basically nailing them that they're not the only person involved, right? So that's so great. That's what, like agree with them. That's wonderful that you're in charge. Like how amazing. I've never seen that at an enterprise company before. How have your deals run before, right? Like how long does it take to get these things through again? You need to ask these questions tactfully and maybe not so boldly, but think of how to get these answers out of them, right? Because they will start to crack, they'll start to open up and they'll be like, oh, you know what, you're right, we do need other people involved. The other thing that you can do, right, is to say again, like be on their side. That's amazing. We typically see anytime I've worked a deal like this before, I've always had to have director of it, director of is, whatever it may be, CMO involved. And that's incredible that you can do it by yourself. So this will be a first for me. Like everything resides with you, right? And just make it kind of open ended like that. What's not really open ended, they'll say yes or no, but get them talking, get them thinking, right? So one, you're excited for them even though we know that they're lying and we're starting to paint the picture of how we normally run deals to maybe even say, have them say, like, oh, you know what? Like actually I think I'm the only decision maker, but you're probably right. Like I probably do need to bring this person, bring that other person in. One other thing I'll say and then I'll stop on this topic. You need to also consider for your buyers any, at any stage of the game, right? Whether you're SMB or whether you're senior, senior enterprise, keep in mind that this person that you're speaking to, this could be their first time buying ever. This kind of technology that you're selling, right? There's so many new disruptive technologies out there these days that it could be their first time buying in your space. It could be their first time buying just ever. Any process whatsoever. Like they're going through this for the first time or it could also be the first time they're going through this at their company. So by asking these questions, right? This is who we typically see that's involved. Every deal I've run in your space has these people involved. You're helping educate them because they frankly may not know who needs to be.

Involved and What I love about what you're doing there too, especially with a champion, is when you're suggesting, not telling, they still feel like it's their idea, right? So you're saying like, hey, so normally, you know, I have to work with this person and this person and this person. And normally you bring in this, like, what do you think about this? And they go like, yeah, we probably should pull in our director of it. They feel like it was their idea, right? And then like, they say, like, okay, like we are working together. So I think that is really, really good stuff that people are paying attention to because you have to have that champion or like the mobilizer, someone to help you internally, because you'll never know. I always laugh when sales reps with me, they're like, okay, like, can I talk to your cfo? And I go, do you really think you're gonna outsell me internally? Like, do you think you have a better chance to convince my CFO than I have? Right? Like, are you even ready for that combo? So leveraging the champion, I think is super, super important. So I'm gonna come back again to something that you said, right? You talked about the research, right? And something that I find happens often with some enterprise rep I speak to, and some of the companies that I work with on the side is they can almost over research. They spend so much time researching, but then nothing happens with it. So, like, what should reps or companies be looking for, right? You know, and then how do they leverage that information to actually break through? Because I've talked to reps that know everything about the company, but I'm like, okay, so like, have you set a meeting yet? Yeah, well, no. So what should they be looking for? But then once they have it, how do they use it to break in?

So I think your point is an excellent one, right? Like, don't invest the time until you've started to book a meeting, right? And there's little things that you can find about the company to at least help book that meeting. But you need to know very high level surfacings, right? One of the things we talk about a lot real quick is the idea of outbound prospecting, what goes into our messaging. And one of the things that we use is compelling event. So one thing I'll tell you just there, like how we do our research on our company and we make sure that we're not investing too much time is look at what compelling events are happening with their company, but dig one level deeper, right? So if I'll give you a Good example that I use all the time. We were trying to target Tesla and after Q2 earnings came out, everyone was like, we'll talk about their Q2 earnings. And I'm like, fantastic. So is everybody else. What else do we know about Tesla? What else can we find out as a compelling event? That's different. So that's one thing. That's where the research will help you, there to at least book the meeting once you've booked it. My advice to you is to take about 15 minutes to start researching that company. That's really all you need to do. Dig in, look at their news, look at their recent earnings reports, see how their stock is performing. If they're publicly traded, which they probably are if their enterprise. Ascertain some information there so you can at least know at a high level what the health of the company is. And then certainly make sure you're researching your buyer as well. Not only personally, but what you can ascertain from them, rather, not only professionally, but what you can ascertain from them personally on their LinkedIn profile. One of the things that frustrates me the most is reps who are in enterprise selling and don't carry executive presence. And one of the easiest ways to do that is when you get on a call and you're like, katie, how's the weather in la? And Katie's like, it's cloudy, thanks. And you're like, oh, cool, right? Don't talk about the weather. Let's find some other things that we can talk about. Now, how to use that information. Right? So how do you use that information? Like you want to show you've done your homework. So every time I get on a call to build rapport with someone, I try to use the personal angle first if I can. Right. And to be clear, we're not getting stalkery. We're not going to their Facebook page or their Instagram and being like, great bikini pictures from your vacation last. No, Right. If they have something like they're a great traveler, they're voracious reader, whatever it may be on their LinkedIn profile, use that. Otherwise, more common connections, if you guys have those, great way to connect the dots. But when you're on a discovery call with this company, the thing that I love to do is to say, first and foremost, I would love to tell you a million things about Sam Sales consulting, but I'd love to hear about everything from your side first. You know, it seems like you guys have great press about xyz. It sounds like your stock has been doing Amazing. But tell me about you. Tell me about your team challenges you're having. Tell me about your landscape overall, if that's okay. Right. And that shows that you've done your homework without having to like just word bomb it for 20 minutes and kicks off the conversation in a great way because you show again that you've done your homework.

So I want to dive into discovery because I know that's a big thing. Something I wanted to, I guess I didn't have as an original question is how are the buyers different? Right? So you said something like, okay, you get a VP on, you get a CIO on and going like, how's the weather? And immediately it's like that. How are the buyers different? Because an enterprise buyer, especially as you get higher up, is different than talking to say the director of IT at a hundred person company. So how are the buyers a little bit different as these deal sizes get bigger?

I think one of the things to keep in mind while you might have this tenure and the seniority in SMB companies that you're talking to, especially in enterprise companies, when you are talking to director and above titles, you are talking to people who are senior, who are tenured, who have been through these processes that they're in working with you or someone like you, probably dozens if not hundreds of times. So one, they've been here, done that before. But the buyers are expecting a higher grade from you and that's exactly where you will stand out, right? I talk to enterprise reps all the time who are like, I don't need to do my homework, I know how to run a discovery call. I'm good on that. The thing that I would say back to the homework piece is that where are you going to be when you join that call? And you say, you know, again, would love to dive in on you first. And they say, sure, tell me what you know about us first. And you're like, and you have no idea what to say. So again, no matter how senior or tenured you are, make sure you're doing your homework. But two, again, the executives are expecting that, right? They're also expecting you. Unless this is a highly transactional sell, they're expecting you to be an expert in what you do, an expert in probably what they do in their market and how you can be a value to them. They're expecting that 30 minute call for them to walk away with you having a thorough understanding of what they're doing and then you having communicated at least a high level, how you can solve their challenges. So if you come in and you talk about the weather. You're going to show that you are a junior rep, that you haven't done your homework, that you don't know where to start a conversation. And they're going to be less likely to trust you as a subject matter expert and as a consultant.

I hope you all caught that because what she's saying there is they expect more from you. You, you have to be better. I think some people do. They think enterprise selling is just like the wine and dine and schmooze and like, hey, like they, they like me, I like them. Like we're good. And it's like, no, they expect more from you. You have to be better at that level. And so now let's go into discovery.

Right?

So okay, you got the meeting you got in there. We didn't ask about the weather. Right. Thank God we're in discovery. What should be some of your key goals in discovery? Because I think so many deals, they're lost in the be. They're not lost in the middle of the end. Something went wrong early. So what should be the goal of that discovery? And then also how do we keep that going throughout the deal cycle? Because these deals can take 6, 9, 12 months sometimes. Sometimes. I've never had more than like a 12 month cycle, but I know there's deals out there that go way past that. So like how, what should the goal of discovery be? But then how do we keep it going?

Yeah. So goal of discovery for me, I always say you've got one job to do on that discovery call and that is to solve their challenge. Whoever is giving your time, solve their challenge by what you do directly or what by someone you know does make sure that that 30 minutes or whatever they're giving you is worth their time. We are going to get on discovery calls, you know, probably hopefully less often than not, where people come on and they say, sam, I'm so glad you took my call. I'm looking for somebody to fly me to the moon. And you're like, okay, great, I don't do that. But right. So just thinking about it, like, how can I make sure that the time you spend with me is valuable to you if I for whatever reason can't sell you what you're looking for, If I can guide in a good way, if I can give you a recommendation or reference and I can validate that for you, I've now been a value to you and you will remember that I'm not just like, oh, it's not me. Take Care. Bye. So, first and foremost, think about that. Now for discovery, how do you solve that challenge? How are you even going to figure out that challenge? It's by asking questions. And it's not by asking your 1700 questions that you have on a script. Right. It's by saying, again, think of that starter. And I've got it on my website, on LinkedIn, exactly how to run. In my humble opinion, the perfect call. But start with that broad question. Tell me about you team, your challenges, your landscape. Just tell me what's going on on your side, if that's okay. One time out of 10, you're going to have someone that says, I actually know a lot about you guys. I would actually love to ask you a few questions directly first. And that's totally fine. More often than not, you're going to have people who just data dump what's in their brain. This is what I call this stream of consciousness. And I start to make bullet after bullet of, like, your top challenges. I try to not interrupt you whatsoever. And then as soon as you're done, I go, that was so helpful. Thank you. I have a million questions. Can I go back to your first point and work my way down? And then I'm digging in, I'm understanding what's going on with them. And even as they answer, talk to me about their challenges, I can then say, we can solve that. This is a. You know, this reminds me of a customer we work with that was in your exact same boat. Right. I can weave in those customer stories and get them really excited. Final point on this, how do we keep discovery going on? So Amy Volis and I were actually talking about this on LinkedIn the other day. But discovery, discovery is an ongoing thing. Right. We know that they're going to have priorities and challenges that they need to tackle, which can change over time, especially working with an enterprise client that might take 12, 18, 24 months to close. So continuing to do that discovery is critical. Even think about your relationships. Katie, you're a married man. I'm an engaged woman. I'm still doing discovery on my fiance. I asked the other day, I was like, what's your scariest movie you've ever seen? And are you an Oktoberfest beer kind of guy? So I'm learning as I go four years in, I'm still learning these questions. It's no different with our clients. So continue to do that discovery. Primarily think about after you have a discovery call and we get on the next call. Maybe it's a demo and maybe they've brought in two or three other people. We haven't done discovery with them. Right. So great opportunity to open that up. And I know a lot of people struggle with that too. Like, well, okay, so maybe I meet with kd, and now he's. Now he's gonna bring his CFO to the call. And how do I manage that balance? So a great way that I can do that when I've got new people on the call is I go to the most senior person that I have a relationship with, and I say, Katie, thanks so much for teeing us all up. So nice to meet everyone. Do you want to do a quick round of introductions? And maybe it'd be great to hear from everybody on the call, kind of what, interested in you, in taking our call, or what your key priorities are and then going from there, because it gives the power to Katie first, and then it allows everybody to voice their opinions. Right. And why they're here, and allow me to do a little discovery at the same time.

I love it. There's a very subtle thing that she's also said, Whether you guys caught it or not, is the note taking. In fact, she can't even help but pantomime the note taking as she's talking about this right now on video. As I'm interviewing her, I'm taking notes on the things that she's saying. Like, as salespeople, we tend to trust our memory too much. Write it down, slow down. To speed up, right? We get to these big presentations, there's seven people. Then we think it's our moment to shine. Here we go.

Go.

Okay, it's go time versus slow down, Ask the questions, take the notes to make sure you're doing the right things there. So there's two other things I want to talk about. I mean, you've given so much away already to people. Like, people should be cutting checks to you in the mail right now. Let's talk about the dreaded deal stall you've been doing the things, Sam. I did the things. I did the research. I got the meeting. I did the discovery. I've got my champion. We're mobilizing. We're doing things. Crickets. I'm five months in, like, now. What? So there's two parts of this question. What are things you can do to prevent? But it's gonna happen. What do you do when it does?

Yeah. So I think you. You nailed it. First and foremost there. There really are no silver bullets in sales, so you will do everything correctly in every step of the process. And then Something will change. I think the things to think about. Remember that the people you're selling to are incredibly complex human beings. Not everybody is as forthcoming maybe with information as other people that you've worked with. There's internal dynamics, right? There are priorities that take place. And they just see your emails come in and they think, like, I know I need to get to this, but not just yet, right? Not everybody really knows how to handle a sales cycle correctly on the other side of the table. So be cognizant of that, too. I think, one, you want mutual action plans. And frankly, I hate that word. The reason I hate that word, or I guess that phrase, the map, is that I think people formalize it too much, right? They're like, okay, Katie, we had this conversation today, and you will do this, and then I will. And I'm like, just kill me now. But I think if you come up with a mutual action plan in terms of a conversation, make it conversational, that's great. The other thing to think about, right, is what is our mutual timeline for getting this done? So if you've done your homework correctly, if you understand core challenges that your company, that your prospect has, and then you also have monetized that pain not only by you telling them, but even more importantly, by them voicing this, right, this is the money it costs us today. This is what we foresee, your challenge, your product, solving for us. And then also, what is the cost of an action for them? If you can get all of that information going, it also allows you to kind of set a timeline on contract signature, right? Case in point, if you say something like, it sounds like every day we don't make this move, it's costing you an unbelievable amount of money, efficiency, whatever it may be. So let's figure out how to get this in your hands as fast as possible. It's October 16th, I think, today. So let's say, honestly, would 1031 be too soon? Can we sign this on Halloween? Would the end of November be too soon? What do we need to do in order to get that there? Making sure that you have that conversation. So that, one, you know that you're both mutually accountable to that date, and then two, that you're making all the right steps and getting all the right people involved is critical. One other thing I would mention for your really large, important deals, especially if the customer is saying, like, it's going to take a lot of work on our side, a lot of different people to keep this deal moving, one of the things that I love to do and again, depending on how long we have until the deadline is, I like to create a weekly, if not bi weekly meeting between us. So I'm just going to put a standing day on our calendar. Every Thursday at 10am we're going to meet and say, how are things going? How have things progressed? Is this for procurement? Have we received T's and C's back yet? Have Infosec done their thing? And if it again, if we know that this isn't going to get signed until January, maybe every other week is fine. But this also includes your stakeholders on your side of the table and theirs. So the last thing we want to do is just no show to a meeting that probably has VPs on our side of the table and that holds everybody accountable. Plus plus one other thing, it just has your name on their calendar all day, every day. And I will say, no matter what level you're at, when you send a meeting invite out, always put your company name first. One of the things I hate is weekly standing meeting in there or Merck plus, whatever. And then you don't get to see the company name. Instead they just see their own name. If you're selling a Merck, been through that sales cycle twice and holy moly, make sure they see you over and over again. So that every time they look at their calendar they think, oh crap, that's right, I need to do something today in preparation for tomorrow.

No, I think that's key. Just getting ahead, right? Getting ahead, making it recurring, getting their agreement. Subtle thing that I love to do in the calendar invites too is like the agenda but also like the problems, right? It's the reminders, right? You see like, you know, weekly meeting with KD versus like, hey, here are the problems we're addressing. Let's just remember this is why we're talking. Because I know, like I see an invite from a sales rep on my calendar, I'm like, oh, I don't want to do that right now. Like, I haven't done the things or I haven't followed up yet. And it's like, but if I'm reminded, like, oh yeah, this is what I'm trying to do right now, it's probably worth it.

Yeah. And consider too guys, that like, while you're going through the contract process, right? So again, if we, if we are here today and we know we're going to get a signature in January, your nurturing is also supposed to be still in full gear, right? This is not the time to say, like, I don't need to support them. Anymore. Think of things that you can send to them that are of value. Invite them to webinars, send them articles that are, tell them you're thinking about them. Because again, all these little things are pings for them to keep thinking about you even as you sail towards the contract.

I love it. I love it. So then let's hit this here real quick for the reps that are listening, right, the reps that are listening. How do you trying to think how I want to phrase this the right way. Like one, like what's a reasonable expectation career wise to get into enterprise selling and how can you prepare for it? Because I think you said it very early on in this conversation of like, you know, it's different, it's hard, but there's this perception that I can just leap into it. I've been selling for two years, make me an enterprise rep. So what is, I think in your eyes, a reasonable expectation of career growth. But then how can they start preparing today? What are the characteristics of a great enterprise sales rep? What are the skill sets? How can they get ready now to become that rep in the next three, four, five years?

Yeah. So I think first and foremost thinking about how to prepare yourself for the future, I would have an honest conversation with your boss. And I know a lot of us have sales leaders that were like, oh my gosh, they're for the birds. If you're in that position with your boss, find somebody internally in your organization or a mentor outside of the organization. There's tons of us available for help. But find somebody where you can say, this is where I am now. Can you listen to some of my sales calls? Can you tell me where you identify a skill gap for me between where I am now and enterprise software? My goal is to be an enterprise rep in 12 months. Do you think I can get there with where I am today? You need somebody who either leads enterprise teams, recruits for enterprise teams, really has an understanding of what enterprise is. Myself, Katie, again, tons of us who can say, here's what you really need and let's look at where you are now and what you need to do to move forward there. For me, in terms of what I look for, for an enterprise rep, I look for process first and foremost. Right. If this, then that throughout everything, I genuinely look for an intelligent person. Right. So how do you think, how do you attack deals? What would you do? Run me through your process there? Because I want to see that they're resourceful, smart and that they pull all of those levers that they need to and I also look for urgency. So for me, one of my taglines is the urgent bird gets the worm. Right? How quickly do you jump on an inbound lead? How quickly do you jump on a job change? Right? I was talking to a rep yesterday, trying to help them get a new deal, and they're like, oh, my champion left a month ago. And I'm like, oh. I'm like, what are you gonna do with that information? And they're like, well, I'm gonna see who replaced them. And I'm like, you're also gonna see where your champion went and sell to them. And they were like, oh. And I'm like, oh, my God. Hello. So I just look forward for how you think for that. I will tell you, too, in the interview process, a couple. Couple of hacks for me if ever you have to interview with me in the future. One, this might seem rude, but I'm always a few minutes late to my interview. I come in at, like, let's say, 11:02 or 11:03. I think, Katie, you and I even talked about this. But I come on and I'm like, I'm so sorry I'm late. We're just working on this huge deal. The call ran late. Even if that's not what happened, because it probably isn't. And I say, you know, again, sorry for being late. And I wait to see if that person says, no problem, or if hopefully they say, like, that's amazing. Like, tell me about the deal. How long have you guys. Is that genuine curiosity there? The other thing on my interviews is I always get to know each other, right? Like, do they have questions? Are they interweaving those? Or are they just answering mine and waiting for the Q and A, which you don't want to do. Like, be conversational, right? Build a rapport together. But then I say, okay, tell me about your process. So if we were. Let's go with Merck again, if we were to give you mercy, an account that we've never been able to open up, never been able to close, what would you do as your process to start cracking that open? And that, honestly, more often than not, tells me whether or not there'll be a fit for enterprise sales, right? So if they're like, well, you know, I'll go and read their annual reports. No. Right. Let's think about where you would start. Run one, look at the history in Salesforce and see what's happened. Two, go into Merc and see who knows who. Can you make introductions and inroads there as quickly as possible. What does your process look like in terms of how you would open that up? And frankly, the quicker they can deliver that information and the more confident in all the ideas that they bring forward. Usually helpful because I know that they're constantly cranking and thinking of how to break these open. So do you think like that? If not, can you learn how and who are you going to look at? Start to ask if you can ride shotgun on some enterprise deals. Find a top performer in your organization. See, could I ride shotgun with you from deal start to a deal close on something? Or are you new in a deal and you think it's going to close? Can I just listen? Could you bcc me on your emails? I just love to see how you run your game because holy moly, you will learn so much just from that.

I love that. I love it, getting ready for it. I think just even the self awareness though too, for the reps that are listening. Enterprise selling isn't for everybody. It's not the right fit for everyone. And you need to know and understand that as well. Like you don't have to go enterprise to make great money. Like if you're, if it's not what calls you. Like I know personally, for me, once it starts going past a year, yeah, I'm too impatient, I get bored. I'm like, oh, I don't want to deal with this anymore. And like it's so I know that about myself. And so then it's like, okay, okay, that's all right. I'll stay away from it. Now let's talk about the leadership side before we wrap on this. We talked about reps coming up and how they can develop. How can you help develop enterprise reps? Because I think sometimes there's this connotation too, is you can just hire an enterprise rep and they already got it figured out, right? Like they've been doing it for a while. Like, how do you lead and develop and make your enterprise reps better? Cause I think, actually I don't think I did you justice in your intro. Like we're talking about how to do, do enterprise selling, but you've been leading enterprise for a long time and so let's talk about this as we wrap.

So I think one of the things I, so we, we inherit teams all the time, right? But in, in terms of at least bringing them on, I want to find somebody who has, you know, 80, 85% of the way there and then they've got foundational cracks that we can improve on. When you've got enterprise Sellers and you think, okay, how do we improve their, their skill, their skill gaps? I like to honestly dive into the basics of their role, right. Because however tenured the rep may be, there are still things missing in terms of their foundational skill sets that they don't know how to do. So perhaps they're not great active listeners, perhaps they're not great conversationalists, perhaps they don't know how to ask open ended questions, perhaps their discovery is okay, but struggles and there's places where we can make enhancements there. So listen to their calls, ride shotgun on a deal, ask to be BCC'd on a deal, start to finish. Invest in them too though and ask where do you want to go? Where do you think your skill gaps are? What would you like to improve upon and where can I be of most help? Again, I think that's only half the battle, right? So hearing what they say and where they want to grow is amazing. But then say like great, like I can address that. But let me, let me listen to some of your calls. Let me get on, you know, especially if you're a frontline manager, right, that's really important. But listen to their calls, identify skill gaps and say, I think we can work on these things that you said for sure. But I also see a great opportunity here. I'll tell you one thing that I find too with a lot of enterprise sellers is that they become relationship sellers and start to shy away from challenger seller. Now I'm a challenger seller first, relationship seller second, right. You can probably reach out to most of every client I've had over the years and they're like, sounds great. But I'm also great because I've pushed on them, right? I've challenged them thought how to get them to think differently. So be aware of that as a leader. I had a rep once who unbelievable relationship seller, right? Just their clients adored him. But the thing that stunk was that his deals normally took two, two and a half years because he wasn't comfortable asking. Yeah, don't even get me started. Wasn't comfortable asking the hard questions, right? Because they were buddies. He was buddies with his clients and then it made it seem like salesy that he was going to push and ask for the deal. And I'm like, hello, that's your job. But just be aware of that, right? Are we asking those tough questions? Do we know how to get those deals done? Or are your sellers traditionally just relationship sellers and keeping the piece until the deal magically comes over the line, just.

Waiting for them to Say, okay, we're ready to buy. Here's the contract. Oh yes, those are the greatest ones. Okay. I have been pulling so much info from you. We got two questions left and I'll let you go on your way here. So the first question is, as we call it, the biggest three, right? So we've been going for about 40 minutes now. You have been dropping bombs left and right on how to do this the right way. If there were three things, the three main takeaways you'd want them to remember from this conversation that would improve their results as an enterprise leader or as an enterprise rep, what would those three key takeaways be?

So I think for the leadership perspective, I would say again, make sure you're taking the time to, to truly invest in your people at the foundational level, right? Just like we just talked about, get in the weeds, listen to their calls, even again, have them bcc you on emails. Because I find that also this is where we lose a lot of people. Are we actually answering all the questions? Do we get around the hidden objections in those emails? Are we doing those things right? The second thing, just like Katie said earlier, enterprise selling is not for everybody. If you love the quick turnover of transactional deals, enterprise sales is not going to be for you. So make sure think about your position right now. What do you love about what you do from a sales perspective? Where do you end the day where you're like, that was a great day. What was it about that that made it a great day? Because if it was the idea of I talked to six different prospects and I've got two new deals going, not going to happen in enterprise sales. The final thing I would just say is really work on your discovery, do your homework, Start with that open ended question, right? And make sure you take notes from that stream of consciousness that you don't interrupt. Like Katie said earlier, discoveries where we lose a lot of our product aspects, but discovery is also where we lose often because that is the engagement we have more often than not. I mean that aside from our outbound emails, discovery is the function that we do the most often with our clients. And if we fail, if we don't capture them, then they're going to go in a different direction and we're going to have a low conversion ratio there.

I think those are huge. Those are three massive takeaways that if people walk away with an apply, they're going to see better results. Last question, Sam, name of the podcast is live better sell better right? Focused on the person in salesperson. I have this really weird belief that if we help people live better, if they take better care of themselves, if they get more joy out of life, that the sales also improves. So what would be your parting advice on the live better side? How can people take better care of themselves or habits to build or have more joy or more fulfillment? What would be the live better advice you'd want to give everybody here?

Yeah, this might be a little atypical, but I would say also pay attention to when you're most motivated and engaged from a time of day perspective. Not everything has to happen within the 8 to 5 window. And a good example I'll give you there is I had a rep who just candidly came to me and said at 3 o' clock every day I hit a wall and I just flounder for two hours at my desk until I can go home at 5. So we switched her schedule, right? We found she was an unbelievable morning person. We had her in from 7 to 3. Her productivity went off the char. So just thinking about that, like, are you a night person? Do you get really productive at night? Can you save your really important tasks for then so you can stay focused? The other thing I would just say is don't forget to just invest in yourself, whether it's working out, going for a walk, getting a breath of fresh air, going and listening to a masterclass or a podcast with us during the day. Like that's professional development and it's personal development just for your own sanity. So don't forget that stuff. It's not all about sitting behind the desk. Desk and doing this all day.

I love it. And actually a free resource for anyone listening that wants to run with Sam's tip there. There's a quiz you can take online. It's called the Power of Win. The Power of Win. And it talks about the four different chronotypes, right, of like your energy levels. It's a, it's a great book, but it's a test you can take. You can find out if you're a wolf, bear, dolphin or lion. And it talks about which times of days are best for your productivity and your energy level. So the power of wind can definitely, definitely get out. So I mean, my goodness. Grac. Sam, you went big. You went big on this one. How can people find more of you? Where can they find you? Where can they get more of this insight? Like where can they follow? Let them know how to get more of you in their lives because they need more of you in their lives right now. I can tell.

Thank you. So I just launched a really beautiful site that we worked on hard this year. So samsalesconsulting.com, tons of resources, all my upcoming speaking engagements. Are there anything that you need? Tons of tips and tricks on my website but connect with me on LinkedIn too. Give me a follow there there Samsales is what I post most days that have great tangible sales tips for you Whether you're a LinkedIn user, whether you're a leader, whether you're an enterprise seller. Tons of tangible advice that I can give you there but feel free to reach out and if I can ever be of help now, you know where to find me.

Hell yeah. Well thank you so much for your time. Thank you so much for your wisdom and your insights. This was amazing. I can't wait to follow up because even I have more questions after this but I won't take any more of your your time. Sam. Thank you so much.

Thanks Katie.

Bye.