How to Sell to the C-Suite

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This is a podcast episode titled, How to Sell to the C-Suite. The summary for this episode is: <p>When it comes to selling to the C-Suite, you only get one shot, but the truth is, most sales pros aren’t equipped to nail these meetings, and it costs them their deal. That’s why Ryan Longfield, CRO at Gong &amp; Rob Perillion, SVP at Corporate Visions, are sharing the science and art of selling to senior decision makers in a 25-minute, can’t-miss webinar. Start nailing the toughest meeting in your sales cycle and say goodbye to late stage heartbreak.</p>
The biggest mistake: Doing too much discovery
00:58 MIN
How many questions should you ask a C-Suite buyer during discovery?
00:54 MIN
What to do instead: Ask your champion for discovery time
01:18 MIN
Misunderstanding the role of the CXO
00:43 MIN
Instead, follow the RAPID framework
02:57 MIN
Tip # 1: Map out the decision-making process
01:36 MIN
Tip #2: Don't confuse role and title
01:54 MIN
Tip #3: Earn the executive's openness to your influence
01:02 MIN
Save the numbers for later...
01:53 MIN

Devin Reed: So thank you everyone for showing up to the event, you made a great decision today because you're going to learn something that is really difficult and really an illusive skill, which is learning how to sell to the C- suite. And so today we're going to go ahead and dive into it. We're going to do our absolute best to stick to our 25 minute mark, because when you sell to the C- suite, it's pretty typical you only get about 25 minutes. So, let's go ahead and dive in. If you're wondering who's talking, I am your host Devin Reed behind the scenes. And our first speaker is Rob. Rob going to do a quick intro?

Rob Perrilleon: Yeah, sure. Thanks Devin. Hey everyone this is Rob Perrilleon, so I'm with Corporate Visions. I look after our delivery organization, so the consultants and trainers that work with clients to think about how people frame up value and make decisions in the B2B sales context. Great to be here and thanks for having us.

Devin Reed: And you're training for your first marathon, you're eating lean in the morning with oatmeal, so it makes sense.

Rob Perrilleon: That's right.

Devin Reed: That's awesome. All right, Ryan, you're up.

Ryan Longfield: Cool. I'm already feeling bad about myself, Rob, oatmeal and marathons... you know. But yeah, hopefully this will shift in my favorite later because I'm not nearly at your caliber just yet. Hey everyone, Ryan Longfield, I'm the Chief Revenue Officer here at Gong. I've been here for about 18 months, before this I was at LinkedIn for 10 years, it says nine on the slides, but it was actually closer to 10. And a little fun fact, I love vintage Jordans, I feel like there's not a lot of things in a male's wardrobe that can add some flare and some pop, but shoes are definitely one of those things. And the host and I share this so he decided to put it on the slide, but nice to be with you all, and I think it'll be a good use of time.

Devin Reed: I was wearing my Jordans to work one day, something I do frequently, and Ryan stopped me in the kitchen, he goes," Hey, I have a pair of those," and my jaw dropped, I was pumped. And then we of course talked about it for a little while.

Ryan Longfield: Yep.

Rob Perrilleon: crosstalk. How many pairs do you have Ryan?

Ryan Longfield: I only have one pair of Jordans. Actually, they're right here and I've never worn them, they're on the shelf, but I love these crosstalk had them when I was a kid, and it's a beautiful shoe.

Devin Reed: It is a beautiful show. Beyond Jordans, we're going to talk about a few things today. First, we're going to cover the biggest mistake that sellers make when selling to the C- suite, then we're going to get into three advanced sales tips that will persuade decision makers to say," Yes," and then we've got some giveaway details that we'll dive into. And so with no delay, there's one thing that sellers are doing all the time, it's a big mistake and backfires. Ryan, you want to take this one away? Yeah,

Ryan Longfield: Yeah, absolutely. So, I remember the last call I was on where I was being sold and the crew came in and it was a very standard meeting, in the normal way that it's structured. And inevitably the question came out at the beginning," So, what keeps you up at night?" And I was almost waiting for it. And so being a person in sales and compassionate and to the person on the other end of the side, I answered the question and answered another question and then answered another question. And right about question four, I started to get a little bit annoyed. And I could feel this thing rising up in me I'm like," Is this going to be a good use of my time?" And when Gong did data, when we pulled a bunch of data around the right amount of discovery questions to ask when you're in a C- suite environment, specifically, it changed dramatically from that of the standard selling environment. And as I was sharing, that's been my experience as well. And so if you could go to the next slide Devin. When we analyzed millions and millions of calls, and we looked for the correlation between closed rates and the number of discovery questions that are asked to the C- level person on the line, what you'll see is right around four, is the sweet spot. And I think what you need to be conscious of when you're selling into the C- suite, is that the time allocation, what I expect to get out of a meeting or the time that I'm willing to spend educating somebody else to solve the things that I'm thinking about, is going to be far shorter. And I think this is such an interesting one because there's so many trainings out there where we're learning, okay, how do you ask great open- ended questions? How do you ask more questions? How do you keep the discovery moment going longer and longer so that you can be educated and then pitch them in the way that is appropriate for their business? And I think this one is somewhat counterintuitive because no, that's not true. In this particular environment, you have about three to four questions before most likely, of course it's a generalization, that C- level person on the other end of the line is going to start to get annoyed and question whether it's a good use of their time. And so we have another piece of data in the next slide that speaks to that as well, which is, this is the length of the response based upon how many questions have been asked. And you can think of this as the shorter and shorter the response gets, the more ready the person is to move on to the next part where they're getting some value. And so the first thing that I would recommend for people, or the biggest mistake that I'd say that I most frequently make is that you don't change the nature of the meeting, there's this big, heavy discovery moment upfront, in the C- level setting, that's actually detrimental to your outcome unless a few things about that discovery are true. And I'm going to kick it over to Rob to share some thoughts on what needs to be true in those discovery meetings in the first part of the meeting in order to make it valuable.

Rob Perrilleon: Yeah, right. Well, I think about this and I remember when you guys first tweeted out that insight and I loved it then, and I still love it, because to me, what it speaks to is something we talk about a lot, which is really be mindful in any interaction, but especially with executives of who's getting value out of the exchange, right? And so if you're just asking questions, you're the one getting value as the seller, right? The executive knows the answer so they're not getting any value. And one way I think about this is, Stephen Covey had the concept of, I think he called it the emotional bank account and he talked about," Are you making deposits or withdrawals?" And I think that applies here. Think about that relationship with your executive contact as a bank account, and are you making withdrawals or you're making deposits? And I would say questions are withdrawals because you're the one who's getting value out of that not the person across the table.

Ryan Longfield: Yeah.

Devin Reed: Right. And so the tip to do instead Ryan, sounds like ask your champion for discovery time instead, right? And so as you guys are saying," Hey, do that before," you should have a few points of contact that are more than happy to prep you for meeting with Rob or meeting with Ryan, so that way when you get on the call, those two to four questions that you use are absolutely sharp, like they're the right questions. And I would say they're something that only that decision maker can answer.

Ryan Longfield: Yep.

Devin Reed: Right.

Ryan Longfield: And I would actually adjust this slide slightly. If you already have a relationship with the decision maker, I would ask the decision maker to send you someone that you can spend time with. If somebody came to me and said," Hey, is there somebody on your team that I could talk to, to make sure I do all of my homework before we have the meeting, so we don't need to spend any time on understanding your business, we can just dive into how we're going to solve?" Immediately they have credibility with me, immediately. And I will get somebody on the line for them to talk to say," Hey, I want you to spend a half an hour with this person, just answer any question they have," and then it's the best discovery opportunity you have as a rep because the person's boss has now told them that their job is to educate you on everything that you need to know in order to sell well, perfect environment. And you can do this through email really well as well, so this is another good reason to do this, it's really simple to pull off, you just craft an email to the C- level person or the DM and you say," Hey, can you provide me someone?" And nine times out of 10, they're going to say" Happily, here you go," otherwise, they'll give you permission to do discovery in the meeting and then you do it that way.

Devin Reed: That's smart, I love that. Well, let's getting into the first tip, which I think we're touching on, is how to get a," Yes."

Ryan Longfield: Great.

Devin Reed: Sellers need to understand the role of the CXO. Can you guys break that open?

Ryan Longfield: Yeah, absolutely. So, let's go to the next slide because I think this hits it on the mark. Sellers often misunderstand the role that the C- level person is playing. And so there's a great quote here from a previous leader of mine, he says," I only do what I can not delegate," and I think this gets you in the mindset of somebody who's in a big job with a lot of responsibility. There's a certain point in your career as you're going up the ladder where you get to a place where your mindset shifts from the primary influence that I have is the work that I actually do, to the primary influence that I have is delegating and empowering other people to do the work. And this is oftentimes how the C- level people are going to be thinking, is if I can delegate it, I'm going to delegate it, and I'm only going to do the things that I can't delegate. And so oftentimes sellers will think that the CXO, the C- level person is making the decision when they've actually delegated that decision to somebody else, and this can be incredibly detrimental to your deal. If you treat them like a decision maker in an environment where they've delegated that decision- making authority, you're going to be misaligned with how they're thinking about decisions being made. And so what I wanted to do is I wanted to share with you all a framework for decision- making. Informally or formally, organizations will use a framework to make decisions, they will have a set of roles internally, it's pretty universal, and they'll probably look like this, so I'm using the RAPID framework, this is from Bain. And I'll go through the different roles and then I'll show it makes a difference in a selling environment. Each letter associates to a role. I want to start with this, I, so an input. In any decision that's being made within an organization, there's going to be a big group of people that are input. Now, the characteristics of input are they give their input on the decisions being made, but there is no obligation by the decision maker or by the recommender to use any of that input. So, this happens quite a bit, you go," Hey, what's your opinion on what tool we should buy for cadencing? Is this one better or is this one better?" And people will give the input. You're not asking them in a way where they have any authority over the decision, they're just getting input. And so, have that as a role that you're thinking about for every deal that you're running, who are the people that are just input, no real authority? The second one is the D, and the D gets the most attention here. The D is the decision maker, and the decision makers is the person who gets close enough to the deal that they know the intricacies of what's going on, but they're not the one that's going out and gathering all of the information and turning it into a codified recommendation, there's somebody else that usually does that. So, this could be your champion in an organization, it could be somebody that's involved in the deal and you can see they carry a large amount of weight in terms of how the decision is being made, but they're not the person with the final authority to say," Okay, after doing all the research, after your presentation to me, this is what we're buying," that's the DM. So, those are the two key roles, the D and the R, those are the big positions of influence that you need to really be careful as to who's playing which role when you're selling, especially in the C- level environment. Just to be comprehensive, the next two, so the perform, that's the person who wants... they purchase the thing, they actually push it through the organization. Big warning here, there can be a time suck in your deal, because they'll ask a ton of questions, they're very interested in getting into the details, but they have no decision making authority. And then the A is the approver, so this is not the decision maker, this is usually someone like a CFO. This is usually somebody who can say," No," but they can't really say," Yes," right? They'll knock down your deal, but they're not going to be the one that wins your deal. And so oftentimes what you need to be careful of is you will assume that the senior most person is the decision maker. And if you assume that the senior most person is the decision maker, you could destroy your deal. Because what could happen is you could get them more involved than they need to be and then all of a sudden you have an extra set of critical eyes on your deal that you didn't want there to begin with. And so you need to be really careful as to like," Is this person actually the one making the decision?" And don't assume that they are just because they're in the deal.

Devin Reed: Absolutely. That's fire, that's so good to know and I think that layout is going to help a lot of folks understand. I think a lot of folks try to sell the same to everyone in the room, right? They just don't really understand like the depth of different roles. And I think once you can speak specifically to those types of folks, understanding who can say," Yes," who can say," No," is going to make a huge difference. If we go a level deeper Rob, we'd love to hear a little bit more on mapping the decision- making process. If you see any room there, or if you think Ryan covered it, we can just keep moving.

Rob Perrilleon: Yeah. Well the one thing I'd add onto it, and Ryan sounds like we have similar mentors in our career paths because the way it was put to me in terms of executive mindset was," Only do what only you can do," right?

Ryan Longfield: Mm-hmm(affirmative).

Rob Perrilleon: Only do what only you can do, and that's the way that executives think, it's all about empowering their teams. But in terms of those roles, the lens that we look at that through is absolutely understand who's who in decision- making process. And then we also look at, think about the decision that each of those roles really is looking to make. So, when you get into a decision maker or recommender, if anyone's familiar with Corporate Vision's work we say," Early on when you you're trying to acquire a new customer, the decision that is really on those people's mind isn't do I choose vendor A or over vendor B? It's as we call it, it's the why change question," meaning do I need to do anything differently from the way I'm conducting my business today? And so you can think about that kind of question. Once you get up to an approver level, their question is different because their question is going to look something what we call," Why invest?" Meaning this may be a perfectly valid question or business issue and it sounds like it's a well thought out solution, but is this the best use of my company's resources and capital at this time? And the secondary question is why now? So do we need to do this now? Or can we defer this decision by a quarter or two because I'd rather conserve those resources, not just the capital and the dollars, but all of the change management that goes along with it. So, when you get up higher in the organization, you can think about those decisions that has implications for how you might conduct the conversation little bit differently and really just stay in point. And to your point Ryan, don't ask them for too much, don't ask them to do something that they weren't prepared to do because they might take you up on it and slow you down.

Ryan Longfield: Yeah.

Devin Reed: Quick question for you, I have to imagine, and to be fair to the folks that are listening, we created this deck about a week or two ago, obviously, we polished it to recently but there's been a small change, and I mean that facetiously, a huge change in the last few days with COVID, does this framework still apply? Does it change in any way given the new landscape?

Rob Perrilleon: Yeah, I'm happy to jump in. The first thing I would say is, obviously the barriers to attention and time commitments are just higher. They're higher particularly now in these days, but they're also higher in the context of... what we're hearing from our clients is, and I'm sure everyone's leaving is, meetings are not being held live anymore, right? They're being held virtually, so you've got the whole COVID- 19 distraction factor, but you've also got the sense that even if someone can carve out some time, probably that meeting's happening virtually, which just means the time pressure, the attention barriers are that much higher. The part about understanding the decision and understanding who's who and really being on point and on message, I think is really important. We've actually got a PhD neuroscientist in our company who looks at memory and retention in messaging. Her conclusion is that really no matter how hard you try, you should expect retention from a meeting to be at about 10%. And it's going to vary, sometimes you're on and it's going to be a little higher, sometimes it's a little bit lower, but she said," You should plan on 10% retention on any messaging." So, what you really need to do, is actually you're better served controlling what that 10% is that they're going to remember as opposed to trying to bump 10% to 12 or 14 or 15. Assume they're going to remember 10 and then think about how do I get them to remember the right 10, the 10% that I want them to remember and make sure that everyone has the consistent recall of 10% that it's not different throughout the group that I'm talking to. So, the first way to do that is to just make sure that you're crystal clear about the question and the decision that you need to answer for that person. And then there's some things, some principles, if we have time, I can talk to a little later, but she talks about making sure you're just very consistent in repeating that message strategically several times and that repetition will build a retention of the 10% that you want. That's a really helpful framing device that I found, I don't know if you guys are seeing similar or different in your research.

Ryan Longfield: Yeah, absolutely. I think the other thing that I'd had-

Devin Reed: inaudible Oh, go ahead.

Ryan Longfield: The other thing that I'd just add quickly on the selling environment that we're in right now is if you think about the way that decisions are made within an organization and how delegation happens, there's like a base level, think of it like the base of the pyramid being this annual planning that happens, and the biggest decisions of the company are made at a single point in time, they'll say," Okay, here's our top line goal, here's our bottom line," and those type of magnitude decisions are being made at a single point in the year and then reassessed over the course of the year. But all the delegation and all the purchasing decisions and hiring decisions and all the spending of money that happens after that is all based on these foundational pieces that are put together and then that is the grid or the way that people then make decisions and delegate following. So, in an environment where those foundational pieces are disrupted, like the one that we're in right now, the reason why you see so much scrambling is because those foundational pieces are adjusting right now. And so you had a deal and it was based on where the foundational pieces were and then those foundational pieces shift and you're like," Hey, why did my deal change?" And it's like," Well, because now it's a different environment, there's a different landscape and there's different foundational principles that are being made for all the decisions that are downstream from that." And so I just say in a time like this, where those foundations are being shaken, it's more important than ever that you're talking to somebody more senior because the decision making goes up in the organization when those foundations are shaken. And so you need to be aware of what's going on with those biggest company decisions and not assume that what was true a month ago about those things and how they're purchasing and thinking about expenses are still true today. So yeah, I'd say it's super relevant and more important than ever.

Devin Reed: Awesome advice guys, that's great. I'm sure a lot of folks are in that bucket right now, deals that are on the last leg, towards the finish line trying to figure out," Hey, how can I adapt and make sure I get there." Let's jump to tip number two, which I think inaudible will be interesting because we're talking about getting higher. And I think every sales person probably knows, even if they don't do it, which is okay for now, that you need to get up the ladder. And we've talked a lot about great sales leaders are delegating more than they're deciding. And some of these outcomes, we'd love to hear from you, I'll go through them and maybe you guys can just elaborate. So, some of the negative outcomes of going too high are, adds unnecessary complexity to the sales cycle, make things a little trickier, you can definitely offend the true decision maker and you can probably even offend the person you're talking to, if you're trying to try to skip over them. I won't say that I've done that once, but I've definitely done it twice. And you also look junior, right? It looks like you don't really understand the organization, you don't really understand how this game works and so you can... people might want to distance themselves from you a little bit if they don't know that you know the game they're playing in. What else do you guys have to add to that?

Rob Perrilleon: One device we use to help, and even on the next slide, Devin, I think there's a really good construct here, is don't don't confuse role and title. And so when we think about defining the target of the message of the conversation, we say think about the right mix of altitude and juice, right? Meaning so who's close enough to the problem to actually care and do something about it? But also high enough to have some decision- making? So, you want to have someone close enough to feel the pain and want to do something, but also someone with enough juice to actually follow through and make a change in the organization, and it's just balancing those two. And that doesn't always mean all roads... not every message is a CEO message, or even a CXO message, find out where that balance is and start from there, right?

Ryan Longfield: Yeah, absolutely. The difference between the role and the title here is so important because if you assume that somebody not on the call, just because they have a big title is the most important person to the deal, you could assume wrong, right? And that's the key. You offend the true decision maker because they're like," No, really, I am the one making the decision and you're assuming otherwise," and I think of titles as the lazy way. Relying on titles is the uninformed way, right? You don't know who's going to be the recommender, the decision maker or the places of input, unless you do the hard work of asking the question," How do you guys make decisions? Who plays different roles? What does that role feel like? Have you made purchasing decisions in the past?" If you're not informed, then you're going to rely upon a title, and often times, that title assumption is going to be wrong. And so you're going to think that you need somebody else on the line to make a deal and you don't. And so just be very careful of that, because then you pull somebody else into your deal and it adds a bunch of complexity.

Devin Reed: Yeah. Well, a lot of folks say," Hey, I know you're the decision maker, sure. But who cuts the check?" And they think that's the real decision maker, right?

Ryan Longfield: Yeah.

Devin Reed: But there's different roles there. All right, we're going to jump into the last tip, we were at 25 minutes, but hopefully you guys are tuned in and enjoying it. We had a couple people say," This is really good material," all caps in the comment section. And one of the early questions I didn't get a chance to get to was how do I handle an agenda? How do I even start this thing? And so tip number three is, earn their openness to your influence. Ryan, do you want to take this one away? Yeah.

Ryan Longfield: Yeah. Rob's going to cover most of this and I'm going to give him the floor to really go deep on this. But, I think that we need to start with the starting premise, that influence is not something that you get just by assumption, it's given to you. In other words, you can't influence somebody unless they give you the gift of influence. And so with a C- level person they're used to going in meetings all day long, back- to- back meetings. And in almost every meeting, the first five minutes in the mindset of the person in the C- level job is thinking," Is this meeting a good use of my time? Do I need to be here? And should I be doing something else?" And so I would suggest that you spend a large amount of time thinking about the first five minutes of that meeting with the lens of," Why does this matter to this person? Why am I going to earn the right to then influence them for the rest of the meeting?" And you need to prove that, don't assume that it's there, so be laser- focused especially in the first three to five minutes because you win it or lose it basically right there in the opening part of the meeting. And so I'll kick it over to Rob to go deeper on that.

Rob Perrilleon: Yeah Ryan. So, I'm going to go through just some recent research that we did and it's actually focused on even before the first three to five minutes, it's about how do you get to those three to five minutes? How do you answer the question to the executive of why should I invest my time in this meeting? By the way, with an eye on the clock, I'm going to go through this very quickly, but at the end we're going to offer a download of this full research report, so if you want to geek out and go deeper, we're going to make all of this available. But the context here was research that we did, we recruited a few hundred executives and put them into a simulation and then asked, what's the most effective messaging strategy for you to accept as an executive, accept a meeting with a vendor that you don't know, haven't been doing business with. The conclusion here is actually going to tie back to the first set of graphs that Ryan showed about questioning, there's a common thread that runs throughout this. So, real quick, the different messaging strategies that we tested were a value proposition, a product centric value proposition, well done there were no clunkers, but a value proposition. We talked about probably the most common way that people are taught to sell to executives, which is show up, reflect and show that you've really done your homework and you know their business, and then bring them a quantified business case with some numbers to show the impact that you can have. We did an industry insight, kind of a provocative insight type of approach and then also some competitive benchmarking executives love to hear how they're doing compared to others. What we found, and to get the winner you'll have to do the download, but I want to talk about here in just the next minute is there was one clear loser in every measure that we looked at. And Devin, I'll talk through if you want to just quickly scroll through the next couple of graphs. Folks, you can see the exact graph values in the research report, but what you're going to see is there was one condition that lost by about double digits on every question that we asked from how confident, how likely are you to take a meeting, how likely are you to turn down and decline a meeting? The loser every time by a big margin was that known business initiative, now think about that's the most common way people are typically taught, show up having done your homework, reflect," Hey, I really understand your business and here's the quantified business impact that we can have," why did that approach lose so convincingly every time? And I would submit that the reason is very similar to the questioning graph that Ryan showed earlier, which is executives are going to value and you're going to get their attention, they latch on to information that they don't know, right? Tell me something that I don't know, that's what's going to get my attention. And if you think about the loser here, that's highlighted in purple, the thing that makes that different from the other is that everything in that condition," I know your business, I've done my homework and I understand your challenges," the executive knows all of that. And so it's in a lot of ways the same dynamic as you asking questions, they're not getting anything new out of it. When it comes to the quantified business, bring the quantified business case, bring the numbers. The credibility that early on from the vendor that they're not working at, we know is going to be very low. And so what our research found is there's a place for the numbers and for the business case, it's later in the process because numbers don't help drive the decision, they actually help someone explain the decision to others, so they're important but they belong later on in your meeting and in the sales cycle. And so the connection here, I think, is in terms of getting the executives attention and earning their influence, bring them some information that they don't know already, that's how you solve that problem.

Devin Reed: I feel like a really good boom is just delivered right now, that was just fire. All right guys, that is the last of it, we're going to skip one slide to get to because we are at time. So, super quick recap, for the three tips, map your decision making... map out that decision making process, that's my typo, higher isn't always better and earn their openness to your influence. And so what we got next is our promise to give away. I've got two folks here, two attendees are going to win a one- on- one, one with Ryan, one with Rob, they're great guys I've been hanging out with the last few weeks, tons of knowledge. So, hopefully you're still on the line, but Allison Sims, congratulations, you won your one- on- one with Ryan. We'll reach out to you after inaudible and Nate inaudible some time, but inaudible just like meeting with him again, if they accept and inaudible. In case you want some more tips and tricks, follow Gong on LinkedIn. And after this, you'll also get an email where you can download the report that Rob talked about, and we'll also send you the recording as well so you can go back, share with your friends, all that good stuff. So, Rob and Ryan, thanks so much for your guys' time. Thanks for your expertise and thanks for everyone who joined, hope you had a good time.

Ryan Longfield: Thanks again.

Rob Perrilleon: Thank you everyone, Bye bye.


When it comes to selling to the C-Suite, you only get one shot, but the truth is, most sales pros aren’t equipped to nail these meetings, and it costs them their deal. That’s why Ryan Longfield, CRO at Gong & Rob Perillion, SVP at Corporate Visions, are sharing the science and art of selling to senior decision makers in a 25-minute, can’t-miss webinar. Start nailing the toughest meeting in your sales cycle and say goodbye to late stage heartbreak.

Today's Guests

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Rob Perrilleon

|SVP at Corporate Visions
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Devin Reed

|Head of Content Strategy at
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Ryan Longfield

|CRO at