Kevin Walkup

Today we’re joined by Kevin Walkup, Enterprise Account Executive at SalesLoft. Kevin shares his progression into sales and some important lessons he’s learned along the way.

View Kevin's Profile


Sahil Mansuri: Hello everyone, welcome to another episode of The Future of Sales, a podcast featuring real B2B salespeople and zero talking heads. We hope you enjoy our authentic conversations as we dig in to the sales process that top sellers use to close deals, learn about their favorite sales technology and tools and even get to hear some fun deal stories of how they close some of their biggest clients. I’m your host, Sahil Mansuri, CEO of Bravado. Bravado is a platform for B2B salespeople to build their credibility by collecting testimonials from their customers. With me today is a name that will be familiar to many in the B2B sales sphere, Kevin Walkup, Head of Strategic Sales at SalesLoft. Welcome, Kevin.


Kevin: Hello. How are you?


Sahil: I’m great, man. How are you?


Kevin: I’m doing fantastic, excited for this today.


Sahil: Yeah. We’re so excited to have you on the show. And to get started, you know, with any good hero story, you got to start at the beginning. You know, we had lunch recently and you shared with me a really interesting story. I said, “Kevin, how did you get into sales and do you mind sharing your origin story with our listeners?”


Kevin: Yeah, absolutely. And this story dates back quite a few years now. It dates back to me as a little kid seeing other kids out there with their lemonade stands. Well, there’s dozens of kids in my neighborhood that were out there slinging lemonade and I felt that there was an opportunity for me to get in there and maybe help out those individuals. So, my very first sales experience was not a kid that was just setting up a lemonade stand, but I was the guy that was selling the lemons to the kids at the lemonade stands.


Sahil: So you saw that there were kids around who are slinging lemonade in the summer and you thought where are they getting their lemons from, huh?


Kevin: Exactly. And a lot of them weren’t even using real lemons. They were using, you know, the lemonade sugar pack and, you know, I think -- well, what a better way to provide a better customer experience by using real lemonade, real lemons. So, my mom being in the catering business, she would go to the store three, four, five times a week and, you know, I was six, seven years old, so she would always log me along. And I’d found the opportunity that I could then use some of the money that I had to buy lemons when I was at the store with her and then, turn those around selling for a profit to the kids so they could then go out sell better lemonade, real, actual lemonade made with real lemons. They could put that on their sign, “made with real lemons.”


Sahil: The part of your story that I find most remarkable is that you are the first kid that I’ve heard -- because I’ve heard the lemonade stand story a number of times in sales interviews. But you’re the first person who actually went above into the supply chain mechanics even at the age of six, it’s amazing.


Kevin: I was -- it’s just an idea and it actually turned out to be a very good one at that time.


Sahil: There you. That’s great. But what about professionally, so after you graduated, how did you end up in sales?


Kevin: Sure. So I actually graduated college in December of 2009 with a degree in real estate. And I had always been very gang hoe about getting into commercial real estate. I wanted to sell real estate. And if everybody remembers, December of 2009 was the absolute worst time in history to get into real estate. So, I had to quickly pivot where, you know, I had been studying for the last four to five years of getting into real estate. And then, I suddenly got myself into the IT tech and recruiting space. A friend of mine was -- had been doing very well there, and he recruited over. And that was my first job was cold calling people based on their resume that looked like a good fit for potential IT role that I knew nothing about at the time.


Sahil: Wow. So you went from selling lemons at the lemonade stand to selling, I guess, helping for staffing, yeah?


Kevin: Yeah. Exactly, right. I was selling people in resumes.


Sahil: Wow. And so how does one go from that experience to the experience of selling at SalesLoft where I think you’ve made quite a name for yourself?


Kevin: You know, it’s another unique story of me being burdened with the cold calling, of following up with my prospects. And, you know, after the recruiting side of things, I quickly moved in to an account management role to be more on the sales side of the house rather than of the recruiter out there finding natural talent, although they’re finding the job recs. And with that came a huge book of business and thousands of people that I could be talking to that have open job requirements and I was persistent in following up with all of those prospects and targeted accounts that I had and I was burdened with, you know, having to follow up with these people, logging in to my CRM, log a follow up task every single day.

And one day, I remember Sean Kester, who’s now a VP of Product Strategy at SalesLoft came to me -- this is in June of 2014. He came to me with this idea behind SalesLoft, this Cadence engine that would help with a lot of that following up and automating the menial tasks of putting all that in my CRM, making sure I didn’t have to put a sticky note on my monitor to remind myself to follow up with somebody in three days if they haven’t called me back or emailed me back. And he actually pitched it to me on a napkin and right then and there I fell in love with the idea not just for myself but for salespeople all over the world.

I knew since it solved my pain as an inside rep that it could solve the pain for other reps all over the world and I wanted to take that upon myself to not just use it but actually to sell it and to help salespeople all over. That same day, I went from that lunch, I’m kind of on a whim, looked at what I saw in that napkin and walked back to my office and quit my job at a multi-billion dollar organization later that day and started at SalesLoft two weeks later.


Sahil: Wow. That is a really fun story. So, from a napkin you were so inspired, it looks like Sean was a pretty good sales guy too, huh?


Kevin: He sold me on it and he likes to say that, you know, he’s never in the sales role that he bats a thousand because he sold me on SalesLoft and that’s what mattered most.


Sahil: That’s awesome. That’s a really great story and I appreciate you sharing your background. So, the first section that we get into here on The Future of Sales of podcast, we call it deal stories. So, the advantage of interviewing real salespeople instead of talking heads is that they actually have stories of fighting in the trenches and closing real customers. You shared a story with me over lunch that I thought was really interesting, talking about upselling, you know, turning a smaller pilot into a larger enterprise deal and what the process there looks like.

Do you mind sharing a little bit about that?


Kevin: Yeah, absolutely. Say, this conversation originally started probably February of this year, so it’s now November, so nine months ago. I was talking with an individual, a Fortune 1000 company in the advertising space and, you know, we’ve really like had a good chemistry together where he was really challenged with a lot of things and, you know, all across their entire organization they were pained with this process, he’s even getting things in the sales force. And it reminded me a lot of myself back when I was with Rod Stud before SalesLoft of not logging anything in my CRM, doing everything manually.

So, kind of getting with him telling, you know, the story of why I even worked at SalesLoft. We hit off and, you know, we started coming up with ideas of how we could take this all the way across his entire enterprise. And he knew it’s going to be a big feet, so what we decided on was let’s get this in the hands of, you know, of one of his 10 markets and let’s move from pitch to prove. You know, we can talk about these ideas all day long but it’s time for us to prove it. Let’s actually get it in the hands of people and let them see the results themselves.

So, they move forward with an initial pilot. And at the end of June of this year and that was, you know, going on five months ago or so. And having stayed in touched with him over time and really making sure that the processes that he implemented were not just the best processes, but actually he was holding that market accountable to making sure that they are leveraging the software in the right way and, you know, really staying in close proximity to him and what was important to them which inevitably was getting things in the sales force and making the reps more efficient.

He helped me kind of understand the entire organization there of, you know, thousands of people that work at this organization. He was like, “Here’s the 60 people that are going to be involved in getting this across the entire enterprise.” And I said, “Okay, here’s your 60 people. Now, I’ll go and talk to all those people and get them sold in on this so we can push this out to the other nine or ten markets. And now, as of November, we should have something rolling out to them by the New Year to have about 250 or 300 sellers fully implemented, trained and ready to roll this out because of that very first initial pilot of the 50 users. They said, “Okay, well, let’s go 6x with this and really take this to the next level so everybody can have this result.


Sahil: Wow, so there was a lot there and I think that there are some really interesting points for us to dig into. Let’s start at the beginning. So you said this is a Fortune 1000 company in the advertising space, you know, I can’t tell you how many sales teams I’ve managed where we are working with one small division of a large enterprise. You know, like one small sales team for Microsoft or one small sales team at Facebook or something, right, and it never expands, right. You’re in this one like silo and you’re working with this one group and you’re always trying to figure out ways to get it to expand and it never really does.

And you have like one champion who has some things they’re interested in but not really sure how to get it out of the silo and every time you try to do a larger overview it turns into like this gnarly behemoth. I’ve seen a lot of challenges with that. How do you think you were able to overcome some of those challenges and actually go from, as you said, you know, pitch to prove, but then how were you able to go from proof of concept to actually, you know, getting that larger strategic deal in place?


Kevin: Yeah. And a lot of times the proof is in the pudding, so leading with actual examples of results. “Hey, you know, Mr. Prospect at market B, I wanted you to take a look at the numbers from market A where they started prior to rolling out the software and now, where they are today four months after, we’ve increased exponentially by X percent. If you do this in market B do you think that would be a value to you?” He says, “Yeah, absolutely, I didn’t even know that team was using software, dude. I thought they just had some, you know, magic bean that started getting them all these results.” I know that was -- the magic bean was our software and I want to help you get it in the hands of your reps and that way you can start talking about it and we can take this to not your market but market C, D, E, and F.


Sahil: So it seems like the strategy that you use was, all right, making sure that that first group, right, market A is truly successful and is able to be kind of like a case study, if you will, an internal case study for them to be able to disseminate through the rest of the markets. How much of your effort as a salesperson do you focus on actually the customer success like? Because I’m sure SalesLoft has a customer success team and I’m sure that you have account managers, and you have people who are, you know, responsible for, you know, once a deal is closed, like, you get handed off to them. But you as a salesperson, how much time do you actually take to make sure that the users of the deals that you close are truly successful?


Kevin: It’s a great question. And to your point, exactly, that we do have customer success and account managers and at SalesLoft we are an entire team, we are all in this together. So, to say that I was the only person involved in the success of that initial pilot would not be true. I would say our customer success and account management team did a fantastic job of leading by example and showing them the customer love that we had talked about that they would receive upon signing and doing that pilot. So, they’ve done a tremendous job on their end. On my end, it was more connecting dots and putting things together, hearing one success story after, you know, maybe getting 10 different stories, hearing one thing that kind of stuck out and taking that little tidbit and taking that over to market B or prospect B at market B and saying, “Hey, here’s a little tidbit of how we improved metrics in the last 12 days and this can be your team too by rolling this out as well.”


Sahil: Yeah, it seems like a big portion of what you did is to help shape the narrative, right, which is it’s another area that often falls or that salespeople often leave to somebody else to do, right. Like, it’s like, “Oh, here’s our marketing material,” or “Here is a static list of benefits that you can get.” And it seems like in this particular case, you were able to craft a narrative that was hyper specific to the company and in fact, to market A so that when market B was looking at the results, it was extremely relevant to them with what they were seeing, would that be fair?


Kevin: I would say you’re spot on there.


Sahil: Yeah. One other thing I just want to touch on before I move on here because I find it really interesting, you told me that the person you were working with initially, you know, basically said, “Here’s the 60 other people that you need to have involved in order to make, you know, this larger enterprise deal come together.” You know, I think there’s two parts to that: first of all is the fact that that’s a lot of people, right, so how do you impress 60 people, I think that’s fun to dig into. But before you go there even, you know, in sales, we talk about having a champion, you want that internal champion, that person that can help you navigate the enterprise sale. And it seems like in this case, your champion was extremely helpful in being able to kind of help you, you know, plot the map and figure out, you know, who the key players were and what you needed to do. How do you build a relationship with a customer such so that they’re willing to be such a strong internal advocate for you?


Kevin: You know, I think building that relationship really comes about where are we today and where do we want to be in the future. So, if I can help take you to where you want to be in the future, would that benefit both of us? And if that answer is yes, you know, that’s going to be much better helping that champion go in and continue making those introductions to those other 60 stakeholders. So, as long as they can make it a win-win situation for everybody, the cost of the software doesn’t matter if they’re getting the results that they need. So once he sees those results, those other 60 people become almost excited to want to talk to you because they have now seen firsthand how the other challenges have been solved through my main key point of contact.


Sahil: Sure. That makes a lot of sense. And just quickly there, you know, you said you get the 60 people excited. Does it get easier to be like, “Well, I’ve already got 54 people who said yes and so, now, you know, we can get the rest onboard faster,” or does it get more nerve wracking that you’re like, “Oh, man, I hope I don’t screw it up now and then, all that work will go for not.”


Kevin: You know, I think you actually hit the nail on the head there. When I’m talking to person number 55, I’m absolutely going to tell them that, “Hey, I’ve got 54 other people that have given their thumbs up,” so that’s a perfect lead in to getting that person excited. Okay, so they haven’t even seen it yet and they know that there’s 108 other thumbs that have already gone up.


Sahil: And you’re good at doing quick math with these.


Kevin: Yeah. Did I get that right? Okay.


Sahil: Yeah, you did, you did. All right, awesome. Well, that was really great and thank you for digging into that. The next section that I want to cover is really talk about the approach to sales, right, or your actual sales process. So, one of the advantages that I have, you know, running Bravado is that I get to see what your customers have to say about you on your Bravado profile. And as it turns out, they love working with you and have really flattering things to say. How does one get one’s customers to love them? What would you describe as your approach to sales?


Kevin: So one of the people that I’ve had always looked up to in the sales space and who I’ve considered mentored me is Ralph Barsi. And one time he was speaking at event and I overheard him saying, one of the, you know, things that you want to do in all sales processes, in all sales cycles is put a 10 on everyone’s head, and that kind of resonate with me like, huh, put a 10 on everybody’s head. So, treat everybody like I would want to be treated. I was like, “Okay, well, that makes a lot of sense.”

So ever since then -- and it kind of resonate back to I’ve kind of always done this as well, but to be intentional about it, to make sure everybody’s experience is as pleasant as possible, and they walk out of that room and say, “Well, Kevin is, you know, a pretty nice guy. I can trust him with, you know, the purchase that I’m going to make. I could trust him with knowledge about the space. I can overall just genuinely trust him.”

And, you know, putting that 10 on someone’s head is very important to me and I even do it outside of the business world, my personal life as well. Treat everybody around me like they have a 10 on their head and that’s been one of the biggest things that I feel that has really helped. Well, people enjoying working with me because they’re going to walk away with a pleasant experience.


Sahil: Well, first of all, Ralph is a legend and I’ve had the opportunity to hear him speak at a couple of conferences as well and he’s really great, you know. And the 10 on the forehead thing, you know, as there’s one part of me that loves what you just said, which is like, yes, of course, we want to treat everyone and make sure everyone has a great experience. I mean, that’s kind of the job of a salesperson, but at the same time, one thing that I have seen a lot of reps struggle with is prioritization, right. Which is, you know, you’re working a lot of accounts, you have a lot of leads, you have a lot of prospects, big pipeline and it can be that as a salesperson you could get stuck in this cycle of spending a lot of time on prospects that are just never going to buy or just that are not great fits but are really interested in engaging with you. And sometimes that comes at, you know, the expense of the amount of time that you can spend with a prospect who might be, you know, more or further down the cycle, might be a better fit or someone who would consider to be kind of a real opportunity. How do you balance that?


Kevin: That’s a really good question. And, you know, one, it goes back to you want to make sure that everybody is getting a pleasurable experience from you because like you mentioned they might not buy now, they’re going to give you all the signs that they’re going to buy, but maybe they’re not going to buy now, but you’ll never know a year and a half from now, maybe they’ll send you a referral, maybe they’ll come back and be ready to buy an they’re going to call you because they remember having that pleasurable experience. So, treating everybody the same, but at the same time being able to quickly gauge, okay, is this person just kicking tires, is this person genuinely engaged in the buying process.

And a lot of times you can feel those out by recommending a mutual execution plan, here’s a plan for us to work together so we can hold each other accountable. If you have someone kind of push me off on that that’s a great way to gauge that this person might just be a tire kicker, they’re not 100% on board with buying. So they’re still going to be treated very pleasantly by me, but what I’ll do is when I’m scheduling next steps with them, I might schedule 30 minutes with them versus someone that has actually agreed to this mutual plan to do business together and they might get a full hour.

So that way I can prioritize, okay, here’s somebody that is genuinely onboard, they’ve come to me with the steps that I’ve outlined for them, and we’re going to spend an hour together going through what’s going to happen next on our next three calls so we have more time together versus other person that hasn’t agreed to that next mutual execution plan. And then, maybe I’ll just give them a little bit less time but still make it a pleasant experience for them so they always do come back with referrals and potentially buying in the future.


Sahil: I love the idea of a mutual execution plan because, you know, I think that if you are actually serious about buying a piece of software, you know that there is going to be some leg work that you’re going to need to do in order to evaluate and figure out who the right vendor is and you’ve budgeted that time in your head. So, I think that, you know, having bought and sold the technology for the last 10 years, and, you know, in the last two years, I think I’ve really focused on the buy side much more than on the sell side. You know, I probably bought like a million dollars or so worth of software. In every instance, you know, I was ready to do work in order to figure out and make sure that it was the right piece of software because I had a pain and a need and a timeline to execute.

And there are times when things just look cool and interesting and I was checking them out, but I wasn’t really serious about the purchase where I probably wouldn’t have been willing to invest the time at that stage, so I think that it makes a ton of sense. And for all of our junior salespeople out there who might be a little bit nervous about, you know, asking the customer to do anything because you’re so excited that someone is actually willing to talk to you, you know, I think that, you know, being respectful of both calendars and separating out the pleasantness and respect that you give someone from the actual, you know, time that you invest in the prospect, I think is a really important point. So, I appreciate you sharing that. I think that was really great.


Kevin: Yeah, absolutely. And for the, you know, junior sellers out there, something that took me a long time to learn and to actually do with confidence is asking prospects, are you okay with telling me no. Some people might just lead you on and on and on down this rabbit hole for months and months just because they’re afraid of telling you no. So, if you ask that question ahead of time, you’re transparent with them, “Hey, are you okay with telling me no?” If they say yes and you know that you’ve got a mutually beneficial relationship where you can be transparent with each other.


Sahil: What a great nugget, Kevin. I feel myself going back to school when I listen to you talk. This is really, really good. I want to go back to one thing that you said just a couple of minutes ago, you know, I heard you emphasize the word trust kind of over and over again. How important is trust when starting a relationship with a new sales prospect?


Kevin: Just as important as trust is important with starting a new relationship with a significant other. You’re married, right?


Sahil: I am.


Kevin: I’m sure that you didn’t get married by convincing your significant other that you were somebody else. You were yourself, you were -- you’re honest, you’re authentic and she was able to see you for who you are. So, building that trust is very similar to that with, you know, a new prospect. And if you’re going to try to be some, some salesy person that’s not you, they’re going to see right through that or they’re eventually going to see through that. So, leading with who you are, I found to be a great way to for me to immediately connect with buyers.

Tell them something personal about myself, what I did last weekend, what I’m looking forward to this coming weekend, that way they see me for me and then, you know, immediately feel, “Hey, you know, Kevin, he’s just one of us, you know. I’m now excited and looking forward to continuing this conversation. I can open up a little bit more now because I’m not just getting interviewed with a bunch of salesy type questions. I want to just have a conversation with this guy.”


Sahil: Okay. So that’s super interesting, Kevin, because I think that most salespeople know that it is important to be authentic, but I think that at the same time most salespeople that I’ve worked with get nervous, right, because they’re like, “Oh, well, the prospect doesn’t really care about what’s happening in my life,” or “I’ve heard a lot of talking heads in the world of sales,” you know, be like, “Get to the point,” right, “You have 27 seconds to capture their attention,” and, you know, “Stick to the value props and stick to the script.” And there’s this mantra that I hear from the world of talking heads in sales that, you know, being over professional and crisp and on message is the thing to do. And you seem to be advocating a more human approach to sales than I hear others out there with, where would you say you fall on that line and how do you get comfortable being a person in front of your prospects?


Kevin: Yeah, you know, that’s another great question. I think, you know, being human is what’s really going to help build that layer of trust. We all went to school, we read textbooks and, you know, we took tests on those, what we learn out of those textbooks; well, a lot of the things that we’ve learned in real life have been human examples, actual things that didn’t require textbook, you know, that gave us those street smarts to understand that. So, it’s almost a balance of, okay, we need to ask these questions, we need to be crisp, at the same time we want to be ourselves and don’t make it feel so scripty.

Even though there might be a script, you know, I gave a demo very similarly every single time, but each time it’s going to have a little bit of my own personality to it, it’s going to go into how that person is interacting with me on the phone, have they been cordial so far, have they been very blunt and to the point, so almost going to mirror the way that they’re acting but also putting in a little bit of my personality so they then start mirroring me on the phone as well.


Sahil: That’s great, great advice, Kevin. And this has been a really fascinating session. All right, so we’re going to take a quick break, give Kevin a chance to grab a glass of water and then, we’ll come back and talk about the second half of the equation outside of process is obviously tools and technology. And Kevin happens to know a thing or two about sales tools, so I think this will be a great session. So, we’ll take a quick break and then, we’ll be back to you on the other side with The Future of Sales podcast.


The Future of Sales is sponsored by no one. We are simply celebrating the modern salesperson, someone who is technical, knowledgeable about their product and an expert in their industry.


Sahil: All right, everyone, welcome back to The Future of Sales, our conversation with Kevin Walkup, the Head of Strategic Sales at SalesLoft. Kevin, I wanted to get into the next section here, which is about sales technology. So, you might know a thing or two about sales technology because of, you know, the whole SalesLoft thing, kind of a household name among salespeople, but in case we have one or two folks who aren’t familiar, why don’t you tell us a bit about what it is that SalesLoft does?


Kevin: Yeah, SalesLoft is the fastest and easiest way for you to take your perspective buyers and turn them into actual buyers. And so, it does that through a cadence of multi-channel touch points: phone, email, social, and streamlines that all into one component for reps to easily be able to execute on, it’s almost like their own personal assistant for the sales cycle.


Sahil: That sounds great. And you know, I think the first product that SalesLoft, and there are a number of other companies in the space, you know, Yesware, ToutApp and Outreach and such, the first kind of core product was around being able to send email, right. I think the first kind of goal that was coming in and being able to send, you know, multiple buyers, a personalized email with one click, which was, you know, extremely powerful for many salespeople. Because before it used to be that you had to customize every single email and then, if someone didn’t get back to you, you had to send a reminder email in two days.

You get to remind yourself on who you needed to send a reminder email to and there was a lot of manual work that technology was able to help automate. You know, I can see why the vision was so compelling to you even on a napkin. The question that I want to dig into a little bit is balancing sales automation with still delivering a human centric personalized approach. Now, can you talk about how you personally leveraged the power of the tools without allowing your process to become automated feeling to the buyer?


Kevin: Yeah, absolutely. And one example is the way that I follow up with my pipeline, being, you know, very busy, having more on thousands and thousands of these demos means I’ve had thousands of opportunities and a thousand opportunities means a lot of follow ups. So, what I did was built a cadence of touch points for following up with my open opportunities. And this cadence is almost like a recipe. You know, back to my mom being a caterer, he sticks me in the kitchen and said, “Kevin, will you bake me a cake?” I’d say, “Absolutely.” Even though my mom is the one that bakes the cake, not me; so I would immediately ask for a recipe of how to follow that recipe so a cake comes out of the oven.

I wanted to build a similar recipe for making sure I’m following up with my prospects. What have I seen, what messages have resonated best with my buyers that they’ve engaged with? So, I took all of these information I built on multi-touch cadences, making sure I’m following up with my prospects, but I didn’t want it to be fully automated. So, the piece that is automated is SalesLoft is saying, “Hey, Kevin, it’s been seven days since you sent that last email, time to send them this one.”

And it’s not going to automatically fire out for me because maybe I have next steps with that person in two days and I want to tailor that message, I want to reference that time that we have on the counter together. I want to reference, you know, their wife’s birthday that they mentioned on the call last time that we had because I want to be more human in the way that I’m engaging with my prospects. So, letting SalesLoft almost key it up for me and then, I customize each message and then, follow up from there or even push somebody out if the buying cycle is a little bit longer.


Sahil: So where do get reps get it wrong, though, because I see on LinkedIn all the time this like public shaming of SDRs and inside sales reps where buyers will post a -- this little like screenshots of emails that they received along with, you know, I’ve seen them call out the person by name, which I think is, you know, offensive and wrong. But I see them call out the company, I see like the CEO of the company got tagged in the email. I looked at the comment section it has like hundreds of likes and hundreds of comments and it’s a ton of other technology buyers jumping in increasingly being frustrated by the outreach that they received being impersonal and feeling very automated. Why are so many reps getting it wrong and what’s the right way to do it?


Kevin: Yeah, I think -- yeah, and to your point, it really does. It’s cringe worthy seeing this on LinkedIn. You know, it’s good for them to put that out there because they are showing that, hey, this is not how you do sales. I think I mentioned this at lunch last week, you know, for those reps out there, they’re trying to do too much or trying to boil the ocean. If you’re trying to take a shortcut, you’re going to get cut short and you really have to lead with that human approach. You can’t just have the generic template of, “Hi, this is me. This is what I do and this is how I do it.” That’s a very me email.

And it should be more focused on, “Hey, I understand your business, I understand the challenges that you are currently having based on my research and here’s a proposed solution to your challenges. We’d love to speak a little bit more about those.” And that way, you can’t be fully templated because you have to show them that you’ve done your research and that’s how I would leverage SalesLoft to say queue that up for me and then, let me take it to the next level, let me add in 20% of customization to this email and make them feel like I spent 100% of this email customizing it just for them.


Sahil: Yeah, it is that mindset of I’m not going to just blast out all of these emails because I know that my SDR manager or my VP sales set this quota for me and I need to make sure I do this many outreaches. You know, one of the things that tools such as SalesLoft has done is it’s made it far -- it’s made it far less expensive, if you will, from a time perspective to send a thousand emails instead of a hundred emails, right. I mean, if you want to send a hundred emails versus a thousand, you know, you had to write 900 more emails once a upon a time.

Now, today, you can just add those 900 names into the cadence and press send. You know, I think that it has created a mechanism that allows people to take shortcuts and still artificially make their numbers look good without realizing that that’s 900 valuable prospects who now have a negative impression of your brand and who have received, you know, an outreach that makes them feel as if this may not be a company or a vendor that I want to do business with in the future because they’re clearly just in the business of spamming us. And I think that the opportunity cost is not being weighed properly by the people who are making these decisions.


Kevin: I agree with you 100%. It’s all about the effectiveness ratio for the rep that sends out a hundred emails and gets 10 replies because those 100 emails were very authentic and sincere versus the rep that sends out a thousand non-sincere and gets 10 positive replies. And they both got 10s for their scores, but the effectiveness ratio is 1/10 versus 1/100. So, you know, rep A is 10 times more effective than the other rep just because they have led with putting a 10 on that person’s head and they’ve genuinely cared about emphasizing with their buyer and showing them that they have done their homework. So, you’re exactly right there to, you know, when those reps are going to send out a thousand emails, I cringe and, you know, kind of say, let’s dial that back, let’s -- are you leading with putting a 10 on that person’s head by sending them this insincere and unauthentic message, and you answer the question and decide if you want to move forward from there.


Sahil: It’s all about the framework, right? If you have that framework of saying, “Hey, I want to make sure every prospect who interacts with me has a great experience regardless of whether they buy or not.” I want to make sure that they walk away thinking that the company that I represent and myself as a personal brand are positive in the mind of that buyer, because you take a long term view, right. I think that that’s the part that goes missing a lot is taking a perspective of the person who today has a six-month, eight-month, ten-month, you know, year long contract with a competitor or who today doesn’t have the right CRM system so that those people, (a) conditions change internally within the company, (b) leadership changes within the company frequently, and (c) those people sometimes end up at other companies where they’re in a much better position to buy. You know, the power of referrals and social selling is something that many sales reps I think undervalue. You shared something interesting with me about when it is the right time to ask for referral. Maybe you can dig a little bit into that.


Kevin: The best time to ask for a referral is all the time. So, many people don’t ask for referrals and it doesn’t matter if it’s after the first call, after the second call, you should be asking for referral in every call. Even if the person is completely 100% disqualified, I’ll still ask them for referral. “Well, based on your network, you know, I know that you’re not the best fit for this. Who would -- who do you know that might be a better fit for this?” And they start rattling off names and my pen can’t write fast enough. So I think all the time is the best time for referrals.


Sahil: Then, why is it that most salespeople don’t ask for referrals? You know, I read a stat recently, we do a ton of research on this here at Bravado and I read a stat recently that 11%, 11% of salespeople ask for a testimonial or a referral, but 71% of buyers are willing to give one. And, you know, salespeople have this reputation for being pushy, right, like they ask for too many things, they send too many messages, et cetera. Well, here’s something that every salesperson knows, referral leads are super valuable and, you know, deals close so much faster when you have a referral and yet 11% of salespeople are willing to ask for one, 71% of buyers are willing to give one. What’s going on?


Kevin: That’s a great question. I have no idea why there’s only 11% of people actually out there asking for referral. I talk about it all the time amongst my team about growing your network and, you know, whether it’s just connecting with somebody on LinkedIn and referencing somebody that you have a mutual connection with. It’s so great to be able to come back to that person down the road, “Hey, Mr. Prospect, you and I did business a month or two ago, I see that you’re also connected with this new prospect I’m working with, would you mind, you know, telling them about our experience working together?” Like you said most of the time, they’re more than happy to do that as long as they’ve had a great experience working with you and you’ve built that trust of a long term partner to them and a consultant that is genuinely there to help their business.


Sahil: You know, it brings me to -- it brings me to such an important point for all kind of young junior salespeople who are getting their start in sales, is the fact that it’s some really small world, right. I think that a lot of salespeople think that, “Oh, I closed a deal with this company that nobody has really heard of, so it doesn’t really matter, right.” You know, the only thing that matters is closing the Googles and Facebooks and Slacks of the world. And as it turns out, you know, buyers, we all know each other, you know, when I was buying, you know, I bought a few applicant tracking systems when I was running a couple of HR departments. And once I bought Lever, once I bought Greenhouse, and in both of those instances, the reason why we ended up buying those products is -- or the different products is because the recruiters on the team had either had positive or negative experiences dealing with members of the Lever and Greenhouse team.

And one example, you know, a couple of the recruiters had really positive experiences with the Lever product team at some conference they’ve met and they were like, “Yeah, the Lever team is amazing. We should totally use their technology.” And another example, somebody had met a couple of salespeople from Greenhouse and it gotten a pitch at another company, they didn’t have the budget for it, so they didn’t move forward with the purchase. But the Greenhouse sales team’s presentations and their ethics stuck with them, so when we were at the next company and we were evaluating technologies, they lobbied really hard for Greenhouse even though I’d had with Lever.

And I said, “Well, sure, if you guys want Greenhouse, we’ll buy Greenhouse, right.” And so, it was a really easy decision for me to just pick the thing that the team was most excited about. What was interesting is that in both of those instances, the recruiters had never either -- had never bought Lever or Greenhouse before, but those companies had done a great job building positive brand experiences for the market and then, they were able to close deals in the future as a result of it. So, I think, again, you know, putting the 10 on the forehead, being conscientious that, you know, today’s unqualified prospect might be tomorrow’s hot deal that you got to close and knowing that if you build that great relationship of that person you’ll be able to take advantage of that relationship later and leverage it to get it in, I think, is so important for salespeople, you know.


Kevin: I totally agree and I couldn’t tell you how many referrals I’ve received from people that have not bought from me in the past.


Sahil: What percentage of your business do you think is referral based?


Kevin: 35%, 40%.


Sahil: Wow, that’s a big portion. And do you feel like deals that come from referrals close -- would you say that they close as fast as normal deals faster than normal deals, what do you think is the likelihood of closing change or what’s the difference do you think?


Kevin: I think they’re all unique, but I think they’re all going to be much -- it’s going to be a much smoother buying process. I’ve had some referrals where, “Okay, Kevin, meet this guy. I just gave them a demo of your product and they’re ready to move forward, where do they put in their credit card?” Those are the best referrals, right, because now that my customers are doing my work for me. And then, there’s also some that have been much longer, much more tedious, completely disrupting the way that they’ve been doing business and have been longer deal cycles. But, you know, that immediate thought of, “Hey, Kevin is a trusted advisor of me and I want to talk about the product that he helped changed my business to this referral,” it’s going to give that person a better, warmer experience right off the bat. They don’t feel like they’re being sold to, they feel like they’re being helped.


Sahil: I love it. You know, to the point of being seen as a trusted advisor, you know, it’s the reason we built Bravado, you know, was because as a salesperson you work so hard in order to create success and win-win situations for your customers. But it’s so hard to tell who are the salespeople who really do that and which are the vendors that are creating really customer centric experiences and who isn’t, which is kind of the backbone behind why we built Bravado was to be able to highlight that for salespeople like yourself who are really pioneering B2B technology sales. So, thank you for sharing that that was super, super insightful. All right, we’re going to take a quick break and when we come back we’ll close with Kevin’s thoughts on the future of sales, how sales will continue to evolve and change. So, one last break and then, we’ll be back.


The Future of Sales is sponsored by no one. We believe that great salespeople are more than just a number and deserved to be celebrated just like everyone else.


Sahil: All right. Welcome back to The Future of Sales. We’re going to conclude our conversation with Kevin Walkup, Head of Strategic Sales at SalesLoft. So, Kevin, what are some of the trends that you’re seeing in terms of how your job is evolving day-to-day?


Kevin: Yeah, I would say the first thing that comes to mind is that buyers are more educated than ever. They have sites out there like G2 crowd that they can do side-by-side comparisons, being educated, they’re leading into some of the sales processes with an upper hand and it’s really going to come down to the experience that they have with that particular rep. If they have two reps that are selling two identical technologies, two different brands, but the same end result, it’s going to come down to the experience that they have, again, that trusted advisor that’s really caring about their business more than, “Hey, I’m just here to sell you something because I was told to.”


Sahil: Okay, so that’s really interesting because what you’re talking about there is the fact that product differentiation is no longer enough to win a deal, is that what I’m hearing there?


Kevin: Yeah. Absolutely, I mean, a lot of times, you have your Coca-Cola and Pepsi side-by-side and, you know, both of them are soft drinks, both of them are delicious, it’s really going to come down to the preference at the end. You know, how was the acquisition process and even though the results are the same, I totally agree there.


Sahil: So then, if product differentiation isn’t enough, then you talked about experience differentiation or what we here at Bravado call delighting the customer, what are the qualities of a modern salesperson and how are they different than perhaps your stereotypical, bro-y, you know, former jock, highly extroverted, you know, gets in and pounds through a thousand calls a day sort of mentality, you know, is that one of the salesperson in the future is going to look like?


Kevin: That’s a tough question. I think there’s a place for those types of salespeople out there forever, but for like the true like big sales, big, you know, generally going to impact someone’s business and disrupt the way things have been done from status quo, I think, the salespeople of the future are going to operate completely different in a way that, you know, they have empathy towards their buyer. They’ll sit down and they’ll even tell you, “I’m not even going to show you product until I understand and we agree together that this conversation is worth continuing because I don’t want to show you a product just to show a product if I don’t understand your business.”

So it’s really important to know, “Hey, is this person a fit before we even continue the conversation.” So, I think the way that salespeople are going to be going is, okay, we got people coming in, they’re more educated than ever, now let’s talk about the space in a whole. You need to be educated around my competitors, what they do differently not just product feature to feature benefit, but who’s the actual thought leader in the space, are they going to walk away from that call having learned something about that space or they just been featured dumped on. Sellers in the future are going to be more educated not just about their product but about the entire market as a whole so they can educate those buyers on what they have and already been educated on.


Sahil: So how much time and effort do you put in staying abreast of your industry, of staying abreast of your competitors, staying informed about, you know, kind of trends in this space, and maybe just as quick follow up to that, where do you get your information?


Kevin: All over because I spent a lot of time, you know, I was reading about multiple different blogs. Again, I love Ralph Barsi’s blog and there’s a couple of others. Thomas Tungans has a good one, John Burrows is talking about, you know, the frontline of selling and the future of sales as well. So, I’m reading a lot of those and part of my morning as I’m getting ready having my coffee, you know, reading through a couple of different posts on a daily basis. And I don’t even use, since I’m relatively slow reader, I’ll even use an app on my computer that will help me read things like 250 or 300 words per minute, so I can just quickly just blast through a blog post in, you know, less than a minute and be able to read five, six seven paragraphs versus, you know, it taking four, five minutes to read that.

So I do that as I’m getting prep for my day as I’m, you know, looking up and preparing for what I’m doing because then, later that day I talk about those things on my calls. “Oh, Mr. Prospect, that’s funny that you just mentioned that and I just read this morning that XYZ is the best thing to do or these modern sales organization are leveraging this with this kind of result, I just read this and I’ll send it to you as a follow up.” And that way I’m becoming an educator and then, I’m putting my money where my mouth is by sending them the post that are top of mind to me that I read that morning and I can send them as a follow up.


Sahil: What is this magic app that you speak of?


Kevin: I think it’s called Speedy Reader; it’s a Google Chrome extension.


Sahil: Great. Well, first of all, that is really cool. So, I’m going to be downloading that because I find myself overwhelmed with content that I should read that I don’t always get around to reading, so Speedy Reader it is. And secondly, to the point of, you know, following up with content to your prospects, you know, this is something that I’ve seen work really well as well is if you can come across as being as informed or more informed than your buyers are about your space, then they’re going to see you as a source of wisdom, as a source of information and that goes right back to that trust, right. I mean, your trust people that you respect and you trust people who are well-informed and you trust people who know what they’re talking about. And, you know, giving your emphasis on trust as a, you know, kind of a core fundamental component of, you know, the sales process really interesting I think to leverage that as well.


Kevin: Yeah, it’s solidifying as well. Instead of just referencing the same piece of content over and over, it’s, you know, two years old. Then, I would say, “Hey, I read this article that came out last night. I read it this morning. Here, this is fresh. It just came out, I want to send it over to you.” It kind of solidifies that, hey, this guy, he doesn’t just reference the same piece of content, he’s actively learning, he’s actively preparing himself for what is to come and knows more about the market than other competitors, than the other people that aren’t reading those blog post that the same people that they’re talking to.


Sahil: And do you think that that helps you actually close more deals?


Kevin: Yeah, absolutely. I think it helps build that trust. It’s definitely helped me get more referrals.


Sahil: Wow, well, that’s great. So there you have it, from the man, the myth, the legend himself. All right, Kevin, well, this has been a really great conversation. I want to thank you so much for joining us here on The Future of Sales. It’s been great.


Kevin: Yeah, this has been a lot of fun. I’ve really enjoyed it today.


Sahil: Kevin, if somebody wants to get a hold of you to ask you any follow up questions or share any thoughts on what you’ve said, what’s the best way to do that?


Kevin: You can always email me at and that’s walkup like walk up the stairs and I’m also @walkupkevin on Twitter as well if you want to follow some of my silly tweets that I put out there as well.


Sahil: I do follow you on Twitter and I think that your tweets are awesome. So, there you go. Thank you so much again, Kevin and congratulations on your many successes and many more to come. I’m your host, Sahil Mansuri. Join us next time on The Future of Sales to hear a fresh perspective from another top salesperson. Thank you very much for joining us and have a great day. Cheers.

Kevin Walkup made his profile using Bravado

Make your own, stand out from others.

Get Started