The Key to Long-Term Sales Success ft. Keith Weightman

What's our mission? What are our core values that should guide everything that we do? And if you don't align, that's okay, but you're probably not in the right place.

Welcome back to another episode of the Revenue Reimagined Podcast. I am stoked we have with us today someone I have been trying to get on this show for what feels like forever. I am so glad that he's finally here. Keith Waitman, who is the RVP of Sales at Bullhorn. And if you're not getting his newsletter, you need to. I don't open a ton of newsletters, but every week—every weekend, excuse me—he delivers simple tips that help deliver big-time impact, combining sales writing, and most importantly, the power of visualization, which we'll talk about in a little bit. Dale, take some notes here.

Keith, thanks for joining the show, man. I'm super excited to be here. I'm glad we could finally make it work out.

So, I mean, other than the fact that Dale was 15 minutes late, we'll give him a pass. We'll give them a pass. We will not make the episode 15 minutes though. We'll make it work.

Awesome. Keith, thanks for joining, and we've known each other for a bit of time ever since, like, back in the Smart Action days. So it's been a bit of time since we've been chatting. But let's start with this question. You've been in sales for a long time. It's time to reimagine your role. Let's say you have to leave sales and go to some other Revenue Department. What department would that be, and why?

That's a good question. I don't think I mean, can I say no? I don't want to go to another?

You got to pick one. One other one.

Other place? Maybe I don't know. Maybe Sales Ops. Ops. Sales operations. Marketing. Like, with all your visualization and all your pieces, I was like he's definitely going to say marketing, but operations?

See operations as well? Yeah, I mean, I like the process side of things. I like to look at the bigger picture. But you know, marketing is another one I could. You know, you threw me with that question. I wasn't prepared for that one this early in the morning.

Let's talk marketing, sales, Sales Ops, as it all comes together. I think, Keith, one of the things that fascinates me—and you and I were talking about this a little before—you've been at Bullhorn almost 12 years, right? Eleven and a half years. That is unheard of in today's day and age for any Revenue leader. They typically have an average tenure of 18 months to be somewhere for that long. And part of me thinks that is because, in part, of cross-collaborative working with marketing, working with Ops, working with everyone, and having these relationships that make you want to stay. But talk to the audience, specifically Founders, who have this general belief: "Oh, no one's going to be here more than a year. It's impossible." You're living proof, man. Eleven and a half years. What does it take? And why did you stay 11 and a half years?

Yeah, it's a loaded question. But I'm a big believer that people work for people. They don't work for companies. And I happened to start at Bullhorn in 2013. I started the same day that my leader started. So we were in the same sales bootcamp, and I've been with him since then. And you know, I look at okay well I've been here for 11 years, and then I look at my CRO—he's been at Bullhorn for 18 years—and our President's been there for 19 years. Our founder is still there. And I didn't come in as a leader. I came in as an AE, and I worked my way up. I had opportunities to grow, and we had good people. We had the best product in our niche. And I was always hitting the number. It was like, why would I look to go somewhere else? Like, I was always overachieving. So I felt like I had the right people, the right product, the right environment for me to succeed. And you know, for Founders out there or for people sellers listening, like, if you find that, think really hard about leaving to try and go get a bigger OTE somewhere else. Because you know, it's hard to get all of those in one single spot.

Yeah, it's funny. So I—and Dale can tell you this because he actually coached me through this a little bit—I certainly was one who suffered from shiny object syndrome. Grass is greener, you know, a little bit more money or a better product, and you know, going to go jump and make that move. And nine, eight times out of ten, it probably backfired. I think there's something to that stability. And I think Founders need to realize how you open this is the most important thing: people work for people. If you surround your team with great people—and I love how you said your leader, not your boss, not your manager. That's a word that Dale and I use a lot—if you surround yourself with great leaders, your people are much more likely to stay, be invested, and help you grow the business. And I promise you, you're going to grow your business better with people who are there three, five, seven, ten years versus this rotating door of 18 months. Kudos to you for staying that long, man.

Yeah, and I can attest like Donnie's amazing. I've worked with Donnie a little bit. He's an amazing leader. And I also think you know, the people that you had working with you as well, like, you know, me and you both know Matt really well. Matt was amazing. Like, it's not only the people that are leaders, it's also the people that work with you or for you. If you go through that process, it's much easier when you're not trying to have to babysit people or bring them along. Like, they're all on that ride together with you. I think it makes it much easier for you to go through that process.

Yeah, yeah. It's really about building the right culture. And I think Bullhorn has done a really good job of that—not only just my leader, but our founder that's still with the organization. Like, I mean, it all starts from him, and it trickles down. He's the one that's created the culture that has permeated through the rest of the organization, and he's part of the big reason why I'm here as well. Like, I believe in him. I believe in the direction, and he's still very actively involved when we need him, which is super helpful as we've continued to get larger.

Awesome. So let's talk. We believe a lot in the idea that there's failure that happens as you're growing the business. I mean, you've been there for 11 years. You've probably seen ups and downs. What's one of the things that you've learned that you failed at, but you learned through it? And give the audience a couple of things on how you can change failure from a setback to a setup.

Yeah, yeah. Well, I've certainly failed a lot. And I think that's part of, you know, I'm a very competitive person, so I don't like losing at anything. But you know, one of the things—go figure, and you're in sales, imagine that—one of the things that I think we failed at early on was acquisitions. So since I've been at Bullhorn, we've made like, I don't know, 13 or 14 different acquisitions. And acquiring these companies and bringing them in—we talk about building a culture, right? Well, a lot of these companies have some shared similarities in the culture, but there's also a lot of differences. So trying to integrate people in and trying to create the right resources to make that seamless was very difficult. And it was hard on customers. Like, customers hated it because it was a change. We lost customers along the way, which was super frustrating. And we had to rethink. The next time we did an acquisition, we got to learn from all the lessons that we did. How do we make it better next time so we can make it a repeatable process? Because that was part of the strategy for us to continue to grow. We were going to acquire companies that complemented our toolset to be able to add more solutions to what we sell and expand the share of wallet.

So I think just integrating new people into the organization and taking their processes and integrating with ours—that was something we failed at for our first couple of acquisitions.

Yeah. What's a couple of things that as Founders are thinking about acquisition, what can they do to prevent some of that stuff? Is it better due diligence? I mean, you do a bunch of due diligence. Like, what are the things that you can do? And you're an operational guy, maybe it's the operational side?

Yeah, I think it was more on the operational side. Like, when we first did an acquisition, there was team and due diligence on the financial pieces of it and all that. But it's more like, okay, now once we do it, what's actually going to happen? What are the action steps? What's the team that's involved? And as we continue to make more acquisitions, we put together operational teams to say, okay, here are the key customers that they're calling on the first day. Let them know what's our strategy? What's our plan? How do we roll down that message to the rest of the field on why we're making this acquisition? Why it matters to them? What's our plan? And what's our strategy so that everybody's on the same page?

So I think it's more around the planning, the messaging, having the right team involved, and making sure the acquisition actually complements what you're actually doing. And systems, right? I mean, someone may be on HubSpot versus Salesforce. Now you've got...

# Transcript

To convert, there's some of these things that you don't think about, and I think it's a little bit like an investment for a founder. Like, when they're going to get a Series A, how do you map the investor to what's happening with the founder? Like, do you kind of drive together? And then if you're converting all of your customers from Salesforce to HubSpot or HubSpot to Salesforce, that's a big migration that could be two, three, four months. We've had to convert a customer to a brand new instance of HubSpot. It's difficult.

Yeah, luckily I'm surrounded by some really smart people that know how to help and make that come to fruition. So again, it goes back to, you know, I'm lucky to be surrounded by a lot of great people at Bullhorn.

That's so refreshing to hear because we talk to a lot of people who are like, "Oh, I have this one person I like, or two people I like," but hearing like there's this whole team, right? A lot of great people. And I think that speaks to the company and probably yourself as a leader as well.

When you look at growing an org and you look at what I'll call broader alignment—you have to align sales, marketing, success, RevOps, pre-sales, and solution engineer. All of that stuff. A lot of people I think get that wrong. And I arguably think alignment is becoming more of what I'll call like a term. Like, we don't have to align. We might have to agree and move forward, but like we probably won't align, but we need to pick the best path.

As you've been growing teams and as you've come up through the ranks over eleven years, what are some creative approaches you take to drive that cross-functional alignment? Because you're working big deals. You're not on the SMB side. That requires a lot of alignment. How do you step outside of the box and encourage your team to step outside of the box to really drive this cross-functional unity instead of alignment?

Yeah, that's a good question. I feel like again, I might be sheltered because I've been at Bullhorn for so long that we built such a good collaborative teamwork between our Solutions Consultants—the PE, the technical experts that are going to demo—Professional Services that will deliver, or we work with a lot of systems integrators that will go and implement the product, support. I think a lot of it comes down to you. The bigger deals that you work, you almost have to build better internal relationships than external. But you can't disregard the need to build those internal relationships because that's what really makes a deal go forward. When you're like, "Crap, I need this customer to have a specific need around understanding our support model, or they want to understand a roadmap better," well, it's better coming from the lead of the product than from a salesperson. So how can I create the picture internally? Like, here's where I need you and here's why. It's building those internal alliances to help you move things forward. And I think it's more around just creating that environment where everybody at Bullhorn is willing to help. And again, I don't know if it's something that I can really break down the why behind it other than that's our culture. It's ownership. It's being human. It's speed and urgency.

So but that's it right there. You actually did just answer the question. That's the culture. The culture is ownership. The culture is being human. The culture is speed and urgency. How many cultures have you worked for where the culture is like, "I'll get to it when I get to it"? Like, there is no urgency. Being human. I, no joke, had a founder get me on a pre-planned PTO in Scottsdale, Arizona and said, "You need to come back because I'm working and you need to be working, and you're not allowed to take time off." Like, what's human about that?

So what you just said is the answer. That's how you drive that alignment. It's that culture. There's not enough emphasis in my mind placed on the importance of what makes culture. And culture isn't wine on tap and beer on tap and bean bags in the office. Culture is everything that you just spoke about.

Yeah, like to me, that scenario that you just mentioned, I think that's so foreign to me. I've never had that. It's the day Dale convinced me to go out on my own that was probably a pretty easy decision after.

Yeah, I mean, I think Dale could have told me I'd make ten dollars a year on that day and I would have been great. Where do I sign? It was months in the making, Keith. Months in the making.

But so let's double-click a little on culture. Because I think it's easy to say it starts at the top, and you know, because I do think that's where it all starts or fails. But how do you instill that culture? Let's give the audience a bit of how do you instill that culture below as you're building your team so that they can see the culture? Because they're probably not seeing as much from the founder that you have. You know, you had such a big long relationship with. How do you instill that culture with your team as they come on board?

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Well, part of that, I'll almost say they actually do have a very, so we do quarterly all-hands. And at the beginning of every all-hands, we go over what's the mission? The mission is to create incredible customer experience. And that's what the entire people at Bullhorn rally around. It's like, if I'm asked to do something and it's going to help create a better experience for the customer, then I'm going to do it because that's our mission as an organization.

And he always goes over the core values of the organization, every single one, and then we focus on one each quarter—a different core value each quarter. And you know, that way, at the end, someone gets an award based on who's exemplifying that core value. Like, you know, service. Who's actually done it? What have they done and why? And we do like a little award ceremony each quarterly all-hands. Because it all goes back to, what's our mission? What are our core values that guide everything that we do? And if you don't align, that's okay, but you're probably not in the right place, right?

It's a good way to weed people out that aren't looking for something different or don't align. But you said something very interesting, which was every quarter you guys are doing this. And I think it's easy when companies are smaller—I don't know if you're under fifty people, under seventy-five people—to have that quarterly meeting. But now that you guys are continuously doing the quarterly meeting even as you grow up over ten years later, I think that's very commendable. Because I think people now want to target toward that quarterly meeting type of thing. So interesting.

Yeah, and we've been doing that since I've been here. And now at Bullhorn, we're about half a billion in revenue, about 1,300 people. So the fact that we've continued to create that consistency, and again, it all comes from Art, who's the founder. And that consistency means a lot to the employees. I don't think I've met one person that I've hired that aren't like, "Man, he's so inspiring," or "He's so genuine. He's not like a rah-rah person. He's very genuine. He's authentic. He's realistic." And when things aren't going well—like, as you guys know, the last 2023 and the beginning of 2024 has been tough—he's not the type that's like, "Okay, we're just going to do more," or like, "Oh, that's not really the case. We just got to do this." It's like, "Look, I understand. The data is there, you know, but we need to focus on the things that we can control, and these are the things that we can control. So this is where we're going to go. Because when there's a snapback, we've already got the foundation to take it to the next level."

Control the controllables. What a concept.

Let's shift gears a little. So this was the first time you and I have met in person. I have subscribed to your newsletter for a while. I actually think I've messaged you many, many months back. I was like, "This is one of the few ones I actually read to benefit from, not just to help our newsletter and see what else is out there." And I do, I read it every morning. I probably have a dozen of them saved in a file that I go back to. And you focus very heavily on the power of visualization. There was a point where I thought that all of those drawings were like things you downloaded from the internet, like I have no artistic ability. So like, anyone who could draw anything other than like a little stick figure blows my mind. But I think you do a really good job at highlighting how visualization can help close sales.

Can help you understand whatever it happens to be. Talk to me about where this mindset came from because most salespeople are not visual people, so I love that you're kind of changing the status quo and driving that in a way that I personally find to be extremely relatable.

Yeah, well first of all, thank you. I appreciate that. So it was 2009. I was working at Ceridian. I was brand new—this was my first job in SaaS. And I was working with a senior solutions consultant on this big deal. It came in as an inbound, and we were going on site to see them. He shows up and he's got this architect tube on his back. I'm like, "What's that?" He's like, "Oh, you'll see."

So we get in there and he unscrews it, he dumps out a bunch of markers, he's got rolled up paper, and he starts putting them all over the wall. He's like, "Hey, this is going to be different than probably meetings that you've done in the past where you sit across the table and ask questions." And this is to the customer—he's like, "We're going to really sit and we're going to write down, we process map, what are the challenges, what are you focused on, what is the current state, where are you looking to go?"

And it was like one of the most—I still remember to this day—it was like the best meeting I've ever been on because it was super collaborative. The customer would pick up the marker and be like, "Actually, it's this," and then they were like, "Hey, can you keep that here or can we take a picture of it?" And from that day I was like, "Okay, I got to learn how to do this."

Because my previous meetings were like, I'm asking them questions from a script or I've got a PowerPoint deck, and I can tell like they've done this with four other people already, and it just wasn't very valuable. So I'm like, "How can I do something different?" Not just to be different, but it's also going to add value to the meeting. And for me it was around learning how to whiteboard and have conversations without the necessity of a deck as a crutch. And it helped me better internalize the message because I don't have that crutch of a deck. You have to practice it. And it was different.

So you know, I've always been a big fan, and I think it also helps with creativity, which is extremely important as a seller—be able to think outside the box and do things differently. So that's kind of the origin story, I guess.

Does your team whiteboard? Certain people on my team whiteboard. I certainly don't press them because it is a skill that you can build, like just like any skill. It's something you've got to work on. Matt, you know Matt? So like, what I love about Matt Dictor, who is a VP of sales now but he used to be on my team, he's the type of seller that he will take action and he prefers messy action over perfection. When I started to say, "Hey, we're gonna start adding this," he jumped right on it. I've got pictures, and you know, I've got pictures of the whiteboard still that he's done. So he picked it up right away. And then I've had a couple others that are really big into it as well.

So I only know of Matt because he's the only person I know that's put up with Dale for a long time in a coaching session. But how do you—sorry, couldn't help myself, Keith—how do you get someone like me who legit has no artistic ability whatsoever? I absolutely whiteboard, but like, I don't draw. And I think most folks are used to whiteboarding in the sense of words. But I do like—again, one of the things I found so powerful is the images versus text—it's just a different way of storytelling. How do you get someone like me to actually learn to do that? And I'm asking for very personal and selfish reasons, to be very clear here.

Yeah, yeah. It's funny. I did a session for Sales Assembly. They were like, "Hey, could you do a session on whiteboarding for our members?" And you'd be surprised how easy it is to do some of the whiteboarding that I do. There's five shapes. If you can learn—if you can do a circle, a triangle, a square, a line, and a dot—you can basically depict anything.

You lost that circle. You lost him at circle. That's the one with three points, right?

You'd be surprised. So I went through an exercise with them and I said, "Okay, let's take some words that you typically hear in your sales cycle, and I'm going to show you just with those five shapes you can draw whatever you want." So we did things like automation, integration, growth. Growth is one line, another line, and then a squiggly arrow. You know, it's just so—it's really about building a visual vocabulary. And the thing is, you can use one icon for multiple different words, so you don't need an expansive visual vocabulary. So it's a lot easier than you may think.

So you know, maybe we'll spend some time and I'll give you some pointers.

I love it. Visual vocabulary. That's a win. That's a WAP, folks. Thanks. No, I'm kidding.

Actually, Keith, set up at some point you guys to see Keith's setup because he's got this board and it's all black. His setup is legit.

Yeah, it's right here. I use a neon blackboard. Neon markers. So it's actually this company called Revolution Light Boards. It's a pane of glass that has lights on around it that illuminate it, and then I just have a black backdrop behind me, and the markers are neon. But I literally pulled this up as we're talking.

This is super cool, isn't it?

Awesome. They're a great company. The product is awesome. And it's just—I love it. Definitely check it out.

Very cool. Very, very cool. You still lost at circle, so that could still be an issue.

Listen, it is what it is.

So from a visual vocabulary perspective, I really like that term. Talk to me a little bit, or talk to the audience a little bit. What are three things that you've seen change in your sales process or the buyer's reaction to that visual vocabulary?

Yeah, I think one: it's just different, right? Corporate Visions did a study a while ago where it was like only 6% of sellers incorporated any type of whiteboarding, and then virtually less than 4%. So right there is a blue ocean. If no one else is doing it and you're doing it, that is clearly you're differentiating yourself.

Also, there's a ton of studies around the way that our brains process images over text, right? It's like 60,000 times faster when you see an image than if you were to read text. So for me, using visuals just adds more. It adds a differentiator. It makes it easier for people to understand because again, I'm not up there drawing the Mona Lisa. I'm drawing squares and circles. And it also helps with memory retention big time.

Not only for me—if I'm planning a talk where I'm going to be using a whiteboard, I've got to plan it out. But the simple visuals help it stick in my brain, and the same is true for a customer. The visuals help with memory retention, which is important as a seller. You want to make sure that you're differentiated, they agree you're differentiated, and they can also remember what you've said amongst all the other competitors that are also vying for their business.

I love it. I think that there's not enough use of visuals out there. We're used to getting these emails that are paragraphs long and these case studies that are paragraphs long. But when you put pictures to it, it simplifies it. I just need to learn to figure out what a circle is.

Last question before we get into some rapid fire and wrap it up: whether you're a startup or whether you are an established company like Bullhorn, I think there's for sellers a struggle between innovation and perfection of execution, right? Do we ship this now or do we wait for it to be perfect? Do we make the slide deck perfect or do we roll with it because we have to go into this meeting? How do you balance that for your team—like when is good enough and when does it need to be perfect?

Yeah, and that's probably one where I can get better at because I'm very detail oriented. I don't want to say I have OCD, but like if you come to me and you have a PowerPoint that has different fonts on it—like you forgot to change the font—yes, that drives me wild. A Google Doc that has all the wrong header levels, should be header two but it's really header three, and you think it's okay to ship that? Yeah, we're speaking the same language. Dale, take note.

No, that's why I send it over to you. I send it over to my EA to fix it, so it's all good.

Yeah, but I really appreciate those people that don't get lost in the details like I do sometimes, where they can just say, "I get that, but you're missing the bigger picture. We've got to go. We've got to go faster, and we can make the changes along the way."

The way to make things better—what we can't do is just be paralyzed saying it needs to be perfect before we actually ship it. And that's something that, like I said, I've struggled with: it's not perfect yet, we can't do it. Where a lot of my other leaders are like, you know, they're already two weeks ahead of me because they're not worried about what the colors and the fonts and things look like. They just go ship it and they iterate over time.

Love it. All right, let's wrap it up with some rapid fire. This was super insightful, certainly for me. But we're not—I'm not the one we're trying to please—but I have no doubt that the founders and revenue leaders who are listening are able to get a ton of value out of this. And we'll talk. I'd love to circle back on what we could do with helping some of those folks with visualization.

All right, so Dale asked you at the beginning of the show: if you weren't in sales, what part of the revenue ecosystem would you be in? I'm actually going to shift this for a second, Keith. You cannot be in tech. Tech is dead to you. What are you doing for the rest of your life? What job? Where are you going to work? What profession?

This is going to seem really, really weird, but over the last two weekends I've been power washing my house, and there's something so satisfying about power washing—just seeing the dirt go away. I honestly think I would start a small power washing business. I love it.

So, little fun fact: we had our house power washed the other day, and I was talking to the guy who owns the company. Former tech sales executive, got burnt out, started this business five years ago, now has three trucks. And according to him, he's like, "I make just under two million a year." He's like, "Yes, it's manual. I'm busting my ass." He's like, "But I love it. No one bothers me."

The sexiest jobs are not necessarily the ones that pay the most, folks.

Yeah, that's funny. So we've been talking to a lot of founders lately, but coming back to the sales leaders world, I've enjoyed this question: What song best describes your revenue strategy?

All I Do Is Win by DJ Khaled.

Nice. That's Dale's walk-out song. That's right.

Keith, early bird or night owl?

Early bird, all day. And everybody in my team knows it.

What's the first app you check when you wake up?

I probably check Todoist, which is my task manager, to see what's on the agenda for the day.

I tried that app a while ago and never got into it, but I need to figure something out. I have so many different places I need to organize.

What would be the one word to describe your sales career so far—eleven and a half years?

Gratitude.

That's a great one. That's awesome. I like it.

Okay, all right, Dale, take us home.

Yep. Keith, earlier in the show you said you were going to be a revenue ops leader. It's tomorrow morning. What's the first thing you're doing as a revops leader?

Lowering quotas.

Everyone wants to work for Keith.

Keith, I cannot thank you enough for joining us, man. This was super insightful, super helpful. If people want to learn more, they want your visualization tips—and we'll include a link—but for anyone listening who isn't reading the show notes, where can they subscribe to your newsletter? How can they get all these great tips every Saturday?

LinkedIn. Just find me on LinkedIn: Keith Waitman. It's right there. You can subscribe in the feature section or I have a link at the top. But yeah, go subscribe. I'm telling you, I don't read a lot of them. You will get value out of this every single week.

Keith, thanks for joining us, man. It was a pleasure.

Thanks, Keith. Thanks, guys. I appreciate you.