Episode #81 She's Conquered the Sales World, Coached Top Sales Reps, and Even BEAT Shaq at Basketball ft. Lindsey Boggs

In this episode of Revenue Reimagined, Adam and Dale sit down with Lindsey Boggs, VP of Global Business Development at DG Matrix, TED speaker, Forbes 30 Under 30, Salesforce Top Influence, and you could even say better basketball player than Hall of Famer Shaquille O'Neal (listen to find out about this one). Lindsay shares her expertise on go-to-market strategies, effective sales enablement, and why listening to customer calls is the ultimate starting point for success.

Get ready for actionable advice on:
✔️ Building and coaching top-performing sales teams
✔️ Using AI to enhance, not replace, human connection in sales
✔️ The power of storytelling in sales outreach
✔️ Lindsay’s unforgettable experience beating Shaq in a free throw contest

Whether you’re a sales leader, an SDR, or a RevOps pro, this episode is packed with insights to help you scale smarter.

Follow Lindsey: https://www.linkedin.com/in/lindseyboggs/


PS - huge shout out to Sendoso for sponsoring our show.

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Transcript

00:00 
This is the Revenue Reimagined podcast where we talk about what else all things revenue with the best senior leaders across sales, marketing, customer success, and RevOps so that you can scale your business by reimagining how you think about revenue. 

00:15 
I'm Adam Jay and I'm Dale Zielinski. As always, thanks for hanging with us. There's a million ways you can be spending your time and we're grateful that you're choosing to spend it with us. Be sure to check out our newsletter if you want the show notes, amazing giveaways, and the tactical advice on how to uncomplicate revenue. 

00:32 
Let's get to it. Welcome back to another episode of the Revenue Reimagined podcast. You are not getting this early in the year but this is our first recording for 2025. We are so excited to have Lindsay Boggs with us today who is the VP of global business development at DG Matrix, a TED speaker, Forbes 30 under 30, four times Salesforce top influencer who just launched her own consulting business last week which we're going to talk about. 

01:01 
And little fun fact, you see that basketball behind her, she actually beat Shaq in a free throw contest. That to me is reason alone to have you here. Lindsay, thanks for joining. Thank you so much for having me both of you. 

01:13 
I appreciate it. Lindsay, I know we've been working on this for a little while and super grateful you're here. I get to know you way early in a bit of my career and your career with Larry Long Jr. and like the stuff we were doing at Pendo through some training pieces. 

01:31 
But now that you kind of evolved and you're starting up your own consulting group, tell us a little bit about what's the thing you like most about go-to-market and what like really likes your passion around go-to-market. 

01:43 
Yeah, my biggest passion around go-to-market is a lot of folks don't even know where to start in terms of go-to-market. And what you'll find is that once you start peeling back the onion, so to speak, they actually do have the tools in their toolkit to do it. 

01:59 
They just didn't know how. And so I love that, you know, expressing to folks, you had this all along, here's a time to leverage it. And here's how you, how you use this tool or here's how you use your voice or here's how you build your brand. 

02:13 
So for me, it's more educational. I love educating people on what they didn't even know they knew they could do. It's funny. Like I feel like, especially in the consultant world, right, and the leadership world, that's such a big part of our roles is that education piece. 

02:31 
And you said something that is near and dear to my heart is like something they didn't even know you could do. When you think you can't sell this way, or you can't achieve this goal, or you can't do this, and you have that aha moment, and we get to witness that. 

02:44 
It's so incredibly powerful. But you talked about people don't know where to start. And I'm gonna, this is normally one of our last questions we asked, but I'm gonna flip it and bring it up here. A lot of times we'll ask folks at the end of the show, like when building go to market. 

02:59 
where do you start? Is it sales? Is it marketing? Is it success? Is it any like, where do you start? And there's probably a little bit of variability. But like, from your mindset, you're going into a new company, let's just say they have a little bit of revenue, but they're broken, right? 

03:15 
As most companies are, sadly, where do you start? The first place I start always is listening to customer calls. So give me that gong access, give me that chorus access, give me whatever you're using to record your calls, give me that access so I can listen. 

03:31 
The worst thing you can do is start at a company and, you know, be told, okay, day two, you're on the phones doing cold calls, I see the I see how that can be effective. But I also am more of a storyteller when I want to cold call or cold email or you know, you know, warm outreach on LinkedIn. 

03:52 
If I don't understand what my customers, how my customers are being successful with this platform, or wherever you're working, you can't story tell. And so the first place I go, it's the customer calls. 

04:02 
And at this company, I'm at now, DG matrix, that's the first place I went, I was like, add me to every customer call, I need to understand how we're being leveraged. And then I need access to our recording. 

04:14 
So how can you make cold calls? If you don't know what to sell, like the value prop, what I've seen, the value prop that the founder or CEO typically gives you is normally at first, this long winded three paragraph, five minute sentence, that is a run on sentence versus I want to hear from the customers why they bought conversely, I want to hear why they didn't buy. 

04:38 
And I joke about this, and Dale makes fun of me for this, I literally have a post it in front of me on my computer, that is what's the number one problem your product solves for your prospects and customers in under 15 seconds. 

04:48 
Very few people can answer that. So I love that you start there. That's where I start. And one of my most successful trainings that I've done at multiple companies, I've done this that will least at five companies is once I onboard an SDR or AE or CXM, the list is long. 

05:09 
I have about 10 people that I'm really close friends with that have bought from me that have become friends. They started out as a prospect, then they became a friend, and I will bring them onto a Zoom, and I will have the team that I'm managing leading, send them a cold email in a Word doc or whatever Google sheet, I will send it to that prospect beforehand, and then the prospect will show up to the Zoom unannounced. 

05:42 
They don't know they're going to be there. The team doesn't know they're going to be there. And I will say, here's your prospect live in the flesh. And I will have that prospect rate their emails or rate their voicemails or rate their cold calls. 

05:56 
And they do it. They do it live. You know, at first the team is panicked. They're like, oh my, oh my gosh. Like I have a real prospect here. He's the CEO of, you know, XYZ company. I better not screw up. 

06:08 
And then they're like, okay, I can ask you questions. And that's been the best. Like I've done a lot of surveys on my enablement in the several years I've been doing it, and that has been my number one, most coveted training program is that exercise alone. 

06:22 
I love that. Yeah, super cool. And, but there's something inherent that you were like that process that you were just talking about started with delivering value for a customer, making sure that you enabled that relationship. 

06:37 
And now they feel to a place of, I want to help Lindsay. I want to help her team get better. Like, I think there's this fundamental challenge in the, the sales world that we all like you, you have to do a hundred calls or you have to do all these calls and, and less about like the quality of what you're trying to produce. 

06:57 
And I love what you were trying to do, like build the relationship, have that for a long period of time, because when we look to hire people, I always think of three things. Can you just grind? Like there's a lot of work that goes around selling all the things you were kind of talking about in the selling space and enablement, there's integrity, like, do you sell properly? 

07:18 
Like, can you sell what you have in your bag and can we deliver that value? And I think that's some challenge that we were just talking about before this in the tech space, like the products aren't delivering what we're selling. 

07:30 
And then the last part of it is like, are you coachable? And like, I love that like coachability and like the coaching part of it. So from the gone calls from bringing prospects on the, on the, I've never heard of that and I love it because like they have to realize like we're just people. 

07:46 
Like it's just a conversation, how you get to that person out of the conversation is completely different and you've done that by the relationships. Um, but since you've been an enablement, what's the. 

07:59 
biggest challenge that you see when you're starting to onboard people, because I think the reason why most sales people are failing or sales teams are failing is because they're never onboarded. Like kind of what you said, two days in, it's like, go do call calling. 

08:12 
And it's like, so what's like two or three things people can do to get prepared to onboard somebody? Yeah. Um, I have onboarded so many people and I can tell you what I see the most in the terms of why they fail is they're not studying. 

08:29 
They're not taking their own time out of their day to rehearse, to inform, to listen, to go to that Gong library. And the way I like to explain it to people that I onboard is look, you may have just spent XYZ amount of money on university. 

08:49 
You paid to get educated. I am paying you to learn now. So I had to flip the script on them a little bit and, and you know, kind of tone it to a point where I am paying you to learn this product, to learn this pitch, to learn this, uh, you know, methodology of sales. 

09:07 
Right. So once they grasp that and figure that out that, Hey, I have eight hours in my day to perform, I can take an hour or two and listen to gong calls. Cause that's what Lindsay wants me to do. So I learn, I can spot it the first week if they're going to be successful. 

09:27 
Take it one step further though. Like some of the best sellers I know have started off with the mindset of, and even continued with the mindset until they have a really good coach of like, I'm the best seller, right? 

09:41 
Like I don't need to train. Like look at Shaquille O'Neal, look at Steph Curry, look at Michael Jordan. What do they do all day, every day when they're not on the court, they train. So when you're not on the phone with a live customer, when you're not building that proposal, what should you be doing? 

09:56 
You should be learning and training and practicing to get better and better and better. I could not agree with you more, but no one does it. And I think that's why when you have folks like yourself who come in and can show them the benefits of why, and I love the mindset of like, I'm actually paying you to do this and get better. 

10:14 
Um, I think that's a really good way to word it. Um, really good takeaway. Lindsay, you you've done a lot of really cool things, right? Things that like transparently I'm envious of, like the Ted speaker, I think is awesome. 

10:26 
Uh, the Salesforce stuff, I Dale laughs at me, but I like accolades like that. Um, I think all that stuff is cool. What stands out to you? Like, what's the one you're proudest of? That's like, wow. Like, holy moly, I did this. 

10:41 
That's a great question. Um, my, my kids were asking me that a couple of nights ago at dinner and I'd have to say that it's twofold, the proudest. There there's two categories to this really. The first is I'm proudest when I get a text from a. 

10:57 
former person on my team, whether it be an SDR, AE, what have you, when I get a text years later, after I've worked with them, and the text is just like, Hey, Lindsay, it's Trent, I just want to let you know, I just got my first director role. 

11:10 
And I like, I'm getting chills right now, like thinking about that, because I just got a text like that last week. And, you know, just the, the pre how appreciative they are of me and and how, you know, they might have been in a cohort with nine other people, but I remember them, you know, I remember certain people, try to remember everybody, to be honest, but sometimes, you know, names get confused, 

11:34 
what have you, but that that is the single most thing that gets me up every morning for work. And then the second thing is going back to the shack thing, like I, I'm six foot one, I've never played basketball in my life. 

11:49 
I rehearsed on my driveway before I flew to Vegas, I through 20 free throws in, I got maybe one in and my husband was like, you know that Shaq can't throw free throws either. So you're going to be fine. 

12:06 
He's like, you don't have to get them in. And I was like, yeah, the plan is not to get them in. The plan was always for him to like dunk it when I missed. But then when I got on stage, somehow Lindsay Boggs, the basketball player appeared and I got both of them in under pressure. 

12:22 
So I worked very well under pressure and that was a single key moment where I was just like, dang, okay, I can get two free throws in what 2000 people are watching me. So that that's a separate thing. 

12:31 
But that's awesome. Those are my two proudest moments, I'd say. I love that. I when you talk about like those folks coming back to you, I think Dale and I talk about this a lot whenever we get those texts. 

12:44 
And I agree with you, there is nothing more rewarding than the out of the blue, like, hey, I got this. And I, I just remember something you did to help me get there. Yeah. Yeah, I think I get chills thinking about it, to be honest. 

12:59 
And I think as you transition into this new journey, Lindsay, with the consulting side of the world and what you're doing for a lot of these companies, like, you're going to be able to provide that like really strategic feedback to them, that sometimes you can't always say like when you're in the company, like, we get to this all the time in our in when we're in our clients, where you can almost have more transparency to the people because like, 

13:23 
they're, they're really trying to pay you to get to like, really where their problems are, versus like, you have to play politics and like a bunch of other stuff that happens internally. So I think that'll be really transformative for you. 

13:36 
Because I like those conversations later as well. Switching up a little bit. You know, when we first were doing some training at Pendo and talking about LinkedIn, and like, like, I remember, like, we were talking about like social selling, like, this was like some like, groundbreaking thing. 

13:54 
And Like people are still trying to go through this evolution of like social selling and, you know, having these conversations, what's the next place where people should really be focusing their time and energy? 

14:06 
Like you still got to do some stuff on LinkedIn and posts and all that stuff. But what are some other things that you're seeing in the market from an enablement perspective to help salespeople be better AI? 

14:17 
And I know that's probably not what everyone wants to hear on this call, but AI has been incredibly profound for the sellers that I coach thinking just about how long it used to take to go through a 10 K or go through an earnings call, have the tools that are out there are phenomenal to help you. 

14:38 
And it's not, I don't consider it a, it's not necessarily a shortcut. It's just leveraging your time better. So if I have a tool that allows me to give it to me in layman's terms, like why not leverage that? 

14:54 
That's the biggest thing I've seen in the shift and I worry a lot of companies transparently are cutting SDRs and replacing with AI. And my hypothesis is that you can't fake the human element. The human element has to be there. 

15:13 
People buy from people. And my hypothesis is in three years, they're all going to be hired back. They're going to have a new motion of SDRing. Because right now I'm just seeing SDRs get cut and have AEs do full cycle, prospect, clothes, all the things. 

15:32 
And I think they're really missing out on having that human element of that first touch. People buy from people. That's why companies who invest in meaningful connections win. The best part, gifting doesn't have to be expensive to drive results. 

15:47 
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16:01 
If you're looking for a proven way to win and retain more customers, visit Sandoso.com. Is there a place in the ARR space where you should have an SDR versus not have an SDR? What's too big or too small to have SDRs? 

16:21 
Is there a timing on the clothes? I always think in my head, if you're under 40k, there's some transactional nature in that that makes it almost very difficult to have a BDR. But I'm just curious your perspective on just getting my head as you were talking. 

16:36 
Yeah, I tend to agree with you, Dale, on that. I'd say I've worked at companies where we've had SDRs for SMB. And it just makes things go more smoothly because they're able to qualify and send it over to the AE and then to close it. 

16:54 
I'd say if you're like a really small startup, that will come later having an SDR, but I think for looking at career development as well, there's so many missed opportunities, having SDRs learn. And that's why I coach SDRs you've got to be continuously learning because when there's an opening for an AE or there's an opening for a CSM, or I've seen a lot of people go this way to account management lately from SDR when there's an opening, 

17:23 
I don't want your name to be read when they get to the interview. I want their name to be recognizable. You've already done the mentorship. You've already done the outreach to that hiring manager. You don't want to be, Oh, I don't know who this person is. 

17:38 
They work here. Oh, okay. You know, like you have to already be in the system. Yeah. And if you're executing at a high level at a SDR level, like, of course you're going to have that, like, I always thought that like you, if you have. 

17:52 
It's a bad analogy, but like the bullpen, and it's like, okay, like you have everybody, but you can see who is actually doing the work. First of all, like, how are you doing the work? How are you educating? 

18:02 
Are you coachable? Like you already have all that stuff. And by definition, they'll filter out the people that don't. For sure. The SDR role, historically, I've always said is one of the hardest roles, right? 

18:14 
And I think AI is going to change a lot for that role, but I think it's going to still have it be one of the hardest roles. Now, SDRs don't have to spend their time, if you're doing it right. SDRs should not be spending their time building lists, reading 10K reports to your point, Lindsay, like going to dig all this information. 

18:35 
It doesn't mean they don't need the information. They don't need to read it. Let the AI summarize it for you. So you could be properly prepared and not have to spend time researching. But you still are the person who has to be that first impression, get that person on the phone or to respond to that email and provide that value. 

18:51 
So they want the demo. I think it's going to increase the value of the SDR role from what it was, which was historically in a lot of people's mind, like, oh, you're the researcher and you just make cold calls to like, you are that first space. 

19:06 
And I think we're going to see SDR salaries increase and the value of that role become much more important than it was in the past. I'm curious, when you think about AI and RevOps and business development, where do you think go-to-market teams are going to go specifically with, are we going to see like heads of AI, heads of like go-to-market infrastructure that's different than RevOps? 

19:31 
Like, where do you see it going with the tech stack and how AI builds into that? Great question. The last company I was at, we actually had a dedicated person working solely on AI and they dotted line. 

19:44 
They were technically on my team. I led the SDRs and go-to-market commercial enablement and they were on my team. and they sort of dotted line to RevOps as well. So I'm seeing kind of a mixture of where they could land. 

19:59 
I see the value in having them on the enablement side because what they're learning in the GPTs they're enabling the teams on makes sense to have them in enablement, but there's also this element of RevOps. 

20:11 
How do we tie in what we're learning about these accounts to your CRM? So I see it in both avenues, to be frank. And I do see this AI pendulum, I'll call it. I do believe every market, every change is gonna be a pendulum. 

20:28 
And we're gonna swing way the other way. We hired a bunch of SDRs and we fire a bunch of SDRs. And the same thing on the sales side. I think a lot of people are like, well, we can just do more with less. 

20:39 
And I think we could do more with less if the people that are doing it are doing the learning, going through the process. So it's like, you still need to learn how to prompt engineer. like you still have to learn how to like utilize and use some of these tools once again going back to I keep going back to like as we were thinking about social selling it's not like we didn't know how to social sell we just got on LinkedIn like we're writing stuff and like putting stuff you were just testing and trying things and I think it's the same thing with AI right now now just like we were talking about in the practice the top one two five percent will be doing this work and they'll be completely fine and they'll make a ton of money and they'll be sought after all over the place from all the different companies the the the where we're going to lose people are the people that aren't going to do the work they're not going to learn they're not going to go through the education process they're not going to fail right because you're going to go through these failing processes so it brings me to my question on what because you're training so many people and you can like you said you can kind of spot them within like a day like are they going to be successful or not how do you help the people that you don't think are going to be successful but they have the drive to kind of go through that process like do you kind of guide them towards a different path in their journey yeah what i do is i put together a survey that i send out to every person in commercial all the aes all the strs etc and it's a skills gap analysis that i put together and it's with a google form super simple and i have them rate themselves on where they feel that they are on let's say objection handling as one scale of one to five how do you rank yourself if they rank themselves a four and their manager raised themselves as a two there's a gap so i take that i'm a big excel wizard i do the delta the conditional formatting and then i look at the bottom and i say okay uh vp of account management it looks like you have a big gap on your team on customer stories here's the you know playbook i made for customer stories when can we get them re-enabled right? 

22:50 
So then I also pair that person that's struggling with customer stories with a superstar that's excellent at that, that's been rated top by me, by them and their manager and partner them with like a buddy system to help them as well. 

23:05 
So I'm not thinking, oh, it's a lost cause. You're done. I'm thinking, okay, here's the gap. Here's the data to support the gap. Let's fix this however we can. And then if they're not willing to work and do it, then that's a separate conversation that you have probably with somebody outside of my department. 

23:25 
Sure. HR. Yeah. The willing to work. I mean, Dale, you said it early, it's being coachable, right? It's probably the number one skill set that I look for no matter what the role I've hired from BDRs all the way up to VPs of sales. 

23:38 
And like, no matter what it is, You need to be coachable Dale certainly doesn't hesitate to coach me daily. Um, so we, we, we all have to be willing to take although, although Lindsay has said, you have a couple of great questions, which usually doesn't happen to me. 

23:51 
So, I mean, let's give you a start occasionally. I show up and I actually add some value. If I start to do it too often, you're going to have this expectation that every meeting we're on, I'm going to add value instead of just sitting there and multitasking. 

24:04 
So let's be real back to coachability. One of the things I do in all of my interviews is I do a coaching section of my interview and what I do is they don't know that it's happening before the interview, but I have them pick their favorite TV show or movie. 

24:21 
And I asked them what streaming platform is it on? And they'll tell me it's on Hulu and I'll say, okay, great. And then I'll tell them I've never seen that show before. And I'll ask them to cold call me as Lindsay and tell me why I should watch the show Breaking Bad. 

24:37 
I've never seen it. And so what I'm looking for now, I'm not asking them to be, I don't want them to be perfect. What I'm asking for them to do is do this role play with me. Then after that, I will ask them, are you open to feedback? 

24:51 
If they say yes, that's a good sign. I know that's the last interview they have. Then after I give them the feedback, I say, okay, we're going to do this again, Adam. And we do it again. And if they've improved from the first time and they've taken what I, uh, you know, gave them for feedback and they've implemented it, I know that they're more coachable than somebody that doesn't now look, I've hired hundreds, 

25:15 
maybe thousands of people in my career. I have hired some bad seeds. I have, you know, I haven't gotten a hundred percent, right. I don't think anyone has it a hundred percent rate, but it does help me. 

25:25 
And there was even one person that was so irritated about this role play that they dismissed themselves from the interview. And I was like, okay, well that helped save me a lot of time. You know, that's crazy to me. 

25:38 
Cause as you're telling the story and like you saw reaction like we do a lot of role play right in interviews I love this because it's it's deeply personal to the person like we all have our shows that we're super passionate about you should be able to off the top it's much different than I hate to say sell me this pen but like sell me any product yeah you don't have to prep you don't need a deck um I'm totally going to steal this in full transparency I think it's absolutely great if someone has an issue with that I like I can't imagine how they feel about some of the other questions all of us would ask and the point of it is is I don't want them to inundate themselves like by overstudying on what our platform does because they're gonna they're gonna be confused they're not gonna know the ins and outs so just tell me they're gonna be nervous because I've never sold this I don't know this right right so I I would rather them sell me something that they know a lot about so or or your or you ask them to talk about their product and it's like you don't know their products then you go research that um I'll give a, 

26:40 
I'll give a quick tip on coaching is like coaching interview questions as well. Usually what I'll do is I'll, I'll give feedback after, after the interview, whether they like it or not, I give them feedback. 

26:51 
And if I progress them to the next stage, I will tell the next interviewer, I told them, I gave them this coaching piece. Make sure that you're testing on this coaching piece, because if they go to like, if I interview and they go to Adam, I'll say to Adam, Hey, I tested on make, make sure you test on this. 

27:08 
If they don't change their perspective on it, then they don't move forward. The coaching part is very hard to actually test on, but I like your, your perspective on it. Yeah. 100%. Was it on me, Dale? 

27:24 
Is it my turn? You've had all the good questions today. So yes, I have. Um, and sadly we are coming up on time, but what I would love is to play a little bit of rapid fire. Um, just throw some questions out here. 

27:38 
Here's the rules. You get 10 words or less to answer. Otherwise, if you go over, I get to Bob Dale next time I say, all right, 10, 10, so feel free to go over as much as you want. All right. Um, every, every time, um, first app you check when you wake up first app, I check when I wake up LinkedIn. 

27:57 
Yeah. Of course. Um, so this is a bit of a cheat because I know, but I know your husband works at Epic games besides Fortnite. What's your other favorite game from Epic, uh, from Epic or Lego Fortnite. 

28:11 
So I just saw that your husband works at Epic, um, specifically on Fortnite. Um, and as I was like, my kid happened to be next to me when I was scrolling, he's like, you know, someone who works on Fortnite huge Fortnite, I should probably mail you some swag. 

28:29 
Oh my. He would die. Um, huge fan. The amount of money I've spent on Fortnite is very sad. Um, early burner night out with Lindsay. I'm becoming more of an early bird becoming becoming. My daughter has to be at school at 6 45 in the morning. 

28:47 
So it's just like, that's just what I do now. I love it. Dale sends emails at 6 10 in the morning. I'm like, dude, I'm still rolling over in bed. It was funny. My daughter came in this morning and I was doing some emails. 

28:59 
She asked me the same question. She's like, how are you doing emails? Um, so if you weren't in tech, besides like sales, go to market tech. If I could go back and redo it, I'd be a journalist. Yeah. I love the next Diane Sawyer, but my, my time has come and gone. 

29:22 
I think what, um, what's your favorite guilty pleasure snack? Rice, crispy treats. Nice. My son makes me, we make those all the time. He's like, can we make race, Christmas, nature? I'm like, okay. Last one, let's wrap this one up. 

29:39 
Dream vacation destination. Maria Tahiti. Nice. Very nice. I love that. Very nice. Lindsay, thank you so much for coming and hanging with us, for sharing your words of wisdom, where obviously people can find you on LinkedIn. 

29:56 
It is LinkedIn, backslash in, backslash. Lindsay Boggs with an E. Look how easy. Awesome. Lindsay, thank you so much. We appreciate it. Thank you. Thank you. Thanks so much for listening. We hope you enjoyed the conversation as much as we did. 

30:09 
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30:25 
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