Will AI Actually Take Over Sales Jobs?

Lindsay Boggs, VP of Global Business Development at DG Matrix, shares her expertise on building a strong go-to-market foundation, starting with the most overlooked step: listening to customer calls. She emphasizes that understanding the customer's actual success and challenges is absolutely critical before any outreach begins, and she trains her teams to master these stories before they ever pick up the phone. The conversation shifts to the impact of AI on the SDR role. While many companies are cutting SDRs to rely entirely on automation, Boggs predicts a massive swing back to human-led outreach, recognizing that 'people buy from people.' She advocates for using AI as a leverage tool to summarize 10Ks and earnings calls, freeing up SDRs to focus on meaningful human connection rather than getting replaced by bots. Boggs also details her elite frameworks for onboarding and hiring. She shares unconventional enablement tactics, including conducting live, unannounced prospect reviews of cold emails, and utilizing an ingenious 'TV show pitch' role-play in interviews to test a candidate's coachability. Her approach proves that investing in targeted education and rigorous coaching is the true differentiator in modern B2B sales.

Discussed in this episode

Starting a go-to-market strategy by demanding access to Gong or Chorus to understand exactly how customers use the product.
Bringing friendly former prospects into live Zoom sessions to grade new reps' cold emails and calls.
Reframing onboarding by telling new hires they are literally being paid to study and learn the product.
Using AI to read 10K reports and earnings calls to save SDRs hours of manual research time.
The impending pendulum swing where companies that fired SDRs for AI will be forced to hire them back.
Conducting a skills gap analysis by comparing a rep's self-rating against their manager's rating to identify targeted coaching needs.
Using an interview role-play where candidates must cold-call and pitch their favorite TV show to test their communication skills.
Evaluating a candidate's true coachability by offering feedback on their TV show pitch and making them do it again immediately.

Episode highlights

0:00 — Will AI take over sales jobs?
1:30 — Where to start with Go-To-Market strategy
4:15 — The live prospect grading exercise
7:00 — Why most sales onboarding fails
9:45 — Proudest moments in sales leadership
12:30 — How AI is changing business development
15:00 — The future value of the SDR role
18:20 — Bridging the skills gap with data
21:10 — Testing coachability with TV show pitches
24:30 — Rapid fire questions

Key takeaways

Start go-to-market strategy by listening to customer calls.
Treat onboarding as paid study time to master the product.
Use AI for research, not for replacing the human element.
Identify coaching gaps comparing rep and manager skill ratings.
Test interview coachability by role-playing a TV show pitch.

Transcript

And my hypothesis is that you can't you can't fake the human element. The human element has to be there. 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. 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.

And a 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.

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

Um, through some training pieces, but now that you've kind of evolved and you're, you're starting up your own consulting group, um, 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? Yeah, my, 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. They just don't know how. And so I love, 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.

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 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 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, it's so incredibly powerful. But you talked about, um, people don't know where to start and I'm going to, this is normally one of our last questions we ask but I'm going to flip it and bring it up here. Um, a lot of times we'll ask folks at the end of the show like, when building go to market, 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 they have a little bit of revenue but they're they're broken, right?

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.

The worst thing you can do is start at a company and, you know, be told, okay, day two, you're on the 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. 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 is the customer calls 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. So. How 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, uh, 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. Um, 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. Mm.

Very few people can answer that. So I 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 at least at five companies, is once I onboard an SDR or AE or CXM, you list, you know, the list is long.

I have a about 10 people that are really, 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 the prospect beforehand, and then the prospect will show up to the Zoom unannounced.

They don't know they're going to be there. The 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.

And they do it they do it live and it 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, X, Y, Z company. I better not screw up. 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. I could 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, 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 100 calls or you have to do all these calls and and less about like the quality of what you're trying to produce. 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? Like, can you sell what you have in your bag and can we deliver that value? And I 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.

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 gong calls, from bringing prospects on the on the I've never heard of it and I love it because, like, they have to realize, like, we're just people, like it's just a conversation. How you get to that person on the conversation is completely different and you've done that by their relationships.

Um, but since you've been in enablement, what's the biggest challenge that you see when you're starting to onboard people? Because I 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 cold calling. It's like, so what's like two or three things people can do to get prepared to onboard somebody?

Yeah, um, I've 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. 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 X, Y, Z amount of money on university. 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, 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 because 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. Take 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? 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? You should be learning and training and practicing to get better and better and better.

I 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. 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.

Uh, the the Salesforce stuff, I Dale laughs at me, but I 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. That's a great question.

Uh, my my kids were asking me that a couple nights ago at dinner and I'd have to say it's twofold. The proudest, there's there's two categories to this really. The first is, I'm proudest when I get a text from a 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. 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, um, 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, um, try to remember everybody to be honest, but sometimes, you know, names get confused, what have you. But that that is the single most thing that gets me up every morning, um, for work.

Um, and then the second thing is going back to the Shaq thing. Like I I'm six foot one. I've never played basketball in my life. I rehearsed on my driveway before I flew to Vegas.

I threw 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 gonna be fine.

He's like, you don't 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.

So I work 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. Watch 2,000 people are watching me. So that that's a separate thing, but um, That's awesome.

Those are my two proudest moments, I'd say. I love that. I 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.

Um, and I agree with you. There is nothing more rewarding than the out of the blue, like, hey, I got this and I I I just remember something you did to help me get there. Um, yeah, I I get chills thinking about it, to be honest. 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 working with our clients, where you can almost have more transparency to the people because like 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.

Um, so I think that'll be really, um, transformative for you because I I like those conversations later as well. Um, switching up a little bit, um, 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 ground breaking thing 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? Like you still get to do some stuff on LinkedIn and post and all that stuff.

But what are some other things that you're seeing in the market from an enablement perspective to help sales people be better? AI, 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. Um, thinking just about how long it used to take to go through a 10K or go through an earnings call. Have the tools that are out there are phenomenal to help you, and it's not, I don't consider it a it's not necessarily a shortcut, it's just leveraging your time better.

Yeah. So if I have a tool that allows me to give it to me in layman's terms, like why not leverage that. So. Exactly.

Um, that's the biggest thing I've seen in the shift and and I worry, a lot of companies, transparently are cutting SDRs and replacing with AI. And my hypothesis is that you can't you can't fake the human element. The human element has to be there. 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. Um, because right now I'm just seeing SDRs get cut and, you know, have AEs do full cycle, prospect, you know, close, all the things. Um, and I think they're really missing out and having that human element of that first touch.

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Like what's too big or too like what's too small to like have SDRs or is it a timing on the close? Like I always think in my head, if you're under like 40K, like 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 it. Just kidding in my head as you were talking. Yeah, I I I tend to agree with you, Dale, on that.

I'd say, you know, I've worked at companies where we've had SDRs for SMB, um, 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. 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 because you 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, 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.

They work here? Oh. Oh, okay. You know, like, you have to already be in the system.

Yeah. And if you're executing at a high level at an SDR level, like, of course you're going to have that. Like, I always thought that. Like, you if you have it's a bad analogy, but like the bullpen and it's like, okay, you like you have everybody, but you can see who is actually doing the work, first of all, like, how are you doing the work?

Are you how are you educating? Are you coachable? Like you already have all that stuff. Um, and by definition, they'll filter out the people that don't.

So. For sure. The SDR role historically, I've always said is one of the hardest roles, right? 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. 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, um, and provide that value 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. Um, to like, you are that first face and I think you're we're going to see SDR salaries increase, um, and the value of that role will 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?

Like where do you see it going with the tech stack and how AI drones into that? Great question. The last company I was at, we actually had a dedicated person working solely on AI. And they dotted line, they they were technically on my team.

Um, I led the SDRs and go to market commercial enablement. And uh they were on my team and they sort of dotted line to RevOps as well. So I'm seeing kind of a a mixture of where they could land. I I see the value in having them on the enablement side because what they're learning and the GPTs they're enabling the teams on makes sense to have them in enablement, but there's also this element of RevOps, 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 and I do see this AI pendulum, I'll call it. I I do believe every market, every change is going to be a pendulum and we're going to swing way the other way. Like we hired a bunch of SDRs, then we fired a bunch of SDRs.

And the same thing on the sales side. Like I think a lot of people are like, well, we could just do more with less. And I think we could do more with less if the people that are doing it are doing the like doing the learning, going through the process. 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 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 and like we're writing stuff and like putting stuff. Like 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, 5% 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. Um, 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 SDRs, et cetera. And it's a skills gap analysis that I put together. And it's with a Google form.

Super simple. And I have them rank 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 rates 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? 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 by me, by them and their manager, and partner them with like a buddy system to help them as well.

So, I'm not thinking, oh, it's a lost cause, you're 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 and 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.

Right. Sure. HR. Yeah.

the the willing to work. I mean, Dale, you said it early, it's it's being coachable, right? It's probably the number one skill set that I I look for no matter what the role. I've hired from BDRs all the way up to VPs of sales 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 all have to be willing to take that. Although although Lindsay has said you have a couple great questions, which usually it doesn't happen, Dean, so I mean, listen, he 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.

So let's let's be real with one another. 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. And I ask 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. I've never seen it. And so what I'm looking for now, I'm not asking 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? If they say yes, that's a good sign. If they say no, that's the last interview they have. That's the last interview.

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, 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, maybe thousands of people in my career.

I have hired some bad seeds. I have, you know, I haven't gotten it 100% right. I don't think anyone has it 100% right. But it does help me 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 because as you're telling the story and like you saw my 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.

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'd feel about some of the other questions all of us would ask in an interview. No. 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 going to they're going to be confused. They're they're not going to know the ins and outs.

So just tell me something And they're going to be nervous because I 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 you're or you ask them to talk about their product and it's like, you don't know their product. So then you go research that.

Um I'll give a I'll give a quick tip on coaching as 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. 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 sure you test on this.

And if they don't change their perspective on it, then they don't move forward. Uh the coaching part is very hard to actually um test on, but I I like your your perspective on it. Yeah, 100%. Was it on me, Dale?

Is it my turn? You've had all the good questions today, so yes. I have. Um, and sadly we 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. Here here's the rules. You got 10 words or less to answer.

Otherwise, if you go over, I get to bop Dale next time I see him. All right, 10 10. So feel free to go over as much as you want. All right.

Okay. That's good. Just every every time. Okay.

Um, first app you check when you wake up? First app I check when I wake up. LinkedIn. 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. Lego.

So I just saw that your husband works at Epic. Um, specifically on Fortnite. Um, and as I was scrolling my kid happened to be next to me when I was scrolling he's like, you know someone who works on Fortnite. He's a huge Fortnite fan.

Like, yeah, I do. Like, yes. Well, it's always like, I should probably mail you some swag. Oh, my goodness.

Yes, he would die. Um, huge fan. The amount of money I've spent on Fortnite. It's very sad.

Um, early bird or night owl, Lindsay? I'm becoming more of an early bird. Becoming. Becoming.

My daughter has to be at school at 6:45 in the morning. 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, like I'm still rolling over in bed. It was funny, my daughter came in this morning and I was doing some emails. She asked me the same question. She's like, how are you doing emails?

Um, so if you weren't in tech, Lindsay, like or you weren't even in in sales, like, what trade would you do besides like sales, go to market, tech? If I could go back and redo it, I'd be a journalist. Yeah, nice. I love it.

Totally makes sense. I want to be the next Diane Sawyer. But my my time has come and gone, 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 a rice crispy treat?

I'm like, okay. So. Last one, let's wrap this one up. Uh, dream vacation destination.

Nice. Oh, 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 uh, obviously people can find you on LinkedIn. Um, it is LinkedIn back in back slash Lindsay Boggs with an E. Look look how easy.

Awesome. Lindsay, thank you so much. We appreciate it. Thank you.

Bye-bye. Thank you.