The Sales Technology & Skills You’ll Need in 2025 for Digitally Enabled Enterprise Sales

The Sales Technology & Skills You’ll Need in 2025 – Digitally Enabled Enterprise Sales

Sales has always been about engaging with customers, but sales technology tools and the way that we connect with people has changed drastically. Robert Beattie discusses the future of enterprise sales, the skills you’ll need in 2025, the keys sales technology adoption and where sales and marketing can intersect at account based engagement. Listen in to learn more.

Justin Michael Welcome back to Quantum Leap on Vendor Neutral in the Neutral Zone; I’m Justin Michael, your intrepid host doing my best William Shatner impression. Today we have Rob Beatty, who is a sales leader and has had a wide array of experience in sales across many verticals and technologies. I’m glad you’re here on the show. How’s life in Ground Zero?

Robert Beattie Yea. No, Hi Justin, thanks for the opportunity to join you. I really appreciate it. It’s been an interesting, what are we up to now? Seven months? nine months? It doesn’t even; it’s hard to even say. You know, we constantly refer to it as it’s Blur’s day. Like, they just blend together, and you sort of show up, do what you need to do, and find ways to stay motivated and just keep fighting.

Justin Michael Yeah, I feel you. People are saying sales has changed. I think the human brain is the same since I checked. But it definitely is pretty weird with so many businesses going out of business. And then there’s other pockets that are just up into the right hockey stick. So, yeah. Yeah.

Robert Beattie Well, I think I think a big piece of it is the sales. Sales itself, the connecting with humans, and why people would change. I think that hasn’t really evolved. But the tools and the ways that we connect with people. I think that has changed drastically.

Justin Michael Talk to me about that, because we’re talking about the future of enterprise sales, what are the similarities, what are the differences? And how can leaders today adapt? Not just because of the current crisis because that will pass, I’m hopeful, but going into this kind of A.I. and M.L. fueled? Yeah, it’s running wild culture. I’m really curious because you’ve had a lot of experience in this area.

Robert Beattie Yeah. So there’s a couple of things, really. I think, one, I think there’s a lot of good lessons to take away from the last couple of months if you’re a more traditional face to face selling outfit, you lost that opportunity. You can’t do that anymore. So how are you engaging with people? And, you know, as you and I join each other on a virtual call, the Zoom call, Teams call Google Meet, whatever it might be. Those meetings have now become very intentional. So when you go to talk to somebody, you’re looking for time on a calendar, your traditional hour to hour and a half demo, sit down in in-person stuff, that’s a thing of the past. You’ve got to figure out ways that you can engage people, engage them virtually, keep them engaged, and provide real value to their business Something I think people always had to do, but you get fewer at bats now to actually do it. So you’ve got to hone your craft. You’ve got to be better. I think that’s a big change. I have often referred to it as maximizing talent within your sales organization as well, which is if you are going to have fewer at bats, if you are going to have fewer sales opportunities, you want to make sure that your best possible team is involved in that. And so I know a lot of companies have been rethinking how and reimagining how they go to market, whether it’s if they’ve never been territory based, starting to go towards that or, you know, going after specific competitors or certain verticals. And so I think that’s an interesting, this is an interesting time, I think, for companies to step back, look at that and say, OK, are we doing this thing where when an opportunity comes in or A.I. or Machine Learning or something, serves something up? Are we engaging that with the best possible resources for that, or are we just doing it the way we’ve always done it? And so there’s a true opportunity during this for people to rethink and reevaluate some of the aspects of that process.

Justin Michael And it’s also interesting, technologies to record people and listen to recordings, I don’t think that was used enough when we could all work together and see each other. This is a bit of a renaissance of listening to remotely train and coach and then what you glean out of listening and then the sales technologies that can parse that and serve insights. I guess I would ask you, what technology are you excited about? What feels like smoke and mirrors? Yeah. What do you see in the industry?

Robert Beattie Yeah. So, I mean, there’s a lot going on with bots. And it was funny; I was having a conversation with somebody today about email and prospecting and sort of the top of the funnel activities that email brings. And I’m beginning to see a distinct difference between the email that has been filled with a bunch of stuff and then given to a bot to fire off and the stuff that a human being has crafted. And now, my eye is drawn far more to the stuff that a human being has done because I don’t have time to read that stuff. And I’m also often reading it from my phone. Right? So if you’re serving me up, you know, seven pages of content and expecting me to draw some conclusion from that, that’s not going to happen. So I think that’s a piece that I think people need to look at. I think from technology that enables more human interaction, I think is going to be very important. Like how do you speed up the number of phone conversations you can have? I think people need to be examining that because, you know, you’re capturing people in a different way than you ever did before. You know, there’s been an awful lot of virtual conferences done this year. There’s been a big switch over to that. Obviously, we had to. But one of the things that people have been telling me is that we lost trade shows like trade shows aren’t a thing anymore. We used to get all our leads from trade shows and thinking, OK, well, what do you do to solve that issue? But at the same time, when people are at virtual conferences when I’m done, I’ve attended a few. When I’m done with the session, I get up, and I go talk to my kids, or I go get a drink of water. I’m not trapped at that conference. And so really figuring out ways to get people’s attention, any technology that can interrupt that pattern I think is important. I think there could be some exciting things coming with text. Somebody who I respect is a thought leader today was tweeting about leaving voice notes for people. And I think there’s ways that you can bring that sort of consumer and friend interaction to the sales process in a new and exciting ways.

Justin Michael I think that’s really true. Sometimes I say what’s old has become new because we used dialer technologies, you contact more, and if you use email automation to personalize it well, you could potentially generate higher volumes of meetings. And then, if you’re meeting face to face or remotely over Zoom, you have to be very strategic. You can’t really lean on you met him at an event, or they just kind of like you. So the deal closes. You have to be really good at active listening over a phone. There’s limitations that bring out the needs to close the gap. So chats, that’s a really cool thing. How are you noticing, like, gaps in new generations of sellers? What should they be looking at and studying to bolster those skills?

Robert Beattie Yeah, you know, back to your everything old is new again. I actually think there’s several of sort of the old schools of thought sales that they should be engaging with. You know, the things that people, there’s a couple of books that I grew up on. “Spin Selling” really like the “Challenger Sale”, “Objections” by Jeb Blunt, like really getting back into psychiatry and how the human mind works and that concept of a pattern interruption. Right? Like human beings love their status quo, and the pandemic reinforces that. Like I said earlier, you call it Blur’s day. Every day seems the same. Everything’s the same; well, there’s opportunity in there to gather and garner somebody’s attention in a new way with a new insight. That’s the type of thing that I think new sellers and people in the sales game who are looking for a refresh should really be thinking about, you know, you used to ask people for an hour of their time or, you know, can I get 15 minutes, well chunk that down to eight. Right? Can you say or do something tactically that gets somebody’s attention that just feels different. Like just sounds different. Right? And so a lot of that has to do with sort of psychiatry. There’s thousands of books about this, obviously. But I, I find that the way to, just how do I stand out from the crowd knowing that I can’t go stand in front of somebody? A big piece of that is garnering attention with something useful to somebody. I’ve lost. I’ve lost the ability to be funny, therefore be likable because I don’t have time. People don’t have time for that anymore. So now I’ve got to bring something of more value to the table.

Justin Michael Yes. That talks about this whole personalization thing, relevance, and timing. I feel like reps are doing a lot of research, maybe ten K’s, ten Qs. Looking at LinkedIn, they’re learning some of the ways to research. They’re putting these into these email blasts, but they might not talk to customers. They’re not talking live with prospects on the phone, over Zoom, and they’re just doing research and program emails. Is that demand gen? Is that marketing? Is that still modern sales? I sometimes wonder.

Robert Beattie Yeah, no, I’m with you completely. And it’s. And how much? How much time and effort is just to create nothing, right? Like I, I said it to a rep of mine; they shared an email with me at a prior job. And they’re like, hey, what do you think of this thing? I said, this is far too long, and there’s nothing in here that that tells anybody anything of value and isn’t going to get them triggered to want to talk to you. This just looks like a thousand other emails that they get.

Justin Michael Yeah, I think I’m a big proponent of that. How about the role of sales and marketing and I’d love to hear more about your background if you could just share maybe a quick overview because I know your sales leader, but kind of how you got to this, the ability to lead these teams and how you’re marketing, how you’ve seen [00:10:11]marketing [0.0s] because I have some marketing has gotten more involved in sales. I’m not sure sales has gotten more involved in marketing. If you can bring the two closer together for these account-based marketing approaches, it’s really effective. How does your background influence that, and what tips do you have for sales leaders trying to get along?

Robert Beattie It’s great, Justin. So I’ve been in sales. It’s funny. I tell people I have a degree in sales from the 90s, which is History. Right? So I got my degree at a liberal arts school. So a lot of people today kind of come up with business degrees, sales degrees. Mine was completely irrelevant to the business that we have, and so but at the time, sales was viewed as a very different occupation than it is today. It wasn’t very, you had people who were sellers, but I don’t know if it was really thought of as a profession; it was sort of this thing that people did. And I don’t really trust them and used car sales guy or whatever. And so my first job was selling computer training. It was during the transition. My first sales job was during the time where people were transitioning from DOS-based systems to Windows-based systems. And it was very intriguing because, within the first couple of weeks of my employment, there was a big conversation going on. Is email a tool we should equip our sellers with? Right? Not, literally, not everybody had it. And so people were thinking, is this something we can communicate with? Is this going to be part of the process? And it wasn’t that it was seen as it was going to get rid of, you know, the voice conversation. But people were having a hard time seeing how it could lead to a voice conversation. And so that was sort of my beginning and got into some leadership roles as a smaller company at the time, which was a great opportunity for me and eventually found my way to Thompson Reuters, where I worked for 15 years up until honestly a month ago, and so was a lot of different leadership roles. Started as a Sales Manager, worked my way up to a Director, eventually became the Vice President of Sales for a group that was selling software, research, and different things to accounting firms. I left there a month ago to take a new opportunity, which I’m super excited about for a company called Modernizing Medicine. Switching Industries. After 15 years, I was kind of ready to do something different: really, really hard choice to go, but a tremendous opportunity. But a big piece of what I’m trying to accomplish is that sales and marketing alignment now. And so, you know, in as far as companies go into, this is what I would say, marketing and sales fill different roles depending on where you are in your product lifecycle. Right? If you’re in a market where everybody knows your name, and you’re really just sort of fighting against the competition and everybody sort of, you know, more or less on par, the role of marketing is somewhat brand awareness. It’s somewhat keep things warm, but it’s run thought leadership events and try to equip your salespeople with as much information as they can to engage those particular clients. If you’re going someplace new, the role of marketing as I see it as to sort of clear the path, right? Like, hey, look, we have the stuff out there. It’s kind of that drip campaign activity, but not a traditional marketing way. Right. You got to do it in small bites because what you’re trying to do is get that buyer to react to the one thing that they’re thinking about at that time, which is, doesn’t happen when I send somebody a big book of things, I hit them with the one thing, nope not today that they, oh, you know what? This is the thing I’m thinking about right now. And so sales and marketing, that relationship, especially with automation, and you mentioned account-based marketing. Account-based marketing is really account-based engagement. And so when I think of the sales process, marketing and sales are trying to get a prospect to engage with your company. Right? That’s what you’re trying to do. That account-based engagement, if it’s somewhat done by persona, by marketing, at some point, a human salesperson has to get involved, but be part of that sort of as they go and in a lot of companies I have seen marketing is doing their thing, sales is doing their thing, and they’re not aligned. I think that tight integration of, OK, what are you doing? What’s hitting the marketplace that we can call on? What’s coming up that we need to be aware of? That’s the stuff that really has to happen between. The territory planning of old, used to be a sales rep, figures it out, says, OK, I’m going to go after this and do these things. Nowadays, I think it’s really account based strategy that marketing and sales do together.

Justin Michael That’s super eloquent, and I can appreciate that and even these terms like account-based sales, and then I talk to senior sales leaders who are very experienced like yourself, and they say, well, just having named accounts has been around for 20 years. It’s the same thing. Lipstick on a pig. It’s the same thing if you’re spraying and praying versus having a really tight ICP. I think we’ve just grown up and had a lot of definitions around this stuff, but I think great sales was occurring in similar ways. That’s why I love talking to veterans of the industry. How does someone who is new in their career develop acumen? How did how do leaders help on that? I guess the big thing is we’re talking about enterprise transformation and digital. And it’s almost you can’t train the troops on the technology of the future. It’s like, what are ways to help people upskill and be ready for all the incoming?

Robert Beattie Yeah, that’s a, I mean, I think. I think so; I’ll step back to twenty thirteen. One of the things to your point about getting people ready for that, because that’s an I think a big piece of it, right? You’ve got to; I think what leaders have to do within their troops is inspire curiosity. You’ve got to kind of give them a reason to be thinking, give them a reason to engage as well. I mentioned it earlier. Human beings like the status quo. And you see that with sales reps a lot, where if I come out, give them a new tool. They may try it for a little bit, as long as I make them, but eventually, they’re going to sort of float back to the way they’ve always done it if that new tool doesn’t do something for them immediately where they can see results. The role of the leader in those cases, I think, is to is, again, sort of prep the field for them to be excited about something new. So that’s my thing, about twenty thirteen, in twenty thirteen I took a look around and said, what’s selling going to look like in twenty twenty? Well, at the time, social networks were new, sales,  sales tech was kind of a new thing. There was there’s a few other aspects of that; video was something that was just brand new that people were starting to think about. And so what I did for my team at that time is I created this vision of the twenty twenty sales rep, and I would talk about it all the time, and we would build our training around it. And there were five pillars of the twenty twenty sales rep, which was you had to be able to leverage new tools, you had to be more of an expert in your industry than ever before because you got to provide those insights, you’ve got to be willing to have a challenger type conversation with somebody. So, you know, there’s all these things that we were saying. These are the things that you have to have to be ready for twenty twenty. And so for seven years, we would talk about, the funny thing was you really needed them in twenty thirteen, right? And so social selling was one of them. And so that became a thing. Starting now, looking out to twenty twenty five, I started thinking about the same thing and again sort of prepping them to be ready for it. And I think there’s a couple of things that’ll be important. I think you’re going to have to be somewhat of a data analyst, right? You’re going to have to be able to bring data in, look at it and have that affect your decisions about where do I go spend my time? Again, back to my earlier point about it is hard to get somebody’s attention, but if I’ve got something that’s telling me this person’s ready to have a conversation with me, I’ve got to be ready to go get them, and the data is the stuff that tells me that. You’re probably going to be in more of a team selling environment. Right? Most organizations now are specializing by task. You have BDRs, SDRs; you have sales reps, you have customer success. Right? There’s different handoffs that occur throughout that process. And so you’ve got to become more adept as an organization about facilitating those handoffs throughout the process and ensuring that the team works together. You’re going to be able to do; you’re going to have to do personalization at scale. I have to be smart enough to know that an email that might work for you won’t work for me. So how do I personalize that to get Justin’s attention, and then how do I personalize that same message? And again, it’s got to be the general same message. I can’t do everything completely new, but I want that scalability of personalization. So as a sales rep, I got to be able to do that. Those are the types of skills that I think people are going to have to have. So what are you doing as a leader today to get them thinking about it? You’re looking at your organization to do that. You know, I always talk about you mentioned it earlier, digital sales. Most big status quo disruptions right now for a customer still require a human being to have that interaction. It’s not something that many will do completely digital. So you’ve got the era right now of digitally assisted. Eventually, we may get to more of that digitally enabled. But, you know, chatbots and A.I. bots two years ago were hard to tell which was human and which was not. Now, if you’ve been around them a lot, it’s pretty obvious. And so, you know, again, you’ve got to be aware of what is the technology that looks really cool today? How is that going to evolve, and what’s going to circle back? So what was cool two years ago, will that be cool again in seven years? Maybe. Is that something to keep track of, too? So to your early-stage career question, as a leader, I think I need to be getting them ready, cueing them up, having them curious, getting them thinking, as that person, you’ve got to kind of go look at a little bit of history. Right? Learn more about sales history. Go read some sales books from two or three years ago. You will gain insight that will help you today, but it will also give you sort of a little bit more of a foundation on how we got here because those who do not learn from history are doomed to repeat it. Right? And history ends up repeating itself. So let’s make sure that we’re paying attention to that as well.

Justin Michael I love it. I learned a lot listening right there; part of Vendor Neutral is figuring out how to buy sales technology stuff. So you’ve been the recipient of endless pitching, and you’ve had the wherewithal to buy tech stacks. And so the fascination is like, how do you do it? How do you wrangle these vendors? There’s going to be five thousand of them; there’s five hundred. Do you bake them off? Do You? Is it ROI? Is it pilots? For folks in your situation trying to make heads or tails of this, maybe buy chatbots or something? How how did you manage that and not be overrun by demo calls and stay within budget?

Robert Beattie Yeah, no, I think I think the important thing is you got to settle on two or three things that you think are key to your process. Two or three things that your sales reps can use and will make a difference. I mean, I’ve bought [00:22:14]sales technology [0.2s] and rolled it out poorly and seen it be awful. And I have bought tech and rolled it out well and seen it be great. And the way that it’s great typically is there is a pilot, there is some form of small group of users that we can tightly control what they do so that we can see in our business is, is it going to make is it going to be a difference maker? Right? There’s, you have to forgive me. I can’t remember if it’s Bill Gates or Steve Jobs, but one of them said when you apply technology to a poor process, you amplify the poor. When you apply technology to a good process, you amplify the good, and you’ve got to make sure that your process is solid, that you have an understanding of how you are doing things so that when you do pick a technology, make sense to your business and it amplifies the good aspects of your business and not just becomes a throwaway for your sales reps. And so pilots help do that because it gives you a chance to experiment. It gives you a chance to check it out and to see, but it also builds; when I’ve rolled it out well, and I’ve had just one or two people using it, you get that jealous impact of other sales reps going, hey, what’s that guy got? You know, hey, how come Holly over here is doing so much better than me? What’s that tool? And so they start to get you know, they get a little FOMO, fear of missing out. And so when the time comes to now deploy the tool, they’re like, oh, yeah, this is the tool that Holly had. I want to make sure I’m on board. When Rob comes out and says, here’s a tool you all need to use, then it becomes management just wants me to do this thing, right? So it’s real different about how that roll up is. That’s the key, right. That’s the key to adoption. And so if you’re a vendor trying to get people to look at their tech stack, give them best practices in adoption, help them see how it can work and what it good should look like. Because if you just are, hey, here’s a bunch of stuff, and let’s see how it works. You know, that’s that people are going to fail, and they’re going to become frustrated, and you’re not going to get the renewal, and you’re in trouble.

Justin Michael Such great advice; how do you, last question, pinpoint great sales talent? There’s good assessment; there’s backchanneling, there’s talk to their former manager, former colleagues. There’s leg work you can do. There’s your gut instinct. You’ve hired a lot of salespeople, but is there a strategy to use interview questions, situation based? But what’s your personal take on this? It’s a hard one to get, especially when it is you can’t meet them in person.

Robert Beattie Yeah, I know it’s tough, but I think it’s really tough. I think hiring right now is as risky as it’s ever been. You know, like I said, I recently switch jobs. I haven’t been to the office of the company I work for yet. Right? Like, it’s weird. It’s a different time. But for me, part of it is experience. Right? You just you got to kind of go through it. You know, sometimes people will tell you I just know good talent when I, I can smell it, I can see it. And I’m always like, yeah, but I will tell you, one of the most influential books that I read is by Pat Lencioni, Patrick Lencioni. It’s called “The Ideal Team Player.” I actually believe very strongly that sales is more of a team sport than a lot of people think it is, and I already mentioned it that it’s evolving, even more that way. And so you want to look for people that fit certain characteristics, and the characteristics he talks about are humble, hungry, and smart. Right? And when you think about it, that’s exactly what I want. I want somebody on my team who’s humble enough to know that they don’t know everything, smart enough to go and learn it, and hungry enough to get it done. So there’s sort of a, I look for proven curiosity. I like people that are are constantly learning that are looking for new things because really that’s what I’m doing when I’m engaging with the prospect is I’m trying to learn about their business. I’m trying to bring a curiosity mindset. If I’m the type of person who’s like big ego, I know what’s best for you. They’re not going to be tremendous salespeople over time because they won’t let people go help people along through that process. Right? Like they truly, people talk about a buyer’s journey. It’s a buyer’s journey. It’s not a sales process. It’s a buyer’s journey. I’ve got to facilitate that journey. I got to get them thinking and curious and trying something new. And so, if I can bring that mindset to the process as well, I think that’s a big piece of it. So, you know, like I said, humble, hungry, and smart. Always be curious. Those are traits that as much as I can find in people, I look for.

Justin Michael Well, this has been a great half hour; it’s flown by. Where can people find you? It’s Rob Beattie B E A T T I E. Find him on Linkedin, and uh yeah. Would love to stay in touch on your career journey and make sure people listening are networking with you and interfacing with you. I hope you don’t mind them reaching out to write a personal request, please. Yeah, exactly. Yeah.

Robert Beattie Just tell me where you heard me. Right. Say on the Quantum Leap, it would be great, but yeah. Hit me up on LinkedIn.

Justin Michael Thank you so much for being on the show today, Rob. And we’ll see in cyberspace.

Robert Beattie Sounds good, Justin. Thank you.

To get started building your optimum sales technology stack, try our Sales Technology Selector. We’ll provide you with a customized report identifying the sales technology solutions that meet your needs. Already know the category of sales technology you need? Use our Certified Sales Technology profiles to find all the details you need to make a decision about which solution is the best sales technology for your organization.

Interested in hearing more Quantum Leap Podcast Episodes?