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Welcome to the inaugural episode of the SaleSage Podcast! In this episode, host Brooks Canavesi sits down with Dr. Shannon Gregg, a renowned expert in sales technology and CRM adoption, to explore how AI and automation are reshaping the sales landscape. Shannon shares her journey from an unconventional start in English literature to becoming an influential figure in sales enablement and technology adoption. Together, Brooks and Shannon dive into the challenges sales professionals face with CRM systems, the role of AI in boosting sales effectiveness, and practical insights on building resilient, adaptable sales teams in today’s tech-driven world. Whether you're a sales leader, tech enthusiast, or simply looking to give your team a competitive edge, this episode offers actionable advice and an inspiring look at the future of sales.
Show Notes
0:00 – Introduction to the SaleSage Podcast
Brooks Canavesi welcomes listeners to the podcast and introduces the show’s mission: providing AI insights, sales strategies, and tech-driven solutions for sales professionals.
3:12 – Meet Dr. Shannon Gregg
Shannon discusses her unique journey from studying English literature to her PhD in community engagement with a focus on sales technology and CRM adoption.
7:45 – From CRM Frustration to Sales Enablement
Shannon explains her early experiences with CRM systems and the realization that technology often isn’t designed with salespeople in mind.
11:22 – The Evolution of Sales Technology and the Role of AI
Brooks and Shannon discuss how AI can eliminate inefficiencies and improve user adoption within CRM platforms, and why sales enablement requires a tech-forward approach.
16:30 – Overcoming Barriers in Sales: Technology, Data, and Interoperability
Exploring the interoperability challenges faced by large companies, Shannon emphasizes the importance of having a unified data strategy and explains how data lakes and AI can streamline sales operations.
22:10 – AI for Just-in-Time Sales Support
Brooks and Shannon explore practical AI applications, from automating prospecting tasks to enabling just-in-time learning that meets sales reps where they are.
27:45 – Training and Development in the AI Era
How AI can transform sales training by making it more personalized, relevant, and immediately applicable to day-to-day activities.
32:30 – Integrating AI with Traditional Sales Tools
A discussion on sales technology trends, including the role of LinkedIn Sales Navigator, document automation, and other tools in the modern sales tech stack.
39:00 – Navigating AI Adoption in Sales
Shannon talks about common misconceptions and fears around AI and offers advice on how sales teams can start small with AI to build comfort and enhance their effectiveness.
43:55 – What Makes a Great Salesperson?
Brooks and Shannon discuss the characteristics of top-performing salespeople and why grit, resilience, and curiosity are essential for success.
50:20 – Advice to New Sales Professionals
Shannon shares her advice to her college-graduate self, focusing on the importance of embracing technology early and leveraging it as a career accelerator.
55:12 – Closing Remarks
Brooks and Shannon wrap up the conversation with a look to the future of sales and an invitation to listeners to join future episodes of the SaleSage Podcast.
Visit: SaleSage.ai
Connect with Shannon Gregg, PhD
LinkedIn: Shannon Gregg
X: @ShannonJGregg
Website: Cloud Adoption Solutions
Creators and Guests
What is SaleSage Podcast?
Unlocking the Future of Sales & Marketing with AI Visionaries
The SaleSage Podcast dives into the transformative world of artificial intelligence, sales, and marketing, featuring in-depth conversations with industry leaders, AI experts, and innovative entrepreneurs. Hosted by Brooks Canavesi, each episode unpacks how cutting-edge AI technologies and data-driven strategies are reshaping the way we sell, market, and grow businesses.
Join us to discover the personal journeys behind today’s tech pioneers, hear firsthand how AI is impacting sales pipelines, and learn actionable insights you can use to stay competitive in a rapidly evolving market. Whether you’re in sales, marketing, or simply passionate about the potential of AI, SaleSage brings you the tools and perspectives you need to thrive in the age of intelligent automation.
Tune in for:
Real-world stories from top sales and AI professionals
Practical applications of AI in business
Key strategies to future-proof your career and business
Inspiration from leaders who are shaping the future of commerce
Unlock the knowledge, trends, and insights to stay ahead of the curve—one conversation at a time.
Brooks Canavesi
Yeah. All right, so we're going to get started here. Okay. All right, everyone, welcome to the SaleSage podcast, where we explore AI insights, sales secrets from top industry leaders, and we aim to help sales leaders and professionals gain their unfair advantage in the marketplace today. I am very excited to be here with Shannon Gregg.
Shannon Gregg
Hey, Brooks. I'm more excited to be here. Thanks for having me.
Brooks Canavesi
Yeah, thanks for making the trip down. I know it was a little bit further than we expected this morning, but I am your host. I'm Brooks Canavesi. I'm the Chief Experience Officer with Problem Solutions and one of the co-founders of SaleSage, where I typically focus on providing our customers with competitive advantages through the use of AI and cutting-edge technology. So when I'm not interviewing sales and technology pioneers like Shannon, typically, you'll find me researching and tinkering. Shannon and I just went next door and were looking at our 3D printers, our laser cutters. We're makers, we're tinkerers, we're software engineers. We really enjoy the art of what is possible. And part of what we want to talk about today and on this podcast is really understanding the art of the possible and how sales can leverage AI to take it to the next level. Regardless of your industry, regardless of the platforms that you use, what CRMs you're in, there are opportunities to use automation in a way that we've just never seen before.
Shannon Gregg
So true. It feels like we're standing on the precipice of something incredibly exciting.
Brooks Canavesi
Absolutely. So Shannon, we just want to welcome you to the show, and to get started, can you tell us a little bit about your education, your experience, and kind of what's brought you to this point in your career?
Shannon Gregg
Absolutely. Like all people who work in technology, I stumbled into it in an unconventional way. I got my degree in English Literature from the University of Pittsburgh, which was, I thought, a really great pre-professional major. I just didn't know my profession would turn out to be technology. So it's been a really interesting journey. And then I moved into getting my MBA in Management, which was a good way to round out the business knowledge that I felt would be helpful in understanding how to really dig into clients' problems, regardless of which department they're coming from. And at some point, I asked myself a question I got really, really mad at, which is why, when there is amazing, incredible technology that will help salespeople do their job better, faster, stronger, are they not using it? So after I did a ton of research on user adoption, I decided I might as well take all of that frenzied activity and put it into a PhD. So I ended up with my PhD in community engagement focused on sales technology and user adoption.
Brooks Canavesi
Wow, what a journey. So you know, today Dr. Shannon Gregg is the president of Cloud Adoption Strategies. She's an adjunct professor at Point Park University. Jazz dancer, music lover, and mom. So tell us a little bit about the jazz dancing.
Shannon Gregg
The jazz dancing is something that I absolutely love to do. It's a team of moms who used to be competitive dancers. Our average age is 42, so every year we learn a new routine. We actually go to competitions and perform. We would compete, but we have yet to find another mom jazz team to compete against. So, you know, you can find us sometimes. Most recently, we competed at an event at Slippery Rock University. So we're standing back there putting our monies where our mouths are when we're telling our kids, you know, go out there and, and do your best. We're trying to do the same thing too.
Brooks Canavesi
That is so fun. Your kids must have a ball with that as well.
Shannon Gregg
It's incredible. You know, it's really interesting to see them turn into the encouragers because they're standing there clapping for us the same way we're clapping for them. And it's a really cool moment to share, for sure.
Brooks Canavesi
That's awesome. So kind of getting into things a little bit. Can you give the listeners just a little background on your journey in your sales career? Like you kind of went through English Literature, MBA, PhD. How has your sales career kind of evolved over time and what kind of got you most interested in that aspect of business?
Shannon Gregg
So I was doing software sales in the nuclear nonproliferation space, which is heavily regulated, highly technical, and a lot of my job was actually writing proposals. So the amount of time I spent actually doing sales was limited. The amount of time I spent coming up with strategy, writing down what we were going to do, figuring out how to translate that into graphics to give whoever was our ultimate end customer, typically the government, an idea of how we would do what we said we were going to do. And I found the operational process of sales to be really thrilling because there, there was a lot of inefficiency. So I was using a CRM at that time that had a black screen and green letters. And when I moved from that space into another regulated space in eClinical, doing clinical trial technology in sales operations, I was introduced to Salesforce. And that's when I started recognizing the flexibility of the no-code, low-code configurable software platform that was available to everybody who used it and allowed a completely different level of user participation. And that's when I started thinking, wow, we can be doing so much more to enable our sales professionals to go out and do the thing they're really good at and help remove the barriers of the things that get in the way of them delighting customers.
Brooks Canavesi
Yeah. So this is a really important topic. When we think about those ingredients for salespeople, what are those things that salespeople find are in their way, the inefficiencies? What are the common things? You've done a lot of research around CRM adoption. What are those things that are keeping salespeople from being effective out in front of customers?
Shannon Gregg
You know, I had to do a lot of qualitative research and go out and ask people these questions without injecting my opinion. And that was hard. That was the hard part about the research. But what came to fruition when we started coding all of the things that we found in these interviews is that technology often isn't designed with a salesperson in mind. So when you think about a technical architect, a developer, they love building juicy things so they can say, "This is the way the code will react when this particular thing is input." Salespeople do not love those things. So a lot of times it really came down to the user experience being designed without the salesperson in mind. A person who's constantly under pressure because they have a quota on their back. And every month is a new time for you to show what it is that you do for the company without thinking about people who are in sales because they generally do not like sitting down at a desk. The same things in their personality that lead them to be really good at creative solutioning, listening well, digging into problems are the same things that prevent them from sitting down and being very good at data entry.
Brooks Canavesi
Yes. And data entry and compliance are the things that finance, operations, and forecasting are looking for. However, salespeople are trying to be out on the road, on the phone, in front of customers because that's where business is getting done—to help their overall quota attainment, commission, and helping the business overall from a top-line revenue standpoint. So that's a very interesting thing that you said. And I am a software engineer. I went to Penn State for software engineering, started building applications at FedEx when I graduated. And so many times, requirements were taken as just text-based requirements from a business unit. And then the developers were interpreting those. This is how I would use this system, not thinking through the true user experience of who is this demographic, what role are they in, and what would be the modality or manifestation of this technology that would make the most sense for them.
Shannon Gregg
So true. Those are really introspective things for a lot of folks who are in other departments who will say, "I can't do my financial projections and the board needs to see them until the salespeople get them into our system." And so a lot of times what we see is sales tools and technology happen to salespeople instead of happening with or for them. And there is a new angle that I think is coming right now where salespeople now recognize they can push back and they can be involved. But we have to figure out where that responsibility aligns based on who holds the budget—is it IT or finance? And they are holding the budget for the sales tools and technology. Is it the sales team? And they hold it and they develop a shadow IT strategy. So there are so many pinnacles that sometimes we hear called silos. And I think we're seeing a new generation of salespeople who were born with technology in their hand, who are willing to say, "This doesn't feel good and this isn't actually what I need to do my job better."
Brooks Canavesi
Right. And I know from a consulting perspective, you've been here, you've done this. I just came from some consulting work over the last two months where large companies still have data interoperability issues, multiple systems, sometimes within the same ecosystem, from the same vendor, that still don't speak to one another. And I'm talking about core systems like finance, like CRM, like contracts, legal, like operations, those types of things. So we hear this all the time. And I just wonder, as you've gone through your consulting efforts, you're talking from a sales strategy perspective, transformation perspective, with C-levels, with CTOs, with COOs, with CROs, as they're looking at this, do they start to see an evolution towards data lakes and not needing this type of interoperability? Let's just get the data out of these systems into something much larger that we can then do all of our jobs more efficiently across those data sets.
Shannon Gregg
One of the things that I find really interesting is when you think about interoperability and CRM and ERP are two easy ones to look at. A lot of CRM systems are built with parent-child account structures in mind, and a lot of ERP systems are built with a three-level account structure in mind. So if you're relying on your CRM for initial opportunities, but in the case of SaaS or something that's repetitively done in terms of opportunity management or fulfillment, if the ERP holds the renewals, it gets really confusing to assign your data dictionary to say, well, if somebody's on a 12-, 24-, or 36-month contract that repeats so we can send invoices out of ERP. If those signals have to go back to CRM, how does it happen? So one of the things that we've been doing for the past five years is, if you're preparing for a data warehouse or a data lake, making sure that the company has a data dictionary first. And so many don't. And I mean of any size. So organizations that you would think, wow, they're an enterprise, they definitely have a strategy, they understand what they mean when they say opportunity or lead and everybody in the company means the same thing. A lot of times they just do not. And then you've got this Excel beast that sits in between where people are still doing beautiful and wonderfully complicated pivot tables that are sitting on somebody's desktop and inevitably are always out of date. And the amount of data that's still stuck in those that has to be pulled out and reevaluated for AI readiness is massive.
Brooks Canavesi
Yeah. And how about how many ways can you spell this customer's name in the data dictionary? Or did we use hyphens? Or did we go humpty case? Or did we go all caps?
Shannon Gregg
Yes, and you know, goodness gracious if they have multiple locations. Is it GlaxoSmithKline, and where is it? And which part are we talking about? And does each department or location get their own account? It is wild, Brooks.
Brooks Canavesi
Yeah. So how do you see AI coming in from that perspective to start to assist salespeople where they're able to get the information that they need at the point of need, just-in-time type of information? Single point of glass, single pane of glass. And how do we also see AI helping with this kind of data normalization, interoperability of systems? Like, where do you kind of see that going?
Shannon Gregg
We've been talking about data hygiene for years, and it feels like it should have been solved with automation. So for a while, it was really exciting to think my opportunity naming convention could be controlled by automation. So we could make sure that the account name is brought in, the business unit is brought in, the timing is brought in, so the opportunity names make really good sense. And we found there were holes with that that didn't always work out the way that people needed to when they were looking at pipeline or projections. Now we see AI coming in to assist not only with hygiene, but also that next best action which humans can't always think about. So where is the white space in an account? Where can we say, hey, dear salesperson, you might not have seen this situation before, but our company has. So here are ways that we can pull in information without you getting on a very expensive call, pulling in 20 SMEs who have other jobs to do while you're trying to formulate this opportunity.
Brooks Canavesi
Yeah, that makes a ton of sense. Where do you see other, maybe more, not as technical, in-the-weeds from a CRM perspective, but just day-to-day sales. Where do you see AI having an impact in day-to-day sales that people could start to employ? And have you started to employ some of these tactics with your teams and with your customers?
Shannon Gregg
There are loads of places that I think we're seeing sales professionals of all designations, from early entry-level salespeople, BDRs to giant enterprise salespeople. In some places, we've got things like LinkedIn Sales Navigator. And I think LinkedIn's had an interesting time of trying to make that make sense, but now it's able to point out to you, "Hey, Brooks is one of your top prospects. Brooks posted this thing here," which we used to rely on our feed or our sort of manual scan and sitting and spending time digging through it now will say to you this has got a little bit greater priority. So there's these simple sort of AI things that are having impact on relationship building. And then you've got things that are even more critical and important, like document automation that can say, hey, you forgot to fill in these things. You don't have this all the way back here. How can we write a contract that you think somebody possibly will sign? And I think one of the things that, you know, when I first saw SaleSage I was so excited about because it felt like an end-to-end enablement platform. And sales enablement has had a real go of it over the last 10 years. No company defines it the same way, no company funds it the same way. It's a really easy place to cut money and positions from whenever there is a looming recession or a challenge with funding. And so I think AI is going to help fill in those areas that we used to very heavily rely on human manual interaction to keep things moving at the speed of personalization, which customers and prospects demand.
Brooks Canavesi
Right. So when you think about training, sales training, that's like a four-letter word to most salespeople, like, "Oh great, another PowerPoint and I'm going to fall asleep here." So what, you know, we see with SaleSage and just in general with AI is that dynamic ability to meet you where you're at, just in time and make it contextually relevant to what you're going after in that day-to-day pursuit. So if I'm focused on the healthcare industry this week, this month, this quarter, maybe that's what I do. I can make all of my training, all of my role plays, all of my just-in-time performance support specifically to that industry, specifically to those customers. Another interesting thing that you mentioned with LinkedIn is kind of that alert about, hey, here's some prospects that are hot to trot. They're posting, maybe you want to go out and like their post and those kind of reminders. One thing that we automated, I did this for my team just last week was getting a list out of Sales Navigator of who our prospects are. So just think Google Sheet, think spreadsheets. Fine, right? And I have names, first name, last name, email address, website. Maybe I have phone number, whatever. But even from their email address, I can determine their website. You can automate to go out to their websites, scrape their websites, then build personalized emails to each one of them and have that output it into additional fields in your spreadsheet. Right. Just using something as easy as Make.com, which is free to start, and that kind of automation, you literally, I learned how to do it on YouTube. You can build that for yourself. That's in the power of the salesperson on a weekend to build. And now you're creating personalized emails to each one of those prospects that has your pitch using the power of AI plus their information. And now it's taking your product and pitching it. We do that in SaleSage because we already know your products and services because the AI has been trained on that. But you can do it more manually using something like ChatGPT. It's simply amazing.
Shannon Gregg
It is amazing. And you think about the hours of research or searching for the right fit and the amount of time that salespeople are spending on that, that truly is not value-added and that gets replaced. So powerful. And reflecting on training, some of the things I learned in my research were based on adult learner theory and change management theory is that adults only remember 10% of what they're taught when they're taught it. So if you've got an eight-hour sales training day where you take everybody out of the field, one, there's the opportunity cost of them spending eight hours away from customer work. But two, you now are relying on the fact that they are going to remember what was the most critical thing you delivered to them when they need it, which may be six weeks, six months from now. So the concept of just-in-time learning addresses these major gaps that exist in holding traditional in-person sales meetings where you're trying to teach a bunch of people who want to be out there talking to customers something that they may not need anytime soon.
Brooks Canavesi
Right. So when you think like taking it down level just to like the, you know, regular salesperson out on the hunt doing their thing, typically they just want to ask a question and get an answer fast. So what do you think about modalities? So I'm on the road. Do you think mobile application? Do you think text message? Do you think a phone call? Where do sales reps, you know, today's reps, as you're going and talking to them, what devices do they have on them? And what is probably the most desirable modality of communication for them to get this information just in time?
Shannon Gregg
You know, I think that answer probably depends a little bit on the industry. You see lots of salespeople who have iPads if they need to show something. So if they have a demo or blueprints or CAD drawings, somebody who needs to see something visually, those folks may be carrying an iPad, and that follows a mobile modality. But if a salesperson is only carrying just a smartphone, the screen is so much more limited, so they're likely not going to use that to show any sort of presentation. However, I think one of the most critical things we have to ask ourselves is how do I allow that salesperson to take the answers that they learned and put it into a place where it's actionable? What are the next steps? What are the things that we have to do to keep this opportunity moving or keep this prospect interested, and how do we meet them where they are? This is one of the places, Brooks, where I think sales is actually trailing behind service. Because I think folks on service teams have been thinking about omnichannel for a really long time. Marketing has been talking about omnichannel for a really long time. And one of the things that we have to give to our sales team is the ability to move seamlessly from their laptop when they have access to it, maybe their monitor if they've got an additional place to look, but when they're traveling, allow them to access that smartphone or iPad so that there is a mobile option as well. Because we know that if they keep all of those notes in their head or even write them down by hand, but don't enter them somewhere to be acted upon. 24 hours, they've already slipped, right.
Brooks Canavesi
So we've been experimenting with voice agents, and we call it "cozy tech." This is—everyone knows how to make a phone call. Salespeople are really good at it. For the right sales audience, that's in the car a lot, on the transit. You know, they're just traveling, flying around the country. Is there a way for them to call into their AI agent? Can they give an update that makes it to the CRM? Can they give action items? Can it send text messages or emails on their behalf? Can it transcribe? The answer to all of those things is, of course, yes. With AI's capabilities, what do you think about voice? And it's an old technology. I still think salespeople need to be on the phone more. I think that it's a way to stand out. There's a lot of keyboard cowboys out there that hide behind LinkedIn messages. And automation leaving a voicemail sometimes is a great way to stand out. But kind of what do you think about the phone, especially with younger generations? It's one thing I'm a little concerned about is I know my age, 45 and older phone, no problem. But like some of the younger generation and you work with a lot of them at Point Park, you're an adjunct professor there. You know, kind of tell me a little bit what you think about, like that type of modality.
Shannon Gregg
So the phone is absolutely a way to stand out now that so many people have put so much automation in LinkedIn outreach and emails. And I agree with you, the phone is going to be something that sets apart a salesperson from one of their peers if they're competing for a job or a promotion. And so one of the things that we've started to do at Point Park is we enter a lot of sales competitions. So our students who are in sales professional classes, they are joining into competitions that often now are incorporating the phone. So they'll have to put together a cold outreach strategy. They actually have to call and leave messages and then they get into a role-playing scenario that is really interesting and fun. We launched just this semester a brand new course called the Playhouse Practicum, where for the first half of the semester they had to devise their outreach strategy. And for the second half of the semester they were literally making cold calls. So they were calling people who had come to the Playhouse before, telling them about the shows that were coming, asking them how many tickets they wanted to buy. And at first, of course, there's apprehension. By the end of the semester, we saw the students who were held to KPIs, they were turning in their call numbers and they were pretty extraordinary. And I fully believe these students are going to have a tenacity that is going to allow them to look really positive in the workplace.
Brooks Canavesi
That's awesome. Now, using the phone, do you think that they will, if they had an AI agent, would they rather text it, would they rather slack it, or would they rather call it?
Shannon Gregg
You know, one of the things that we find about students, salespeople, managers, is that everybody has a modality they sort of like the most. But I think we're seeing now in consumer tech the ability to speak to an AI assistant. And I think we've got loads of people out there who expect the same types of things out of their enterprise applications. So if I can go onto my Snapchat and ask my Snapchat assistant, "Hey, I'm in Boston right now, where's a really good place I can go to eat?" And it says, "Hey, based on the things we know about you from when you entered your data to download this application, here are some places we think you would like. And here are photos of them." Our enterprise salespeople want that same sort of thing out of their sales tech stack, right?
Brooks Canavesi
Agreed. What are some misconceptions that you've seen around using AI in sales? And how have your customers started to either adopt or ban or not allow AI? Because they're scared of it.
Shannon Gregg
So I think we've got that same fear, uncertainty, and doubt with sales professionals as we do with general consumers. And that is, "Is AI going to take my job?" And we all know AI is not going to take your job. But those who know how to use AI are going to have a better time in their jobs, a better time finding jobs, and a better time doing what they need to do as a sales professional. So yes, people are scared of AI. People are curious about AI, and in a lot of cases, people are overwhelmed by AI, so they don't know where to start. They're not sure exactly what the best place is for them. And so with a lot of our customers, when we're talking about AI and AI readiness, we try to hone in on what is the biggest challenge that you have and how can we solve that in snackable pieces. So when you try to give somebody a concept and you imagine, Brooks, building an entirely new house, that's a lot. You have to choose paint colors, size of rooms. You know, what does the outside look like? What does the inside look like? Are you doing carpet? Are you doing hardwood? That's so much for people to think about that they go into cognitive overload and they make no decision. So when we're talking about AI for salespeople, it's like, how do we use a small decision? So is that just guiding you along and saying, "If they made this decision, here's the next place on the path that you should take them?" That's a great way for them to start. Where is the analysis paralysis happening? And how can we help you use AI to dig you out of that hole so that you don't have to rely on yourself to remember what should come next? But there's a pretty easy pathway that says if A, then B, sure.
Brooks Canavesi
And I think it's very clear, and I think I agree with you that those that can use AI are going to excel much faster. The train's left the station. The analogy I use all the time is like, the gun went off, we're on the track. Are you in the blocks or are you working your way down the track? Right. Like, we're in the race, whether you like it or not. So for those salespeople that are looking for a place to start, what are some suggestions on, "I don't want to be outpaced." Most salespeople are very competitive. How do they start to gain that competitive edge? Where's a place that you think are just a few things that they can start with?
Shannon Gregg
Right. So I think, first of all, it's important to know, are there regulations that are happening in your industry or in your company so you don't act outside of that? And second of all, making sure that you know when you do get started, and if it's ChatGPT or some type of generative AI, great. Start with that. To see how it feels and understand what the power could be, but also understand who holds that data, what are the terms and conditions, making sure that you're not teaching an unregulated, unknown backend a lot of details about you. Right. A lot of people learned that via social media. When they're like, "Oh, my goodness, I think my phone's always listening to me." You better believe it is. So if you and I are sitting here talking about, you know, buying new kayaks or how you really like kayaking, guess what? Both of our phones, as soon as we walk out of here today, are going to start showing us kayak ads. Right?
Brooks Canavesi
Right.
Shannon Gregg
So really understanding, you know, what. What is the landscape to make sure that you're keeping yourself safe? Because when you talked about salespeople being cowboys, that's one of the things I love about them. They want to explore how do I do more, better, faster? So I think for most salespeople, it's understanding where am I doing things over and over and over again. So what is repetitive that I could allow AI to come in and give me the assist on, or what are the things that I'm doing where I get caught? I don't do it very often. This is a new customer or industry for me. What types of signals can AI give me to help me keep this moving so I don't get stuck in internal bureaucracy trying to figure out how do I solve this problem?
Brooks Canavesi
Yeah, that's really sound advice. And I think that people need to understand that it's not that scary. It's natural language. You speak to it. So there's a term called prompt engineering, and that can be overwhelming. But there's a lot of just really good information out there that you can read, watch YouTube videos on that just get you a little bit further. And all of this generative AI is natural language first. So how you prompt it is going to be the types of outcomes that you get, right? The results that come from either a large language model or diffusion model. So I think that's also a skill set that any salesperson could spend 15, 25 minutes just upping their game. 10% can mean a world of difference in using these types of tools.
Shannon Gregg
I totally agree with you. And if somebody who is older has been around you, and I remember learning how to ask Google questions, right? Asking Google questions was different than the way that you asked Bing or Yahoo a question. And so learning how to prompt is something that you're absolutely right, will help to set somebody apart. And I recommend doing that in soft ways when there isn't a critical quota or closing date sitting on top of you and just asking it a question and seeing what its response will be and learning how to reframe that. And I think that is such an interesting skill. Five years ago, there was no such thing as a job description, a job title that said prompt engineer. But there sure is now, right?
Brooks Canavesi
What do you think? You know, this is one of the questions that I struggle with all the time. And everyone has different ingredients that go into it. What makes up a great salesperson? So when you're thinking about hiring salespeople, can you give the listeners some advice on what you found? Are some of those definable characteristics, maybe undefinable characteristics? And then when making hiring, some tips and tricks to find great salespeople.
Shannon Gregg
I think number one is grit and resilience. I think without grit and resilience, it's really challenging to be a salesperson because we're told no. And we have to try new strategies very often to be good salespeople. So understanding how somebody deals with rejection is something that you should get out on the first interview, right? So how do you deal with it when something doesn't go your way? Grit and resilience, those are things that I think a salesperson cannot come to the table without, because this is not for the weak. However, I do think it's the most exciting profession. I think sales is an absolute window of opportunity to so many different people. And so I think if you're looking to hire salespeople, you've got to establish that. And then next is natural curiosity. So we have to be creative problem solvers. When we're salespeople, our clients only need us if we can solve a problem for them. Right. They're not going to bring us in and hand us money if they can figure it out themselves. So that same sort of natural curiosity will spill over into the way that they move around internally. So will they want to figure out how they can do something a little bit easier, a little bit better? Will they want to say, hey, AI can come in and help us develop our battle sheets. It can help us understand our ICP. It can help us format our proposals in a way that makes more sense to the person who's reading it, who maybe is non-technical. So I think for me, those three things are imperative. Everything else you can teach, I can teach somebody a little bit more about an industry or I can help them to understand what the challenges are that our customers currently have. But if they don't have grit, resiliency, and a natural curiosity, I don't know how much we could do with them as a salesperson.
Brooks Canavesi
And do you have a series of questions or activities to try to bring some of that out in an interview process?
Shannon Gregg
So one of the best things I ever learned, and this came from our friends at Development Dimensions International.
Brooks Canavesi
Yeah, DDI.
Shannon Gregg
DDI so tremendous at helping you learn how to interview people to predict results. And one of the things that I learned from them was asking them how they have done something in the past instead of how they would do something. Because what they've done in the past helps you understand where they are on tasks. So asking them, "Tell me about a time when you…" [fill in the blank] is much better than saying, "How would you handle?" Because then you're getting the real-life perception with a story. So you can evaluate their storytelling and how they deal on task without saying, "What kind of answer do you think I want to hear as the interviewer?"
Brooks Canavesi
Right. That's great advice. When you think about hiring and those ingredients, and you talked a little bit about this, you said you really love sales. Right. And finding someone that's done this that is passionate about it, you know, there's so many things that go into it. And I like your three ingredients. I agree with those wholeheartedly. Mine are different terminology. I usually say discipline. So I ask people things like, have you ever run a marathon? Have you ever been on a diet more than six months? Like, have you ever wrestled in high school? Like, things like that that require severe discipline, then I kind of know some of that past experience. But when you think about sales, what is it? If you were going to give, like, two big things, what is it that makes you the most excited about the profession?
Shannon Gregg
Well, I think one of the things that's most exciting about sales is you are continually getting better because you're getting consistent feedback from your clients. You're understanding how to be coachable. So I'm not a great salesperson today in 2024 without an idea that I have to continue to change my game because once things get really easy and they're plugged in, that means that my customers know how to buy it without me. So if I don't understand a little bit more about an industry, a little bit more about the way the economy is changing, if I don't constantly pump my brain with new information, I'm dead on arrival. And that's when I'm not going to be any good in sales. So I love that. I think that's one of the things that's really exciting. I think a second thing that is really exciting is the technology use amongst salespeople. I think we've seen that change majorly. And if you look at the martech landscape, it's like an eye test, right? There's like 5,000 logos on that. It used to be that the sales tech landscape was an adorable little thing that had about a tenth of the number of logos as martech, which made me feel like, what? Why are the marketers out there taking all the technology and showing us how great they are with their martech landscape? And now the sales tech landscape has evolved to a point where it is as much of an eye test as the martech landscape. That means there's loads of things we can play around with once we figure out what are the problems we're trying to solve with our sales process and our go-to-market approach.
Brooks Canavesi
Yeah, I love the lifelong learning aspect of it. And I totally agree. Like, for me it's about really, it's learning about other businesses. That is what gets me up every day is getting to speak with new customers, learning about their business, what makes them tick, how their employees handle situations, who's their ideal customer, what products they build, how they build them. All of that just fascinates me. And like, I just invest in it. And for me, like, because I'm that invested in the customer and I want to learn everything about it, it shows. And then you build a really strong relationship. And I think that curiosity, lifelong learning, I think those are very key elements, and you hit it on the head.
Shannon Gregg
I don't know how we could exist without it. Yeah, people can understand and smell when you're being authentic. And a salesperson who's authentically interested in how their business works and what sets them apart from everybody else is what's going to drive that relationship. And there are no sales without relationships.
Brooks Canavesi
Correct. So kind of closing out here. If you were going to give advice to your college grad self, so you just came out of English Lit before your MBA, knowing what you know today, what would you say for yourself?
Shannon Gregg
I absolutely would tell myself, coming out as a college grad, understand a little bit more about how technology can impact the way you do your job. Because for a long time, I allowed that to happen to me instead of getting involved and saying, I need to understand how I can exploit this, how I can use this better, how I can understand the data to help me drive my decisions. And so I think that's something that I figured out a little later than I wish I would have. So I would tell myself, get in there and figure out how the technology that helps you do your job isn't just a lubricant to get to an end, but instead can help propel you further, faster than you even thought possible.
Brooks Canavesi
Fantastic. That's great. So we're kind of running up to time here. Wanted to just say thank you so much. This has been a great conversation. I learned a ton. When we first met, you were on stage, actually, and you were talking through change management, sales tech, and being the salesperson that I am, I came up, gave you my business card, wrote ideas on the back that we should talk about so that you had some context around it. And I'm very grateful that we met at that conference and really grateful that you were able to join us today. Thank you.
Shannon Gregg
Thank you so much. I am also really grateful. I'd love to tell everybody that it's been a long time since I've seen something that made me literally fall off my chair. And when you first showed me SaleSage, I said, "Brooks, this can't be possible." And I did fall off my chair. That was cool. And I think one of the things that is so great about that is there are still experiences to be had. You know, there are still things that we can learn that will set our minds on fire. And that's the type of reason that we get up every single day. Right. We like to try something new and experience something new and be wowed and have a sense of wonder about what is possible. And that is why I think we are absolutely in the golden age of sales right now.
Brooks Canavesi
For sure. We are living in the future. We say this all the time. I'm literally talking to my phone, talking to my AI agent. It's transcribing things for me. It's sending summaries. I am, you know, building music that I showed you today before the podcast. We're making music, music videos with prompt engineering in less than two hours. Like, we are living in the future. It is amazing.
Shannon Gregg
What a time to be alive.
Brooks Canavesi
Yeah. Well, thank you so much and thank you all for listening in. We will have new episodes. Please come back and listen to the SaleSage podcast. And thank you so much for your time.
Shannon Gregg
Thanks for having me.