EPISODE 669: How Large Sales Deal Expert Barbara Weaver Smith is Using AI Right Now

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Today’s show featured an interview with Women in Sales legend Barbara Weaver Smith, the author of Whale Hunting: How to Land Big Sales and Transform Your Company.

Find Barbara on LinkedIn.

BARBARA’S ADVICE:  “The Whale Hunters model is scout, hunt, harvest. It’s loosely derived from how the Inuit people hunted whales. We use a lot of their terminology and a lot of their belief and value system in our work. A whale hunting company is one that everybody in the company understands how they make money and their role in it. We do a lot of work with targeting ideal customers, which would be whales. A whale could give you a deal that’s 10 to 20 times bigger than your current average deal.”


Fred Diamond: I’m excited today because I have Barbara Weaver Smith, the founder and CEO of The Whale Hunters, and she’s the co-author of Whale Hunting: How to Land Big Sales and Transform your Company, and also the author of Whale Hunting with Global Accounts: Four Critical Sale Strategies to Win Global Customers. Barbara, we’ve been associated for years. You’ve been one of my go-to resources for selling to big companies. We’re going to be talking today specifically about some of the things that you’re using for AI and how AI is changing sales coaching. I’m excited to talk to you about that, but get us caught up. What exactly is the Whale Hunters Institute and what do you want our listeners to know about you?

Barbara Weaver Smith: Thanks, Fred. The Whale Hunters Institute is our newest project, our newest product. It’s an online learning environment for everyone involved in large account sales. In whale hunting, we believe in a collaborative approach. I mostly work with mid-size companies who as they move up market, they’re running into much bigger competition. The big competitors have sales teams, dedicated sales teams, dedicated sales engineers, and people who write the proposals and do the bid and all that stuff. But mid-size companies don’t have that. They just have a couple of salespeople, but they have subject matter experts all over their company. My basic training involves how to get a whole company to be a whale-hunting community.

The Whale Hunters Institute is just a step in that we’ve gathered many, many of our materials and a bunch of new courses that would allow people to get the equivalent of a whale-hunting coaching and training engagement. It’s more for smaller businesses that couldn’t afford to do a big training but we want to make sure that we have everything available for them. It has courses, it has lots of tools and templates. It has audio and video, lots of ways to learn about how to manage large account sales. It’s not just for the sales person, it’s for the leaders, for the sales leaders, for the CEOs, and for subject matter experts who are involved or want to get involved in large accounts sales.

Fred Diamond: Let’s get everyone on the same page here. What exactly is a whale, in terms, so people understand specifically what we’re talking about? You’ve mentioned large accounts of course, but give us some insights into what does a whale company look like so people understand where we’re going to here.

Barbara Weaver Smith: The Whale Hunters model is scout, hunt, harvest. That’s the whole sales process. It’s loosely derived from how the Inuit people hunted whales. We use a lot of their terminology and a lot of their belief and value system in our work. A whale hunting company is one that everybody in the company understands how they make money and their role in it. Whale hunting is about those three parts, scout, hunt, harvest. We do a lot of work with targeting ideal customers, which would be whales. Now a whale is a company that could give you a deal that’s 10 to 20 times bigger than your current average deal. A whale is different size for different companies. If you’re just starting out, maybe you’re going after a $800-million company, or a billion-dollar company would be a whale, and other people are going after the Walmarts and the Costcos and the big box stores. Well, all kinds of multinational and global companies.

I use Caterpillar as an example sometimes. Caterpillar, the last time I looked, they owned 789 companies. You could do a lifetime of business with Caterpillar if you just studied where they are and move from one to the other. But typically, companies don’t do that, so we leave millions of dollars on the table. Whale hunting is about being really strategic about what are the qualities of a large account that would need what you’re selling. Then you define those characteristics, find companies that meet those characteristics, learn everything you can about them, and start introducing yourself to them. That’s the start of the process.

Fred Diamond: Just a very basic question here. Can every company be successful in going after whales or is it a specific type of mentality that your company needs, or mindset that they need? Or do companies come to you and say, “Hey, we want to get bigger companies, what do we need to do?” Do you sometimes say to them, “You know what? Maybe that’s not the market for you.”

Barbara Weaver Smith: Well, there are some characteristics. First of all, it’s got to be a B2B company, or primarily B2B. There are some retail companies that can build a B2B component, but it’s not retail. All other kinds of products and services will work. My characteristics, my requirements actually for companies, they have to have good leadership. They have to have strong leadership because this is the kind of thing that comes from the top. It can’t even really come from the sales leader unless the sales leader gets the CEO on top, because you need the whole scope of the executive team involved at some level. Certainly encouraging it and keeping it going. If they hand it off, it’s not going to work because ultimately, it’s a cultural change in your company. I don’t sell cultural change, but that’s what they get, a big transformation. Companies that are in trouble, they’re floundering, they’re not ready to do this.

Most of the companies I work with are at some kind of plateau, and they’ve often outgrown their current client base. They’ve gotten really good, they’ve done a lot of innovative things, and the companies they’ve been selling to really can’t afford them anymore, or don’t need all the things they have. They need to move up market. They have very good reasons for doing that or they want to introduce something new.

Salesforce is a great example. They have a service that the biggest companies in the world can use, but they started out selling to small companies, almost on a retail level, to get going. That’s an example of they came to a point where they were ready and they wanted to sell their same product to much bigger companies, that kind of thing.

Fred Diamond: You mentioned Caterpillar, which you said has over 790 entities. Is going after one whale hunting? Or is the definition that you’re going after Caterpillar? For example, when I was a consultant, I had Microsoft as a client for close to 10 years. Bill Gates had no idea who I was or if I even existed. But a VP of a particular division knew who I was, liked me, had budget authority, who was a great client for five to seven years. I had to get into the flow and understand the pricing, et cetera. Give us the delineation about that. Is it do you have to go after Caterpillar or is it just as successful going after one of those 790 entities?

Barbara Weaver Smith: Well, that’s where you would start, with one of the 790. But your example of Microsoft is great. What you had with Microsoft was all you needed and all you wanted. But if you were a bigger company and you had that piece of Microsoft, then we would teach you how to move from that piece to the next piece, to the next piece, to the next piece. That’s part of our process, is how to grow that business.

You would start with maybe what’s in your backyard, or the first introduction you got, or the first person that wanted to talk to you. Then you could systematically explore and strategically define, where’s our next best opportunity? You might do that in concert with people that you’re working with at Caterpillar who could maybe make an introduction to someone that stepped out from where they are. It’s very strategic and systematic, if that’s what you want to do. But if you want to grow, you want to have big companies, don’t think that you just want one piece of one, because the easiest way to grow, if we have a piece of a big company, is to get another piece of that company.

Fred Diamond: Actually, having those logos on your PowerPoints and being able just to say, “Hey, some of our customers include brand names,” definitely go a long way in the sales process. Matter of fact, one of the key messages that I used to work with customers, my clients, was a key differentiator is we’re the leading CRM company and some of our customers include Microsoft, IBM, whatever it might be.

Let’s talk about AI and let’s talk about how AI is changing sales coaching. You’ve done some specific things. Give us some of your insights into generally where you think it’s going, and tell us some of the specific things that you’ve been doing at the Whale Hunters Institute to utilize AI for your customer’s value.

Barbara Weaver Smith: Well, the first thing I did that’s really worth talking about is I created a clone of myself, which is called Barbara AI. By creating a clone, what that involves is feeding it data information. The clone knows all my books, and it knows tons of materials that I’ve used with my clients. It knows almost as much about whale hunting as I do. There’s still more that I could give it, but it’s not a whole bunch. It’s designed to be a coach. It speaks in my voice. It also types answers. If you’re a member of the Whale Hunters Institute, for example, and you have a question about whale hunting, you can ask Barbara AI this question, and it’s available 24/7, wherever you are.

I’ve seen other clones now that are also designed to help salespeople. That’s how you create them. People can type a question and see a typed answer come up, or they can use the little phone icon and actually speak to the clone, and the clone speaks back to them, which many people would prefer to typing in their questions, especially salespeople.

Fred Diamond: Can you tell us specifically what tools you used to create the Barbara AI?

Barbara Weaver Smith: To create Barbara AI, I used a company called Delphi.ai, and that’s their whole business, is helping you create clones. They’re just adding a lot of features so that you can teach the clone to do more things. My clone is extremely powerful. In one way, it’s more powerful than I am because I don’t have the ability to go through everything in my mind. I don’t remember everything that’s in every book. I can’t bring that to bear when I need it, but the clone can do that. Anything that it knows, it can synthesize and give you a creative solid answer, really good answers to questions.

Fred Diamond: How much investment did you have to make? What does it look like for you specifically, Barbara Weaver Smith, working with this company or preparing? Was this a three-month effort? Is it an hour a day? Give us some insight into how you were able to get to the point where you’ve created everything using these tools and services.

Barbara Weaver Smith: I would say it probably took somewhere between 20 and 30 hours, and it was very cheap. Delphi AI, you can start at $25 a month. It’s such an incredibly powerful thing. Then I upgraded to $99 a month. It’s one of the cheapest tools that I use really for the power that I get from it.

Fred Diamond: You’re talking about books. I’ve written two books, as people know. Insights for Sales Game Changers. I also wrote a book on Lyme disease awareness. Someone interviewed me recently about something that was in the sales book and I was like, “I forgot about that.” There’s a huge amount of value here for sales professionals and sales trainers. How has this differentiated the Whale Hunters Institute being able to move everything to create this second platform, if you will? How has it helped you increase your leadership as a sales training organization?

Barbara Weaver Smith: Well, for one thing, like many other platforms, it has courses that people take. It’s interactive, but it’s a relatively passive way of learning. It’s not a way of learning that typically sticks. You don’t get really deep learning that you can apply. I believe that having the clone there, if people choose to interact with the clone, it’s like interacting with another person. It really is, even though you know you’re not. I’m not pretending it’s me, but the clone gives you good answers, and then it always asks you a question. It prompts you to think, it prompts you to apply, like a good coach would do, if you work with it. I think that transforms the typical online learning into something that’s much more interactive and much more powerful.

Fred Diamond: How about from a business development perspective for you? Has it helped you get clients that you didn’t have to meet with and talk to? Having this whole model, has it led to getting customers that you don’t even know or you haven’t had to interact with?

Barbara Weaver Smith: Yes, it has, so far, on a very small level. So far, we’ve only had a handful of people in it because it’s brand new. But we’re looking for people in two ways, individuals and also sales teams and collaborative teams that would benefit from it. Certainly, people who have already been through the whale-hunting process, I think will find this advantageous. We need to reach out to all of them, which we’re doing. It’s a big lift, there’s no question about that. Having something new and unknown to people, but I think it’s going really well.

Fred Diamond: Now that you’ve invested and you’ve launched, what are some things that you’ve learned? I see a lot of applications for what you’re talking about here with not just sales training or sales coaching, but sales in general. As I’m sitting here thinking, I’ve done over 700 Sales Game Changers episodes. Each one is like a course. I’m sitting here banging my head thinking like, “Why am I waiting to make this transformation?”

What are some of the things that has occurred to you that you didn’t expect now that you’ve gone across the chasm to get into this space?

Barbara Weaver Smith: Well, for one thing, I’ve learned a whole lot about AI. I’ve used a lot of other AI tools in building the institute. I was an early adopter of ChatGPT. I was an English professor in my first life, so I just love this concept of this large language learning. ChatGPT, from when I first learned it, it seemed to have limits. There were some things that it would help me do, but I couldn’t really see the whole vision of it. Once I started working on the clone, the power of it just exploded for me. I’ve gotten deep into many other tools. Tools that translate text into video, for example, tools that extract any kind of information you want from any kind of document. I’m thinking, if you were to create a clone, you could upload all your episodes. The clone can learn from any medium. It can learn from video, it transcribes everything from the video almost instantly. It has enormous power.

Now, I know that there’s enormous possibility for misuse of AI, just like there is for any technology. But I’m a positive person, I’m an optimist, and I wanted to be in on this power. For salespeople, it has unbelievable power, not just something like a clone. Although I think any sales organization should clone all their training material, put it in a clone so everybody has access to it in the way they need by asking it a question. I would certainly recommend that. But so many other AI tools, AI can do a lot of research for salespeople. I’m big on research, and it’s not something that most salespeople really enjoy doing, that I recommend that they have. We call them scouts of people that do the research. I think they should be from marketing or they should be from sales enablement, or they should be admin people, feed the salespeople all the knowledge they need and work back and forth with them very interactively.

Fred Diamond: Are there other AI tools that you’re using that you want to mention as well? You mentioned Delphi, if you want to just share some as well.

Barbara Weaver Smith: I used one called Salespeak.ai. It started with uploading PowerPoints, but you can upload any kind of document. When I build my courses, typically I start with a PowerPoint and then it’s narrated, et cetera, turned into a video. I can upload a PowerPoint and I can ask for a 50-word summary. I can ask for a full summary. I can ask for a list of all the topics. I can ask for it to extract the key topics. All this is helpful in the institute for people to understand what’s going to happen in this lesson. Then I can ask it to create a quiz. It created all the quizzes for all the courses. I wanted four questions in each quiz, and I would ask for eight questions so I could select the best ones that I got. When I asked for eight questions, typically, seven of the eight would be completely usable, and I could get multiple choice questions with the answers. It gave all the wrong answers as well as the right answers, which is a huge time saver for someone like me. It might be useful to a salesperson if they want to summarize a document that they have to understand. It’s just instantaneous. That one’s really good.

Fred Diamond: A lot of the people who listen and are listening right now to the Sales Game Changers Podcast, I’m based in Northern Virginia, right outside of Washington DC. A lot of the companies that are members of the Institute for Excellence in Sales focus on the public sector marketplace. There’s a lot you need to know about regulations, budgeting.

As a matter of fact, I interviewed recently a guy named Jim Kelly who runs Dell’s public sector business. He talked about how he and one of his reps were preparing for a meeting with a customer. There’s something called continuing resolution, which is when the government budget isn’t approved, there’s stop gaps along the way to ensure that there’s money allocated so that we can keep paying for military and keep fixing roads and all those things. He said before in preparation for a meeting, they typed in status of continuing resolution. He said that reams and reams of data came up and they went back and forth. There’s a lot of complexities in certain sale.

I’m wondering, for your customers as well, again, if you’re selling to large companies, the whales, they’re all in their industry. If you’re selling to a CFO of a global 2000 company, they just don’t want to know a bullet point about your product. They want to know that you know, do you agree with this, that you know how your solution is going to affect compliance or multinational growth and ability to work? I got to imagine that AI is going to be a tremendous value to help with that research.

Barbara Weaver Smith: I think they will. You’re exactly right about what they expect. They don’t care how you do what you do until they decide they want it. The reason they decide they want it is it solves a business issue for them. It gives them a new opportunity, or it solves a problem. That’s what they care about. You have to go in understanding what that might be so you can begin to talk about it. The way you add value is bring them something new, bring them something that they haven’t heard yet that you’ve researched. There’s another way AI can help you. What’s going on in X, Y, Z industry? Give me some examples, et cetera. Some of the AI tools are not completely up to date.

One that I use called Claude.ai, it’s a version of ChatGPT I think, but it is made to support people. It goes through 2023, so it’s pretty up to date, but you have to watch out for that. Otherwise, you can get really good information. When I’m going in to talk to somebody about whale hunting, I like to bring them an example from another industry or an idea that’s new to them, something of value.

Fred Diamond: For smaller companies, and even for large companies, mostly smaller companies, as they’re going for the whale hunting, a lot of cases, again, we talked about how they could find some chunks. But when they get the opportunity to get to the C-suite, at the whales, give us some insights into what is on their mind. We just alluded to a little bit of it, but again, if I have the opportunity to get in front of CIO, CTO, CFO, even a CEO or COO, what are some of the things that they think about on a daily basis? Again, they’re not really interested in the minutia of how my technology is going to help. But give us some of your insights, Barbara Weaver Smith, and what they think about that I, as the sales professional, need to be aware of.

Barbara Weaver Smith: Well, first of all, they’re thinking about their company strategy and what they need to do to be part of that, which is why I never go in until I’ve read their SEC report. I’ve read their K10, I know what their strategy is. I always ask them, “What’s your responsibility for fulfilling this strategy?” and I put myself up to date on it. That’s one thing. They’re worried, most of them, at that level, are worried about all kinds of problems and what they ought to do about them, external things.

Different industries have different challenges. A lot of industries are being disrupted. AI is going to disrupt all of, in ways that we can’t imagine. They’re trying to think about that, and they’re thinking about the threats that they face from competition. They’re thinking about the CFO, they’re thinking about the cost of it. They’re thinking about how to manage what should they invest in and what should they hold onto because the market is wonky. They have a lot of worries. You can learn a lot about what might be worrying them by looking at their SEC documents and also looking them up online, seeing what their news is and stuff like that. You have to be prepared before you go in. You have to feel like a peer. The hardest thing for salespeople is to not be afraid to talk to an executive.

I use the example, when I first started my business, I came out of the academic world. I was afraid that business people think academics are not serious enough, they’re not practical enough for business. Then I had a role as a president of an organization, but it was a nonprofit, it was a humanities council. I thought, “Well, that’ll never fly.” I was thinking all my credentials don’t count anymore. How am I going to feel okay going in to talk to people? Because I’m used to being in charge, but I’m in a new environment where I’m not in charge. I don’t have any reputation. Nobody knows me. You have to get a mindset that you are a peer to them in a different way.

Then I learned, of course, I was wrong about how business people feel about academics for the most part. My credentials started to matter again, but do anything you can to feel like a peer. The best way to do that is to be prepared before you go in. I have a friend who’s a CEO, and he said, “Whenever I talk to a salesperson, I ask them a question about EBITDA. If they say, ‘What’s that?’ I don’t talk to them anymore.” You have to have your sales acumen.

Fred Diamond: Actually, if you’re going to be speaking at that level at these types of companies that we’re talking about, the people who’ve gotten to the C-suite at the companies that we’re talking about, the whales, they just didn’t wake up and say, “I’m done flipping burgers. I’m going to be a CFO at McDonald’s.” It’s been a 20, 30-year journey, with education as well. They’re not thinking about little things. They’re thinking about big things. The sales professionals who we deal with at the Institute for Excellence in Sales, and many who are listening to the show right now, understand that, is that they need to be interested, prepared, do the research, and not just BS research, but really true, valuable research into what’s happening macro and micro level.

Barbara, thank you so much for the great insights. Congratulations to you also, you’ve created a great brand for yourself and the Whale Hunters Institute. Just want to applaud you for being on the leading edge of this. Although we talk about AI all the time, and it’s on everybody’s lips, not everybody has made the leap yet into truly implementing AI into their business and have thought it through. I know that I’m taking a lot of value from this. We’ve been implementing a lot of things, but I’m excited to research this Delphi company and start shifting a lot of the tons of content we have at the Institute for Excellence in Sales into some additional platforms. Congratulations to all your success, and thank you so much. Thank you for being a great resource to me over the years whenever I’ve had questions related to this, although this is the first time we physically have met, even virtually.

Give us a final action step. You’ve given us a lot of great ideas. Give us one thing specifically people should do right now after listening to today’s show or reading the transcript.

Barbara Weaver Smith: They should up their preparation. Everybody you go to talk to, be sure you’re bringing them one interesting thing, something of value, not tangible, intangible value. Something you’ve learned that they could benefit from.

Fred Diamond: The preparation is so key. We’ve talked today about so many different ways that they can get the research that they need. Barbara Weaver Smith, I want to thank you. I want to thank everyone who listened today. My name is Fred Diamond and this is the Sales Game Changers Podcast.

Transcribed by Mariana Badillo

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