Selling to Fortune 500.

In this episode of How To Sell More, host Mark Drager sits down with Dr. Barbara Weaver Smith, the founder and CEO of The Whale Hunters. Dr. Smith shares practical insights on how small and midsize businesses can successfully land big enterprise clients. From using account-based sales tactics to improving internal communication, she walks us through the steps needed to build long-lasting relationships and grow your presence within larger organizations.

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"If you're going after big companies, the most important thing you can do is research before you go in. Learn everything you can about them." — Dr. Barbara Weaver Smith

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Listen to The Episode!

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Top 3 Reasons to Listen

Strategic Insights on Landing Big Clients: Learn how to shift from winning individual contacts to securing entire departments and organizations as clients.

The Whale Hunter's Process: Discover a proven methodology for targeting, landing, and expanding within large enterprise clients.

Overcoming Sales Challenges: Gain practical advice on addressing common fears and obstacles when selling to big companies.

Follow Dr. Barbara Weaver Smith on Social

Website: https://thewhalehunters.com/

LinkedIn: https://www.linkedin.com/in/barbaraweaversmith/

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More About Today's Guest, Dr. Barbara Weaver Smith

Your guide to bigger deals with bigger customers

As the founder and CEO of The Whale Hunters, Dr. Barbara Weaver Smith specializes in helping businesses land big sales and transform their companies. With a unique background that spans academia and business consulting, she has dedicated her career to guiding small and midsize companies in strategically targeting larger organizations. Dr. Smith is the author of "Whale Hunting with Global Accounts: Four Critical Sales Strategies to Win Global Customers" and co-author of "Whale Hunting: How to Land Big Sales and Transform Your Company."

Before establishing The Whale Hunters, Dr. Smith served as an English professor, college dean, and president of a statewide nonprofit agency, bringing a wealth of leadership and educational experience to her business endeavors. She is renowned for her expertise in bridging gaps among corporate silos, building powerful cross-functional teams, and fostering internal cooperation within organizations.

Dr. Smith has successfully helped numerous companies build strategies for big, complex deals, working with both small and midsize businesses as well as large corporations. Her mission is to help businesses understand the importance of an account-based approach, improve internal communication, and strategically expand their reach within larger organizations. Through her proven methodologies and deep understanding of sales processes, she empowers companies to develop trusted advisor relationships and achieve significant growth.

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Key Topics Discussed

• Landing and Expanding in Large Organizations: Dr. Smith emphasizes the importance of not just winning over individual contacts but securing entire departments and organizations as clients.

• The Whale Hunters Methodology: Inspired by Inuit whale hunting practices, this methodology involves a systematic approach—Scout, Hunt, and Harvest—to land big clients.

• Team-Based Selling: The significance of approaching sales as a team effort to match up with all influencers and decision-makers within a large organization.

• Understanding and Mitigating Buyer Fears: Identifying potential fears that large clients may have when dealing with smaller vendors and developing "fear busters" to alleviate those concerns.

• Account Management and Expansion: The importance of separating sales and delivery teams to focus on both providing excellent service and seeking new opportunities within the same organization.‍

• Systematic Growth Strategies: Utilizing a structured process to evaluate and plan the next steps in expanding within a large account, ensuring no opportunities are left on the table.

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Key Takeaways

• Research is Crucial - Before approaching a large client, thorough research is essential to understand their needs and how your services align with their goals.

• Develop Fear Busters - Create strategies to address and alleviate the fears that large organizations may have when considering a smaller vendor.

• Team Collaboration is Key - Foster strong communication between sales and delivery teams to ensure consistent service and uncover new opportunities.

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A Transcription of The Talk

Mark Drager: So Barbara, I used to tell my team that we win over people and not accounts. And that's because I would win over an amazing prospect and an amazing client, we would work with them for a few years, and then they would be promoted, or they would move to a different company, or they would leave the role. And then suddenly, we would just kind of stop working with that company or organization. And I think if you're listening today, and you've had that experience yourself, where you tend to win over people and not organizations, I think this conversation is going to be really impactful for you. Because you are an expert with the whale hunters at helping business owners like me win over more large accounts, more enterprise clients, more Fortune 100, Fortune 500, international clients. Rather than just win over the person, we want to win over the departments, we want to win over the companies, and we want to keep our clients forever. Help me with this challenge I faced and others face.

Barbara Weaver: But you're absolutely right about the challenge. That's why it's so different. It's so hard for companies like yours to take that step because it's not like anything you're already doing for the most part. And you're absolutely right, it's about how you land the organization and then keep expanding inside that organization.

Barbara Weaver: I think small business owners leave millions of dollars on the table when they do get a hold of a bigger company because they settle for that piece of it that one person or that one little group is responsible for, instead of using that opportunity to grow it throughout the whole company. So one thing that I always recommend people do as a small or midsize company is to make that sale as a team, not just send one lone ranger in, but send people who match up with all the people who are going to be the influencers of that deal.

Barbara Weaver: When you get into bigger companies, they have more buyers, they have a group of people that are going to influence the sale. And so you have to meet them, to begin with, and you have to be able to speak their own language, which usually one person can't speak the language of all the people that are influencers or the end buyer. We do a lot of work teaching the salespeople how to be orchestrators and how to engage subject matter experts who are not salespersons in the sale, which terrifies the salespeople. And it terrifies the SMEs as well because they don't want to do that. They don't want to sell anything, they can't be part of that.

Barbara Weaver: So there's a lot of internal training that happens to make that really work. And when you get good at it, it's just amazing what you can accomplish because you have a whole team of people who know how to speak to a buyer. Because that person is not usually in the role of buyer, they're usually in the role of an IT person or a marketing person or some kind of customer service or something. So the better you can match up with them. I mean, that's one big thing that we do at the beginning, is get that happening.

Mark Drager: And so what you're really describing is a shift from sales, where we know that there's a buyer or a customer, whether this is a complex situation or not, we know that we have our customer. And then once we've won over that customer and we notice, oh, they're part of a department, or they're part of one location where there are multiple locations, or there's more depth we can go into with this client in this account. It really does require a shift in thinking approach and investment.

Mark Drager: It seems to be a very different game. I mean, I've built most of my agency and most of my career working with two types of clients. We had our corporate 100, and corporate 500 clients, and we found ourselves within a large insurance company working with, let's say, group benefits. And then from group benefits to retirement planning, and from retirement to retail ops, and then from retail ops to events. And we were able to, over the course of six, seven, eight years, spread across the organization. But for me, it was all very organic. It was not a planned, targeted piece where I asked Department One to connect me with Department Two to pitch over here. And so this is a very different type of thinking and a different type of approach. And if we do not have that account-based approach to sales, what would be the first few steps for us to be able to start to make this shift to essentially stop leaving money on the table?

Barbara Weaver: Yeah, well, the whale hunters model is loosely derived from how the Inuit people hunted whales. That's how we got the name of the company. The process is called Scout, Hunt, and Harvest. And so we start with scouting, which is identifying the characteristics of your ideal bigger customer. Now, the size of a bigger customer varies according to the size of your company and what you're doing now.

Barbara Weaver: Now, if you have an average sale size of 50,000, you want to look for something that's 10 to 20 times bigger than that, to define what's big for you. So not everybody's going after the Fortune 100 right away. And so the first step is that scouting piece, figuring out who in the world or in the vicinity, or whatever you decide is that region that you're going after, would be likely prospects for you to talk to. So it flips marketing on its ear because you're not just sending a message out to the market to see who responds to it, you're deciding these are the people that I want to do business with. So your marketing is directly to those people. That's how you start and then I'll let you speak.

Mark Drager: And so in my mind, it's helpful to consider each business unit by department or by region or by P&L if you can get insight on that. Organize Business Units, consider each one a customer within a larger organization that you can then leverage. Like any customer, you would leverage the sale, you would leverage internal referrals. It's almost like its own marketplace. You have to consider that. Market more clients.

Barbara Weaver: Yeah, exactly. Think of the mass market. Whenever I speak to a group, I always like to give an example of a big company. They have no idea how big it is. I'll just give one example. Caterpillar has 789 companies that are part of it. So you could do your whole life's work, selling things to Caterpillar if you had the right things to sell. And so it's worth a lot of time and effort to learn everything you can about Caterpillar before you go and talk to anyone in your little corner of that world.

Mark Drager: And then once you have them in, once you have, let's say, the first win, and you want to turn that first into a second, into a third, into a fourth. Is it as simple as saying, "Hey, Jane, this has been a great project, and I'm looking forward to doing more work with you. But I've noticed that X department over here on the West Coast or the East Coast, or there are other people who have your responsibilities or your roles in other departments. I would love an introduction to them." And we can just simply do internal referral-based intros?

Barbara Weaver: Well, that's part of it. But it's not going to just be you who's inside. So if we're talking about service businesses like yours, like mine, you may have many people that are delivering that service. And what typically happens is the sales team doesn't have any more communication with those people. Salespeople are working on something new. These people are all in that company getting to know lots of people and delivering good work. So the first thing is to make sure that the salespeople and the delivery people are always connected. So that learning becomes company learning, not just learning by the individuals. So that's a huge piece of it.

Mark Drager: That'd be establishing more of an account management team as opposed to maybe direct outbound sales or inbound sales.

Barbara Weaver: Well, yeah, you'd have to think of that as a team. And there has to be some sharing of some kind of systematic sharing of information at different points, say quarterly, or every six months, or whatever, depending on the length of the contract. So your company is learning about their company. So you don't just have one point of contact, you have multiple points of contact. And multiple people from your company have those points of contact. And then when it's time for sales to come back in and lead that next sale, these are the resource people that need to be involved in that decision-making. Otherwise, you've lost a huge amount of knowledge that can tell you where those issues are, or if you know how to imagine where the issues are. For example, if you're a sales trainer, you're always going to sell to the sales VP or sales unit. So the people that you're working with, some of them are going to know other people. So you do it all systematically. That's the biggest thing, make it a system, not just a lone salesperson going in and the delivery people are no longer part of it.

Mark Drager: But the real trick is to sit down on some kind of cadence, whether that's monthly or quarterly, right, and look at the entire account, look at the entire organization. And strategically pick, select, and plan for ways that you can move deeper into the organization. So where are our current clients? How do we sell to them more often? How do we increase our average deal value? How do we get more deeply into the business unit we're part of? But then, how do we actively go after the other units as well? So this is no longer a passive approach. This is very targeted.

Barbara Weaver: Very targeted. Absolutely. So we have a system that teaches companies exactly how to do that when you're ready to sell your next thing to that company. We call it "search for ambergris" because ambergris is a substance that whales secrete. And when it lands on a beach, it kind of turns into gold. It's fragrant, and it's been used in perfumes, and it's not even legal to have it in the US anymore. But in other places in the world, it’s the most valuable substance. So that's what we're looking for inside that whale: where's the ambergris in the whale?

Barbara Weaver: We train people to do a workshop. We usually do three companies at a time. So we have three groups of people in this workshop, going through a 10-step process of how to decide what's their next move. It has to do with what we know or think we know about the company? Who do we know or think we know? What do they think about us? You know, things like that. And then what are the possibilities of what we sell down one side of the paper? And across the top, what are the buying groups that either we know or we don't know yet? And then we kind of figure out how much of that buying group's buy do we have already? Most of it, we don't have any. And then we strategically calculate what's the next best move. We make that calculation based on two numbers, from one to 10. One to 10, how hard is it gonna be for us to do this, one being easy and 10 being hard. And the other spectrum is, how much value would it bring to the customer. So is this like a five-point value or a 10-point value? And then you get kind of a little number that suggests which are the most likely places for you to go next. So we do it all really systematically so that you have a process that you do over and over. Like maybe when you do your strategic plan every year, you do that with your big accounts, or you can do it on a different kind of cadence, but cadence is the word. Have a plan.

Mark Drager: That's great. It's almost like lead scoring in terms of an opportunity point of view. Now, you don't know exactly. Now, in my experience, I've run an agency since 2006. And we've been fortunate enough that the vast majority of our work is direct to clients. But we've also, you know, been not white-labeled, but we've been brought in as a trusted vendor for other organizations, for consulting firms, for ad agencies, for others. One thing I've noticed, by our business model approach, we were project-based. Even if we had repeat clients, repeat accounts, and repeat business logic-based. And the deeper we would get into an organization, and again, I've noticed this with others, the more the account is worth, the trickier everything becomes. Now every business unit, every touchpoint, every client experience, every story runs the risk of tarnishing all of the hard work you've built up.

Mark Drager: You push too much into a business unit that maybe frankly, you kind of oversold or didn't have any business. Maybe you tried something new, or maybe for whatever reason, you had a very challenging prospect who did not understand what was going on. And now they are walking the halls or on the Slack chats of your client, and they did not have the experience that you wanted. And so what I have noticed with others especially is the more the account is worth, the higher the risk of losing that account is, which is the higher impact on the business. And it makes everyone afraid, cautious, and conservative, and they stop focusing on value. And for me, frankly, it's a great competitive edge because we can come in and just go so much further faster. But how do you build a moat? Or how do you protect these accounts so that way you don't run the risk of losing them, but also you don't build it up so much so high that one mistake, you've just lost, you know, 30 million off of your revenue because that one client disappears?

Barbara Weaver: Well, one way is to not think of having a single account manager, which usually we do. We have an account manager who's supposed to manage the account and sell the new business. And if they manage the account really well, they don't have time to sell the new business. So I think always you should have an account manager who's only responsible for doing what you've promised to do. And keeping track of doing that, keeping track of all. I mean, they spend their time putting out fires in many businesses, especially if it's a software business. I'm sure that's probably true in agency businesses, we've worked with a lot of agencies, and that's one of our biggest types of clients. So I always recommend that you separate the delivery process from the new sale process, which means you have to have complete transparency and communication all the time between the sales team and the delivery team.

Barbara Weaver: Because you're right, the quality of that delivery, and the more people that are engaged in it, the more possibility you have for mistakes or misinterpretations or whatever. What I have found in most companies, the account executive is very frazzled with putting out fires, managing the scope, exceeding the scope, making sure that the client gets everything they want, and everything we promised, and more. And they don't have the time, they don't typically have the mindset of where's our next work coming from. I don't think typically the same person unless you're the CEO, and that's what you do, you're usually not the right person to do both of those roles.

Barbara Weaver: And I think that account management is a role that involves a team of people who are providing the service and then selling. It involves a team of people to go after the next

sale, and there's some overlap in those teams because that's where your SMEs are gonna come in for your next sale. But that might be in a different department down the hall, it might be in a different country, you know. So everything about that is how to manage your resources, especially your human resources. I don't know if you know, the second book I wrote, which is "Whale Hunting with Global Accounts." And that's for somebody that's already, they're still small. They've got a few big accounts, one of them, maybe they really could go to another country with that account. And so how do you just think your way through that?

Mark Drager: I think you've really hit on a great point. And I've noticed it with my clients. I've noticed that with our own business as well. When we separate those who are responsible for selling from those who are responsible for delivering, sales go up. And part of that is, I think there's a natural hesitancy. No matter how confident you are, no matter how good you are, there's a natural hesitancy. If you're the one pitching, selling, and spotting the opportunity, in the back of your mind, you're like, "Ah, dang, I got it. Oh, my goodness, this delivery is so complex and so much work." And like when you're just thinking about how do we actually make this happen, someone has to make it happen. And if the person looking at the opportunity is in a very positive, optimistic point of view, which you need from sales, you need excitement, and all of those things, if you're coming in, trying to be that engineering mind going, "Oh, gosh, what are all the details?" you're gonna take the deal, you're gonna kill the deal. You don't have the optimism because you're so worried about delivery. And if you're the type of person who spends all day, every day realizing just how challenging and complex delivery and putting out fires can be, you're gonna come into everything very suppressed, quote-unquote, realistic. So I think those should be completely separated in my opinion as well.

Barbara Weaver: I agree. And it's an investment that's well worth it with big companies. And that's why I say think of them as a market of one. Because when you get really ingrained in a company and you know a part of it really well, then you're so much better equipped to do the next piece of work or the next piece of work. It's so much easier to do it within the same company. Even if nobody knows you in the new place you need to go, you have a reputation, you're already one of them. You know, that's the way you need to present yourself. "We're already part of you. We're already here. We may be over here, but we're already part of this organization. And so we know enough, we don't know everything we need to know, but we know enough to get this off the ground with you."

Mark Drager: It also helps cover some of the expenses of the challenging legal work of filling in through the MSA and becoming a preferred vendor of choice or whatever hoops it is you must jump through to become a preferred vendor. Being able to have that status, making purchasing easy, and having everything set up on the finance side. The more you can do with an organization, the more, as you mentioned, the reputation and the trust that you've already paid. Someone else in the organization has vetted you. You are there to help. And it does come with a little bit more trust.

Barbara Weaver: Yeah, well, whenever you're smaller than the company you're going after if you're smaller by some degree that matters, those buyers are afraid you'll screw it up. They're making a buying decision primarily not looking for the best thing that can solve their problem, but something that will work and that they're not afraid of. And so, once you're already inside, you've proven yourself with one part of their company, that greatly diminishes their fear. And also, if somebody else in their company chose you if they chose you, they won't get blamed for making a big mistake on somebody unknown. So it just, it's so much easier than it is to get in the first time because they're buying out of fear. They really want what you can do, they really believe you can do it better than some big companies that they know. But they're afraid. Either they'll put you under, which they could do, or, you know, you'll fail in some way, and they'll be held responsible.

Mark Drager: That is most people's largest fear when you work in a large corporate environment. And, you know, if you're an entrepreneur, if you're in a scale-up, startup, whatever it might be, but you're the entrepreneur, you're the business owner, you work for a team like that, small and medium-sized customers, we're focused on results, right? Large enterprise clients, the people making the purchasing decision, want results, but they want results that don't... they would rather eliminate risk and uncertainty. Because they need to be able to manage up, they need to be able to justify the spend, and they need to be able to... it needs to look good for their resume and their career path. And at the end of the day, their role matters most to them.

Barbara Weaver: And if they make a mistake in a big sale, you know, they're very vulnerable. They could lose their job.

Mark Drager: You know, they could lose their job, but it could take their career within a smaller industry as well. Yeah, exactly. Word gets out. They can spend 10, 15, or 20 years building their career, and it can be gone in a matter of a few sideways projects.

Barbara Weaver: So one of the things we do with our clients is we call it whale fears and fear busters. Before they ever talk to a client prospect, figure out all the ways that they might be afraid of you. We talk about four kinds of fears: fear of change, fear of internal conflict, fear of more work, and fear of making a mistake, which is the biggest fear. So they just write down what are all the ways they would be afraid of us in those categories. And then what do we have as fear busters, which is where marketing comes in, you know, specific tangible things that we can use.

Mark Drager: This has been a great conversation. I've been speaking with Dr. Barbara Weaver, who is the author of "Whale Hunting with Global Accounts: Four Critical Sales Strategies to Win Global Customers" as well as the co-author of "Whale Hunting: How to Land Big Sales and Transform Your Company." I have one more question for you, and it's the question I love to end every interview with: if you had one tip or one strategy that would help all of us sell more, what would that be?

Barbara Weaver: If you're going after big companies, the most important thing you can do is research before you go in. Learn everything you can about them.

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Resources & Go Deeper

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"5 Keys to Successfully Selling to Fortune 500 Companies" – HubSpot Blog

This article outlines essential strategies for selling to Fortune 500 companies. It emphasizes identifying the right contacts, mapping out the decision-making process, and preparing for extended sales cycles. Establishing credibility and providing immediate value are key to building lasting relationships with these large enterprises.

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"Largest Sales Organizations in 2023" – Selling Power

This article provides insights into the largest sales forces in America, offering a breakdown by industry and showing how businesses with large sales teams approach Fortune 500 clients. It also explores the challenges and trends post-pandemic, which are crucial when navigating sales to large organizations.

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"Enterprise Selling: 5 Tips to Land Fortune 500 Accounts" – Inside Sales Solutions

This article focuses on mastering enterprise selling, particularly when working with large companies like those in the Fortune 500. It includes practical tips like pinpointing the purchasing power within large organizations, being persistent throughout long sales cycles, and refining your strategy as you engage multiple stakeholders.

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