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Walter Crosby is the CEO of Helix Sales Development, helping growth-minded entrepreneurs build high-performance sales teams and drive repeatable revenue growth with margin integrity. He works with leaders frustrated by underperformance, guiding them toward a performance-based sales culture with transformative results. A University of Michigan alum with a degree from the School of Hard-Won Wisdom, Walter’s sales career spans B2B industries like LED luminaires, financial services, and commercial fire alarm systems. His expertise covers K-12 education, higher ed, contractors, and commercial firms. Known for his love of fine cigars, Walter often reflects in his private lounge and shares insights on sales and cigars as host of the Sales and Cigars podcast.

 

In this episode, Jason and Walter discuss:

  • Align salespeople with company values through a tailored recruitment process
  • Prioritize strong communication skills over industry experience in hiring
  • Implement a unified "Sifter message" to align sales with marketing strategy
  • Ensure effective onboarding and cultivate a self-motivated sales culture
  • Insights from hosting a podcast that blends business strategies with cigar appreciation

Key Takeaways:

  • Sales success stems from a commitment to helping customers make informed decisions, emphasizing insightful questioning over traditional pitching.
  • A tailored hiring approach prioritizes communication skills and cultural fit, ensuring alignment with target customers rather than focusing solely on industry experience.
  • The foundation of a high-performing sales culture lies in effective onboarding, self-motivation, and goal alignment, fostering both individual and organizational growth.
  • A salesperson’s values must align with the company’s culture, making the interview process a crucial two-way evaluation rather than a one-sided selection.
  • By equipping salespeople with a clear "Sifter message" that integrates sales and marketing strategies, companies can enhance consistency and effectiveness in their sales efforts.

 


“Salespeople should be helping their customers. We should be helping them make better decisions. We should be helping them think differently about a problem they may have.”

 - Walter Crosby

Connect with Walter Crosby:


Connect with Steve and Jason:

 

Listen to the podcast here:

 

Walter Crosby- Salespeople Should Help Their Customers

 

Hello and welcome everybody to this episode of The Insight Interviews. This is your host, Jason Abell, and I've got a guest today that I don't know that I've ever had a guest that I said I'm not excited about, I don't know that I would have a guest that I'm not excited about, but I am particularly excited about this one. This guy's a dad, which is very cool to me. We talked about our kids prerecording, which was a lot of fun, but my guest today is Walter Crosby. Walter is an elite salesperson, period, end of story. He sold things from signs to complex B to B systems. He is just a sales guru. Those are my words, not his, but anything about sales Walter knows about. Walter is the CEO of Helix Sales Development. He's also the host of sales and cigars podcast, which is very intriguing to me. Maybe we'll talk a little bit about cigars today, but Walter, without further ado, welcome to the show.

Jason, Thanks for having me. I appreciate the kind words. I'm just a sales guy, long time,
38 years of sales and that's how I look at myself.

We're going to get into sales big time, but I'm going to ask you a question that we ask all of our guests to start off the show, which is today, as you and I engage each other, and you know, the dead of winter, February of 2025, who or what, Walter, are you especially grateful for today?

My wife today, especially. I'm going to get personal, but I've got a lot of family stuff. My parents are aging, they're older, they're in their 80s. One's got dementia, one's just a knucklehead, and it's trying to find that balance of managing, helping, without taking over. So, about 20 years ago, we moved them into our house. They have their own quarters, a space; they’d both be dead if they weren't living with us. This was my wife's idea 20 years ago. Why don't we move them in? Your mom and our daughter are best friends. It'd be really good for both of them to have this continuity. They're like, yeah. My dad comes along with that, and that's a long-term situation, so we're on the other side of that now and she has always stepped up and said, this is we're in this together, and it's complex. I'm not sure I could do the same thing with my mother in law, so I have to be grateful for that.

Man, I really appreciate that answer. You know, we've asked that question over 300 times, and as you can expect, we've just gotten a wide range of answers and that one, I will tell you that that's centering me this morning. As a guy that's in his 50s, I very much understand this sandwich generation that you and I think share with aging parents and kids that still need us from time to time, whether they know it or not, right? You and I talked about that prerecording. So anyways, either way, I appreciate the transparency there, and I feel like we're centered now for a really good discussion on sales. So, you want to move over to sales?

Sure. One last thing about my kid. She's still on the payroll, literally and figuratively,

You and I both. We could definitely have a podcast episode about that. Both of mine are as well but certainly headed in the right direction. So, good stuff there. So, gosh, where to start? You've got, as I did my research, Walter, one of the things that I really appreciate about where we are right now with me interviewing you is you're not a theoretical, this is what I've researched and find out what works for companies, you're in the mix right now. Like, your boots are on the ground, selling things and helping other organizations sell things, and so I just really appreciate that, because our listeners are founders, CEO, C suite, high level salespeople, and I want to start maybe 10,000-foot view, but then get real micro with you. So, 10,000-foot view on sales. If an alien were to come down and not understand sales at all, and you were just gonna riff for a few minutes on what the heck even is sales, how does that work, where would you start, 10,000-foot view?

Actually, I think that's pretty easy. A way to explain it, the way I explain is it, salespeople should be helping their customers. We should be helping them make better decisions. We should be helping them think differently about a problem they may have. It's not about pitching. It's really not about pushing people. I hear salespeople say, well, you know, I'm pushing them in this direction, or I haven't pushed this product. You shouldn't be. You really should be helping them figure out if what you have to offer is of any value to your prospect or to your buyer, and that comes with asking questions and getting that person to think a little differently about what their situation is. So, if I'm having a conversation with this alien, it's really about helping somebody understand their situation and determine if you can help them make improvements, if you can help them get to where they want to go, right? Because we're always trying to get away from the pain and the fear and go someplace that's going to be better, and to me, sales is, if it's done well, it should be fun, we should be adding value to the community, to our customers, and we should be compensated for it. So, it's a great way to make money, but if you're in it for the money, then you're probably going to go askew at some point. And I got into it for money. Actually, that's not true. I got into it because I didn't know what else to do, but in reality, the money was like, oh, wow, this is nice. But helping people and enjoying that process and feeling good about it. Most people think of salespeople as that used car salesman with the blazer that's loud and the short sleeve weight shirt and a clip-on tie and if I could show you a way, right? We need to change that.

Yeah, I've already taken notes just on question number one there. Salespeople should help their customers. All right. Well, let's start to get to get micro. I know you've got very specific things and thoughts that you have on sales, tried and true, I don't want to say theories, but things that that you practice in particular, and you mentioned even before we hit record, even about the hiring process, recruiting. I know at Rewire, we're helping executives all the time. I mean, recruiting is such a big topic of discussion, and there's an element of this that it starts with just getting the right people on board. So, what do you have to tell us about recruiting or hiring?

I mean, at a very high level, we go back to that 10,000-foot level. If you're hiring sales people the same way you hire everyone else in your organization, an engineer, a marketing person, an admin, a manufacturing, a laborer, if you hire everybody the same way, you're probably going to get it wrong with sales, because sales people are different. And when I say that to a leader, to a CEO, they're like, yeah, you guys are weird. You're pain in the ass, you're difficult, you're demanding, and I'm like, all of those things are true.

Yep.

But during the interview process, the salesperson is often better at interviewing than the interviewer, the hiring manager. We can, we can read them, maybe better than they can read us. We can control the conversation better. And when you lose control of the conversation, you're not going to get to where you really need to go. So, at a very high level, I think that is one thing that a business owner can think about, is how can they change their process when they're when they're looking at salespeople and taking them through that that hiring process? Because you want to attract the right people. You want them to self-select in, and you want people that aren't a fit to self-select out. And then during the process, the idea is that we should be challenging them. We should be treating them a little bit like a prospect treats them. And then don't sell the company. Don't sell the role. Don't sell your company until the end. We need to figure out if these folks have the skill sets that we need. So, if we go down into being a little bit more granular, yeah, what is it that you want your salesperson to do every day, every week? What do they need to do to be successful? Who do they need to know how to talk to? And that's where it starts with. If we're not clear about what this individual looks like, sounds like, feels like, you're already off track. And the thing that I've noticed is that if you know it's like, okay, what do they need to be good at? Well, they got to be good at sales. Account Management? Business Development? Farming? What do you want them to do? Cold call? Well, sure, like, okay. So, we have to sort of start there. And, you know, we use a tool to help us figure this out, but I think the big thing for your audience is to understand that they have biases
in their process, and we need to try to, as an interviewer, try to figure out that and keep that out of our conversation. We need try to be objective. And I think there's a there's a big fallacy that maybe we could talk about. The fallacy being, I need somebody who understands my industry. They have to have industry experience, because we're so unique.

Yeah, I want to talk more about this one. Go ahead.

So, you know, and it's a real, it's a real fight, right? This is ingrained, like I have a complex piece of equipment, or I have a complex piece of software, or my offering is very difficult to understand, so I need somebody who sold it before. My argument there to start the conversation to go a little different is, who does your salespeople need to talk to. Is it a CEO? Is it a CFO? Is it a product manager? Like, let's talk about that. Who is the customer that we need to reach that can make a decision? Not say no, not get in the way, not procurement, but who can say yes? Who owns the problem in the budget? And when you get them to focus on that, then you can say to them, okay, who else sells? Let's pretend it's a CFO. Who else sells to the CFO?

What do you mean?

Well, there's lots of people from a sales perspective, that call on that CFO. Who else is adjacent to your industry that already knows that CFO? Already knows their lingo. I'll show my age. Already has a Rolodex of CFOs? If your product is complicated and complex, I get it, but if you can't explain your product, and you're offering to somebody in six to eight hours, then you don't know your product well enough.

That's right.

So we if they know how to talk to a CFO, and the CFO is your buyer, and you teach them the right questions to ask that CFO to help uncover whether or not they're a good prospect, then they're already three quarters of the way there. They know how to speak here, so we don't need the actual industry experience. That might work out great, but let's not limit ourselves, because I truly believe it's a fallacy.

You talked about tools that that you use in the hiring process. Besides that, the fallacy of needing to know the industry, what type of tools were you alluding to?

I mean, we write a very specific ad where the ad describes the individual, so, I consider that a tool that that we're using to like change. If you look at most ads, it's list of accountabilities and responsibility.

Yep, yep.

Boring. They're all the same. If you have an expensive product, it's a premium product, and it does something that other people don't, then that salesperson needs to sell value. That salesperson needs to be able to differentiate themselves. So, we write an ad that describes what they have to do. You got to call on these people, in these industries, and you have to be able to talk about value. You have business acumen. You got to talk about ROI. That's one tool I use a particular assessment that's predictive of success in sales. There's lots of great assessments out there, right? It depends upon what you want to measure. If you want to understand how to manage somebody, there's great tools. You want to understand somebody's mental ability? Great tools. If you want to understand if a salesperson is likely to be successful selling your product to your customers, the assessment that we use dials that in and is predictive to about 90%. 90% being that they will rise to the top half of your sales team in 12 months. More importantly, 75% of them, if we say bad candidate, you shouldn't go there, we're not recommending them, and you hire them anyway, 75% of them are going to fail in six months. Bad news is they don't usually get fired; they stick around.

Yeah, yeah. And then, gosh, as much as we're talking about recruiting and hiring, yeah, it's probably a whole other episode about firing, coaching up, coaching out, firing quickly, or whatever you want to call it. But that might be the subject of a of another show. So, we've got the right people on board. You’ve got something that I read where performance-based sales culture, that's something that's important to you. Tell me more about that.

I'd like to add one more thing. If you hire the right candidate and you don't onboard them well, they're going to leave. So, I got hired in 2008 at a new job. Awful time in this country.

I remember that time. It was tough.

So, I got hired. I show up on a Monday morning as I was requested. They weren't ready for me. It was like a big surprise. HR wasn't even ready. I sat in a conference room for an hour and a half, right? They finally get paperwork going. The VP of sales wasn't ready. Nobody took me to lunch. It was an awful first day, awful experience. The next day, I was like, you know, what are we doing guys? And the guy handed me three books. They looked like textbooks, engineering books, and he said, you know, read these over and we'll talk again tomorrow. So, I go back to my little cubicle, and I open up the books, and it's math and formulas, looked like calculus, all the stuff I hated in college.
So, I spend the day looking at them to make sure, and then at the end of the day, I went into his office and threw the books on his desk. I said, I think we made think we made a mistake. He’s like, what are you talking about? I'm like, if I have to know this and I have to understand this to be able to sell the product, then you got the wrong guy. Because, like, I'm not going to do that.

Good for you.

It doesn’t make any sense. And he called me a couple of names, right, which got us off on a great foot, and I'm like, just let me go play with the equipment. Let me go talk to somebody that's smart here, that can help me understand the big things. So had it not been 2008, 2009, and there was another job opportunity out there, I wouldn't have stayed. I was with that company for 10 years, top salesperson, sales manager, all that stuff that happens, but I almost left in two days, because their onboarding was nonexistent. So, if you're going to bring somebody on, you need to book a salesperson’s first two weeks. Make sure that they are learning what they need to learn that matters to sales, the right words, the right messaging, the right balance. And it's not product. That's not the most important thing. It's, how do you talk about the product? How do we ask the questions? What's our ideal prospect? What do they care about? What are their fears? So, you need to have all of that ready before you find good talent and then get them through that. So, I think that's the continuation of the hiring piece.

Yeah, so well said. I've experienced bad onboarding processes like you're talking about, and then I've experienced the opposite of that, which is everything is lined up. Here's your expectation for day one. Here's what's going to happen. Here's what it's going to look like week one. After two weeks, you should be able to do these three items. At the end of 30 days, we're going to have a sit-down review and talk about how it went. Here's what you're expected to do. The opposite of what you experienced in 2008 also exists, and there is clarity. And when there's clarity, there's just a path for success. Not that that guarantees success, but it's a path to success. But moreover, what I've seen out there is kind of what you experienced, you know? And if it weren't for your own kind of taking control of things there, which I don't know, Walter, I want to say most people don't do, and how much money is spent on hiring and onboarding and all these things to just have it not work right?

It's incredibly expensive to go out and try to find the right talent. And I don't care if you're using a recruiter or not. Making a bad hire is expensive, not just with the hard cost, but what does it do to your marketplace, you know? What does it do for your customer base? I mean, that company I was talking about, I show up at a couple of weeks later, I show up and I give the guy my business card. It's like, hey, I'm the new guy. And he pulls out five business cards from the last five salespeople and says this is the last four years. I grabbed the five cards out of his hand and handed him mine and threw the other ones away. I'm like, this is the only one you need.

There you go.


But most people aren't willing to take the fight. They think that the company should do some certain things, and the company should, but you know, what I try to coach salespeople to understand is that you are responsible for your growth as an individual. Companies should help you. Absolutely. However, there's lots of books available through Amazon, Audible, right? Go read a freaking book on sales to get a little bit better.

Right on.

Go ask people questions. There's plenty of people that are successful, that are willing to help, if you ask, and you're responsible for that.

Yeah. Anything else on the performance-based sales culture? You know, I listen to that, and I think, well, that could be rough, but it also could be just amazingly clear and wonderful. So, in any other aspects, when you say performance-based sales culture that you want to talk about today?

Yeah, if you have the right people on the team, you root out the mediocrity, right? Once you start accepting somebody's less than your standards, the people that are performing look at that like, why are we busting our butt, and these guys over here just coasted along? So, I like to look at it this way. I got invited into an Italian family, very tight knit family. I got invited to their Sunday dinner because I helped out the daughter once. Some boys were picking on her, and I stopped them from picking on her and her old man found out about it and invited me over. That dinner table they would fight and yell and scream at each other all the time with love, right? But they were fighting with each other and yelling at each other. It was very loud and boisterous. Fun. It was exciting. That's what a sales meeting should be like, right? There should be a lot of like, you got me this month, but I'm going to get you next month, and we're gonna compete and all for fun. But you bring an outsider into that sales performance culture, you're not part of the group here, right? Call it a marketing person, engineering person, or whatever, like, you're gonna look at it with a little skepticism. They looked at me with skepticism, and it wasn't till the old man said, hey, he helped out Tina, da, da, da and all of a sudden, I'm getting picked on like everybody else, which was great. So, I think that metaphor is really what a sales team needs to be. You get clear expectations of what you want your people to do, and you explain it to them and then you explain them what that looks like. How they're going to be tracked, how where the accountability is, what that looks like, how we do accountability here, you explain all of that to them in the first couple of weeks, and then you actually do it.

Yeah.

This is important that you actually hold people accountable, and you can do it with a carrot, not necessarily have to use the stick to start, and there's a simple trick to that. Now maybe this helps your audience.

Yeah, talk about the trick.

If you want to create positive accountability, sit down and have a serious conversation with that new salesperson. What is it you want? What is it that you're you're dreaming about that you want to get? And this is sort of materialistic and capitalistic and all those things that people don't like, but if they can tell me that they want to go from a 24 foot boat to a 42 foot boat, or they want to buy a cottage out in the mountains, or they want something that's going to take some resources and some time, that's what I'm looking for, because if they want that boat, we can identify what they got to save to get to the boat. And then, over the course of two or three years, now we have a leverage point. If you don't make the calls, how are you going to get the boat? If you don't do the behaviors that we're looking for you to do, how are you going to get the boat? You told your wife you wanted the boat, right? You told me that you wanted to have your kids go out on a boat and be able to go out for a weekend and everybody comfortable and have fun. I'm using this as a leverage point, but it's for something they want. Now there has to be alignment between that boat and the company goals.

That's right.

And there has to be integrity there, right? It has to be for the right reasons and ethics involved, but if you can find that goal that they want, that they you can help them see a path to saving the dollars that they need to save to earn extra money to do that, boom. Now you've got positive accountability, and you just got to keep that consistent. You gotta help them see the way.

Well, that story, what that’s making me think of is, yeah, you gave an example of a materialistic type of thing, but what I'm hearing from you is the deeper meaning is, you're finding out what's important to them and then helping them get to where it is that they want to go. The tool, the mechanism, the vehicle is, sure, selling the thing, but it's ultimately to get them where they want to go, and that just brings us back to the top of our conversation today. Walter. I'm seeing a thread with you that's weaving its way through our conversation, which is, when we opened up, you talked about a salesperson being able to help their customers. It sounds like when you're hiring salespeople, they're now your customers, and you're helping them get to where it is that that they want to go. Am I connecting things that shouldn't be connected here?

No, no, no, you're 100% on target, because if we don't look at those sales people as our customers from an entrepreneurial point of view, we need to understand their why, and they need to understand our why, right? And that's part of the interview process as well. If we believe certain things and our core values are thing, are these and they're real, right? The entrepreneur created those core values out of authenticity, right? Not just saying oh, this should be good. We should do this. This is what people think we should do. If they're real and the owners are living it, then that needs to be part of your guiding light when you're hiring people, right? This is our culture. This is what we expect our people to do. And you might be the greatest salesperson on earth, but if you're not willing to participate and be part of our culture, then you're not a fit, right?

Yeah.

So that's part of this. That's why we don't sell at the beginning. We got to figure this person out. But you're 100% right? It's a two way street. Everybody's got to win. The company, the salesperson and your customers. If we're not having that that sort of triumphant, it ultimately is going to fall apart.

Yeah. Any particular projects or things as you look over the horizon into the future that you're particularly excited about these days?

I figured something out here in the last six months that I've been struggling with for years. I call it a sifter message, but it’s that idea that the business owner hires a salesperson, and they think the salesperson will figure out how to talk about the product, the service, and then be able to relate that to your buyer, and, you know, it goes back to the onboarding conversation we had. It goes back to being prepared to look for what we really need in a salesperson in the hiring process. We got to give them the tools. The Navy SEALs are an elite military operation. They're highly trained. They train all the time. But when they go out on a mission, there's a strategy in place, everybody knows what they're supposed to do, they're checking their equipment, right? And they know exactly what's supposed to happen and then they can improvise if they have to, if something weird happens in the field. But we send our salespeople out with empty pockets, just assuming that they're going to go figure it out, and I'm here to tell you, it's hard. It's very difficult. You have to have a salesperson that just hates to lose, that will go figure it out and try and try and try. We can be a lot more successful if we give them the information that they need to be successful. That growth, instead of it being really flat, it starts to go quickly, right? We can grow faster if we help them. So, what we figured out is how to get that, get the right stakeholders of the company, facilitate a conversation, and then we come back and provide them that arsenal of weapons or tools, however you want to look at it.

Yep.

And then we can help that sales team know how to use them, how to position them, how to use the questions, when to use them. So, that's what I'm really excited about, is it was a missing piece in what I've been experiencing the last seven, eight years of trying to help business owners get over that, create that culture. Marketing and sales have to be congruent, and this will help that that process.

That does seem exciting. Training and giving your salespeople the same training, the same tools, the preparedness as the Navy SEALs. I like how you connected that there. Walter, tell me, what do we need to know about your podcast, Sales and Cigars? Cigars and sales? What are we doing over there?

Two of my passions, right? Sales and cigars. My wife tells a story that, I don't know, 18 years ago I developed two bad habits, one summer, playing golf, and then cigars. Cigars was something that was social for me. It was outside with my friends. Maybe there was a libation or two involved, usually. So, I retired from golf, but cigars are still a thing. So, I have people on my podcast, and we talk about how we can add value to an audience. The audience is similar to yours. It’s CEOs, senior leaders in sales, sales managers. Sales is a slight edge business, right? You can win or lose for just the silliest of reasons.

Yep, true.

And if we can give somebody just a little tip in every episode we're trying to fill them full of little nuggets. Sometimes it's about marketing, sometimes it's directly about sales, and it always ends with cigars. So, I always ask one question at the end that's always the same. Any relationship with cigars? And what's beautiful is that I had this lady on that I was fully expecting her to tell me, yeah, cigars suck, they're awful, you shouldn't even be allowed to buy them. That was what I was expecting, and she was prepared. She pulled out this fedora and pulled it into frame. This is my grandfather's hat. Oh, and then she proceeded to tell a story about her grandfather; the hat still smelt like cigars, and it brought her back to a 10-year-old girl who was very fond of him. I mean, it was just like, it brought tears to your eyes. So, for me, it's like, I'm having conversations that where I learned something, I have some fun, and the audience gets some tips on sales and how to think a little differently. As you know, these are not easy to pull off. It takes time and resources, so you have to be having some fun with it, otherwise, it's not worth it.

Yeah. So good. I appreciate that story. Well, I know I'll go and check it out, Sales and Cigars, I'm sure wherever podcasts are found. I'm assuming some people in my audience will as well. How would they find you, Walter?

You know, I'm on LinkedIn. It's really the simplest of ways. I post things that I think are value to our audience. I have a website, HelixSalesDevelopment.com. There are a lot of resources there. LinkedIn, you can just ping me. I'm pretty accessible. And what we need to talk about, Jason, is having you on my podcast so we can continue this conversation.

Audience, you see how he did that there while we're recording. So, what am I going to say? No? Come on. It would be an honor to be your guest. I've got relationships with cigars that I can talk about and sales is one of my favorite topics, so it would be an honor to be a guest on your show. I'd love to further some of this conversation as well, so, we can make that happen. Walter, we’re winding down our time here. I just see it where you and I are having further conversations. So, thank you for your time, thank you for your expertise. I mean, starting off with the answer to your very first question, and then ending with your story of your guest on your show with the fedora and the grandfather, yeah, I just appreciate your authenticity, your transparency, and it sure does seem like you know a thing or two about sales. So, thanks for your insights today. I very much appreciate it.

Thank you. I appreciate the opportunity. It was fun.

We'll talk again soon. Walter Crosby, the guy is such a good salesman that he sold me on being a guest on his show before we were recording our show. So, I don't know. That's the epitome of a great salesperson, but I really enjoyed that conversation. The guy is definitely the real deal. I just I really like how he started and how he finished, which is salespeople should help their customers. And there's all kinds of things around there, from how you recruit, how you onboard, clarity is key in equipping your people to do the job that you've tasked them to do, not just assuming that that they can go ahead and go do it. So really appreciate that from Walter Crosby, but as we say at the end of every episode of The Insight Interviews, it doesn't much matter what my insights are, but what really matters is what were your insights?

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