Ep. 2 | What the Early Days of Salesforce Can Teach Today’s Sellers with Joe Williams - Part 2
The Selling Economy, hosted by Jeff "Yosh" Yoshimura. Guest: Joe Williams.
https://www.youtube.com/watch?v=RRcGlY0BLok

Introduction

[0:00] Somewhere out there right now, a sales rep is walking into a meeting and sitting across from them is a buyer who already knows more than they do. That's no accident. AI has created the biggest shift in selling in 30 years. And millions of sellers and the leaders behind them are living it every single day. I'm Yosh and this is The Selling Economy, a show about the people in the middle of that shift and the stories of what's working now and the lessons that they've learned along the way. The Selling Economy is presented by AnyTeam, the team behind every rep.

DIY AI and the Limits of Building Your Own

[0:36] Let's talk about DIY. What's your perspective on DIY AI? And DIY AI could mean a lot of things to different people. It could be, let me go take Claude and go build uh agents inside of Claude and then connect it to to the different apps within the enterprise using MCP. Uh it could also mean that I'm going to have a GTM engineer build bridges between multiple AI applications. In the early days of Salesforce, DIY was also very common. It was like, "Oh, hey, I can just take a spreadsheet or I can just take a contact manager. I can go do DIY." What is your perspective on DIY today?

[1:08] Yeah. Well, I just want to comment on that last statement because when we were selling against Siebel, most of the end users weren't using Siebel. They were supposed to, but they were doing things in Word and Excel because they were sick of Siebel. So, the DIY always existed. But today with AI, to answer your direct question, I'm a good example of it. Personally, I use Claude. I have Claude, but it doesn't do anything to update the context of what I'm doing around me. Like, anybody else I'm working with, anybody else I'm dealing with doesn't have insight into what I just did in Claude. It's not a doing it yourself is definitely a reality. There's a lot of opportunity to do things to better my personal experience as a seller, but from a business perspective, if I have a team of three or four people, I need to update those people. They need to be in real time in sync with what we're doing.

[1:59] And a build it your own, do it yourself doesn't really cut it. I mean, I just made this comment to a friend the other day. He just started at another company as a regional salesperson. I was talking to him about what he's doing and I go, "You have a nice house. You have a nice car. You didn't build your car, you bought it. You didn't build your house, you bought it." And even if you said you built your house, you gcded it and you had people build it. You just oversaw what they did on that. Put AI into the same class. Like there's tools out there, great tools, but I would use a platform for building an enterprise class solution as opposed to trying to build my own AI.

[2:33] Yeah. And I think we're seeing, you know, really strong proof points of that in the applied AI application space. So companies in the legal space, in the customer service space, building kind of full-scale applications where you're not seeing teams say, "Oh, I'll just go build my own legal AI application." There's companies that have already done that. And I think you'll see that in other areas of the applied AI kind of in the app space across the board.

Why Automating More Activity Does Not Create More Pipeline

[2:57] Yeah, there's an example that I just posted on LinkedIn recently a few weeks ago where a company with their SDR specifically, which is an area that you could definitely use AI for, but they ultimately, and I'm going to concatenate the response, they automated the existing behavior that they didn't change the structure. They didn't change how they they just did more of the same and they ended up with a bunch of noise. It wasn't more pipeline. They didn't displace their SDRs. They just did more of the same. They just spammed a bunch more emails out there to people outbound. That's not the right way to do it. You need to take advantage of the tool, the platform, and apply it to the new rigger that you're going to use to be of more value to that end user.

[3:39] Yeah. I remember the iceberg slide. Yeah. The famous iceberg slide of little tip of the iceberg up top and everything underneath there underneath. And that was when I think about DIY AI, I think about everything that's under the covers there that somebody is going to need to to maintain, update, and be responsible for ongoing. The pendulum's swinging back the other way, Yosh, already, right? People are starting to think about, well, how much is this costing me in tokens if I'm a CFO, right? How how are we avoiding the AI slop and hallucinations? What about data? What are we risking anything? we like people are starting to think about this in a more holistic way like you say that under the water iceberg that is looming that they got to watch out for.

[4:23] I'd say six to eight months ago people were rushing to AI and even some of the existing tech stack were bolting an AI onto their solution and now people are seeing the results of that going that's not the right way to do this.

How Sales Leaders Should Think About AI

[4:35] Yeah. So what do you think is happening in like B2B sales? If you were a a sales manager, a sales VP, a CRO, how would you you coach and lead a team today? Yeah. So I I would definitely look to deploy an AI platform that supported us in a way that I would reshape how we went to market. That's a bigger thing. people are instituting AI as just a scale or velocity as opposed to it's going to be a different approach because it's a different tool and we want to use it properly. So if I was leading a team today, I would definitely employ some form of AI, but I would do it in a way that augmented what my end users like we talked about this not too long ago about getting that time back. So if AI is a time savers, okay, great. What are you doing with that extra time? Are you giving your team back time where they're in front of the buyer, the end user in a meaningful way? And to me, that needs rethinking the process in which you're running things. It's not just I'm going to add some hypers scale to my sales team. I'm going to change what my sales team needs to do to give them more value added time. And that's what I would do.

[5:47] I would focus on an approach that added real valuable time to the end user which ultimately is going to result in more value to the buying community and they're going to see that and feel that and things going to snowball from there. Yeah. If you ultimately give a seller more time back, you're also going to give the buyer and the customer more time back because now you're you're not going back to that customer back to the buyer with the same questions they already have had answered. or in the role of post sales. Imagine that the sales team had five to 10 to 15 conversations and imagine that when you transition to a post sales team instead of starting off that conversation as as new, you have context from from every conversation that had already happened so that ultimately you can focus on time to value, time to implement and getting that those those users and those customers deployed as quickly and rapidly as possible. And what? Here's the thing, and Gartner said this a couple of years ago at a cso, a chief sales officer conference that I was at.

Why Buyers Still Need Human Sellers

[6:48] The buyer wants the human interaction, but they want it when they need it. And they want it to validate what they think they already know. Remember, buyers are enabled. They're doing a lot on their own. They don't need a seller until they actually want and need a seller. But when they need a seller, they're expecting him or her to come to the table with something that tells them something they don't know or validates what they think they know. Because what the Gartner report suggested at that time was there's buyer remorse. If they try to do this all on their own, they're like, "What did I miss?" Like, "Did I make a bad decision because I didn't speak to a seller?" So it we don't go away. Professional sellers are needed, but they're needed when they're needed and they're needed at the right point in time. If, like you say, we give back time to the seller. We're giving back time to the buyer for that last bit of validation where the buyer's like, "Yeah, I'm talking to Joe because I think this is what we're going to do.

[7:37] This is where I think we are in the process. And again, it's another cliche, but like Lindsay Armstrong's a woman that knows I said this a lot back in the day. No gets you to yes every time. When a seller in a room tells a buyer, "No, we don't do that." Or, "No, that's not how we work." Your credibility goes through the roof. No gets you to yes every time. And I'm telling you, AI gives you the ability to be intelligent enough to say, "No, we're not a good fit for that, but we're a really good fit for that." You've now just educated the buyer, stop them from making a bad decision because you're going to try to deploy your product the wrong way and you had enough moxy, enough intelligence to say, don't do that. You know, you're going to run that Ferrari into the tree.

[8:16] We don't want you to do that. We want you to have a great experience. So, I'm going to say no. That's where we're we're getting to that point where we're going to arm the sales professional to be able to do that, to be able to direct and augment the process where Beller is like, "Thank goodness I spoke to him or her because that helped me." Yeah. Imagine that that flip in that relationship. That's a seller that the buyer is probably going to want to to engage with again over and over because of that that rapport and that trust building. So, I love that. Love that quote.

AI, Trust, and the Buyer Relationship

[8:44] And one other thing on the trust from a buyer perspective, we're talking about the seller in AI. With all this AI, buyers are suspect. They're worried. They're like, "What did I this real? What what I'm seeing there's a real concern. Trust from the buyer perspective is going down because of AI, not up going down. all the more reason for a human to be involved.

Defining the New Selling Economy

[9:03] Yeah, it's uh it comes down to getting close to the business, getting close to to to to your buyer, your champion, but not just the champion, everybody who who is part of that team and really standing behind what you're selling. So that ultimately you can bridge that into a long-term relationship which which leads to an improvement of many ratios that that companies kind of meter and monitor. So NER or NRR is right, net retention revenue. you can start small and grow into into a long-term engagement with that customer. And one of the things that this this podcast is about is about what we call the New Selling Economy. And the New Selling Economy is about not just deploying technology, but it's about a structural shift in how organizations think about adopting and deploying AI. Meaning that if you take the topline numbers of an organization and if it's a public company CFO is reporting on uh the percentage of sales and marketing dollars spent as a percentage of revenue on a quarter by quarter basis. If a company is spending 70% or 60% of that number on sales and marketing of which generally in my experience sales is is roughly 85 to 90% of that number. I've had very slim marketing budgets. But what that really means is like if you deploy AI and if AI was really working, you should see a a change in those numbers. Meaning that you should be able to to impact the organization and have a lower cost of sale, improvement of CAC ratios, improvement of NE or NR numbers, uh the ability to kind of rapidly deploy and ramp reps. So what used to take 3 to 6 months should happen in days and weeks. the amount of time when organizations go through massive account transitions where at the fiscal year you move out a certain number of reps or some some people just kind of move out on their own, but then you do account transition. So you move people into new roles because they've been promoted. So they get a new territory, a new segment, a new set of accounts. The amount of of of really kind of transition that happens there is massive. And all of that at the end of the day hurts the customer because now the customer is sitting on the other side like I have a new account team. I have a new sales rep. That team is not educated on my business. I like the person I had before. So the New Selling Economy is is really about an organizational shift where uh it's not just deploying technology. It's about kind of how do these new organizations look in the future if AI is deployed in the right way.

Rethinking Sales Efficiency and the Tech Stack

[11:30] Yeah. And and I've heard you say this multiple times in recent weeks, Yosh, there truly is a New Selling Economy that's happening right now. It's just whether companies are adopting the new way in which to really take advantage of that, right? We talked about it ad nauseam. Buyers behavior has changed. That's not going backwards. It's going forward. They're enabled. They're intelligent. They they're able to do things on their own. And there's still this stack of technology that companies are holding on to and trying to just put brute force into that instead of realizing there's a massive change and I need to change as well. And you hit a broad brush stroke there because you're talking about like just the headcount allocation, bringing new people on board, the year-to-year process of transitioning from different territories to different accounts, all that adds to that cost of sale and ultimately hurts the buyer experience. like you said, I don't know if anybody's really looking at that that holistically. And then the other thing that you touched upon is nobody's buying product for the sake of buying product today. Everybody wants to make sure there's real value in what I'm purchasing because they have a plethora of technology already. They're like I was on a deal not too long ago, like three years ago at a company and it was ADP to be honest. And they go, we have 200 applications. Why do we need 2011?

[12:46] They they were making a joke, but they were making a point like because we were selling them on this new product and they're like, we have over 200 different applications in this company right now. Why do we need 2011? I mean, they were making a point and I think that's where we are like in this New Selling Economy, companies are being real cautious about, do I really need yet a new widget because I have a lot of widgets, you know? And I think the answer is is you do, but you also need to rationalize what you're currently doing in a way that lowers the cost, lowers the overhead, and makes the bodies that you have more efficient. I'm not a I'm not a big fan of saying you need to reduce headcount. I mean, like there's always a reason to look at rightsizing your business, but human bodies can be used in a number of ways if you're effective.

[13:29] And I think there's a chance for us to be more efficient with the staff that we have, whether they're direct sellers or indirect sellers or supporters. there's a role for everybody. If you can utilize that horsepower, that asset in a more efficient way, your cost will ultimately go down, not up. And again, there's there's always a reason to rightsize, but I'm not a big fan of saying, well, AI is going to displace the amount of people I need because I think you could just repurpose those people to be much more effective and much more valuable and grow your company at the same time.

From On-Premise to SaaS to AI

[13:58] Yeah. I think it's our job to to help kind of educate the world and the world of sellers out there that there there is going to be a new norm. We haven't reached that euphoria yet, but it's coming. Uh, talk us through, you've been through the journey of on-prem, cloud, SaaS, cloud, and now AI. Every one of these journeys required some sort of like technology structural shift, meaning that the companies had to go and replace legacy tools and it's not easy to replace tools that are sitting inside of enterprise. So talk talk the audience through kind of what that experience was was like going from on-prem to cloud and now what your perspective is as these new AI technologies or these AI native technologies emerge.

[14:38] Yeah. Well I mean first and foremost old habits die hard right it's especially if you're the RevOps professional or owner that chose that tech stack and now I'm coming in and inadvertently calling your baby ugly. Right? Like you have something in place. You worked very hard to get budget and resource to deploy this. you have a team that may not be getting the value you want out of it and you're working on adoption metrics and usage metrics and here I come in with this new shiny toy going, "Hey, you're all wrong. You need this." And I'm using that as an example because no matter where we were in those technology shifts, that's what you're doing. You're going from one thing that they have and they're trying to make work and you're telling them they're wrong. I'm being per for a reason because there's other ways of going around it where it's not that dramatic, but that's ultimately what you're doing. you're telling them stop doing this and start doing that. So in order to do that effectively I think one you got to see where people are in the process. Are they objective? Meaning are they willing to think about something different? Because it's a different selling approach. Like so if I hit an account that has a current technology in place that I believe is obsolete. That's one man's opinion. I believe it's obsolete. If they don't believe that I'm selling very differently than if I know they know they have a problem and they want to fix it. if that makes sense. Right? So I would take a very different I say look I understand you're very happy with your new but I do want to let there is something different available to you today to understand and I'll just send them or get them engaged in listening right in some way. Hey I'm hosting this you know me like a lot of my calls aren't cold at this point. I've been alive long enough where people know me. I'm like hey just come have some drinks.

[16:17] Just listen. I'm not selling you anything. but they'll leave going maybe I didn't think I needed it and now maybe I'm more closer to the middle right so that's that's the first thing to understand and respect where that buyer is in their belief system and then from there you have an opportunity to longer some of these sales cycles take over a year right because they didn't believe and they didn't need or quite frankly they didn't need your product at that time it's no other way when a buyer tells you no sometimes it's an okay answer no there's 10 other prospects that you're not focused on right now.

[16:51] Sometimes sales reps get so entrenched and I need to sell Citibank. No, you don't. You want to sell Citibank, but if they're not ready, they're not ready. And that's a hard thing to message up to management. We're like, "No, you got to win that deal. You got to win. There's no deal to win at this point." Yeah. It's about meeting them where they are, right? So, yeah, meeting them where they are matters a lot. But like again, when you have this kind of massive technology shift that we're in right now, I don't

Meeting Buyers Where They Are

[17:17] Think there's any organization out there that's not thinking or talking or deciding about an AI based solution in some way, shape, or form in their business. And I think sales is a ripe opportunity to take advantage of this. So because of that, I have this unbelievable confidence that whoever I'm talking to needs to listen because it's the right time with the right technology shift. And if you don't start thinking about it now, you're going to be left behind because the New Selling Economy is here. Those that take advantage of it early on will be the winners. There's not not everybody's going to win. And there's always lagards and you know there's a price to pay for being a lagard. But uh so it's a long-winded answer to your question, but I think with every shift in technology, there's an opportunity to displace what they have. But you got to be very, like you said, in the moment where they are in the point in time. It doesn't mean that you stop talking to them or educating them, but you can't sell somebody that's not ready to be sold.

[18:10] Yeah. I'm I'm excited to see what uh what transpires over the next 5 to 10 years. I think this world is going to going to look much much different. I think my kids uh your kids and your your grandkids uh their future is going to be bright, but it's going to be much different than how how you and I grew up. So, I just spoke on AI, a place where my parents are. It's an assisted living place. You didn't you didn't know this Yosh, but I literally I just did a

AI, Jobs, and the Future of Work

[18:36] Session on AI and it was for everybody that was a senior. So there they're 70 and older and there's about 60 people in the room and one I'm trying to educate them on what it is and like that. And I said to them I said there will be more new opportunity than displaced opportunity. And they didn't hear that from the media. They didn't hear that. all this job displacement c conversation. There will be changes in what happens. But that doesn't mean you're out of a job. It just means your job's going to be different. And there are jobs that will go away. Just like with the horse and buggy, I didn't need as many horse farms as I do automobile manufacturers. But there will be new jobs. There'll be new opportunity. And the human critical thinking that's required to leverage the new technologies that we're talking about with AI doesn't go away. It's just another tool to be used and employed by by people in the right way.

[19:28] Yeah. So that's that's that's amazing. First of all, amazing that you're you're doing that and giving back. You've always been somebody that that gives back to to the community, gives back to to your colleagues and um that's Joe. You're you're one of a kind when it comes to to to that. I want to kind of close this with a with a rapid fire. You know, quick oneline answers. It could be

Joe’s Favorite Sales Moments

[19:48] A short sentence, but three three real quick quick questions. Your all-time favorite sales moment is question number one. I have a lot of very interesting positive moments. I got I got to talk about two because one is like very meaningful to me. I had spent over 12 months without a sale at a brand new startup. I was one of the first hundred people in the company and I'd been working really hard on a number of deals and I hadn't sold anything yet. Now, I had kids in diapers at the time and everything like that. So, lack of a commission check over a 12-month period is a very long time. But in one evening on a quota of $2.5 million, I closed $6 million worth of business in one evening. It was a Lucent deal and an ADP deal. I'm not ashamed to say that I cried when I when I hugged my boss at the time because it was an incredible validation to the work that I was doing that we were doing came to fruition. But in one night, we closed over $6 million of business against the 2.5 million quot. It was an incredible time. But one of the more fun stories I like to tell that isn't about me. My boss's boss at Oracle, Joe Dartmaleo. I used to call him Joe D. He's a legend at a at Oracle for a reason. The guy was incredible. He was my boss's boss. My boss was Gabe Caviculi. We had an account called Russ Berrie. Now, if anybody knows who the company is, Russ Berrie, they'll know what I'm talking about. Any gift store in any hotel lobby or any hospital when you go downstairs to buy that poor sick person upstairs a gift, that's a Russ Berrie item. They sell the little stuffed bears with a heart in it. They sell little candies. Russ Berrie is the name of a company that does that. Well, we were trying to sell them Oracle Financials against SAP. SAP was a much better application than we were at the time. Oracle was known as a database company, not an application company. But I I knew we had the right solution. I spent enough time with the team to know that we should win this deal. But we had to meet with the CIO who was very biased towards SAP. So I brought my big gun in, not Gabe. I brought my big boss in, Joe D. Joe Debartleo and we're in front of this CIO. You gota you got to listen to this. So we're in front of the CIO and we're literally like 45% higher than SAP. I mean literally like a lot more money and we weren't known as being the better application, but I knew we did well. So I gave Joe all that context before we walked in. The CIO opens the meeting with he's like guys, he goes, "I appreciate you taking the time." He goes, "But unless you come down and meet their price, this deal isn't going to happen." So Joe D sits back and in his Long Island way rubs his nose and goes, "Listen." He goes, "I want a full head of hair. You want a better price.

[22:19] Certain things we're both just going to have to realize ain't going to happen." He literally told the CIO, "I want a full head of hair." Joey D's bald. He goes, "But certain things ain't going to happen." We got the deal. Like it was it was unbelievable. I mean, I'm sitting there as a rep going, "What are you doing?" But again, you learn a couple things, right? Diffuse the situation. It could have been a very tur meeting. The guy laughed. He's like, "Well, listen." He goes, "I'm not paying you the same thing I'm pay." The guy opened up and it and he was willing to do the deal with us, but he didn't want to pay such a premium, but like when Joe said that, it just changed the whole demeanor room. It was human touch. Absolutely.

[22:56] It was it was unbelievable. And again, the good news is we got the deal and won the deal. But I'll never forget like people like Joe taught me how to sell from a human perspective. I had so many examples of where break the tension with something a little bit more human, a little bit more realistic, but you've built the value to be able to do that too, right? It's not just shooting from the hip. So, amazingly, you answered kind of number two, which is like one of your your favorite sales rep manager moments and uh that that that Joe story is is amazing. But if there's another story, please do share. So, favorite sales rep or manager that you ever

Lessons From Great Sales Leaders

[23:28] So, I was working I was out of college two years. So I'm young. Think young 20s. I don't know about selling. I just I was an athlete. So I knew how to work hard. I knew how to persevere and I knew how to compete. So like that made me, you know, in my eyes a good salesperson. So I'm working for this woman, Sharon Dunl. She was the daughter of a Jewish furrier in the garment district in New York. So you can imagine how she grew up like tough hard knock worker, right? We walk into this meeting and I'm selling ADP payroll at this point. And we had never met these people before. We sit down. She reaches across the desk and in a very obtrus loudmouth way, she's like, "Give me your hand.

[24:06] Give me your hand." The guy's like, "What? What are you talking about?" The guy's like, "Okay." He hand he reaches across. She shakes his hand with both hands and goes, "I know we're going to do business together. I can feel it." And I'm like 20 something years old. I'm like, "This is selling like what are we doing here?" But again, she just she taught me how relationships matter and how just the human approach. And again, now she backed it up later in the meeting. She knows what she's talking about about tax filing and all these other capabilities that ADP brought to the table. But she literally met this person by reaching out, grabbing his hand, making him feel like, who is this woman? She's like larger than life and like give me your hand. I'm going to do business. I know we're going to do business together. But again, it taught me like there's a human side to everything that we do. And to to fall short of that and fall into this AI trap that everything's going to be automated is just crazy.

Who Joe Wants to See on The Selling Economy

[24:55] Yeah. I think uh it'd be be awesome to be able to go back to those days of just walking the streets, walking in companies, knocking on doors, building relationship. Amazing. Uh my last question is uh the nomination. Who is one person that you would like to see on The Selling Economy? Who is that one person you would nominate and why? I Well, when it comes to selling, there's one person that I consider a brother from another mother and he's taught me more about this profession than anybody who it is. It's David Renitzki without a doubt. I mean, he's done more for my personal career and for literally hundreds of other people's personal career because he looks at the art, the profession of selling as just that, the art and the profession of selling. And he'll take advantage of technology. And quite frankly, he'll tell you self-professed. He's the worst user of technology a lot of times. He he, you know, I've seen him slam phones.

[25:49] I've seen him throw an iPad like because he doesn't know how to use either device correctly. But uh there's nobody else I would think of Dave Reniski. He he he knows more about this than most and he cares more importantly he cares more about this than most.

Closing Thoughts

[26:02] You and I love Dave and we'd love to have Dave on on the show. So it's our job to get him to be one of our guests someday in the future. So Joe, this was amazing. First episode The Selling Economy. It cherishes and brings back so many good memories. Everything that I've learned from you over the past 25 years. excited for you giving back uh to the future and actually this podcast is part of you giving back is really the best way for us to kind of instruct and inform the future is to learn from the past. I truly believe that and uh I want to just thank you for everything that you've done for me and my career and also for really believing in what we're doing uh with this The Selling Economy and what I'm trying to build with my new company. So, thank you very much uh Joe and uh any parting thoughts from from you?

[26:47] Just we've been blessed to be involved in this industry that's a really interesting industry. The innovation is always there and always feel like we're playing catch-up, but just to be involved with the great people and again, one of my earliest memories of you is your great hair and that hasn't changed. You still got great hair. Well, I don't have as much hair. So, it still looks good to me. But no, listen, we've met and worked with some great people and I never want to lose sight of that. That's what makes this all so special. All right. Thank you much, Joe. Uh, we're gonna close up this episode. Till the next one. Take care, everybody.

[27:17] That's the show. If this one sharpened how you think about selling, send it to one person on your team who should hear it. Follow The Selling Economy wherever you get your podcast and subscribe on YouTube so you never miss a conversation. To learn more about AnyTeam, visit anyteam.com. New episodes every Wednesday. I'm Yosh. So long. Thanks for listening.