#107: Mentoring the Next Generation of Successful Sales Leaders

Speaker A: And what I see happening is a rethinking of go to market models around the ratio, let's say, of uh, how many people are hunting for new logos, how many people are nurturing existing customers, who's focusing on filling the funnel, who's focusing on nurturing that funnel and qualifying and developing deals and closing deals. And I see companies experimenting with that in the chasing the holy grail of increased sales productivity per sales rep headcount. And, and as a measure that I know you and I and our customers appropriately obsess over is how do we get more yield out of the go to market teams that we have in place now and as we grow them and evolve them, how do we do so in a way that better matches the way our customers want to buy? And that's where the Challenger Sale, I think has never been more relevant than it is now.

Speaker B: Welcome to Winning the Challenger Sale where we help you win the sales moments that matter every day. Today we're doing things a little differently as the podcast is taking a hiatus in 2024. This will be our last episode of Winning the Childer Sale for now. So we wanted to take a moment and celebrate. We started this show nearly three years ago and since then we've produced over 100 episodes. We've hosted incredible guests like Alice Hyman, Sam McKenna, Chantelle George, just to name a few. And we've gained so many valuable insights to to reflect on those insights and our experiences. I knew I wanted to bring in someone who truly understands the Challenger journey. And Dan Daldegan is just that, or as I call him, Triple D. Triple D serves as an operational engaged member of our board. He has several high growth enterprises including cloud, software and services portfolio companies including Ziliant, Great Gray, saleshood, revenuewell, Exigy, and of course Challenger. He has had an exceptional career when he served as the CEO of SpringCM and that led to their acquisition by DocuSign in August of 2018 for more than 270 million. He spent 11 years building and leading Salesforce teams in the central US and nationwide. Dan, I could go on and on, but I'm so honored to have you here today. So welcome to Winning the Challenger Sale.

Speaker A: Thank you, Andy. It is my honor and I'm delighted to join you. We have chats like this so often, so it feels very natural.

Speaker B: Yes, I know. I was actually joking earlier that this, to keep this to 35 or 40 minutes is going to be the hardest part. So we're all both going to have to be disciplined on this and usually we have some tequila drink or some bourbon with us. So, um, you know, it's, it's 9:00am

Speaker A: so, uh, you know, this morning it's coffee. Very pedestrian.

Speaker B: It's coffee. Lots of coffee. Yes, yes. So like I said to our listeners today, we're going to run things a little bit differently. So for those of you that don't know Dan Del Degan, he's an incredible mentor and he's my mentor. I've known Dan since 2018. We first met at a Cubs game and I knew right off the bat that we would continue to do great things together. I actually have pictures still, uh, of the day we met, which is pretty awesome. So since I'm the one normally asking the questions, I thought it'd be fun for Dan to ask me some questions and help me kind of reflect. But before we do that, I would be remiss if I didn't have Dan answer a few questions because once again, like I said, he's my mentor. He has so much insight into this space, into this vertical. So, Dan, I'd love the listeners to get a little understanding of your relationship with Challenger. You're obviously a board member. You've been here since the 2020, since I came in. Um, and how and why did you take on that role?

Speaker A: Great question. Well, thank you, Andy. And I'm eager to turn the tables on you and ask some questions too. Uh, I'm sure your viewers will find that novel and refreshing and enlightening. It's a great question because when I joined Marlon after selling SpringCM, um, to DocuSign and I took some time off and I thought what I want to do is go back to doing board work and investing. And I joined a private equity firm, which was a great decision. And the Marlin team had already invested in Challenger. And when I discovered that, I thought, wow, this is the intersection of two of my passions. The investment thesis that I signed up for there, which focuses on expansion stage companies in the technology and tech enabled services space. And then Challenger, which is a, uh, I don't think it's inappropriate to say a spiritual movement, almost a religion that I signed up for in the mid 2000s when I first read Matt Dixon's book. And then at Salesforce, where I was building and leading the enterprise sales team, we adopted Challenger and we started using Challenger with great returns on that investment. And that was the first probably moment in my career when I came to the realization that what I had been saying for a long time, I started finally really feeling, which is that the way you sell can be as much of a differentiator as what you sell. And the Challenger sale, that whole rhythm that we established at Salesforce, really proved that out. And so then later on, every organization I went to, we'd talk about and implement Challenger. And so then it was. There was certain, certain, like, serendipity almost when I came to Marlin and they said, well, Challenger is one of our companies and we'd love for you to come over here and work with the team. And of course, the first thing I did is say, okay, we're looking for a new CEO. I know just the person. And a recruiter said, well, we're already talking to this person in Chicago named Andy Harris. I said, what a coincidence. That's who I want to recommend and go after. And I'm delighted you joined us over three years ago. And so the journey since then has really proven that out that the organizations that you and your team work with achieve these really transformational, to use an overused buzz phrase, outcomes. And I think even today in this economy, it's never been more important to make the way that you sell and the way your go to market team is aligned and trained in the narrative they're using and the methods they follow to be a differentiator for you.

Speaker B: No, that's amazing. And I really appreciate, obviously, all the leadership and just all the institutional knowledge that you've brought to Challenger.

Speaker A: Well, thank you. You know, these playbooks, as we call them, at some level, just become a matter of me sharing all the mistakes I've made in my career. I've been doing this long enough.

Speaker B: Well, as I tell most people, I'm, uh, a recovering relationship sell. You know, until I read Challenger, I was like, oh, uh, that's why, you know, that's where I'm falling down.

Speaker A: Indeed. And it's, you know, the battle scars or the mileage that we have through so many sales interactions and sales cycles, we've been through, you know, victory and loss, including the worst kind of loss to no decision, which I love talking about with sales organizations and sales leaders. And what I really get a charge out of now at this stage of my career is helping accelerate the journey, the learning journey and the productivity curve of young sellers and young sales leaders and in many cases, young CEOs. Of course, to me now, everybody feels young.

Speaker B: I get it. I just got my AARP card in the mail. So, um, I'm with you, Trinity.

Speaker A: That's pretty sharing, right?

Speaker B: So speaking of that, the mentorship, um, which is something you and I have Been talking about a lot recently. You started a company called Talas, and that's a curated mentorship program for sales leaders. You know, obviously we know the importance of mentorship, but talk to me a little bit more about your inspiration for it and why is it kind of fitting that perfect niche in the market of, like, obviously, Challenger, we sell, um, you know, we train large volumes of sellers or big companies. But, you know, where does Talas kind of fit into that?

Speaker A: That's a great point. Thales really was born out of a recognition. And you and I have talked about this so many times, too. And this conversation originally started with a dear friend of mine, Casey Gandham, who's the founder and CEO of a company here in Chicago called Packback. And he's also in a band that I support, and we're in a 501, uh, charitable organization together on a board. You know, Casey and his wife Jess, we had this recognition that mentoring, as we'd often call it when we'd sit down for these dinner meetings. And you and I talk about this so often, the joke was, boy, if we charge for all the time we spent mentoring, we could retire. And we joked about monetizing it, but I think what we were really talking about was, wouldn't it be great if you could operationalize it? Because it feels like formalize it. There's only so many hours in a day that you can set aside for personal mentoring and friends that you've met through the industry and people that you've worked with who reach back out to you. And for you, that includes this very large universe of students which must, you know, double and triple down on that volume for you.

Speaker B: Yeah, I just taught this weekend, So I got 50 new, uh, people that want to chat.

Speaker A: Exactly. So, you know, and it's, it's. There's only so much time you can spend on that. And as gratifying as it is to be the mentor, paying back those many hours in my life when I was the mentee and didn't even realize at the time how, how lucky I was. And now I'm very grateful for it. I want to pay that back, and I want to do it in a way that there's actually some scalability to it and an operational rhythm where we can help many people. And so Casey, and then later on, two more teammates, uh, Derek and Ein, um, who are operationally running now, Thales, this services organization, think of it as a managed service that operationalizes mentoring in a cohort of a small handful, in this case the first one is four players. And we're using the player coach metaphor, very sports oriented. We have seasons, you know, not. Not fiscal quarters. There's a season just like the NFL season we just wrapped up. And these players in the cohort complement each other with similar experiences, but different enough they can learn from each other. The common denominator is it's all SaaS, software, sales, leadership. And that's the swim lane, of course, that you and I grew up in, and so many of our close friends who are, you know, probably going to be coaches in these cohorts going forward. I'm doing the first one now. It's very gratifying. We're learning a lot about how to scale it, and we're very excited about what the future holds for it.

Speaker B: That's fantastic. And what would you say, you know, of this first generation of sales leaders, this first cohort, what are you focusing on the most? Like, where do you think the biggest gap is? From a skill development perspective, there's two

Speaker A: overarching realizations that I suppose shouldn't surprise us, but it's fun to see it unfold anyway. One is it's a very old school, tried and true fundamental. Just like in sports, you grew up as an athlete, you know the importance of fundamentals and being drilled in the fundamentals. And it is how important it is to get your team to follow process and fundamentals and even the most rudimentary things like planning for a sales call, having a sales plan at the beginning of the year, knowing your ideal customer profile and knowing how to qualify opportunities against that. We're used to training reps in that, but training and mentoring leaders and how to coach their reps through that is a, is a different level, a different layer of that journey. And I really enjoy that. So that's one, one thing. It reinforces that the fundamentals still matter, and winners typically are the ones who do the fundamentals better than anybody. Just like a, uh, Michael Jordan, a Kobe Bryant, um, a Tom Brady, a Patrick Mahomes.

Speaker B: Right, right, right.

Speaker A: The other realization is more of a. I, uh, think it's topical given, you know, the post Covid era. And that is that leaders who are trying to figure out, how do you inspire and lead a team that is mostly remote? And, you know, you and I had the benefit of being in an office and learning from mentors around the office, at the coffee machine, walking in the hallway, going out to lunch together, and all that unstructured learning that happens from witnessing the conversations, listening in, asking great questions. A lot of that most of it's not happening today because we're not in the office. So, uh, I think increases the degree of difficulty for a first line sales leader all the way up to a CRO or even a CEO to mobilize, inspire and operationalize a team around a process. And I think we have to be that much better as leaders to overcome that. As we're getting back into rhythm with some partial. Hopefully most companies I'm seeing are two to three days a week in the office and trying to get back to some kind of a rhythm. But leaders have, I think, a bigger learning curve to scale to get their teams productive in this generation of leadership. It's harder now, I think, than it was when you and I came up.

Speaker B: Yeah, no, I completely agree. I learned so much by just listening to other people on sales calls, listening even to our CS team on, you know, what they were hearing from the customers. And I know just that, that you know, we all had the big gong in the office. You know, someone would get a call or, you know, like just all that excitement and energy. And I do generally feel bad, especially for, you know, those, those SDRs and you know, some of those earlier, more junior, uh, people in their careers, because it is definitely a loss. But like you said, we are trying to sort of rectify it and get, you know, people at least in one or two days a week, which I think, you know, certainly helps.

Speaker A: Yeah.

Speaker B: So, you know, one of the things that I know you love to talk about and Challenger loves to talk about, I should say love to talk about it because it is like almost like a horrible thing. But, you know, we know that a lot of sales executives have been struggling with forecasting, um, because of all the uncertainty in the market right now. And you know, indecision being such a huge piece of this, we actually a Challenger did a webinar, uh, last week on indecision. We had 1200 people register just just to show you how prevalent this is. Right. Because people are like, how do I get my buyers to, to be more ready to buy? How do I get urgency around, you know, the problem? And so, you know, what are you thinking from your perspective? You know, as the economy seems to be getting a little bit better. Right. We're all hoping that seems to be the direction. But yet there still seems to be a lot of indecision in the marketplace.

Speaker A: There is. And I think again, uh, as a theme of returning to fundamentals, my observation has been when we come out of economic cycles like this, and I've seen a few of them uh, back in 08, back in 01, I can even go back to 1987. And that's where I lose a lot of the audience. Oftentimes when people start looking around and going, I think that was most audiences, it was their parents that dealt with that one. Um, and coming out of those cycles, what I have found, and I'm seeing the same characteristics now in this, let's call it a recovery, if I can optimistically throw that label on. This period we're in is a return to, on, um, the part of a lot of CEOs. Not just enterprise software companies like the ones I serve as an advisor and board member, but the customers to whom they sell and they work with. Manufacturing, distribution, healthcare, government, financial services, all these industries. There's a return to the fundamentals of getting productivity out of our current go to market team. Evolving and growing go to market teams in a way that makes sense for the contemporary go to market models, including what is a combination of work in the office, work at home, not just for our sellers, but for the customers with whom they're working and to whom they're selling. And what I see happening is a rethinking of go to market models around the ratio, let's say, of uh, how many people are hunting for new logos, how many people are nurturing existing customers, who's focusing on filling the funnel, who's focusing on nurturing that funnel and qualifying and developing deals and closing deals. And I see companies experimenting with that in the chasing the holy grail of increased sales productivity per sales rep headcount. And as a measure that I know you and I and our customers appropriately obsess over is how do we get more yield out of the go to market teams that we have in place now and as we grow them and evolve them, how do we do so in a way that better matches the way our customers want to buy? And that's where the Challenger sale, I think has never been more relevant than it is now is. Matt was one of the first people in his writing that articulated something I had never thought about before, which there's not just a selling process happening, there's a buying process and the customer thinks of their buying process, not their selling process and their rhythm, um, and their culture is determinant of how they go about making decisions. And there's science and art to it. And so I think it's, it's good for Challenger as the, as the performance you and your team are driving is a strong reflection of it because there's a return to that, that fundamental and the pent up demand that any organizations in 23 who are saying, okay, we're going to hold off on that for now. The pent up demand we're seeing the effect of now and pipelines, uh, of organizations that are trying to get to that holy grail of increased sales productivity.

Speaker B: Yeah, I couldn't agree more. And I think that that's, you know, like you said, it's really understanding not just the, you know, your process as a seller, but the buyer journey. And I know I've had, you know, somebody fantastic guests on the show who give me so many good insights, but one of the things that I always, that always sticks with me is that salespeople are on their timeline. Like I want something to close by the end of Q1 because that's my timeline. Right. But your buyer really could care less whether you're hitting your quota. You're not. Right. Their timeline is. So the way to work back is, well, when do you want this, you know, product or service in place? Right, right when needed by. So, you know, almost like a kickoff. Right. Like, you know, what is that kickoff date that you want? And stop thinking about the close date, which is really hard for us as sellers because we're thinking quota. You know, I want to make Presidents Club, I got to get this deal closed. Right. So I do think it's like having sort of that understanding of what your process is and then how do you push backwards from what their process is? And I do think that that shows really a lot of understanding and empathy that we're asking from, from our sales leaders and from our, from our A's, frankly, you, our sales reps. Which is, leads me kind of to my next question. You know, when you think about, as we think about sales leaders and what we're asking of them to do, because I think we're asking more than ever, right? You've got to coach, you've got to have empathy, you've got to, you know, you have a lot on your plate. Um, you got to work with marketing and there's so many different marketing channels. And so we're, you know, obviously expecting a lot of our leadership team, especially that, that middle management, you know, so when they start to think about, and I know you're great at doing this when you're starting to think about your path of, you know, whether it's um, you're going from CRO to CEO or you know, a VP to a CRO, you know, what are some of the things that you really feel like people Need. Need to focus on.

Speaker A: That's a great question. And I came to this realization, as I know you did, because we've talked about this before around really handling your blind spots as a traditional sales leader. When we grow up in the discipline of sales and sales leadership and on our way to. If we're. If all the stars align and we have the opportunity, if we aspire to it, which isn't for everybody, but if we become CEOs, it's natural that we lean in on the conversations we're comfortable with. Like, do you notice every time I go thumbs up, the fireworks? Thank you. Zoom, um, keeps going up. So what I tended to lean in on was the conversations. I felt like, oh, I know what we're talking about here. This is comfortable me. We're reviewing revenue forecasts. We're talking about problem accounts, we're talking about customer success, diving catch saves that we need to do to renew a customer. Talking about marketing campaigns. I know this vernacular. And then I was less comfortable and less likely to sit down with the engineering team, the product team, the finance and GA team. So those blind spots I'm referring to. For somebody who grew up in sales like you and me, I think it's necessary to be conscious of a couple of things. One is know your strengths and know where you are likely to become maybe redundant for that. For that leader. Like, what's really hard for a sales leader is working with a CEO who was a sales leader.

Speaker B: Who's a sales leader. Yeah.

Speaker A: And, um, so I think it's m important to be conscious of that, is let that person do her or his job and not be a helicopter parent as a CEO. Former CRO CEO. Micromanaging your CRO, there's a natural tendency for that. The other is to know where your blind spots are. For me, it was definitely in operations and gna. I mean, I majored in computer science and then went to business school, but I was miles away from being an accountant. I had a rudimentary understanding of how to read an income statement and a balance sheet and interpret it and budgetary conversations. I could feel myself just instinctively saying, okay, this is for somebody else to focus on. I want to get back to a conversation about go to m market and resisting that temptation and being fully present in those discussions with those teams and helping them understand that is an important conversation. Your presence there, your participation, asking intelligent questions, you know, and it doesn't mean you have to drive every decision you want to collaborate. But I found I needed to achieve that balance and not just be CRO plus plus as a CEO.

Speaker B: Right? No, I think that's a really good point. Right, like, we don't, we don't need two CROs.

Speaker A: Right? Exactly.

Speaker B: Yeah. That's fantastic. So I think, you know, this has been a great conversation. I know you want to flip the table now and ask me some questions. I want to give you the opportunity to, uh, to flip the script a little bit. Um, hopefully they will not be too hard, but I think, I think I can go with it.

Speaker A: Now, this is, this is lightweight and probably nothing you haven't heard me ask and talk about before. So, first of all, on this podcast, I'm a huge fan. I've been watching all the episodes and I love the guests that you have from your extended network of customers and partners and friends who are all together on this journey in sales and sales leadership. Uh, what was the original inspiration? And it's amazing going through 100 episodes now, it's been a great run. What do you think the future holds because you've developed this great audience and this, this following, what inspired originally and where do you think it evolves from here?

Speaker B: Yeah, I mean, I can go back to sort of, you know, how I think I learned these days. Right. For me, so much of how I learn is through podcasts. I think as we think about generations and you think about, like, what's easy. And, you know, we all like to do what's easy sometimes. And I think for, for me, there's like four or five podcasts that really help me every week that I listen to that help me, whether it's to your point, like, how do I be a better, uh, leader, helping develop more strengths, how do I, I listen to all in, which is all around finance. And because it's not my strength, right? Finance and the economy. And so I feel like I can really understand that. And so I think for me, that the thought of, and I even think about my students, um, that I teach at Kellogg and really the way they learn and I teach an entrepreneurship class and how I built this is like the best podcast for them to learn from. Right. So if I think about just how we learn these days and where we have sort of the extra time, um, it's great to learn in like 30 minute segments. Right? So that was kind of the inspiration for the podcast was how can we help our prospective clients, our current customers and clients, our, our team members, our employees, like, continue to learn. And also, you know, because we do, we, we tackle different topic each month. How do we help them really understand, you know, what people are concerned about or what they're thinking about. You know, this month, that's great. Different perspectives on that by having four different guests with different titles, roles and perspectives.

Speaker A: I love it. And I think what you're going to find as this audience grows and you continue to evolve this after this, this little hiatus is the, it's going to evolve organically and the audience and these interests and these, these topic areas you're talking about will inspire those conversations and the guests that you'll invite on. And that's the beauty of this. There's an unlimited supply of really interesting people with cool experiences to share that the audience can learn from. Uh, you'll never run out of really, you know, cool, interesting people reach out to. And even in your own network, you could, you could do 10 years of podcasts and schedule them out now.

Speaker B: Yeah, exactly. No, I mean, that's what's kind of cool about sales. Is that what I love about sales? And when I interview people in sales, everyone had a different way that they got to sales. Sales isn't like becoming a lawyer or a doctor where you're like, okay, then I went to school, you know. You know, although I believe sales is very much a profession, you know, some people just kind of fall into it. You know, I've had women, uh, on who were single moms and they were like, oh my God, I have to figure out how to make money. And the sales is the fastest and easiest way for me personally to make money. Or, you know, you, you see a lot of athletes who are like, okay, I'm, um, you know, I played sports in college, I played sports in the NFL and now I don't know what to do next with my career. And so often sales is not that it's just a catch all, but it is something that you don't have to go to school and say, I have to go back to school for four years to learn how to sell. To your point, if you go back to the basics and you really think about, it's something you can learn if you just take the time and you are willing to have kind of that resiliency and grit around it, you just,

Speaker A: I couldn't agree more. And you just hit on m something Andy, that I find, and I know you do too, almost comical. And I'm glad to see the trend is changing. And that was when you and I were in college, when you were in Ann Arbor. How many Michigan professors ever talked to you about professional sales?

Speaker B: Yeah, no one? No, no, I was, I was a psychology major. Which was probably communication. Psychology was probably the closest to. Right. Uh, sales.

Speaker A: Yeah, right, probably. And same for me at Illinois. There was, you know, in the computer science, business curriculum, engineering, you know, communications, all these majors, if there was ever a mention of professional sales, it was tangential or it would be right. And the first exposure I had to is when an alumni alumnus, uh, came back who made a real impression on me and her career had been in sales and she was this bright student from the engineering curriculum at Illinois. They brought this woman back. She was at the time probably, I don't know, 35, 40 years old, which is kind of funny. My, my 20 year old self thought, oh my God, that's ancient. How old? Wow. Yeah. And she was talking about her career path and I was fascinated by it. And it was the first time anybody really had addressed us on this notion of a career path that could be very lucrative and exciting and fulfilling in professional sales and with an engineering or, um, technical background. So that opened up my eyes. It wasn't my professors at the curriculum at Illinois that inspired me, it was talking to alums, which was probably the first time that mentoring ever took a shape in front of me. Like, oh, professional mentoring. That's. Even though I didn't call it that at the time. So the universities now, including your own experience as an adjunct professor at Northwestern, where you're teaching entrepreneurship, it's invariably includes go to market and sales. You know, DePaul has a sales curriculum. Now a lot of universities are adding it. What's been your experience with this changing? So now that our children, and someday their children will not have to wait till they're 22, graduated from college to hear sales for the first time and wonder, oh, well, what's this?

Speaker B: Right, right. I think it's um, like everything, I think having options for people and having, you know, more diversity in sales too. I think part of the problem with sales. Right. You know, currently is that there's not enough diversity in sales. And why I think that is, is because it wasn't widely accessible to a lot of people to either get trained, uh, or to really have those experiences. And so I think what's I'm most excited about is when I look at, you know, Northwestern, I look at any of the programs I'm seeing around, you know, undergrad or graduate programs, I'm seeing a lot more women, a lot more minorities, so people that are really gravitating to, towards sales. And I think that also that notion of like the used car salesman, you know, that like image at least we're probably too old now. The good news is that that image has probably gone away because there's Carvana. No one has to deal with this anymore. But I do think that, you know, that used car salesmen that we all grew up with thinking, oh, well, like, you go into sales because, like, you don't really have any skills or you weren't, you know, you don't have a degree or. And now I think because it's. It's so professionalized and you do get. People are like, oh, actually, this is a really great opportunity for me, and here's a way I can actually learn and hit the ground running versus, you know, you talked about, like, a lot of trial and error in your career. I know for me, I didn't naturally go into sales, but, you know, I realized that, um, you know, product engineering consulting wasn't for me. And I was like, I love sales, I love marketing, but I had to learn the hard way, right? Like, there was no guidebook for me. There was no course I could take. I mean, I never went back to graduate school for that reason, because I was like, I love sales. And there's actually nothing that's going to help me do this better than just, you know, getting back up again every single time I got knocked down. Right?

Speaker A: So, yeah, that's a great point. And, um, you know, a lot of people face that conundrum that was another inspiration for Tallis is that, you know, when you get that stage of your career and it's what's next? Do I go back and get an mba? Do I get an advanced degree? You know, a lot of the learning, the most relevant learning these days comes from these mentoring relationships. And, boy, is it time and cost expensive to go back to school. And, you know, especially if you're at that stage of your career where you're married and you're starting a family, it's a lot to take on. So as you look to this next generation and as parents, it's hard not to. When we look forward and think, okay, what's it going to be like for our children as they get into their professional careers? What do you see changing in professional sales that is not just a function of the technology and the industry you and I work in and the services like Challenger and the methodologies and the religions, if you will, that help us understand buyer's intent and achieve that intersection more reliably. When above a buyer's timing and the seller's availability that creates that magic that we call closure, what do you see happening in the future in sales, especially as we talk about maybe fundamental changes in go to market models, not just in technology companies, but all the customers that Challenger serves.

Speaker B: Yeah, I mean, I think your point about back to basics is so critical, Right. I do think that at the end of the day you need to understand like fundamentally how to sell and following a process around that. But I think that what's really cool is that you have now the intersection of AI and you know, those great skills coming together. So, you know, a lot of people, you know, you always hear the panic, AI is going to replace jobs. We're not, you know, and I don't think that at all. I actually think just like any technology, if used for good, I do think it can be a one plus one equals three. I'm really excited about the opportunity for our sellers to have more value added conversations to be able to really curate that experience for their customers. You know, a Challenger, we talk about Teach, Taylor, take control. And that teach piece is so important. And how do you teach somebody if you don't know as much about their business? You read their annual reports, you read, you know, you find them on LinkedIn, you, you figure out what they're talking about. So you do a ton of research up front before you even have that discovery call, right? The biggest difference, you know, or one of the biggest differences with Challenger is just how much time we spend before we even pick up the phone to talk to that customer versus just jumping on a call and saying what keeps you up at night, right? You know, hate it. Like it's the most cringeworthy thing to me now, right? If I. Two things. If a sales rep literally says to me, what keeps you up at night in the first five minutes? Or opens up and says, hey, I'm just gonna share my screen because I want to do a demo, I'm like, I'm done. Take me out now. And you know, sorry, technical difficulties, I'm out. So I do think that what's nice is like, there's no excuse. I used to say this. I mean, God, 25 years ago, I used to say this to my marketing team when the Internet Internet first came out. So now I'm aging myself triple D. But I used to say there's no excuse for not knowing what your competitors are doing. You have the Internet, like we didn't have the Internet. And I had to figure that out, right? So I say the same thing with AI. There's no excuse to not know. You know, revenues or charts, all those things that help you be incredibly Successful because it's literally at your fingertips. You can type in chat, GBT and get so much information. So.

Speaker A: That's right. Yeah, yeah. It's not hard to show up in a sales interaction with relevance in your questioning.

Speaker B: Right.

Speaker A: And do, and do project genuine curiosity. Right. Which, which leads me to another question. Curiosity we often talk about as being one of those attributes of great sellers. That boy, if you're born with it, beautiful, but you can develop it. It is a muscle that can be developed. What else do you see as some of the fundamental characteristics that somebody can either say, oh lucky me, I was born with it. And that's a good thing about sales is most of these skills you can develop, you don't have to be born with. It's not like, you know, in the NBA if you weren't 66 with a 35 inch vertical or more, you know, good luck. So what, what characteristics do you see that like, like the theme here is kind of timeless. It was just as true when we started our careers as it is now that, that translate to sales success.

Speaker B: Yeah, I mean, I think you touched on a little bit with like preparation. Right. Like I think, you know, there's no, there's no shortcuts in sales. Like, I truly believe you have to be prepared for every interaction possible. Um, you know, based on our Challenger research, we know that people are 57% through the buying process before they often even pick up, you know, the phone to, to get a seller, you know, on the phone. And if they didn't need a price, they probably would go be 85% through the sales process. So we're, we live in a society now where people choose not to talk to people. Right. Like even I see it with myself, if there's a chat function versus a phone call function on a website, I will immediately take that chat function. Right. So if I can send an email versus actually picking up the phone. So we've become a little bit accustomed to that. So I think it's like really making sure that we're actually being like prepared, thoughtful about the conversations that we are having. Because knowing that people, if they're actually getting on the phone with you, it's a pretty big deal that they're actually taking your call. I think the other things that go along with, you know, even being an entrepreneur, you know, obviously I started my career like you as an entrepreneur. I think sales and entrepreneur have a lot of, you know, overlap, I would say like that grit, that resiliency, you know, that and then really, truly being empathetic. To what your customers are trying to do in this day and age. I think, um, you know, we talk about indecision, and a lot of indecision is understanding that your customer has a lot of fear about making a decision because they're scared that we call it fomu. But they're scared of messing up, right? Because in this economy, nobody wants to make that decision that causes them to get fired, to, you know, have something happen with their bonus. Right? Like, we, you know, there's still a lot of uncertainty and fear in the economy. And I think really good sales people have that empathy and are willing to, you know, hold that space for that, that, uh, customer and say, hey, like, I know this is a big decision. I know there's a lot on the line, right. To be really, I don't say, like, confrontational, but really, you know, kind of that trusted advisor with them and really hold that. That space. And so I think those are some things that really translate into not only being a good seller, but being a good CEO.

Speaker A: Uh, that's great. I couldn't agree more. And that's probably why we're seeing. I think there's. There's been an increase since. Since I started my career before you did. Clearly, I started at least a decade before you did in this. And the line of sight I've seen over these few decades is I've seen increase in the frequency with which somebody who grew up in sales ends up in the CEO job. I'd love to double click on that with you because many, you know, you can take many paths to that destination. And I was somewhat of an accidental CEO. I was on a board where we were going to do a CEO search, and it was a logical choice that we all agreed on, and we ended up having a great outcome, and it was a very gratifying experience. But I hadn't put on the board, if you will, early on in my career that, okay, I need or want to be a CEO. I'm curious, what do you see today? And do you think there's value in doing that and having that North Star? Or was your philosophy sort of let the game come to you, and opportunities will present themselves in a natural rhythm, and you got to be ready for them. How did you navigate that?

Speaker B: Yeah, I would say it was a little bit of both. I mean, you know, I was. Early on in my career, I was at Anderson Consulting, and, you know, at 26, I was like, I can do this better. Which I still, to this day, my partner loves to. I mean, we still are Close. He loves to joke with me. He goes, I like one of my favorite conversations ever with you is like, yeah, I don't really think your business model makes sense,

Speaker A: because at 26, you had seen everything already, right?

Speaker B: I seen everything. I knew it. All, right. You know, now that my kids are that age, I'm like, oh, you know, like, you don't know everything. They're like, mom, you thought you knew everything. You know, but. But obviously, like, I didn't, um, know everything. Still don't know everything. But I do think, you know, I always had a vision for myself of, like, wanting to be. Do things a little bit differently or just really connecting the dots on how things could be done differently. One of my favorite, um, articles is, uh, Red Ocean, Blue Ocean. And it's really this idea of thinking about, you know, often a lot of businesses that are started are just taking something that's a competitive space. So Red Ocean, you know, lots of competition. You think about the sharks in the water and just finding kind of this little piece of, like, that blue vision, that little niche of something that's just. You're just tweaking something, doing something a little bit differently. Like, if you think of Uber, right, a great example of where, you know, you had taxis and car services and limos, you had all of that available. They just took something and changed the way you access that. Right. And so it wasn't like they created this whole new company, right. I mean, of course, there are, like, the Teslas of the world and all of that, but I think most entrepreneurs. And so for me, it was really just identifying, like, how can I do things a little bit differently? I think it's also just. I really leaned into my strengths, to your point, uh, Triple D. But also knew when to ask for help and knew, you know, for example, I've always said, like, the second person you should always hire after you hire me is a really good cfo, you know, So I am very aware that, like. Like you, that I get excited about products, sales, you know, marketing, right? Customer, um, success. But you start. You stick a bunch of numbers in front of me. You start talking about, you know, bank covenants and all of that. I'm like, whatever, you know, so. So I think, you know, it's a little bit of knowing your strengths and a little bit of also, um, just that grit, that determination. And then I think. And Triple D, you can. I know this about you, so I can say this. I think. I think salespeople or CEOs are a little bit rebellious. Like, we're a little bit of rebels. We don't always. I remember. So I'm left handed and I used to have trouble coloring in the, in the lines. I mean, literally, you know, when people say, like, you do the box. Right. And like, I remember, you know, being in preschool and in, you know, kindergarten having really a hard time coloring because I was left handed. And at that day and age, people didn't really know how to deal with the lefty. And everything was built for people with right hand. They were right handed. And so I think I've always just been just a little bit of a rebel. And so that has, I think, actually served me well. Whether it's sales or, you know, or any. Or anything to be that matter.

Speaker A: Yes, that makes sense. And you probably really realized what an asset it was when you picked up a field.

Speaker B: Yes. And now a tennis racket. I realize being a lefty in tennis is, uh, you know, I try to find. And that's actually a really good point. Right. Because, you know, for those of that have never seen me in person, I'm only 5:1. Um, I'm relatively small, but yet I always tried to find that sport that like, I could excel at even being short or even, you know, so field hockey is one of the few sports where being short is actually an advantage. Also being left handed is an advantage. And so I'm always trying to say, like, play with what you got. Don't try to be something you're not. Right. You know, so that's.

Speaker A: That's a great mantra. You know, we talk about often the parallels between being a parent and being a leader, not just a sales leader, but being a business leader, and how the life lessons in each of those domains can feed on each other and inform and inspire each other. What thoughts do you have, especially as you have friends who are embarking on, um, parenthood and you give them that sage advice, which I know we've talked about. When you're an expecting parent, it all kind of flies past you like, yeah, whatever, because you're just overwhelmed.

Speaker B: It goes by so fast and you're like, it's actually, you know, like in that moment, it doesn't seem like it's ever going to go by that fast, but that's right.

Speaker A: So what are some highlights of lessons in parenting or in business that for you have crossed over?

Speaker B: Yeah, I mean, so much. Right. I think the biggest one is choose your battles. Right. Um, as, you know, triple. Do you have five kids, which I always joke because I like, I can barely handle the two. I have and the dog. But, you know, I do think it is, um, it is really ultimately choosing your battles, I think, priority. And it helps you prioritize, right? Choosing your battles helps you prioritize what's most important. And I think, you know, having kids and being a working mom helps me think about quality versus quantity. So, you know, I always try to give people, and, you know, this about me, triple D, like, I'll give you 110 in everything I do, but I might say no to something because I can't give it 110. So I think it's one really prioritizing your time and focusing on what's most important and setting those boundaries. And I don't always do a great job of this, so I, you know, I preach sometimes to this, but, uh, really trying to set those boundaries of, like, what are you going to do that's most impactful. And I think it's the same thing with your kids. Like, you know, being a working mom, I'm not around all the time, but when I am with my kids, they are my number one priority. They know that. They know how important they are to me. And so I think that is, you know, number one. And number two, like I said, choosing your battles, whether it's with my executive team, whether it's with customers, you know, just being like, is this really worth going to the mat for? Because I think sometimes we get in our head around, like, we've got to win something for our own ego versus realizing that the outcome should just be the outcome that that makes the most sense.

Speaker A: So that makes sense. It also can help you more judiciously use your energy for the battles that really matter. Because we. It's not an unlimited supply.

Speaker B: I used to always, uh, I had a leader used to always say, there's only so many calories in the day. Right. And so you do have to think about, you know, think about it like calories, right? Like, if you're going to spend 600 calories on this, it better be worth it, you know, so that's a great point.

Speaker A: Yeah. Well, then I'll just go get a snack and get 600 more calories from chocolate.

Speaker B: Right. I was going to say I'm really good at replenishing calories, so I love it.

Speaker A: Well, this has been so much fun. I'd love to continue this and hope, uh, to do so again with you.

Speaker B: Yes, yes. I would say this is, it's so fun to have you on the podcast. I'm so used to, like I said, you know, in person over a drink, but this is. This is just. Just as well. And thank you so much. I couldn't think of a better way to sort of wrap up the podcast as. As we go into hiatus with, um, without having you here to. To join me. So thank you. Appreciate the time.

Speaker A: Well, I'm delighted and honored that you invited me, and I've had a lot of fun with it and look forward to reconnecting again soon.

Speaker B: Awesome. Thanks, Triple D. Thank you. Cheers. Cheers.

Speaker A: Take care.