Avoiding the Five Sales Pitfalls That Prevent Long-Term Success

Some of the best work we’ve all done here on the call has been in situations where we’re relaxed. Right? We don’t feel that pressure. We don’t feel like something’s gonna be judged if I don’t go in the right direction. And when you have that ability to feel that calmness go over you, you’re able to make some of the best decisions. You’re able to make it with some more authority and with confidence. And that’s what I always teach those new leaders is take your own shackles off and be who you are. This is Revenue Makers, the podcast by Six Cent, investigating successful revenue strategies that pushed companies ahead. So Simon, what do you think it would be like to have worked at Salesforce or salesforce dot com right before the IPO? They’re under a hundred million dollars and you’re selling right next to Marc Benioff. I mean, that’s crazy. Imagine telling a David and Goliath story and Salesforce not being the Goliath in that story. Well, today’s guest is Chris Lee. He’s a CRO of Zilliant who’s actually a CPQ software platform, but his background is exactly that. He was at Salesforce in the early days. He was at Siebel. He was at DocuSign before all these companies were the companies they are now. And he has got some pretty amazing stories and insights. And he talks about capturing lightning in a bottle, and he takes it with him in terms of how he builds his next team. So what a great conversation today about team building, success, and failure. And I think, you know, just having had those experiences, for him to take those learnings and, like, do it again and again and again at the next series of companies, I think there’s a whole lot of learning for us in just hearing what makes a great team and hearing how to hire the right people and hearing how to promote the right people and establish the right culture. It was just really unique and an interesting perspective. Absolutely. So let’s dive into this conversation. There’s a lot to learn here. Let’s do it. Chris, thanks so much for joining us. Really looking forward to the conversation today. So just to throw a baseball bat right at you, because why not? You have this background of having been at some pretty amazing companies in the early days, Salesforce, Siebel. And I can’t even imagine the learnings from taking those companies from sub hundred million dollar and being on these journeys with them. As you’re continuing on in this career of yours, which is epic, I would say, at this point, what are some of the learnings or some of the things you’ve taken with you? Like, if you hearken back to those days at Salesforce, for example, that you apply even now if you were to move even into a new role or if you’re building a new team, like, what goes with you? Because I can’t even imagine there must be so much. First of all, thank you for having me. It’s an absolute pleasure. And it’s these type of questions and conversations that I love to have because it takes me back in time to those really special moments. And to answer your question, Adam, I think that the things that come with me as I move through my career, I think the learning points are companies like Siebel Systems, salesforce dot com, DocuSign. These are all organizations that when you’re with a company in the early stage, you get to see the potholes. You get to understand what is it that you can’t solve because you don’t have the dollars or the resources, and you figure it out. So when you run into an issue or a challenge, suddenly it’s more about, hey. What can I do to solve it on my own versus let me call this division of the company and hope I can get ten people to jump in or a partner or so on and so forth? So it’s just learning experiences that you respect as you go through and go in some of these other organizations that you can learn from those and you can put them into action in some of the more global companies that I start to work with. And they’re learning experiences that helps you understand what your capabilities are as an individual, and it’s not always the sky is falling. You always know that there’s a way out of it. Yeah. And that’s so great. And I feel having had the experiences that you’ve had, do you find that when you’re jumping into a new role, it’s like, okay, all over again. Like, the same principles are a thread through each of them where it’s about getting a great team in place, great sellers, great culture. Like, how do you really go about building that? Saima, great question. It’s almost like you have this blueprint. There’s this idea of trying to capture lightning in a bottle of what I experienced at Salesforce early stage pre IPO. And it’s that blueprint of what was it that made that company so great, why for ten years nobody left the organization. And it was a lot about building a team that believed in each other, that helped each other, that really wasn’t about playing politics. It wasn’t about backstabbing to try to figure out how one can look better within the organization. It was really about this David versus Goliath kind of mentality where you brought folks in that we had a common enemy, which was the big eight hundred pound gorillas at the time, which were Siebel and Oracle and Vantive and Clarify and Microsoft. And you really came together as a group to try and win. And that’s all you were really trying to do was win. And there was so much pride in doing it. And it’s something that as I’ve continued to grow and move into different positions and different organizations, and there is a recipe. But if you have one of those pieces that’s ever so slightly off, you can’t capture that lightning in a bottle. But even if you get ninety percent there, you’re still a lot better than anyone else that hasn’t grown up and reminds me of the saying that we have internally at sixth sense, and it permeates everything. You gotta wanna. And if we can find more people who will hold on tight to that, we’re gonna be great. Yeah. And it’s also bringing in folks that haven’t been through that experience yet that you can see that excitement on their face. They have the hunger to want to do great things, And it’s also being able to bring folks in to the company that they haven’t experienced big success yet, and they want to learn. They’re hungry to learn. And there’s something in their why. Like, why do they do it every day? And there’s something in them that’s driving them, and you wanna also embrace that. And it’s a special type of person. But when you see them, you’ll know that’s who they are, and that’s who I bring into each one of those organizations. If you double click a second on, we talk about the blueprint itself. Right? And obviously, the largest piece of that is people. What are some of the other major pieces that brought that lightning into the bottle beyond people? It’s also just the overall view or messaging coming from the top. Right? It’s the CEO. And they also have to have that energy that want to succeed, but do it in a way that you’re enjoying it. You’re having fun with it. And I can tell you that working with CEOs like Marc Benioff and Keith Kroc when I was at DocuSign, These are folks that enjoyed the hunt, if you will. And that permeates across the entire organization, that level of energy, that level of confidence and excitement. You know, I remember two situations where one with Marc Benioff, it was classic. It was David versus Goliath. And here we were this little company and he takes out a page in USA Today that says, as a little boy on a blackboard saying, I will not give Siebel my lunch money. I will not give Siebel my lunch money. And then the caption was, don’t be bullied by the big CRMs. It was a classic, and the response that he got from it was even better. So suddenly, the publicity went through the roof of this little tiny company, which was great. The other is someone like Keith Crock. Keith was so energetic at DocuSign, he would literally come out on a corporate kickoff and be doing high kicks of the level of excitement and tell a great story about how DocuSign was you know, he was living an experience using DocuSign and would tell this unbelievable story. And the passion that would come through was, again, just so contagious. And I think that a great company, it starts from the top. And that’s one of the other key pieces of the blueprint is making sure that you have a leader that believes in the same success for the company as you do and we’ll back it and get behind it. And then the third piece is just making sure that you do have the right product and making sure that it is at least eighty percent of the way there. The other component to it of a blueprint is having people that can build the relationships with their customers and provide a white glove service. Because at the end of the day, I’ve been in situations where I may have had only, I don’t know, seventy five percent of the feature functions of a competitor, but they knew that I would be with them throughout the entire process and the journey together. And, yes, in due time, we’ll have those feature functions, but they wanna know that I’m in the foxhole with them. And I think being able to create that white glove service is also a part of that blueprint so that customers understand that it’s not just about product, it’s about relationships. It’s about the partnerships and knowing that you’re with them through thick and thin and it’s a phone call away. Absolutely. And b to b sometimes people think it isn’t so much about the people because we’ve taken that c out of it. But my god, you know, at the end of the day, we’re still people buying from people, and we’ve gotta be together in this. It really is a game changer. The companies that do the best that I’ve been with and I’ve observed are the ones that really connect with their customers, not just in a product sense or a feature function sense, but it’s really about being able to connect with them on on a personal level. And I’ll give you another example. I one of my customers that typically what you do is you’ll before you go on a sales call, you’ll do research. You understand who you’re meeting with in the background. So I did the research and I found out that this person, every morning, would wake up to his three children and make sure that he made breakfast for them, make sure that he did his workout in the morning before they woke up. So that was the best thing I ever heard because as soon as I walked in, we talked about running, which I love to do. We talked about my knees were hurting that morning because of the run, and I was the same way with my children and making sure that I was there for breakfast and lunch and dinner and so on and so forth. And it just connected us beyond anything a competitor could do to come in because we had this relationship suddenly in just a matter of moments. There’s so much to unpack there, but I’m just thinking about the huge advantage that any group of people that’s been in these companies has throughout their entire career. You take it with you, And I think everyone can look at their career and say, okay. There’s that catalyst or really provided such a base for everything going forward. But when you think about somebody who’s sitting, maybe they’re a first time sales leader. They’re a couple years in. They haven’t had that experience. They haven’t captured lightning in a bottle. They haven’t worked at one of these amazing startups in early stage. What’s your advice to them to sort of, okay, you haven’t seen it, but you wanna build it. And you don’t wanna look at it as a disadvantage, but, like, you’re new, and you’re green. And it’s, like, where do I go? And what can I do to contribute? Maybe I can build the next blueprint myself. Yeah. No. That’s a great question. I would advise or coach that sales leader. For one, I’m always a big fan of having mentors. Right? And I’m a big fan of making sure that as a sales leader, I’m always offering to be a mentor who has experienced it So you can do it through a connection and relationship. And I do think having someone there for you that has experienced it will be a coach for you as you are managing for the first time. And I think it’s also helpful because a lot of the sales managers, in particular, are moved into that role because they’ve been a great salesperson. But at the end of the day, that doesn’t necessarily equate. You could have a fantastic, amazing salesperson, but they’re not necessarily a leader or a sales manager. So it’s important that you do have someone that can coach you through that. That’s first and foremost. And the second piece is my advice or coaching on that also is never hesitate to make a decision. You’ll have wrong decisions, you’ll have right decisions, but just make sure you make the decision. Don’t get analysis paralysis and just know that you can always pivot. And I think what I explained to a sales manager is take your own shackles off and allow yourself to be comfortable with who you are and understand that you’re not being judged and that the person who’s your leader above you will be there to protect you and know that you’re not being questioned over everything. And once you can see someone take their shackles off, I mean, think about it. Some of the best work we’ve all done here on the call has been in situations where we’re relaxed. Right? We don’t feel that pressure. We don’t feel like something’s gonna be judged if I don’t go in the right direction. And when you have that ability to feel that calmness go over you, you’re able to make some of the best decisions. You’re able to make it with some more authority and with confidence. And that’s what I always teach those new leaders is take your own shackles off and be who you are. Be who the person that brought you here, but be humble enough to know that you don’t know everything and leverage your mentors and leverage others within the organization. And it’s never embarrassing to ask for help because we all have been there. For some reason, everyone believes that you miraculously went into a leadership role, and you didn’t have to go through the learning process at all. You just were that great. Well, that doesn’t happen. Right? There’s a couple that have it, but that doesn’t always happen. That’s what I would probably give as advice to any of the new sales leaders. And, also, the one piece I’ll also mention is don’t focus on hiring people that you’re friends with. It’s good if they’re great, but you also have to have some tough discussions and conversations. And it’s comforting to know that they’re around you because you know them. But at the end of the day, you also want a team that respects you for the work, not just as a friend. But it is that combination that you have to strike a nice balance with, but it is something that’s, something to think about. For sure. And so, you know, it’s great. I think that we hit on the fact that, yes, hiring is crucial and getting the right people in. But even just promoting from within and bringing, I think, the folks who are exhibiting the behaviors that you wanna have across the organization, like, recognizing that going beyond just the metrics. Creating a great culture is important, but then holding on to it and really cultivating it throughout is even more important. I do have a question, though. I mean, you’re a really successful CRO. We’ve talked a lot about the intangibles. But tangibly, like, how are you measuring success within your team, within your reps? Like, what are those metrics and those KPIs that are great indicators for you? When you think about reps, you also have to think about it’s not just about hitting a number. Everyone thinks about it hitting a number. That’s the way you build a culture around the sales folks, and that’s the way you determine the best. That’s really not the case. Yes. That’s a component of it, but not the end all be all of it. You have to think about what it is in their career also that they’re trying to get out of being in this sales role. What is it that their next step is? And I think being able to look at the sales reps that are on your team, looking at who’s going over and above in the sense that really doing the extra effort to be successful. And I’ll give you an example. As a salesperson, not having to rely on all the systems, what I find today is, like, any of the new folks coming into sales, it’s like, well, I need a software package that can do this, and I need one that can let me do this. And when the reality is that it’s also some of the most successful is just really doing your own research. Right? Finding out about the company, knowing them better than they know themselves, and building out an organizational chart and understanding each individual and making a phone call and being personable and building that relationship. And I think a lot of that is not what happens today. So many folks are like, I need to get this software package in order to remind me to call the customer three times over the next three months. No. You don’t need that. How about just picking up the phone and saying, I need to make the phone call? Or how about just a nice personal email that doesn’t have to be one that’s prewritten? Simple things like that go a long way. And I think when you can find a salesperson that’s not only focused on how do I drive the number and hit the number, but it’s how do I get there and do it. They’ll find a way to do it because they wanna be successful. And that’s the way I would look at those sales folks and looking at what is their career path and helping them along the way. What I do is I wanna make sure that I’m talking to my BDRs, my business development reps, the lower stage of the sales spectrum because I want them to know I believe in them. They’re gonna work that much harder because I know their career path is they wanna be in sales, and then they wanna be in sales leadership. And I help coach them along the way, but it’s seeing those folks early stage and the hunger and being able to help promote that from within so that they can drive their career path as well. But that’s what I look at is, like, how does the six most successful find a way to do it without using technology to do it oftentimes? Yeah. That’s funny that all this talk about AI and, like, oh, it’s gonna do this. It’s gonna do that. But really, at the end of the day, like, nail the fundamentals of your job and the way you get it done before you start thinking about whatever machine or software, like you said, is gonna help you. Because I I was at a conference a couple months ago, and, like, what’s the next big thing gonna happen to AI in twenty twenty four? And what’s your advice to people that haven’t implemented or aren’t using AI? I said, like, make sure you’re actually doing your stuff right first. And, yeah, obviously, there’s a place for AI, and it’s pretty remarkable what it does. But I think people just jump ahead to, like, oh, shiny object, cool toy, but did you learn how to build the toy or did you learn how to build the process first? It’s not about really anything that’s going to change how you go about your business, and it’s not going to eliminate what you’re saying, which is you gotta roll up your sleeves, and you’ve gotta be willing to get dirty and still do the basics. You know, tech is great. We’ve all bought a ton of tech in our careers, I’m sure. But at the end of the day, it’s still good selling, good marketing. And so we have the saying internally, ideas are easy, but execution is everything. And that is the one piece that is in our control. No matter where the economy is going, no matter where the budgets are going, if we are executing well and we have a North Star that we’re all working towards, we’ll be okay. And so talk to us a little bit, Chris, about setting that vision, setting that goal for the year, getting your reps all aligned. Yeah. So I love what you said, Saima, on it is all about execution. But I think a lot of it also is really being a realist as to what is it that we need to do as a team. What I always like to do is I never want to make it feel like that salesperson is someone that has to do something individually. As a group, this is what we’re doing. So it’s being able to look at what is in front of us together as a team and march to that in one direction for twenty twenty four. So we’re all in the same boat rowing in the same direction. The great thing is that now once we know how to get there, it’s how do you execute. And then it’s, okay, what are some of the ways that we can execute on this strategy and this plan? What do we need to do? What’s the talk track to our practices across North America into EMEA and vice versa so that we’re seeing different ways that they’re expanding their customer base, but doing in such a way that you’re enabling the customer to be successful in what they’re doing. But, again, to your point, which is it is all about the execution, but it’s also about putting that plan in place, that strategy for the year, and making sure we’re all rowing in the same direction. We all know what we need to do to get there. It does feel a lot more like a team approach, and you can also leverage, like I said, the best practice of others that are executing faster or more volume than some of the others. That’s solid stage advice. So you’ve seen so much success, clearly. You’ve helped so many people be successful. You’ve been successful companies. Let’s talk a little bit about the opposite. When things go wrong. So talk a little bit about in your world, with your teams, how you look at failure. And in my mind, it’s sort of like, if we’re not screwing up, we’re doing something wrong because we’re not pushing ourselves versus like, okay, well, we fell down. Let’s get back up. I could go on that. But, like, how do you think about that with your teams? Adam, it’s gonna sound crazy. I’m gonna say this, but I embrace failure. All the way back to my days of selling door to door copiers and understanding that as a new salesperson and selling copiers, that was the master class of selling because, man, you’re walking door to door, you’re freezing, the weather’s changing on you, and you’re being rejected everywhere you go. But the thing that I always talk to my sales folks about are always about, one, you always wanna be pushing the envelope. You always want to break glass. You always want to push it so far that, yeah, you might fail. But the great thing is and I equate this back to a Rubik’s cube. Now, Saima, Adam, you guys may be too young for a Rubik’s cube. We know when the Rubik’s cube is. Yeah. And I’m not talking about just taking the little pieces off and then sticking them back. But with the Rubik’s cube is a prime example of selling, right, which is you can solve for one side, but you failed essentially. You missed all the other sides. But you then take that idea of how you got to the first one and then you kinda make adjustments to what you did to get the first side, and now you have two. Guess what? You still failed. And then you make adjustments again. You got three. Right? And this goes on and on until you finally have solved the Rubik’s cube. And then it’s time to replicate it. So now you’ve mastered it. Now you replicate it. And I think that’s what sales is all about is it’s those that are willing to adjust your process, adjust your way of selling to that failure in order to get closer to success. And it’s really literally spinning that Rubik’s cube until you find what that process is or what that exact winning solution is, and then you replicate it across. But failure is just something if you welcome it and you become used to it and comfortable with it, it doesn’t scare you. It doesn’t frighten you. When I grew up, I was the youngest of five kids. I didn’t grow up with anything. And to me, I wasn’t afraid of the bottom. I wasn’t afraid of failure because if you’re coming from the bottom, there’s no place else to go, right, but up to make a decision and go, well, you’re gonna be back at the bottom. Well, great. Guess what? I’ll embrace it and I’ll bring myself back up again. Having that mentality of I’m not afraid to break glass and back to my point, which was I’m not afraid to take the shackles off. I’m not afraid of someone judging me because I made the wrong decision. And if you have a leader or a manager above you or working with you that’s not putting that pressure on you, I’m telling you, failure is brilliant. It will help you embrace everything that you need to do to get closer to success. And that’s, I think, absolute recipe for a great salesperson. Absolutely. Some of the best learnings come from those darkest moments, frankly, because that’s where you’re really innovating and figuring out the best path forward. Chris, let’s talk a little bit about sales in the sense that going beyond the sale itself. Obviously, the role of the seller particularly in complex b to b cycles is bringing that customer along the journey, making them really successful, driving high adoption. So I don’t let the sales folks walk away from a customer. It’s never a, we close the deal, we sign the contract. Now I’m off to the next shiny penny. No. No. No. No. No. The way I look at it is that if you were there with the customer, you made commitments. You were there with them. You built the relationship. To now turn around and hand it off to someone in customer success to say, hey. Now you build your own relationship. I’m over here. If they need something, you handle it. No. That’s not the way we do it. You’re there with a customer for life. And if you were there, you built that relationship, you need to be there from the beginning of gathering that lead to working the sales cycle to implementation all the way through to the point where you’re there at the renewal. In the SaaS world, the interesting thing is customers have choices. Right? It’s like, okay, that renewal is up. I can go somewhere else and get a better product or a cheaper price. And that’s why you need to stay on top of being a salesperson that is helping your customer throughout the entire journey. And being able to also yes. You’ll leverage your customer success team, but it’ll be a team environment that you are the quarterback of. You’re the one who owns that relationship. So that has a lot to do with why I think we’ve been very fortunate, and I’ve been fortunate in my past of having a great retention because it’s about staying with the customer, like I said, in the foxhole, and then also going back all the way through to renewal and making sure that they’re constantly feeling as if you’re with them. And that’s why salespeople also need to do that. And I can tell you, Saima, I still have customers from twenty years ago that I’m still in contact with exchanging holiday cards and birthdays and so on and so forth, and it’s because we build trust in one another. And the only way you do that is making sure that you’re with the customer throughout the entire customer journey so that you have the customer for life. And you’ll have a friend for life too, which is a bonus along the way. So much great, great sage advice. We said the only the only kind of advice that you serve out. We have a question that we ask all our guests as we get towards the end. It’s not meant to stump you. It’s not meant to throw you off your game. If I were to go to heaven, what would Saint Peter say, or what would I want him to say to me? I feel like I’m on, the actor’s studio. What’s your favorite word? What’s your favorite word? The question is, what is the most ridiculous thing you’ve had to do or been asked to do in your career? There’s positive ridiculous, and there’s negative ridiculous. And we’ve gotten from smuggling goods to doing bad things to clients with turning off their product, you know, all sorts of crazy things. So what do you got? My god. You’re killing me. You’re killing me because I have two that come to my head, and I’m like, should I say them, or should I, like well, how far can I go here? So I’ll say the first one that’s clean because the second one, you can always one that hears the second one. You can always edit out. It’s at the back end of it. I used to say it’s a family show, but I think we’re beyond that at this point. So Yeah. So back when I was with Siebel Systems, my only account was Merrill Lynch. So you always had to have a badge. I never had a badge. So what I found a way was that, one, I ingratiated myself with the person at the front desk, and they kinda knew me, but you can’t always just go in every day. So I found a way that once I was in past the front desk, I knew that if you go to the bottom basement of this huge building, you could walk freely back and forth. So I literally would be in one part of, like, asset management over here and then selling to them, and then I go into a fire door down in the basement, literally, where people were keeping lights on and whatever, and I would walk all the way to the other side and then pop up through another fire door. And I did this like a champ for probably almost two years, sold the biggest deal at Siebel Systems, one of the biggest ones ever. And it was all because I was found a way to navigate under this building, and I would take my management team through there. I think we had Tom Siebel walking through one time. I still think I could do it, but there’s always a way. If there’s a will, there’s a way. You could never tell me that I can’t get in to talk to someone. I would always find a way. And I try to tell my sales folks, there’s always a way. I don’t care if I have to dress up and bring balloons in and act like I’m somebody who’s coming in to deliver a birthday greeting. There’s always a way. It may not be the best way for you, but there’s always a way. Well, there you go. Chris, thank you so much. This has been such an interesting conversation. I think it went places that we didn’t think it would go when we first started, which is always the best type of conversation, by the way. Yeah. No. I listen. I really appreciate it. It was absolutely one of the best podcast I’ve been on, and I enjoyed it thoroughly. My last parting words is that for anyone that’s in my position or in a leadership role is always to pay it forward. And, you know, I think it’s really important for the new generation of folks that are coming up in software and technology is to have a mentor, to have someone that they can rely on, to help them pave the way. I would have loved to have had it, and I think that anyone that’s in our position, we should do that. We should do it for folks that don’t have necessarily the opportunities that were presented to us or they don’t have the mentorship or they don’t have access to the right knowledge bases and so on and so forth. And I think it’s really important to give back because why do we do this? Right? At the end of the day, it’s about giving back. It’s about putting a smile on someone’s face. And I can tell you that at the stage that I’m in my career, it’s not about how much money you can make and what level you can get to. I’m really happy watching somebody else buy their first home or buy their first car because it’s something that I was able to help them with. And I just think that my recommendation and advice for anyone that hops onto your show is that please pay it forward. What a great way to end. Yeah. Absolutely. Thank you so much. Thank you, Chris. Thank you, guys. It was great. Pleasure. You’ve been listening to Revenue Makers. Do you have a revenue project you were asked to execute that had wild success? Share your story with us at six cents dot com slash revenue, and we might just ask you to come on the show. And if you don’t wanna miss the next episode, be sure to follow along on your favorite podcast app.