11: Debe Rapson - Find Your Motivation, Drive Your Destiny

0:08 Scott Ingram: You're listening to the Sales Success Stories podcast, where we deconstruct world-class sales performers to provide insights and strategies to help you improve. To learn more, visit us at top1.fm.

0:21 Scott Ingram: Here's your host, Scott Ingram. I'm really excited to be talking with Debe Rapson again today. Debe is the top director of strategic accounts at Demandbase, and has been for the last 7 years running. Now, if you've been listening to this show for a while, you'll know that Debe was the star of episode number 4, which we recorded in person, but we didn't discover that there had been a major audio issue until well after we were done recording. So I've taken down that recording, and the only people who can access it now are those who are part of our Sales Success Community. You too can become part of that community. Just head over to top1.fm Enter your email address, and that'll prompt an invite, and you'll get access to all sorts of bonus material in there, and it's all free. So, with that out of the way, welcome back to the show, Deb.

1:08 Debe Rapson: Thanks, Scott.

1:09 Scott Ingram: So, let's start like we always do with the top 3 things that you believe have allowed you to get to and stay in that number 1 position for all these years.

1:17 Debe Rapson: Okay. So, as we all know, it's really challenging to get to the top of your game. There's no question about it. It takes a lot of years and a lot of experience. Experience. And once you've arrived, of course, it's, it's tough to stay there, right? It takes a lot of work to keep you on top. Probably, I mean, I don't know, I think 3 things that kind of set me apart and allow me to really stay at the top of my game. And all my attributes that I'm going to talk about here are really, really focused on kind of doing the right thing, doing the right thing by my customer, doing the right thing by my prospect. I'd say probably the first is my genuine curiosity. I really am interested hearing about my clients, about their business problems, their challenges, their pain points, and really interested in hearing what initiatives they have. What are their goals and the things that are going to not only make them look good, but make their, their organization look good. And people can always tell when you're genuinely interested or just kind of asking questions going along, waiting to pitch. And I think that my, my genuine curiosity, you know, in asking questions and probing, you know, pretty broad and deep in the conversation really give me the ability to stand out to my clients because I spend my time listening and not pitching. So discovery in my book is all about listening, not pitching. And it's a theme that's kind of ridden out throughout my career and really helps me set the stage in understanding, you know, what my clients are up against. And I think that people really appreciate listening and not pitching, especially in the first exchanges. So that's probably the top of my list that really makes me stand out, I think. Secondly is really along the same lines, doing what I say I'm going to do, whether it be following up with a client when I say that I'm going to, following up with an email or a phone call at the time that they've asked me to, really sticking to the promise. If I say I'm going to do something, I do it. And I think unfortunately we don't do that enough. Along the way, and it really makes those who do stand out. And then probably the last is that I'm a challenger. I love problem solving. I love evangelizing and educating, and I don't mind standing up to a client when I think that they're kind of going rogue or going the wrong way and saying, hey, you know, based on my experience, and I have lots of years of wisdom and experience, You know, this is probably a better approach, or you might want to think about doing it this way or that way, or that way is going to get you into a whole lot of trouble. So I've probably won my biggest deals and my most challenging deals in challenging my clients. And once you do it, you gain a lot of credibility. It's probably one of the sharpest tools in my toolbox that I have. And I really come across it honestly, just naturally.

4:23 Scott Ingram: Such good stuff. And I look forward to talking about that a little bit more. But before I start to dig deeper into my conversation with Debe, I wanted to quickly suggest that you set yourself up with a free account on Nudge. Nudge is a modern sales platform that uses AI to find actionable insights on your prospects and customers without all the grunt work. So sign up for Nudge to start building real relationships with your buyers. Just type top1.fm/nudge. That's N-U-D-G-E, top1.fm/nudge, and get started today. So, Debe, talk a little bit more about how you structure that discovery and that first conversation. You know, what are some of the most powerful questions you like to ask?

5:08 Debe Rapson: Yeah, so I always try to start in asking general questions that aren't going to threaten people or make them more uncomfortable, right? So I want to ease right into it. So I want to understand a little bit about how their marketing organization… so I sell marketing technology… so how their organization is structured. What are the, you know, what are the different goals that they're looking to achieve in supporting the business? I typically ask broad-based questions about their business. What is the company? Where are they trying to grow their revenue? What are the key initiatives that the C-level folks are pushing forward in the coming year, etc.? So starting broad and then narrowing in to what are their challenges and what are their goals. And I typically like to ask the same question a little bit differently, maybe 3 or 4 times, because when I do, I find that I get a different answer. So, and I typically do that around their challenges and their pain points and what's really hurting, what's really keeping them up at night, if you will, in a less canned way than that. But, um, I think it's really valuable to go deep and to ask those questions a little bit different way because it nudges additional information out of them. And then I'd like to They're very often to different areas, probing deeper around some of those pain points, uh, how they support the business, uh, what is going to make them look good? How do they measure their success? Those types of things. My first discovery call is never any less than an hour where I'm just probing and asking questions and giving a little nugget here and there so that I'm keeping them engaged and feel like they're getting something out of it, but really focusing on their story.

7:00 Scott Ingram: How are you preparing for that? Are you… do you have a plan for where you think that conversation will go and then you kind of follow it once you get there? What's, what's that look like?

7:10 Debe Rapson: Yeah, I spend a lot of time doing research before I have that first conversation. I work really closely with my SDR who helps me do a lot of research on the company, who's who in the zoo, who the power players are, who the blockers might be, those kinds of things. And then just understand a little bit more by reading, you know, their 10-K and their annual report. We have a tool called Spiderbook. Demandbase has it, and it provides insights into not only companies that are kind of low-hanging fruit for you, but also, uh, those contacts at those companies. And I can see what they're blogging about, what they're speaking about at conferences, et cetera. So I prep by really understanding my, my contacts and those companies and what they're trying to achieve so that when I go in, I'm really validating, I'm demonstrating credibility, but also validating that I understand what I think I understand.

8:11 Scott Ingram: And let's pivot a little bit. You talked about kind of the challenger being really key. Can you give a specific example or 2 of how that's manifested? I think you mentioned a couple of your biggest deals have come because you took that kind of approach. What did that actually look like?

8:27 Debe Rapson: Not long ago, I was in a deal with a company that we'll rename nameless, but they're a large telecom manufacturing equipment equipment company, and we, uh, we were in a sales cycle and it was getting very competitive. And because I had done so much discovery up front, I really understood what the client was trying to achieve. But my competitor was kind of wooing the client with gifts and tickets to places, and unfortunately the solution that the competitor was offering really and truly didn't make sense for the client. It wasn't going to help that person achieve their, you know, their goals. And it was actually, you know, probably going to be one of the, one of the sticky decisions that sometimes clients make that, that make them look bad. And we've seen folks get fired over sometimes those kinds of decisions. So instead of letting it go, I decided to just have a heart-to-heart with the client and say, look, you know, whether you decide to move forward with me now or whether you decide to move forward with Demandbase later, you know, here's what I know. And I kind of took it back to what I had learned in the discovery and provided documentation on why that competitor's solution wasn't going to meet their needs. And it was a risk. Right? Because this person was being wooed and, and I could tell that this person was kind of moving in that direction to go with a decision that wasn't really going to be good for her or her business. So I kind of stood up and said, look, whether you decide now or later, you know, you need to know this because at the end of the day, we're going to do business at some point in my career and yours. And I want to make sure that I have done all that I can do to steer you in the right direction and to be transparent with you. And the client did a 180 turnaround and thanked me. And this person had a pretty big ego. So it was, that was part of the risky stuff of telling this person, hey, you're going down the wrong path here. Right. And did a 180 turnaround and we ended up getting the business. And she told me she really valued me doing that. You know, providing the evidence that she needed to really understand why.

11:03 Scott Ingram: That's a great story. Thanks for sharing that.

11:06 Debe Rapson: Yeah.

11:07 Scott Ingram: So, Debe, talk about your role today at Demandbase and how you got to number 1 there.

11:13 Debe Rapson: So I joined Demandbase when we were 18 employees. It was without a doubt the biggest risk in my career. I've never been with such a small company. And I, you know, I came in as their first enterprise rep with a named account. Account list. And because I came from the same industry, I was able to get some pretty quick traction with my network and really just kind of grew from there every year, getting about, you know, 200% or so of, of my quota and really growing and developing Demandbase's revenue and bringing on some great logos. So it was really just about understanding and having that background. Of, uh, and network and background in that industry, and, uh, very strategically going after the business that I thought made good sense for Demandbase where we'd really bring value to our customers.

12:11 Scott Ingram: How big of a factor do you think that staying in the same industry and leveraging the both the knowledge base that you have and the, uh, the network that you have, how big of a role does, does that play, and, and how did you think about that?

12:26 Debe Rapson: That is a great question. I now think it has played a huge role in my success, but 20 years ago, if you'd asked me that question, I probably would have said I don't think it matters at all. But through the experience that I've gotten and the expertise that you get by staying in one industry, I think it matters a lot, not only for the experience that you get in the industry, and it really helps you to become an expert and provide credibility to your customers that you really know your stuff. But the networking factor is absolutely huge. I've had customers for the last 10 years that I've been in this industry buy from me 3 and 4 times because, you know, they know that I'm not going to steer them wrong, that I'm always going to be straight up with them, and I'm going to make sure that they're well taken care of. And that's That's huge in just getting that repeat business because our clients move around to other companies and we move around to, you know, to other companies. But staying in that same industry, I think, has, has really benefited me.

13:35 Scott Ingram: Yeah. I'm glad you said that. It's funny. That to me was one of my original premises for this show and, and kind of the hypothesis of what makes the most consistent top performers. And I've seen over my career just this thread of those that are, I mean, like you, just year after year after year in that number one spot. I think they're benefiting from all of those things. And I think you have to be really careful if you're experienced in sales and thinking about making a significant move that you can really lose a lot of that. And, and I've really been cognizant of that myself in where I've positioned myself in the work that I do today and staying very, very close to where I've been for the last… losing count now… 7 or 8 years.

14:28 Debe Rapson: Yeah, I think that early on it's great to experiment to understand where is your passion, where are you successful. Do you prefer talking to finance, or do you prefer talking to marketing and sales or HR? Once you find your people and you getting success, I think it's a great idea to stay in the same industry. I started my career in advertising sales. I moved over to software and telecommunications, and then I went into learning management systems, and I found myself drawn back to the marketing and advertising space. And it's definitely where I've had phenomenal success in my career.

15:10 Scott Ingram: You know, it's interesting that you say that because I went through a very similar process. I mean, I've sold to virtually every part of the organization. I've sold to IT, I've sold to finance, I've sold to operations, and I've sold to sales and marketing. And I got to a point in my career a number of years ago where I was at a fork and decided, you know, my people are the sales and marketing. I feel like a lot of the rest of the organization, they are much more risk-averse. They are backwards lurking and kind of CYA-ish, whereas sales and marketing, those the, the future-focused folks, and, and that's how I operate and how I like to play, and, and it's, it's a, it's a good, good match. So let's keep going with that. Talk a little bit more about your origin story and, and how you got into the sales game.

15:56 Debe Rapson: Yeah, so I think I shared this with you before with bad audio, so I'll… we'll, we'll hopefully do it better this time. So I, I was doing an internship in college And I went to Indiana University and I decided to try, uh, going into news reporting. And, uh, I checked out a couple of radio stations in Indianapolis, which was about an hour away, and landed an internship. Sold myself right into it. And about 2 weeks into the internship where they sent me out with a microphone and a tape recorder and wanted me to go and interview people and attend, uh, you know, um, commerce meetings and local types of events. I realized I was pretty bored by it, and that's probably not such a great idea 2 weeks into an internship and what you thought was your career path to get bored. So I, I happened to pass the general manager in the radio station, and he said, hey, how's it going? And I said to him, actually, I'm not really enjoying it that much. I'm a little bit bored. And he just looked at me and started laughing. And I said, what, you know, what's so funny? And he said, well, he said, you seem like a real natural salesperson. He said, why don't you go out and ride with my top sales rep for a couple of weeks and come back and let me know what you think of it? And so I did. I went out with his top rep, who happened to be a woman, and spent a couple of days with her. And I immediately knew that sales was the right career for me. And the reason why was because she was kind of going around in her car, um, you know, meeting with clients, taking them out to lunch. It was kind of like running errands, being out of the office, right? Always kind of going out, meeting with clients, listening, kibitzing with them. And, uh, and the one thing that attracted me, and this is back in the very late '80s, is she had one of those big block cell phones in her car. And I was like, wow, you can talk on a phone in your car? I thought that was pretty neat. So between that and how she was spending her days, I said, wow, this is really it. And I went back into the general manager's office and thanked him for that opportunity because it really set me on my path. And after that internship, I moved out to California and sold myself right into a radio station sales job. With coffee, coffee radio.

18:28 Scott Ingram: That's great. And along the way, I mean, I'm sure there were a few steps between where you started and where you are today. What were the most important steps or the most important lessons or maybe the pit that you fell in? What… give us some ideas there about what was most impactful through the rest of that journey.

18:48 Debe Rapson: Yeah, I think that I had the opportunity to really experience selling different things early on. So I started in radio, I made some really good friends. I got the opportunity… KOFY owned a television station. I got the opportunity to also sell television advertising. So the first was air and the second was time. And then after that, I went to selling magazines, which is space. So in the first 7 years of my career, I got to sell airtime and space. And if you can sell air, time, and space, you can pretty much sell anything. So I, I was really fortunate in not selling necessarily a product, but something that was concept… conceptual and something that evaporates. And that is a skill set, right? Because you've got to be able to build out a story, evangelize what it is that you're offering, and it's something that disappears after. So I think advertising was just a great training ground for me, and it also really gave me the opportunity to really learn what I was passionate about. And from there, I got the opportunity to manage, and that in itself, I think, in many ways has made me a better rep. I worked for MCI, which WorldCom bought not long after. So I worked there for 4 years and managed a team. I wasn't going in to manage I was actually looking for an enterprise type of sales position, but the general manager there said, hey, I'd really love to, to, you know, put you in a management position if you're interested. So it was kind of a neat opportunity for me to do something a little bit different early on. And I managed… I took over 4 people and grew it to a team of 21 and managed another manager under me. And it was actually a really fun job because I had a Hawaii and Bay Area territory, and that was really fun to take those quarterly trips to Hawaii to manage my team there.

21:04 Scott Ingram: That's awesome. And, and par for the course for Debbie, you had 500% growth while you were doing it.

21:10 Debe Rapson: Pretty much, yeah. It was great. I did. I, I had great growth, and, and we went from being, uh, the worst team, uh, at that company to being the, the number one team at the company. So it was a just a really neat you know, opportunity to really see how you grow something, especially from the management position. What I learned in that job that was a, just a perfect lesson for that time is that middle management is not a lot of fun. Um, they ended up closing out that, uh, those territory sales reps, which was kind of like the, the young pups, um, selling B2B. They ended up closing out that division. And letting everyone go. And I ended up leaving as well during that time and changed the course out of telecommunications and into software to kind of change the course of, in direction of my career and started selling to HR. So it was, you know, it was tough lessons in that, you know, companies make decisions and when you're middle management, you, you know, you don't really have a seat at the table. But one of the things that management did for me, it really helped me to become a better rep. I, I understood very quickly after that when I decided to go back into sales and carry a bag, I decided that it, it, uh, it really gave me some great insights into really how to be a better rep. The things that managers think about, the, you know, solving problems for myself and bringing solutions to management, etc. So it was Really neat, neat experience.

22:53 Scott Ingram: And why did you decide to go back into the individual contributor role versus continuing down a management path?

23:01 Debe Rapson: Because the thing that motivates me, Scott, is freedom. And money buys you freedom. And I made a good living, definitely for that time in my life. Um, you know, I made a good living in management, but I could make a lot better living, a lot more money by changing my trajectory and going into software and going back to carrying a bag. So for me, it was not about climbing the ladder. I'm not interested in the power. I'm interested in the money. And I learned that about myself, which, which it was, you know, just great insights.

23:40 Scott Ingram: That's awesome. So, Debi, in our first conversation, we talked a lot about kind of qualifying an actual sales role. Um, and, and you talked about Demandbase as one of the biggest risks you took on in your career. So how are you thinking about that? What questions are you asking going into a new role type opportunity?

24:04 Debe Rapson: Yeah, I, I ask all the hard questions. I don't typically, again, I don't start with them. I almost treat it like a sales cycle, right? I start with, tell me about your organization. Who are the key players? What's your management style, right? All those kinds of things when you go through that first kind of discovery interview. And I really like to run that interview like any good sales rep. I want to take control of things. So I really like to start by asking those questions and really qualifying them. Is this an organization that I want to be a part of? And then what I like to do is I like to speak to the players in the organization that I'm going to work with and that are making the decisions in the organization. So as an example, when I interviewed at Demandbase 7 years ago, I spoke with, of course, the director of sales… actually, I think it was the VP of sales at the time who was the hiring manager… but then I also spoke with the CMO, the CTO, the VP of Biz Dev, and the CEO. And I asked to speak with them. And then the last person, which typically most people don't request, is I asked to speak to one of their board members because it was such a young startup. I wanted to make sure that the company was going to be viable, that I liked the, the path that they were taking. I wanted to make sure that the product was solid. And what I did was I asked similar, some different, but some similar questions to all those different folks in the organization so that I could triangulate and really understand, is everybody singing the same tune or am I getting different answers, which, which, you know, intimates that there's an issue there in, in the way things are going at that company.

26:03 Scott Ingram: That's really interesting. And what's most important? I mean, when you're looking at that, and typically you're not talking to just one company, is it the comp plan? Is it the culture? Is it the product? What are you looking for as the most important factors to determine where you're ultimately going to go?

26:21 Debe Rapson: Yeah, I think you actually beautifully stated it. I think it is first, does the product work? Is it vaporware or does it work? And you've really got to talk to the right people. You've got to get a demo of it. So, I didn't mention But I also talk to the folks that, you know, the SEs that do the demo. You've really got to know, am I selling vaporware here or does this thing really work? And, and are their clients successful? Right. Sometimes I even backchannel and we'll call a couple of their clients to find out companies that are listed, et cetera, through my network, you know, hey, how happy are you? What are you happy with? What aren't you happy with kind of thing? So, you know, Is the, is the solution solid? Can I sell it? The second thing I look at is what does the comp plan look like and what does the territory look like? And territory is probably one of the most important pieces for me. I want to understand, you know, what my opportunity is in that territory. So I'll go pretty deep in my research there. And then the third piece is definitely culture because I'm a challenger, I'm best suited for a startup culture. Large companies don't love people like me. So, so, so I definitely look at that. You know, you kind of create that criteria and create your checklist and, you know, interview with your top 4 or 5 companies. And very quickly, I think you can weed out, you know, who are your top 2 or 3 choices.

28:01 Scott Ingram: And any red flags? Like what What, what sets your alarm off?

28:05 Debe Rapson: Well, vaporware for sure. Oh yeah, we're working on that. It's, it's, uh, gonna be fully cooked in the next quarter. Yeah, that, that definitely makes me concerned. Vaporware is a huge one. Um, when I ask questions and I'm triangulating with different folks in the organization and I'm getting different answers, that's a red flag. I also, if I have the opportunity to talk to the top brass, I always do that. That's typically, I'm in a final stage with the company and I'll ask to speak with their top rep first. Of course, being competitive, I want to assess their top rep, right? And, and, uh, secondly, I want to understand what do they think about the organization, what they like about working there, and what don't they like about working there. I really want to understand what are the warts so that every company has warts. I just want to be able to assess what are your warts.

29:03 Scott Ingram: Yeah, great stuff. So Debbie, what if… let's take kind of the, the flip side and take us to a time where things weren't so easy and you were struggling a bit more. What was one of those biggest challenges and how did you get through it?

29:18 Debe Rapson: So that's a great question. Um, I would say 2 of my biggest challenges in my career have been Um, the first is, you know, probably the toughest is getting fired. Um, you're not a great sales rep if you've never been fired.

29:40 Scott Ingram: Well, good. I didn't, I didn't know I had checked that box of greatness. That's fantastic to know.

29:47 Debe Rapson: You totally have. So I, I really think that, uh, picking yourself up, putting on your big girl pants, your big boy pants, and, you know, dusting off your knees and moving forward is, you know, probably one of the greatest challenges because it hits you in a lot of areas, right? It hits your, your ego for sure. It's also scary and, you know, that feeling of unstable and your world kind of feels rocked. And so inside, um, it's, you know, it's hard and you kind of have to put on your game face because you're interviewing for sales positions. So showing confidence is absolutely key. In, in getting a sales job. So it's, you know, putting on that mask, if you will, and saying, hey, I got this, and feeling that inside. Because I think that people can feel when you are genuine and when you're not genuine. So getting fired definitely is a tough one. And for me, the 2 times that I've been fired in my job are when I was the number one sales rep, and that was pretty jolting. One of those was, you know, the president of the company… we were being acquired, and the president of the company, the new president, you know, didn't like the way that I was doing things. You know, it was a personality clash. Maybe that person was threatened by me, not sure, felt that way, you know, wanted uniformity, etc. And they let me go. And that was pretty jolting, especially being, you know, the number one rep globally. And the second was a similar situation. They laid off half of their sales reps. I had a big salary and a huge commission, and it was a great cost-cutting factor to let me go. So those are definitely really tough times to be in that position and realize that there is no loyalty in business. Business is business, although business is also personal. So it's something definitely that was a big one to get over. And then I would say the other time that I've really felt jolted was changes in territory, when somebody else is telling you what your new territory is or what you're going to be doing next year, and you have to really, you know, take a step back and reevaluate, do I want to be here? For that? Is that the job that I want? And sometimes, of course, you know, you weigh it out with the, you know, the things that you love about the company, the things that you hate about the company, your comp plan, um, you know, ability to grow your revenue, your commission, you know, all of those things. Do I, do I still love the people that I work with, right? All of those things. So, you know, those are probably my 2 biggest challenges of my career are getting fired and changes in territory.

32:51 Scott Ingram: And let's talk about the change in territory, or just change in general, right? Maybe it's a big change in the comp plan, or it's territory, or any of those kinds of things, or all of that, or all of the… exactly, all at once every quarter. I've been there, done that. What… how are you dealing with that, right? What, what is your process? What is your approach to not let it completely throw you for a loop throw you off your game so that you're, you're still effective?

33:19 Debe Rapson: Great question. You are definitely crawling in my brain right now. I think that what goes through my mind is a complete reassessment when those things happen. And they pretty much… territory doesn't change every year, although some segment of my territory definitely changes every year. You know, maybe it's adding accounts or cutting accounts or Focusing more on customers versus prospects. So certainly there's an element of change every year. I really sit down and go right into research mode and put together, you know, and evaluate what is my opportunity here? How can I, can I capitalize? Can I make the numbers that I want to make? Can I make the money that I want to make? Is my situation still ideal? And I've got I've got, you know, a list of things. Like, just as an example, for me, working in the office is a non-starter. So if somebody said to me, okay, now next year we want you to, you know, come 100% into the office every day, that, that would be a no-go decision for me. Um, you know, making a certain amount of money, you know, if I can make over, great. If it's less, it's a no-go decision for me. So I'm very clear about what that criteria is. And I just go into evaluation mode. Can I do it with what I'm given here? And I also don't hesitate to negotiate whatever it is that's changing. So if, you know, just because somebody is in management doesn't mean that they're always right. And I have a lot of experience under my belt, and of course I'm a challenger. So, you know, I obviously try not to you know, combat the situation, but more thoughtfully challenge the decision that's being made if I think it's not right or not going to work.

35:28 Scott Ingram: Yeah. And so it sounds like once you've done that, then, then, you know, and you make a decision one way or the other and then, and then it's fully commitment and go.

35:39 Debe Rapson: Exactly. That's exactly right. The key is you want to be in control of the decision. You don't want to things to happen to you. You want to drive your destiny. And although sometimes it feels like things are happening to us, I think it's important to realize that, that we actually do get to drive our destiny. And the more proactive you are about it, the better life you'll lead, both professionally and personally.

36:11 Scott Ingram: Yeah. Awesome. Awesome. So, the next line of questioning, I've done half a dozen interviews since the last time we talked, and I'm getting better at this. So, now I know, and I actually think I know your answer, but I know that the first question I have to ask is, are you more of a morning person or are you a night owl?

36:30 Debe Rapson: I'm a night owl.

36:32 Scott Ingram: I knew that. So, the next question, because you're a night owl then, is what is your evening routine look like?

36:40 Debe Rapson: That's a good question. You know, I typically, I end my day about 5:30, 6:00, 6:30. I get my tushy over to the gym and get a workout in, or go up into the Oakland Hills and have a hike or grab a yoga class, and then come home and do dinner with my family and have some good connection with them. And my husband's a teacher, so he goes to bed pretty early because he wakes up at 5. And, and then I go back and organize myself for the next day, whether it's finishing up a presentation that I'm building or taking a look at, you know, kind of what my plan of attack is gonna be the next day, or, you know, what was left over that I wasn't able to accomplish today and plan it throughout the week. So I always kind of jump back in at night, typically, you know, for about an hour. Sometimes it goes into 2, 2 and a half hours. I try not to, um, you know, I try to relax and kind of meditate a little, chill out before I, I go to sleep at night. But, uh, definitely I spend a little bit of time pulling together whatever it was from today and figuring out, you know, getting myself prepared for tomorrow.

37:57 Scott Ingram: Yeah. And talk about that in a little bit more detail. I mean, when you're going through that prep for the next day. How are you doing that? How are you trying to structure, um, your, your day so it's most effective?

38:10 Debe Rapson: Yeah, I look at the things that I need to do to move the needle in my deals. Sometimes that's, uh, following up on stuff that is in process. Um, you know, uh, follow-up thank you notes, uh, after meeting with a client or sending case studies or, you know, research white papers, etc. Sometimes it's just making a list of folks that I need to follow up with, right? Hey, tomorrow I've really got to check the box here with these 4 companies and make sure that I touch base and that we move the needle. Sometimes it's preparing. I always take a look at my calendar, you know, a little, a day or 2 ahead, and, you know, what do I need to really focus on for tomorrow? Do I have to prepare for a presentation? You know, do I need to make a list of companies that I want to attack, right, that I want to kind of start going after and really working with? And maybe I've got to do a little bit of research before discovery calls the next day, etc. So it's kind of whatever's on my plate. I'll take a look at typically every Sunday night. I do that for the week ahead, and then I do that on a daily basis. So So really just so I kind of stay on top of my game and I continue to move the needle forward. So I'm not a naturally organized person, so I have to have a discipline around it. Otherwise I wouldn't be organized at all.

39:46 Scott Ingram: And talk about the Sunday piece, because I know that's a big part for you. How much time are you spending on, on Sunday and how are you using that to kind of lay out the, the week to come?

39:56 Debe Rapson: You know, typically I'm just spending an hour on Sunday and typically it's kind of that Sunday night timeframe where I'm kind of looking at, hey, what do I need to do this week? What are the things that I want to accomplish? Where do I need to move that needle? And I schedule those things into my week. So I literally go through, I make a list of what my goals are for the week. And that, you know, includes kind of what do I want to accomplish? And then what are the tasks and things that I need to do to accomplish those goals? And then I take the time to actually schedule them in. And then the other piece that'll probably make you laugh, but the other piece that I do is I schedule in my workout. So, you know, Tuesdays and Thursdays I like to go to yoga, and, you know, Monday, Wednesday, and Friday I want to hit the TRX at the gym. And, um, on the weekends, I'm, you know, on Sunday I want to do a hike with a friend kind of thing. So I really also schedule that stuff in. I mean, obviously the weekends I don't schedule as much, but I really try to schedule it into my work week. Otherwise it doesn't happen.

41:03 Scott Ingram: Yeah, well, I, I mean, I wouldn't laugh at that. It makes a lot of sense, right? If, if working out and being healthy is one of your priorities, the, the way you make it a priority is you put it on the calendar.

41:15 Debe Rapson: Exactly. You get it.

41:17 Scott Ingram: I get it. So before we continue, I've got one more little bonus for our listeners, and the deadline on this is coming up fast. My friend Craig Rosenberg, who many people know as the Funnelholic, is getting ready to host the 2nd annual TOPO Summit in San Francisco on April 12th and What makes this event unique is nearly all of the presenters are actual practitioners, kind of like the show. And I'll be there and recommend you join me. And you can do that at top1.fm/topo, T-O-P-O. And we actually have a ticket to the event that we're going to give away in our Sales Success Community on February 24th. So if you're not already in the community, you can head over to top1.fm, get on that mailing list, and that'll again automatically prompt an invite, and you can find the Topo Challenge from there. So would love to see you in San Francisco, Debbie. Maybe I'll, I'll come see you while I'm there.

42:07 Debe Rapson: Oh, I'd love that, and I want to go to that. How do I get that ticket?

42:12 Scott Ingram: You go to top1.fm and you get on the mailing list and you get on that community.

42:17 Debe Rapson: Yeah, I've heard great stuff about that, actually. I've heard great stuff about that conference. That's awesome that you'll be there.

42:23 Scott Ingram: Yeah, absolutely. And Craig just does a, a great, great job. And it is, um, actually, I think my script is wrong. It is all practitioners. There's none of these, I wrote a book on sales, I haven't sold anything in 20 years, but you should listen to me. It's all people who are active, uh, in, in leading and part of very fast-growing sales organizations and learning what they're doing. So, it's very, very much aligned with what we're trying to do with this show. So, worth, worth checking out.

42:50 Debe Rapson: Yeah, sounds awesome.

42:52 Scott Ingram: So, Debe, what, what motivates you?

42:56 Debe Rapson: Uh, I think I said earlier, and it really is always true throughout, you know, all the time that I've been selling, it's really freedom. Freedom motivates me. I, and freedom is tightly tied to money. I really want to be able to make choices in my life based on really what I want, whether it's, I want this car, I want this house, I want this vacation. I need to, you know, I wanna spend time with my family. I wanna have that freedom to choose. It's, it's kind of like, um, you know, when you're in school, you have… if you have great grades, you have choices. If you don't have great grades, the choices, you know, you don't have a choice. You're…

43:43 Scott Ingram: they get made for you the way they have to go.

43:44 Debe Rapson: Exactly. It's made for you. And, uh, and I really like choices, and I like freedom. I want to run my day how I want to run it. If I want to do yoga in the afternoon on Tuesday, I want to be able to do it. And so that's kind of what rules my… the way that I move in the world. And making money gives me choices and gives me freedom, and it's truly what motivates me and propels me forward to do that hour on Sunday night when I'm kind of tired and just want to chill out to the Netflix. It motivates me to take a little bit of time to prepare because I know that when I do I perform better.

44:26 Scott Ingram: Love it. What about when you're having an off day? What do you do?

44:33 Debe Rapson: Well, if everything's going wrong that day, I walk away from the day. I listen and watch to what's happening around me, and if things aren't going my way, not just in one meeting or, you know, you know, a bad interaction, but if things just kind of seem like they're are not going well that day, and we all have those days, typically, honestly, I walk away and I go for a hike. It's really what I do. Don't tell my boss. But no, actually, my boss knows. But, but, um, you know, typically that's what I'll do if it's not that situation and things just aren't going well. I, you know, you know, some things happened or this meeting went really wrong. I typically, typically can pretty quickly identify what happened. I'm very analytical and want to understand where things went wrong, where I goofed, or, or where as a team we didn't perform. So I, I really look inside of myself, and typically when I look inside of myself, the answer is right there.

45:39 Scott Ingram: Nice, nice. And, and if you can't find it right away, it's, it's up in the Oakland Hills somewhere.

45:45 Debe Rapson: Exactly.

45:48 Scott Ingram: Awesome. So I'm curious about just belief systems or actions and things like that. When you look at average sales reps or the B players who aren't performing consistently at the top, what are some things that you see that they do where they believe that you think is nuts or is standing between them and significant success?

46:12 Debe Rapson: Yeah, the one thing that I… well, I won't say one, I'll probably say 2 or 3. The thing that really stands out kind of jumps to my mind when you ask that question. Is that folks don't take enough time to really properly do discovery. And people who know me know that I talk about discovery a lot because it is the thing that I believe sets me apart and all the top players apart from the B players and the C players is taking the time to really understand what this client is trying to achieve and what are this client's roadblocks and the company culture that is, you know, helping them, you know, to excel to success or holding them back? You know, are they evangelists, people who are on the cutting edge, or not so much? So, you know, really taking the time to fully do discovery and listen and not pitch during discovery is probably, you know, the number one thing that jumps out at me. And, and I do think it's crazy to pitch during discovery, and I haven't done it for probably 25 years. I mean, it is a solid process that I'm loyal to because it's really moved me forward. And I see it as something that really sets the stage for everything else that happens in the sales cycle. Once you understand what's going on in that company and you understand what their motivations are and you understand how they make decisions and what's going to make this person look good or bad and how they measure success and what their real pain points are, not just, hey, I've got this challenge or that, but where's it really hurt? What's, where's the friction behind that's really standing in the way of them getting success? Once you understand those things, you, it sets the table for really being prescriptive in your solution and really being relevant to that prospect. And that's how you get deal, deals done. So listening and not pitching during discovery is, is I think very important. And I can't understand why people pitch during discovery. I just don't get it because it shuts out all their opportunity to really learn about their prospect. And then, yeah, and then, and then the second thing that kind of jumps out at me is just folks not following through on what they said that they were going to do. You know, I mean, sometimes it's laziness or not being organized, you know, or getting distracted, whatever it is. But I think that it takes away from our credibility as salespeople when we don't deliver what we, what we said. And I think it's crazy when people do that. If you have the opportunity to be in front of someone, you know, do, do the right thing, take care of them, do what you say you're going to do. So those are probably the 2 things that I think are obvious. Obvious to me and a little bit crazy when folks don't do it.

49:28 Scott Ingram: Yeah. Debbie, talk about how you're setting up a pure discovery call like that, because I will tell you, I watched a train wreck this week by somebody who, one, they weren't prepared. So that was, that was the bigger issue. But the client expectation was, wait, I thought I was seeing a demo, you know, and it just wasn't set up properly. So how are you setting up that conversation so that it's clear what's gonna happen.

49:54 Debe Rapson: Yeah, any SDR that has worked with me before and made that mistake once never made it again. And it has happened where the client has said to me, hey, I thought I was getting a demo. Wait, what? And it's probably happened 3 times in the last 7 years at Demandbase, but it never happens again with each SDR. You know, the way that, that I set it up is is I really try to help the rep understand the SDR who's typically setting up my appointments. And if it's me setting up my appointments, I'm in the same way very clear. I help them to understand, you know, our first discussion. So when we get together next week, I really want to spend the time to understand your business, the things that you're trying to achieve, your goals and initiatives. And I also want to understand your challenges that are keeping you from being successful here, and I want to understand how you're measured. So let's spend, you know, an hour together. I'll ask you a bunch of questions and happy to share some information about what we do as well, but then I want to just ask you a lot of questions and really understand, you know, what's happening in your world. And then I'll come back and I'll show you what Demandbase can do for you. I'll talk to you about the value that it's going to bring you. I'm not going to show up and throw up. I'm going to be really prescriptive and focus on your business. And I never have somebody say, yeah, no, I don't want that.

51:30 Scott Ingram: I don't want real help, just write me a prescription, right?

51:33 Debe Rapson: Exactly. And once I help the SDRs kind of understand… I mean, they're young reps also, the SDRs, and, and, uh, typically they They don't necessarily understand how important it is to do that kind of discovery. So I spend a lot of time working with the SDRs and mentoring the SDRs so that we can sell business together and they make money and I make money. It's a lot of time. You got to invest, right? You got to invest in your team and invest in your clients to be successful. Yeah.

52:09 Scott Ingram: Oh, that's great. What's, what's your favorite bit of advice or coaching that you do with your new SDRs?

52:17 Debe Rapson: Uh, I really sit down and walk through my territory with them. I spend typically the first month with them when, when they're kind of brand new working with me. I spend the first month or so meeting with them twice a week. Week and walking through kind of the different things that I know are proven for, you know, that will make them successful. So I look at things like how are they prospecting. I want to understand how they write because most sales reps don't write well, don't write emails well. So I really spend some time upfront on that and pass some templates and help them to understand how to send out emails to that are relevant and interesting to prospects versus just canned kind of emails trying to get an appointment. I really focus on that relevancy. So spending time with the emails, walking through my target account list and guiding them to either specific stakeholders, specific roles that I call on where I know I can get good success And, and then of course, you know, how I would like them to communicate with that person. And part of that communication is how are they going to ask for the meeting and, you know, setting the expectation around that hour discovery. So that's definitely part of that process. And then I meet with them on a regular basis after that initial 30 days is, you know, we're, we're along the journey together. I meet with them typically where, you know, where I am 2 or 3 times, 4 times week. And typically I'm, you know, meeting with them once or twice a week. Hey, let's set our goals for the week. Who are you going to call on? What folks are you going to get into? Um, you know, this organization over here, we need to understand who's who in the zoo. We need some org structure information, etc. So, you know, you have different stages, um, of sales cycles that you're in with a company. If you're at the beginning stage, I help them to understand how to do the research. And Demandbase, like I said, has a great tool, SpyderBook. So it's nice that we have that and we definitely drink our own champagne. So we use that tool, um, as well as a plethora of other tools like SpiderBook, et cetera. And we're really working together. I'm not just letting them kind of go fish and hopefully have good luck. I want to maximize their opportunity and help them to optimize the time that, you know, that they're prospecting for me, I really want to help them optimize it so that we get good results. So I invest for sure heavily.

55:06 Scott Ingram: Well, it makes sense, right? I mean, you're investing in somebody who the more successful they are, the more successful you're going to be.

55:12 Debe Rapson: Exactly.

55:14 Scott Ingram: So, Debbie, let's… I think that's a pretty good transition to talk about kind of mentoring in general. I mean, obviously in those cases you are being the mentor, but, but how do you think about mentors and foster those kinds of relationships?

55:31 Debe Rapson: Well, that's a great question. I wish I had a mentor. I'm mentorless. It's really unfortunate. If maybe… would you like to be my mentor?

55:43 Scott Ingram: I think it's the other way around. That's why I keep calling you.

55:46 Debe Rapson: I don't know. I, um, I, you know, I really don't have a mentor. There have been a couple of women along the way in my career who have provided some guidance and advice. But I, I think that the industry that I'm in, which is, you know, which is software solutions, I don't think there are a lot of women before me who are ahead of me, who are on the same track that I'm on. I, I think I'm, I think I'm that generation. I, I look at the other women that are my peers and kind of in my age group who are very senior. And, um, and I'd look, you know, and they're all kind of with me barnstorming, if you will. You know, typically we're the only women sitting at the table in a meeting, and we're all typically top performers. Um, and we'd like to stay in the sales game, right, for, you know, for maybe throughout the rest of our career. And there aren't that many people in software sales that are number one women that are career, you know, lifetime career salespeople. And it's not to say that a mentor couldn't be a man. Absolutely. You know, I'd love again to have a mentor, but I haven't really found anyone who I've come up against that, you know, who I've met up with, who I have that kind of relationship with, which, which makes it challenging because there are just not that many folks kind of ahead ahead of me, um, in a similar position. So it makes it challenging. It makes me kind of have to make up things as I go. I talk to my mom a lot. She's a strong woman.

57:37 Scott Ingram: Well, Debbie, it's, it's so interesting because we talked about this again in, in the first, uh, conversation, but it's become even more pronounced. So obviously women are a minority in the sales profession. I am finding more and more that they are at the top a lot. And in addition to that, I think that rarely do you see a woman who is a C-player in the sales organization, right? They're not at the bottom. So, I'm curious as to… I won't plant any seeds. I have some ideas that I've been developing, but I'm curious into your perspective as why do you think that is?

58:18 Debe Rapson: Well, I think it's because I think women are raised to be aware of their surroundings, and I think women are picking up the social cues and they're watching all around them as they grow up. You know, they're watching their moms, you know, when they they're getting dragged to the store with their moms and they're, they're, you know, they're watching and observing how people communicate and how they interact in the world. And I think naturally that's what we do. And I think guys lead a little bit differently. I think they're a little bit more in their own body, if you will, and kind of charging forward. Don't pay as much attention to kind of what's going on around them, their surroundings. I'm being really general, obviously, so, um, you'll have to forgive me for that. Uh-oh, Kona's gonna start barking here. Um, sorry about that. My, my cute little 15-pound dog is acting like an alpha chick here.

59:31 Scott Ingram: I was gonna say we'll cut this out, but now we have to leave it in.

59:34 Debe Rapson: Yeah. So, um, but you know what I, what I would say is that, um, you know, that, that those kinds of, um, you know, those, those kinds of skills… watching and listening… really help make a strong sales rep because you're aware of what's going on around you. You are listening to people and engaging in, you know, in kind of that curious way, asking questions. And I think that that really helps. And I, you know, I think it really helps in dealing with people in those interpersonal skills area.

1:00:11 Scott Ingram: Yeah, that's, that's pretty interesting. And it's, it's along the lines of where my, where my theories are too. And it just, it has to do with the level of, uh, empathy and a stronger listening ability. And it goes back, it really goes back to your discovery and, and genuine caring. It's, it's all those things that you said at the very beginning were what set you apart.

1:00:35 Debe Rapson: Yeah, I think so. I, I really do. Good point. I, I really think so. I think those are the kinds of things that, that make a difference in good sales reps, you know, just picking up those cues. It's one of the reasons I love, Scott, to be in the room when I'm pitching. I don't really like pitching over the phone or over the web because you don't get the ability to read the, the visual cues, and I think it's so important. And even when I do And every once in a while I do have to pitch over a web meeting. I always turn on the video and say hello. And if they'll keep the video on the whole way through, I'll keep it on too, because I really do want to read their facial expressions.

1:01:17 Scott Ingram: Yeah, that's, that's smart and getting easier and easier to do. It's funny, although it's a two-edged sword. Again, I've got funny story. This has been a very interesting week. But the BlueJeans, for example, as we get these newer kind of web meeting platforms, platforms, if, if any of you have used BlueJeans, it launches right in, like default is camera on. So, um, if you, if you haven't been down that road before and you work from home and you get a BlueJeans meeting, you might wanna put your thumb over your camera. And because it takes a minute to turn it off, it's pretty interesting.

1:01:50 Debe Rapson: That's funny. My Zoom meeting does the exact same thing. And if I, you know, I work outta my house, so if I've got the ponytail on top of my head, my client's gonna see it.

1:01:59 Scott Ingram: Yep. Yep. Yeah, it's too bad we have to be so mindful of those things again. I know. So, Debbie, I'm playing with a little bit of a new idea. I don't know if I call this a soapbox session or section, or I kind of want to reward the folks who have invested the time with us. They're obviously committed to their learning. They've been with us for an hour or so. So, is there a, is there a fun story that you really like to tell or, uh, or, or something that you feel like somebody that's listening to this, that's obviously committed to their own success really should know and take to heart, uh, going forward?

1:02:42 Debe Rapson: You know, I, unfortunately, I don't really have a fun story to tell. Um, but I would just say, you know, listening to yourself and being genuine and listening to your own intuition inside of yourself is a little kid who's gonna tell it to you straight. And listening to yourself about how you should be behaving is a really important thing to do. You know, reading a situation, there's always that voice inside of you that says, oh man, I really screwed that up, or wow, I hit a home run there. Listen to that and, you know, pay attention and, and, you know, and find that natural curiosity and passion. And if you don't love what you do, stop doing it and go do something else because Because whatever it is that you love to do, you'll be able to make money at it. You know, it's, it's really about listening to that voice inside, I think. And, you know, and treating people well, you know, treating clients like they're friends. You know, would you, would you not return a phone call from a client? Or I'm sorry, from a friend? No, of course. Would you do that follow-up? Of course you would. Know, just treating people well and, um, and listening to yourself. And I think you, your path will unfold in front of you.

1:04:02 Scott Ingram: Yeah. It's so, I'm glad you brought up the belief thing because I feel like that is probably one of the most consistent, maybe even the most important themes that has started to emerge from this as well. Right. If, if you don't believe in your product wholeheartedly, it's just, it's just not going to work. Right. And the rule I've always had, I mean, whether it's belief in product or, or anything else. I've, I've always said if you don't love what you do, it's work, and work sucks.

1:04:33 Debe Rapson: It really does. Totally agree.

1:04:38 Scott Ingram: Good. Well, I think we have done a fantastic job here. Any, any parting thoughts, or shall we, uh, shall we call it a day?

1:04:45 Debe Rapson: Let's call it a day. But I just want to thank you for, for, uh, retaping, um, and giving me the opportunity. It's been really fun, and really fun getting to know you, you as well. And I'm looking forward to listening to some of these other Show, so thank you.

1:04:59 Scott Ingram: Beautiful. Thanks again, Debbie.

1:05:02 Scott Ingram: Thanks for listening to the Sales Success Stories podcast. To be sure you never miss an episode and for an invitation to our Sales Success Community powered by Influitive, subscribe to our newsletter at top1.fm.