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What Got You Here Won't Get You There — From Founder-Led Sales to Scale · Selling AI

• Warren Kucker: ⁓ Hey and welcome to another episode of Selling AI. Today we're getting into something I think a lot about. What makes a sales rep a top 10 % salesperson? And what the line actually looks like now that we have AI in the room with all kinds of new tools and selling AI products. I have Christy Jones on the show today. Christy is a sales coach, speaker, and founders of the Sales Acceleration Group, ⁓ where spent the better part of a decade helping B2B SaaS founders and sales leaders build the processes and the people that actually drive revenue for businesses. Before that, she spent 20 years in the trenches, hiring, coaching, and training nearly 1,000 sales reps. She's the author of Selling Your Way In, which makes the case that there are jobs where someone else sets your income and jobs where you can set your own income, sales being a prime example of this. What I love about Christy's work is this, early stage companies bring her in, hopefully at exactly the right moment, before they try to to scale. Because if the process is broken at two reps, five reps, 10 reps, It's disaster at 50 reps. In today's episode, Kristy and I are going to talk about what the top 10 % look like in an AI-assisted sales world, how AI is changing founder-led sales motions, and what accountability actually means when the excuses get harder to hide. All right, let's get to it. Kristy, thank you so much for being on the show with us today. Super pumped to have you. Welcome to the show. Kristie K. Jones - Author: Warren, thanks so much for having me. I know we're gonna have a great conversation. Warren Kucker: Great, awesome. Well, let's dive in. Tell me a little bit about your journey. You mentioned in your book that your family is a family of entrepreneurs. You learned about sales and a direct relationship between work and income at an early age. And then you used that three-year career, you know, a server through high school and college, moved your way through B2B sales, VP of sales, and then basically a VP of sales, let's say founder, coach, and implementer at the early stage. Tell us about that progression and how you got where you are now. Kristie K. Jones - Author: I say I got my MBA at the kitchen table. So my father was an owner broker of a real estate franchise. My mom was a top agent in town. so ⁓ ironically, despite the fact that they were working in the same office, they did not see each other throughout the day. And so everybody came together at the dinner table for an hour or so before. She probably had to scoot off to show a house or present a contract. So everybody got to debrief their day, and that included my parents. So my brother and I were paying close attention. We learned about buyers and sellers and commission checks and all of the things that went into running a business when my dad was and wasn't taking a paycheck so that he could make payroll for his own employees. Money was a very transparent topic at our... dinner table in our household in general. so, you know, we, through osmosis, if you will, we both, you know, went through life, but at an early age had, you know, financial acumen, business acumen, and we got it by, through modeling. So although my dad was very open about talking to us about money and giving us tips and tricks, a lot of it just came through paying attention or even, you know, through not paying attention, but just hearing it, thinking you weren't paying attention, but it was getting, it was getting in. And so no surprise that my brother and I both went into sales. He went into the he took the individual contributor route Whereas I took the sales leader route and followed on my dad's footsteps But that was really the foundation I think ⁓ a lot of people didn't have the experience that I had growing up either because their parents didn't own a business or money was still a taboo topic and I I'm a big advocate about talking openly with your children about money because you know, nobody really teaches you how to manage money or how other people you know, spend or make money. And so I always say, if we were all more open about sharing what we made and how we spend money and how we invest money, we'd all probably be better off and we'd all probably have more money. So my parents live by that rule and I live by that rule with my child and so does my brother with his children. Warren Kucker: That's not something to put it and I can do it through a whole podcast. don't know what I'm probably doing wrong parenting and what scars I have from my own childhood in this space. But I would guess that most people probably accidentally end up into how they manage money as adults based on how they interact with it as children. So I really like that philosophy. Different podcasts, I dive into that really heavily. Tell me a little bit about, let's say the mid to later stage of your career. So you were a VP of sales, B2B SaaS company. You were looking for a new role. You were asking people, you know anybody who would be... VP of Sales, B2B SaaS kind of scenario, and you ended up doing consulting work for multiple companies, fractional VP of Sales work. Tell me about your full-time experience and then your transition to the work that you do now. Kristie K. Jones - Author: It's been my first eight years out of college in retail as a buyer for a major department store that still exists today. ⁓ And I got, but I got a really bad taste about corporate in my mouth. And I think part of it had been with how I'd grown up. You know, and I, we had to such a small company and it felt sort of like a family and I felt sort of like a number. would be sitting in the New York showroom at, know, Tommy Hill figure and you know, the president, the GMM, the DMM and down to the buyers. And then we were really just, you know, taking notes. ⁓ And, know, and being admins, if you will, in that situation. I really wanted in the situation where could be a knight, sit at the knights of the round table, as I call it, be an important part of those important conversations that were happening. ⁓ And so I took a leap of faith and joined a company that I think at the time I went from this major Fortune 500 organization to a company with about 15 or 17 employees working directly for the owner of the company without a title. I think my first title was ops manager, but that was not probably an accurate picture of what I what I was going to be asked to do. So for the first few weeks there was no formal onboarding. I followed him around like a puppy and went to all these meetings and sat in on all these meetings. And then he started handing me, he said, why don't you handle benefits? I was like, I don't really think about benefits. I don't have an HR degree. And then at some point he said, we need to hire some more salespeople. You've done a lot of hiring. Why don't you do some hiring? And I was like, okay, but I never really hired salespeople. So yeah, there was a lot of on the job training. I spent 10 years at that B2B SaaS company. I say I'm so old that we called it subscription model back in the day. We didn't even have the fancy SaaS acronym. were calling a subscription model. And that was when people were literally moving from like we had to convince them to get off on-prem. So I mean, they would be like, what do you mean? Like, what do mean the cloud? Like, what does that even mean? That's not safe. You know, like we just we're going to need a server. Like we're going to need you to mail us a server. And we were like, yeah, we're going to do that. So I mean, it was it's been a very like from all like I'll tell you one from that from like talking to people about moving from on-prem to cloud to now. I feel like I've lived through a lot of very big changes in the software world. After I did that for about, I don't know, 16 years. ⁓ like, you mentioned, I actually lost my job, ⁓ at a B2B SaaS corporation. was running their very first SDR team, ⁓ was under the sales umbrella. They made a decision, ⁓ that I had actually encouraged and was advocating for to move it under the marketing umbrella. ⁓ unfortunately the marketing team was out of, ⁓ Arizona, not in St. Louis, Missouri. And so they, ⁓ blew up the team, ⁓ paid me nicely to stay on for three months while they rebuilt it in Phoenix under a new manager and a new team, ⁓ under the CM. And at that point, like you said, I went out looking for my next VP of Sales job in some capacity. I was working for a startup at that time and I loved that world. I wanted to stay in B2B SaaS VC-backed And as I started to network, ⁓ I had met with a VC company here locally and the general manager that I'd met with had called me a few weeks later and said, hey, like we just invested in this cybersecurity company and they need to build out the first sales team. And the founder has no clue what to do. Like, could you meet with him and have coffee and give him some pointers? And I said, sure. And at the end of that 90 minutes, he became client number one. ⁓ And then two other companies that I was talking to tangentially became clients number two and three and as you mentioned I built my business on fractional. I don't do it much anymore I know it's very trendy now to be a fractional VP of sales But in general, I don't do much fractional work anymore at all but that is how I built my business in the first 18 months and Normally run about four or five clients at a time and that works just well for my personality like different stages Some are doing playbook building some are doing hiring. I'm doing some executive coaching with a couple of founders right now who aren't quite ready to build out their first sales team. all of the, know, every day is a little different and that works just perfectly for my personality. Warren Kucker: That's That's awesome. That's some great experience. You know, my last two roles are both still trying to get people from on-prem into the cloud. This is an example all the time that people, I mean, we were worried about like blockchain is something everything in the late ⁓ teens. Now ⁓ AI is the topic, which it's a big topic. It's a good one. It's a pretty solid shift. It could be too solid of a shift at some point, but we've been through this before, right? So like where cloud was the biggest, I'd say like, You're still looking at 50 % of businesses that could be in the cloud, but are on-prem, are still on-prem. It's wild. It's a really good awakening as to these things move in their own time. ⁓ And it's not lightning fast. So it's a fun... I have people that would stay on-prem and they wouldn't buy my cloud software because they're afraid when the phone lines go down in their area. So they want a server. So it's still there. So that's really ⁓ still prevalent. That's great. Kristie K. Jones - Author: Interesting. Yeah. Warren Kucker: Cool, let's talk about your work in let's say early stage, right? So, or like this founder led sales to like a transition there. From your perspective, what's like one of the top three lessons learned in this part of the growth journey for a company where they're getting out of that like let's say first founder led most of the sales, maybe they have a founding AE, but it's kind of like just ⁓ beg, borrow, and steal your way to revenue. Two, like we have something and we might have product market fit, but we need to figure out how to start to build this out with other people selling. What are a couple valuable lessons there? Kristie K. Jones - Author: you Mm-hmm. Yeah, less is more is the first lesson. ⁓ Trying to boil the ocean, but everybody can use our product or everybody would benefit from our product. You have one human, right? Like either you as the founder or the sole human, if you'd like, you said you have a founding AE, you have one human. That one human can't sell everything to everybody. ⁓ And so I think one of the things that I tell people, said, I build out the playbook for really ⁓ other reasons than I put in the SOW. ⁓ you know, 46 page playbook. But what I'm really doing is creating alignment and discipline within the organization through the exercise of going through the playbook. So I don't build a playbook in a bubble. I do them as workshops. So I require that everybody who's important within the organization, and that could be everything from an SDR to customer success are present so that everybody understands and is growing together and makes, you know, we're in alignment. But once we, you know, once we get into that alignment, the ICP is so important and, you know, really like In some cases, you don't need more than 200 companies, target companies. And the bigger and the broader, I said that I'm kind of snotty sometimes. So I say, Tam isn't for business. Tam is for VCs. So once you get your pitch deck and you got your VC money, forget about TAM because it doesn't matter anymore. Now you have to really get small. And so I think that's one of the biggest mistakes that people make. I worked for a startup out of Romania. And when I first got to them, they were selling globally, including Australia, which was a crazy time zone for everyone. had one, we ended up hiring one European rep that included Australia and one North American rep. And I mean, I I fought it the whole way. I was like, this is crazy. Like this is two humans, an entire globe. And it just like, you just don't need it. initially I kind of say like, why don't we just own, what do we want to own first, right? And in general, I kind of encourage people to own their backyard, right? You've got the network, you your founder is, you know, lived, probably lived in that area or are they, you know, they know the industry, but I think the other big mistake they make is trying to do bite off more than they can chew initially with one single human. Warren Kucker: Yeah. That's ⁓ I talk about this all the time. It's actually a frustration with it in this space, especially when you start venturing into, I'd say, should I have venture capital? Should I take venture capital money? Right. There's no one then that has an incentive to actually truly understand what your TAM, SAM and SAM are, right? Like your, your target potential market, your addressable market and your observable market, right? Both the VC and the founder both have an incentive to inflate this, right? But you're, you're right. The smart thing would do, okay, we have to play the game that we're playing here, but then once it comes time to get on the field, let's really pin this down, right? And what I talk about with companies is the opposite of over-revoiding your TAM is going into a market that you're, what you need to do next, I need to get to four million in revenue to support my staff and get to a next level of funding or buy both of those. There's not enough companies in your potential market to do that actually for what you're trying to do with and while having that focus. So it's a balance, but you're absolutely right. Everyone over-inflates who they can sell to. And I love that focus. The problem isn't just lower. How do you convince founders that, hey, you have to focus on this one market. You have to try to win 5 % of the work in this space over the next 12 to 18 months. And how you do it, do you ever get any pushback from the founders you're talking to? Kristie K. Jones - Author: Sure, absolutely do. I think part of the problem is by time I come in, they've probably gotten to a million dollars in revenue, right? That's how you get your first round of that VC money. But when you look at the clients, like the very first thing I do is an ICP workshop, right? And I go like, who are the clients today? And then I say, what do they have in common? And there are very few things that those first few clients have in common. So I go, okay, well they only have five things in common. So we have to find other companies that also have these five things in common. And that's not that many people. Because you've been selling to anybody who had money, or who believed in you, or who knew you from before. And I said, you went through your friends and family Rolodex. But I said, what you haven't done, and this is where I'm starting to talk to founders about, and VCs as well, by the way. Like you really need to get to two million. That first million can be the friends and family plan, but that second million needs to be cold, right? Needs to be people that don't know you, who don't know how to spell the name of your product, who don't really understand what it does. Right? Because they haven't lived through giving the birth, you know, the nine months of birthing the baby, as I say. And so, you know, I think that's, know, what I say to them is when you look at what really these have in common and then what really makes sense, because in some cases, like those first few customers, some of those are miscells, just like mis-hires, right? You should not have sold to them. Because I asked that question, who do you wish you hadn't sold to? And they're like, well, they go, who do you when you see that caller ID number pop up on your phone, you do not want to answer. Right? And a lot of times it was, they're too small, right? They were too small. And now they think we're their admin, right? They don't have infrastructure inside the organization. And so they call us and be like, well, can you just build this for us? Can you just do this for us? So it really is like, I spend a lot of time on that ICP workshop because there are very few, like we're gonna come away with very few, when I say objective traits and then subjective traits. of an organization, right? The firmographics are the objective, like this is what they look like. And even then I'm like, you know, what's the floor and what's the ceiling? Cause it can't be floor and the ceiling is infinity, right? You need to have a floor and a ceiling. And so just getting people like really helping them understand. Cause then I say to them, like, you know, the very first question I ask is, well, so like forget about your TAM, but within this thing, do we even know how many people fit that? And they go, no. I know. I'm like, and then when they come back and I said, that's their homework, and they come back and they're like, there are 47,000 companies. And I go, great. You still only have one human. Warren Kucker: Yeah, right. Yeah. No. This is I just got this conversation because I just go through this. This is my entire experience in like the venture capital space, right? It's just like country like ⁓ need in order to hire ahead of your growth. This is like what that's what really you're doing with VC, right? You need to like get aggressive with these metrics. But the result is you're absolutely right. I'd too many revenue. To get to a product market fit, you need like one million in revenue with like at least 20 customers that look alike and use the same product. Oftentimes even at two million, a couple of customers are using kind of like a side product. They're not using your product fully. Couple of customers are nothing like the other customers. And then you really boil it down. like, I have to talk to companies that have seven million revenue. I'm like, you don't have product market fit. I don't know what to tell you. Like you have such a wide range of revenue. great. It'd be cool. I'll take eight million in revenue with like a few enough people to be profitable, but to be in the VC world. Kristie K. Jones - Author: in. Warren Kucker: You can't give a rep territory of about $15 million in potential revenue and have them turn that into 700,000 because they don't look alike. And that's really what you're trying to do at this stage. What have you found? I really struggle with this. I'm a founder. I'm founder, founder-led sales, turned VP of sales, back to a founder, sounding like a founder, and breaking every rule in the book in a bad way. How do you coach founders through that transition? Great, you are ready to hire. You should bring in like three reps. Kristie K. Jones - Author: Mm-hmm. That's right. Warren Kucker: right, to target this market, to hit two million in new bookings next year and into your next stage. How do you coach them through that transition? It's a really stark transition that people take for granted. How do you do that? Kristie K. Jones - Author: Yeah, I make sure they're ready. ⁓ You know, and I actually just have a checklist to be honest with you about the things that you should be able to check off. Right. And that is like, you know, things are documented formally. We have processes, you know, we understand what's worked and what hasn't worked. We have, you know, we have a commission structure that. mirrors what we want to have happen. Like we have quotas, we know how to ramp, we know how we're gonna get there. Some of it is still little fuzzy math, right? mean, some of it we're not, like this is what we think can happen, but we're not 100 % sure. But I think the most important conversation I have with founders is, are you ready to give your baby up for adoption and only visit it on the holidays? Because like if you're, I say if you're gonna continue to micromanage and keep your hand in the cookie jar, then nobody, no matter how good a person I find for you and bring into the house, you're gonna push them out or you're gonna tell them, so you're gonna tell them that this is not how it's done. But what I have to explain to them, and that's why I say, really starting to push people to take that second million, between million and two, and go do cold, right? Because I say to them, go, I call it founder advantage. I have a whole keynote on the founder advantage because they're not you. They didn't give birth to the baby. Their name isn't founder or CEO. They didn't spend 25 years in the industry. know, like they don't have all the advantages that you have as founder. And in some cases that, you know, cause you know, founders, you know, I just send these LinkedIn messages and people agree to speak to me. I'm like, no kidding. Wow. You know, I go that's not gonna happen. And so the very first thing I do is try to prepare them for that. Because, you what I don't want to do is run off an A player, I find for them, because they keep telling them, well, that's not how I did it, that's how I did it. That's why I really make everybody go through that playbook exercise. Like I refuse, I will not hire a sales professional for you if you have not either had a fully built playbook done by you or somebody else, or I've been involved in that process. ⁓ Because the playbook that we're building should not be built on the Rolodex that they used, right? So when they start to say, I just send these LinkedIn messages and I go, well, that's great. That's not gonna work for the next person. So now what are we gonna do, right? Are we gonna hire marketing? Are we gonna have a marketing content plan? Are we gonna go to conferences? Like, what's our go-to-market strategy? Because that's one of the things, ⁓ I know you're gonna smile. There's no go-to-market strategy. You have product, market, and they think they won the lottery. And I'm like, there's no go-to-market strategy because they've just been using the friends and family plan. Warren Kucker: Yeah. Kristie K. Jones - Author: That conversation is so important and a couple of times, had to, because I stay, we do hiring a little differently around here. I call it project managing the hiring process. So we never leave the founder alone with the candidate. We lead all those interviews. We're around for onboarding. We're hand holding them through the whole process. ⁓ But you can tell during onboarding, I sometimes have to pull them aside and say, you're doing it again. We're going to work the playbook. What you did work, I'm with you. Warren Kucker: Yeah. Right. Kristie K. Jones - Author: Congratulations, right? It's a big deal. Most companies don't ever make a million, right? They never get there. They never get VC funding. They never get PE funding. Like that's a big deal. But the other Christ-ism that I use all the time is what got you here won't get you there. Right? And so, and that includes the people, right? The people that you built the $1 million company on will probably not be there when you get to five. They just won't, right? They're not the right, you needed this skill set for zero to one, but you're gonna need a different skill set from one to five. Warren Kucker: Yeah, it's like there's a saying in sports that like the playoff series hasn't started until the road team wins a game, right? Like you're trying to build like a growth scale company. That bootstrap, bootstrap's wonderful. You can get to 10 million with six different product lines and different customers and a core team of people. That doesn't, that scales literally. Like you're just gonna add that revenue, but you can't build the. I'm gonna, this sales team eventually is gonna be 25 reps in the next like four years to really hit that kind of like hockey stick growth curve. You can't do that without being really intentional about those first few. You're absolutely right. One thing I've actually struggled with, so you're gonna answer a question that I actually don't know the answer to is still to this day, ⁓ would be this. What's the level of involvement from the founder that should be with those first few reps? I feel like sometimes there's two things that happen. You're way over involved and you do exactly what you just talked about. Or you pull yourself out entirely and you're like, I'm going to trust the experts. Right now the experts are here. I'm going to pull myself out. And I don't know that that's necessarily the right approach. Eventually, the CEO should be involved in big deals, later stage, or mid-stage, exact-to-exact conversation with large customers in your song. So that should happen. Is there an in-between? What's the in-between for a founder with those first three reps that first year and a half? Kristie K. Jones - Author: Yeah, I actually encourage the founder to become the sales leader. Right? Warren Kucker: Okay, right. Kristie K. Jones - Author: And so that's sort of how I, you cause then they can help figure out when to insert themselves into deals when, they think they can be of help. And so, you know, sometimes, like I said, sometimes that's where the fractional sales leader part, um, sometimes, you know, I get them on boarded or whatever and they're like, well, you're not going anywhere. Right. I'm like, I would like to, uh, I'd like to leave at this point, but, I'm, but I'm happy to train the trainer for three months. Right. So I think the CEO needs to understand how to run a pipeline meeting, how to run a one-on-one meeting, how to provide. Warren Kucker: you Kristie K. Jones - Author: coaching, you know, how to understand when the pipeline is a fantasy versus a reality. ⁓ And so I would rather they take that mid-level role so that they're not, again, they're not doing it, they're not fishing for them. but they're providing the support that's needed and that gives them the ability that they don't feel like they're being left out of the game either, right? So they still get information, but they get it in a more structured way as opposed to calling all day long or pinging them on Teams or Slack and being like, what's going on with this deal? I don't see another whatever and your notes aren't in here. Like, let's put a structure together for that. ⁓ And so I think that's, you and I do a lot of that, by the way, like I'm already building the bridge during the interview process. and I think that's really important because I'm leading those interviews and I've got the founder and the candidate in the room, I start to talk about how do you like to be led and how do you like to lead? And then I ask a very important question at some point. said, hey, Warren, what will have to happen in order for you to start to build trust with Christie? to the point where you don't need to feel like, yes, you're gonna do pipeline review every week or whatever, but you don't need to be in HubSpot every single day with the deals screen up or the deal dashboard up every day, poking around. How does trust get built? And that's the most important question I probably ask during the interview process. And everybody needs to be honest with themselves because if it's... you know, if it's like, I'm not a really trusting person and it's probably gonna take a few months, now the candidate gets to choose whether they wanna deal with that or not. Warren Kucker: That's a really good way to look at it. Okay, cool. Let's pivot to, say, the excellent individual contributor, right? ⁓ What I'd say is like, what people, laypeople outside of sales think make great salespeople is generally not anywhere close to what actually makes great salespeople. We had like a pretty solid framework that challenged the notion and the challenge of sales like a decade ago and use some science and some math to be like, great, this is a quadrant of potential salespeople and this is the type of salesperson you want. on way I framed it as a founder to people is like, there are some sales reps that people have found hard, they're hard to work with, right? Like from an organizational standpoint on a sales process. But like, there's hard to work with, that's not fun. But then there's hard to work with, like the personality trait that you're struggling with is what actually makes them a great salesperson. So you just have to leave it alone. So like, you have to deal with it because that's what makes them great on the sales process, right? From your perspective, the Christie Jones process, like. What do you think makes a great seller a seller? How can a seller become that great seller in your framework? Kristie K. Jones - Author: Yeah, that's a question. think initially, and again, I always take it from the lens of kind of an early stage because the early stage, the one, two or three sales professional needs to be maybe different than four, five and six. But I affectionately say, I'm looking for people who aren't gonna check their brain at the door. Right, so if you need full SOPs, if you just need to execute someone else's full plan, this is probably not a good place for you. And I think in general, even if you're in a more structured or let's say a $25 million company, your best reps are gonna be people who are always looking for process improvement ⁓ within the organization and within themselves. And so those with strategic and critical thinking skills, those who challenge in an appropriate and professional way how things are done, and are willing to be that early adopter, meaning, a lot of times, I always said to reps, when they came to me, I said, when the first three months you start, you are gonna follow the playbook, right? And then if that's working for you and you're getting to that top 10 % realm, at some point, you will have earned the right to come to me and say, I wanna try to do it this way. And I'll say, fine, I'll let you and only you do it that way, but you have to commit to doing it for 60 days, are you willing to do that? Because not committing, like just deciding to try it for one week is not, that doesn't give us a good sample size, right? You have to get better at it. You got to try a few things. But I said, are you willing to commit to it for 60 days? And if you are, then yes, you can go off and do that. And if at any point during that 60 days, we don't think it's working and we don't think it's going to work, we all agree to abort. But I like those kinds of people, right? And they're not, like you said, they're not lone wolves, right? When you think about Challenger, they're not lone wolves. ⁓ They are challenger sales reps. They are people who look at something and say, this probably isn't completely as good as it could be. And how do we make that better? ⁓ I think the other thing that I really stress in the book is that top 10 percenters do everything a little differently in their life. They probably don't drink a lot of alcohol. They probably put whole foods in their body. They probably have a religious or spiritual practice. They probably get exercised. may have some sort of a, like, you know, they may do yoga. They may do something like that. ⁓ They care about their circle and they only bring the right people into their circle that they think support the mission, if you will. ⁓ They seek out mentors and they mentor. They have that give back mentality because, you know, they understand that that's how everybody gets better. And so, you I ask a lot of questions around things like that. I want to understand, you know, how do you start your day? You know, and I, and a lot of, and the top 10 %ers I hear I started at the gym or I started with a meditation practice. Um, you know, something along those lines. So I think, you know, I always use the example I said, you know, like two, back in the day when we were in the QB world, you know, like you'd be sitting next to your QB mate. It was over here. Right. And you know, the QB mate is outselling you, but you're hearing the QB mate all day long. You're hearing Sally and what she says all day long and you are mirroring that and yet you're not getting the results What you don't understand is what Sally does after hours? When she leaves the office right who she spends her time with the book she reads, you know the podcast she listens to You know the you know the exercise that she know that she's going straight to the gym Like you know that you know about the gym, you know, she you know eats salads instead of fries or whatever But you don't understand that that's part of the entire plan. that, so I think those are the things that I think people, people spend a lot of time when they're interviewing on skills, past, know, past successes and experiences. And I don't disagree with that. But if you really want to know who a true top 10 percenter is, you know, they're treating their body like a temple. They're putting in the reps just like a professional athlete would put in, you know, they're practicing like they play, if you will. Warren Kucker: Yeah, so let's get into the why. So let me throw out a proposition. you tell me when I'm wrong or tell me what you've seen has worked and what I said. when I talk to reps about this, right, I think over the past six, seven years in B2B SaaS with a lot of cash and a 0 % interest rate kind of scenario. And B2B SaaS isn't all there is selling, but this example works really well. Actually, most selling is not like this, to be clear. We just expect, like, great, like in order to make all the math work, you're going to sell a million dollars worth of work a year, right? Cool. Sounds good. Great. That makes the math work for what we need to do overall. Selling a million dollars in new business a year is hard work. Like it is not, that is not something that we've expected that it should happen because we had to set the metric there, but it's not usual. I think it's 38 % of people made their quota in this space according to Pavilion and probably 2024. I don't know if the 2025 numbers are out. So it's hard work. On top of it, if you can consistently sell 1 million plus in revenue, You're going to bring home 350,000 plus in revenue and your own cash, right? A $350,000 a year job is a hard job. it's just like, it's not, if it was easy, then everyone would have $350,000 a year jobs and everyone would sell a million and the bar would move. Right? So like to me, what you're talking about, it's not that any of these are like vanity exercises. So you're like, Hey, I meditate and I eat well and I exercise and I choose my circle. Right? It's that. Kristie K. Jones - Author: That's right. Warren Kucker: In order to get to the level where you're a top 10 % and you're consistently making $350,000 plus in your role, you have to kind of optimize a lot of the fringe parts of your life in order to do well at a hard job. Is there something I'm missing there, something I'm wrong about, something I'm right about, something that you've kind of pulled through in that experience there when you talk about this problem? Kristie K. Jones - Author: I don't think that you're wrong. do think it gets easier because the other thing that these people have is discipline. And so when this becomes a habit, when the discipline becomes a habit, it's just how we do things. Right? Like this is just the culture we've built. Um, you know, again, like a big, I'm a big sports person. Um, so Kelvin Sampson, university of Houston, right? And my big 12th world. I'm a Jayhawk. I love him. I would love him to be our coach at KU when Bill Self leaves because he builds culture, right? He builds like, this is just how we do things here. And if you don't fit it, then, you know, sayonara to you. And I think top 10 % are building their own culture, right? Like this is just how we do things, right? right way and a wrong way to do things. And I do think, like I say to people, go, one of the things that makes me crazy, and it happens with top 10 percenters too, is people don't ask me as much as they used to, but they'd be like, how can I be successful? What is the thing I need to do to be successful at this job? And my answer is always, stay three years. Stay three years. Like, year one, you don't know what the hell you're doing. You're just building your pipeline. You don't even know if you can close anything because sometimes it's gonna take six to 12 months to close something. you know, like I eliminate, I've been eliminating, I've been doing hiring for two. I'm looking for, I was looking for three enterprise reps in the last two to three months for two different clients. And I was eliminating people that only stayed 18 months. And people were criticizing me. They were like, that's the average time people stay. And I said, if you are an enterprise sales rep and your sales cycle is 12 to 18 months, that means you've only sold one to two deals. That's not a track record of success for me. If you can't do it five to 10 times, then how do I know you just didn't get lucky? Right? Or how do I know that that deal wasn't already get started before you showed up to close it? Warren Kucker: Okay. All right. Kristie K. Jones - Author: And I mean, so I'm like, I do think that the longer you stay, so I always say like, year one, you're figuring it out, building your pipeline. Year two, you're figuring out how to close it, because year one is figuring out how to get into the pipeline. Year two is figuring out how to close them consistently. And year three, all those, I call them NRNs, all those not right nows, I mean, we're only closing 15 % of deals in SaaS. 85 % of people are saying no for one reason or another. If you actually stayed into year three, Warren Kucker: Yeah. Kristie K. Jones - Author: How many of those NRNs would show back up, right? Because the problem got big enough, the pain and problem got big enough to pay for, they got more money, something happened. like, I do think the job gets easier, but no one stays long enough for that to happen. Warren Kucker: Yes. Now, that's a really good take, because I completely agree. I think one of the bigger flaws in how we've tried to operate this type of sales motion over the past half a decade to a decade is that honestly, most of the time, you have to open up an opportunity with a company two and a half, three and a half times before they close. Not everyone's in a logical buying window at any sort of time. Even if we could solve the most important problem they have right now for an ROI that's through the roof. right, with very little risk, right? That's why I'm talking. Some people, they're just not ready to buy yet, right? So it's just like, it's great if you can make it for long enough to build more innate awareness in your targeted market pretty narrow, where everybody knows who you are, right? They've heard of you a lot, right? Like they told you no several times. I'll say a lot of those nos come around to a yes, but I've only really thought about that from a company perspective, not a rep perspective. How do you feel like a, how does a rep know the difference between like, hey, you know what, like I'm at year two and a half. It's going, I feel like I'm really good seller. It's going pretty well. If I stick this out, like I'm almost at the precipice of again, having like a solid five year run and like stacking up big money years on top of a lean year or two. How do you think reps can tell the difference between the two? Kristie K. Jones - Author: mean, what is the company doing, right? Are they investing in R &D? Like, is the product getting better? You know, are they expanding into maybe other markets? Like, where's your opportunity going forward? And I think it really is looking at, I think product is one of the main things to be looking at. Is the product continually improving? We're coming out with new feature functionalities that are being driven by customers who say, I'd really like it if it could do this. Are we staying competitive? If we have competitors within that space, are we staying competitive? ⁓ Things are like, you Are we recession proof a little bit? Right? mean, right now it's it's harder, right? It's much harder to close. I put out a poll, I know, a few days ago that said like, what's the big difference between now and then? it's like the buying, know, buyers are, it's just taking longer. It's taking a whole lot longer to get a deal closed, which is another reason why you shouldn't leave because you're to leave that pipeline behind. ⁓ But really, you know, but like looking at your, like, you know, do some predictive analytics, right? What does the future look like for the company? What direction is the company headed? Is this a direction you think you can win in? Or are they going down a path or a different direction that you're like, yeah, I don't know that that fits with my sales superpower. ⁓ I spent a lot of time in the book, and that first time I in the book. I think so many salespeople mismatch their sales superpower with the organization. I just got off a call right before this with a candidate for one of those enterprise account executive jobs ⁓ in health tech. And we have a pure SaaS product. And he's been selling product plus SAS. He's been selling equipment, medical equipment plus SAS. And after 30 minutes, said to him, said, this isn't a good fit. And I'm to tell you why I'm always very direct. they don't get the dear John or dear Jane email from me. You get, unfortunately get to hear it over zoom. But I told him, said, it's very different. You know, and the other thing he didn't have was startup experience. And I said, it's really like, go, you know, he's like, yeah, but I've, I've come into places where they didn't have this, that or the collateral or whatever. I go, you don't know what you don't know. Like I can't explain what a startup life is like, like to the point where you would really believe, like you would believe me, but you really wouldn't understand. Warren Kucker: address. Kristie K. Jones - Author: And so, you know, I think that's the other thing is like pick I told him I said you have had five jobs where you've sold equipment plus sass That's your swim lane Stay in your lane friend Like that the chances of you succeeding outside of your lane at this point because you've figured so many things I go you've spent all of these years like 12 years figuring this out Why would you want to leave now? Warren Kucker: Yeah, yeah. Yeah, because you're starting from, then you're starting from like a pretty tough starting point. You could figure it out, but it's gonna be hard and it's gonna be lean years, right? It's gonna be an intentional shift. And I think most reps take an unintentional shift for good reasons and some bad. Yeah. Kristie K. Jones - Author: Yeah, they take the recruiter. I go, you took a job because a recruiter called. That is the worst. That's the worst reason to take a job. You know what? And top temper centers don't do that, by the way. Top temper centers, if they leave, they use the same prospecting strategies that they use to get clients to get the next job. They know, again, they don't have a TAM. They've got a very small ICP, ideal company profile. Warren Kucker: Right. I know. Kristie K. Jones - Author: And then because of that, I told this guy, go reach out to companies that look like these last five companies. They would love to have you. You know, he thinks SAS is cool. I think SAS is cool too, but I think he'll struggle. And I think he'll make a lot more money if he stays in the swim lane. Warren Kucker: Yeah, right, making money is more funny. Right, agreed. Cool, okay, maybe two last questions. This is great. So let's put yourself in the shoes of a sales rep. Let's say you're a five, seven year sales rep. This would be a hard hypothetical, but we're gonna go through it anyway. Five, seven year sales rep, right? You're like really good. You have a taste for it. You've done pretty well. Like you made your quota. You're trying to level up, right? And there's two things involved here. I'm moving on to a new company no matter what is happening. Kristie K. Jones - Author: Hahaha Warren Kucker: How would you select what company to work for? What criteria would you look for? And what sales skill do you feel like that person probably has to level up on the most there? Now, if you have to put yourself in a specific vertical or a sales process in order to get there, what would you focus on as a sales rep right now in 2026, really trying to get into that top 10 %? You're at the 70 % mark and you're trying to get that boost. How would you select your company and how would you boost yourself? Kristie K. Jones - Author: Well, what's the next level mean? So I call it step changes. And so when I'm looking, the other thing I look for in candidates is has everything made sense in their career progression? Did they take a step back? When you see the step change, I call them step changes, I'm like, everything should be bigger and better. The job should either be more complex. The compensation should be better. There should be more bonus structure. You should maybe decide you're going to be involved in, maybe you get to be involved in expansion, where before the customer success rep was involved in expansion and renewals. So what does more complex look like for you? Because if you're trying to get to 100 and you're at 70, you're going to have to do something uncomfortable. that you haven't done before, but what's, but like, you can't go from here to here, right? It's like, what's the next like step level up, step level up, step level up. And you can look at someone's, like you can look at someone's resume progression and you're like, and when something doesn't make sense, there's normally a reason. And a lot of times reasons are personal, right? Like sometimes I'll reach out to somebody and say, Hey, before I interview you, I noticed that you took a job, like you moved and took a job that was like lateral. And it doesn't make sense to me because all the other things you've been doing were progression. And they're like, yeah, my mom got sick and I needed to go be near to her so I could take care of her. And I couldn't handle taking on a bigger role. I needed to do something that I really felt comfortable with and understood. I hear that all the time, right? There's a personal reason for that. And so what does NEXT look like for you as far as the skills and then as far as your question about the skills that you're missing, it probably is something about complexity, right? Like ⁓ multi-threading, like you're gonna need multiple departments, like the health tech company that we talked to, you know, it's wellness, it's HR, it's IT, it's the chief medical officer in a lot of cases. And so do you understand before maybe you've been selling to two departments, but now you're selling to four. Do you understand how to continually keep the ball rolling with all four people or all the committees and all those departments? So it's just a little more complex than what you're doing now. But I think a lot of people go like, go, oh, I've been selling SMB or I've been selling mid-market. I'm just going to go into enterprise. That in some cases is a really big job. If you've been selling $40,000 deals to go to selling $240,000 deals. And if you don't understand a 12-month sales cycle, so I'm saying like, the smart step level changes and you know think about what skills you know as you're looking at those job descriptions and starting to interview you'll figure out what you don't know and what you're gonna have to like again we always say is you know like we're building the plane in the air in some cases it's okay to take a job where you're building the skill as you're going through it if you have the right people lined up that's why that circle matters if you have mentors so your mentor if you're if your next level is let's say enterprise you want to jump to enterprise then you should already be being mentored by by someone who's been there done that. You should already have that person in your back pocket to support you. Warren Kucker: I think it's underrated that this like mentoring aspect until before I go to the last question. People look at this with too much complexity. Honestly, you could reach out to 20 people on LinkedIn that seem to have the experience and the role that you would want next. And five of those will respond and take the time with you, right? And one of those will take repeat time with you. It's really not, the math is actually pretty, we don't do a good enough job of like reaching out to those who have been there is four years ahead in the journey that you're on. like, Kristie K. Jones - Author: Absolutely. Warren Kucker: are perceived to be where you want to take the next step. It's like you think a mentor has to be someone you worked with in the past that's four levels up or any of these types of things. No, just find like an enterprise account executive who have been there for five years and have some quota numbers that make sense on their resume in a space that you think you like. And I don't see that it's also where jobs come from and when you need one in a pickle later on. So navigating around LinkedIn is way easier than people give it credit for. Kristie K. Jones - Author: That's right. Warren Kucker: So let's say ⁓ from your perspective over the next couple years, obviously a pretty big change in happening technology wise. ⁓ Do you have any thoughts on like a shift in how people buy and how sell over the next couple of years that we should be starting to be mindful of or should already be mindful of? Kristie K. Jones - Author: Yeah, you should already be mindful of, and I'm writing a of ⁓ blog posts and things like this on this topic, but the buyer's journey has changed, And we as sellers are not there yet, from what I'm seeing. So with the buyer coming in more educated than ever before, before we forced them into the discovery so they could jump through that hoop to get to the demo, they're not gonna do that anymore, right? They're gonna get mad, and they're not gonna do that, and they're just gonna go to your competitor. They're gonna go to somebody who's not making them do that. And so if you're a seller, you need to be thinking that the skill you probably don't have because we didn't need the skill up until just recently is how do I build trust and relationship with someone who's coming in at the 80 % mark? You know, we made them go through the qualification with the SDR, the discovery with the AE, the demo, maybe we brought in the SE along with that, because part of the reason we did that is so that we could build trust to when we finally said it's time to buy. They were comfortable doing that. Well, how do you do that when you only have 30 % of the time you used to have to do that? so, know, figuring out and getting sales leaders, I'm putting this on you because sales, mean, you know, top 10 % are might figure this out on their own, but in general, they shouldn't have to figure this out on their own. And so what is it? What is it? What does that first conversation now look like? And how do you build trust and credibility and a relationship with a fraction of the time that you used to have so that someone, and by the way, the buyer, it's less important for the buyer than it used to be too. Like this whole like people buy from people. I got it, I like it. And then we went from like people buy from people they trust. Well, guess who they're trusting now? AI. So they have to trust AI. And they are trusting AI in a lot of cases. they're gonna, like, you're gonna have, they're gonna be less trusting of you than they are of AI. And so how do you, and again, it'll probably be less important. This trust thing I think will be less important, but it's still gonna be there. And so if I were a sales leader or if I were a sales rep, I'd be going to my sales leader and saying, so what I've been publicly saying for the while is the first two stages of the sales cycle are now going to be owned by marketing. Qualification, discovery, and demo. Because if they go to your website and they can't, like your FAQs, like they want every single question somebody would ask you during qualification, discovery and demo, better be on your website. They better be able to find an answer to that. And that's marketing's job, right? So we're gonna come in, we're coming in at alignment, right? They're trying to figure out about alignment. and whether or not, they've already got three people, like you're one of three people, congratulations, you made the short list and you didn't have to do any work. But now the work really begins, right? Because now you're at the worst stage. You didn't help write the qualification or the questions you are here, whatever, right? And so if I was a sales rep and my sales leader hasn't started to train me on how that first conversation goes. Warren Kucker: Yeah, you don't know anything, right? Kristie K. Jones - Author: when they've already seen the demo that was on the website and they've already pre-qualified themselves in, and I start talking about, like, what are the business problems that you've been facing that got you to this point? They're gonna kill you. They're gonna be like, we're out, out. Yeah, I already know what my business problems are and I think you can solve them, prove it. They're gonna come in with a prove it part. And so that's what we need to be, we need to be shifting really quickly to what is the new first call look like? New first conversation look like. Warren Kucker: Yeah. I couldn't agree more with this first call paradigm and I totally agree. think a marketing leader had some research that like 82 % of research is done now. They call it dark research, right? They're not coming and getting your PDF. They're figuring out about you in ways that you don't understand, right? So like, and when I talk about from a rep and CS standpoint, I think the shift in what you're talking about here is like, are no longer, the table stakes, I don't think quite yet, because I don't think buyers have gotten there. And I think there's actually gonna be a subconscious move. I actually didn't know if they're gonna consciously be here. But what's going to happen is this, it's going be table stakes that you know everything you could know about your prospect and your customer across the board without having to ask them. And that doesn't mean everything internal, everything external. I was talking to an account executive at a FAANG company that talked about, they have customers in there, spend several million dollars a year, been doing it for 20 years, their account manager switches every six months and then they have to teach their account manager why they use their product every six months. That's infuriating on a subconscious level and it doesn't have to happen anymore. We can get away. is kind of like had to happen before. Now recording every conversation running in through LLMs, you don't have to deal with this anymore. Your AM should know exactly why your customer uses you and understand your entire journey. You're absolutely right. We need to, as a salesperson, if I was going to be really blunt, be like, listen, I'm happy to give you any information you need to decide to make this decision. All I need to know is this. What's the reason you would potentially buy us? And what do you think the impact of that is? And if you could tell me that so that I could use that throughout the process to understand whether it's worth my time to continue this. Then the rest is yours. The rest of my time is yours. Hey, we have $1.5 million in claims that last quarter that I need to get down to $750,000. Otherwise our gross margin is going to work. And the claims are because of X and Y. Cool. Sounds good. We could solve X and Y and we cost $50,000 a year. So here's the ROI. Let's agree on it. How do I get you to a point where you understand that you can justify the purchase, you understand what post-purchase is going to look like? And honestly, I talk about people want to buy from people. You just want to vet, do I want to enter a three year relationship with this company? And the sales to me is the first gateway of this. They're good to work with, I think customer success would be good to work with. And I think all of the rest will really get to elevate the time we spend together and eliminate all the other back and forth. We spend a lot of time in the sales process with the salesperson being taught by the buyer what needs to happen in order to move things forward. We could really get away from that process, which I'm looking forward to, if you ask me. Sorry, that went longer than I expected. ⁓ Cool. Kristie K. Jones - Author: you Agreed. Agreed. Warren Kucker: Great, well, Kristy, this is phenomenal. I really appreciate taking the time. I could keep on going. I would if I could. ⁓ Where can people find you to hear about what your thoughts are? Like you mentioned a blog specifically on what shifts are happening. Where can people find you? Kristie K. Jones - Author: Thank Yeah, easiest place to start is LinkedIn, because I've got all my information on there. Go connect with me after you hear this, and then message me. Tell me what the one takeaway that you're going to do or that you got out of this that really was your aha moment. I always love hearing what it is that you and I talk about that really resonates. Warren Kucker: awesome. If I could say this one, Christy writes about this in her book. She's always got 30 minutes for people and don't abuse it if you don't need it. But two, I reached out to Christy, she's way too cool for school and she gave me 30 minutes and a heartbeat and here we are. So I highly recommend anybody reach out that would love a chat. Christy, really appreciate taking the time. You're really thoughtful about this space. I love the founder led to a growth scale motion myself so I could spend hours. I appreciate you taking the time. You have a good rest of your day. Take care. Kristie K. Jones - Author: Thank you.