585: Getting better at sales through PRACTICE and being UNIQUE w/ Christi Loucks — Wantrepreneur to Entrepreneur | Start and Grow Your Own Business

Hey, what is up? Welcome to this episode of the Wentrepreneur to Entrepreneur podcast. As always, I'm your host, Brian Lofermento, and today we're talking about a big topic. In fact, this topic is so big that I feel if you do everything right in the entrepreneurial journey but you get this one thing wrong, then you're always going to struggle to grow your company. And that one thing is sales. Now, I have brought in someone who is incredible at sales. She's so intentional about the way that she talks about sales, especially in the words that she chooses. So I'm really excited Excited to pick her brain about all things sales. I want to tell you about today's guest. Her name is Christie Loucks. She's the owner and founder of Crafted Sales Co., a consultancy aimed at helping high-growth startups drive revenue through strategic sales enablement programs. You see the way that she chooses the words to describe her work. I'm so excited to get into the nitty-gritty of that. Prior to starting her business, Christie worked for 10 years leading sales enablement and operations at multiple cybersecurity software companies, including Ping Identity and Chainalysis. She also works alongside her husband at Heritage Oak Holdings, a holding company focused on acquiring and operating small businesses across North America. And with all of that said, the thing I also really love about Christie's approach is that she is an entrepreneur at heart. She's driven by her values. She's driven by the pursuit of freedom and everything that she does since starting her business. So I'm so excited to dive into my interview today with Christie Laox. All right, Christie, welcome to the Wentrepreneur to Entrepreneur podcast.

Thanks, Brian. Good to be here.

So obviously I teased quite a bit about this episode. So many things that I'm excited to dive into with you here today. But before we get into all that stuff that I'm excited to ask you about, I'd love for you to fill in the gaps for listeners. Take them beyond the bio. Who is Christy?

Yeah, so I guess I'll go back to where I started my career and tell the behind-the-resume story. So, I started my career in human resources. I actually worked, my first job out of college was working for the US Antarctic Program by way of Raytheon Polar Services. So, started there, was helping train and onboard personnel deploying down to the ice, as we call it. So, I had a really fun start to my career, then moved over into the tech world where I joined Ping Identity in 2013 as an HR associate. And, you know, it's so funny looking back, I was one of, I know I was one of the lowest paid people at the company at the time because I would run all the compensation reports for HR so I could see everybody's salaries. And I know I was at kind of the lowest rung in the totem pole. I worked in HR for 2, almost 2 years there, kind of got promoted, you know, moved up the ladder. I created our onboarding program for Ping Identity. And a myriad of other programs that we ran within the HR function. In 2015, I, well, Ping had a new CRO come on board, and that's Chief Revenue Officer, and he wanted to run a sales kickoff program in early 2016, I believe. I might have those dates wrong, 2014 into 2015, something like that. Anyhow, He didn't have a team at the time because he was brand new. And somehow I think because I ran our onboarding program, I got tapped on the shoulder to say, hey, you know, you can get things done, you know how to execute and you're detail-oriented and you know how to run events and programs, so why don't you come help with this sales kickoff event? I didn't even know what a sales kickoff was. I didn't know what a forecast call was. I had absolutely no real inkling into what sales entailed, but I said, sure, you know, sign me up, I'll help with this event. So we did the sales kickoff. It was the worst sales kickoff we ever did, but it was the first one. So, you know, we were, we were learning. And post-event, that CRO came to me and basically started including me in all of these sales enablement related meetings. And I finally told him, you know, Dave, like, This is really interesting to me, but I work in HR, not sales. So if you want me to help with continued efforts, then it needs to be a full-time job and, you know, I need to actually make a cutover. So he ended up carving out a position for me. I jumped from HR into sales enablement and started, um, started the organization from the ground up. I then grew it at Ping to, uh, we had a team of 13 people by the time I left. So, you know, going back to that lowest on the totem pole, I'm very, you know, I'm very proud of what we built at Ping. We ended up, you know, covering not just sales enablement but also partner enablement, technical enablement, so all the pre-sales, you know, kind of smart guys in the room resources. And then we also owned customer training, so external training as well as internal enablement. So it was Um, it was a really fun almost 7 years. And since then I've continued to run enablement and build it from the ground up at a few other startups. And here I am today with my own consultancy.

Yeah, Christie, so much of that overview that I absolutely love, including the thing that really stands out to me is your open admission about how bad your first sales kickoff call was. And I think it's something that we all need to embrace as entrepreneurs that I always say the first anything is always going to be your worst. My first podcast interview was for sure the worst interview. My first video was the, was the worst that I ever did. And I think that that's evident in the way that you talk about sales. Obviously, I've researched so much about you and your business and the way that you operate. And the thing that really stands out to me is how much you talk about sales being a practice. And Christie, a lot of our listeners, they're wantrepreneurs, they're entrepreneurs, and they're thinking, gosh, I've never had formal sales training. How the heck am I supposed to be good at it? And obviously practice is one element of it. And hearing your story, it's clear that that's been part of your journey as well. I would love for you to talk about why you view sales as that practice. What does that mean to you? Is it just about reps? Is it about being more focused and strategic in the areas that you can improve? How do you think about improving in this practice?

Yeah, I, I think it's all of that. Um, I think there are salespeople out there, there are founders out there, entrepreneurs out there that have a natural call it gift of gab or a natural ability to persuade and have easy conversations. That is an inherent skill that not everyone, um, has. And so to that end, practice is required even for those people that have the, the quote gift of gab. I think you may have really natural skills, but there is a refinement to sales there is, um, a finesse, both kind of an art and a science to it that you have to employ intentionally. Um, you can't just, you know, especially in today's world, you can't just send a generic email. You can't just show up on a call not prepared. Um, you can't just spew, you know, call it show up and throw up, or my new favorite is a pitch slap where you just show up and start talking about your own product without any listening, like you have to be active in your listening. There's so many things you have to be intentional with in sales that I don't think people pay attention to, especially if they do have an inherent aptitude for sales. So to that end, you know, I think it does take repetition. I think it takes refinement. You know, when you're, as an example, when you're crafting outbound messaging, right? You can send out a bunch of generic emails, but it's more impactful if you take the time to finesse your words. If it doesn't work, you have to change, you have to edit, you have to modify. It's just this ongoing dedication to the craft that I think is really important and very underrated.

Yeah, I like that, particularly because really early on here, you've already called out the fact that everybody has different personality types. For people. I talk for a living. That's exactly what I do. I love humans. I'm super extroverted. People go, well, yeah, of course sales is easy for you. But the reality is I see people— you already mentioned active listening, for example. I see deeply introverted people who are just incredible listeners that crush at sales because they have that gift. So I like the fact that you've called that out. And Christy, I knew that you wouldn't be able to help yourself today and you'd already say the word craft quite a few times. It's already in the name of your company. And it's one thing that really stood out to me is that you always talk about you your sales craft. You don't talk about like salesmanship or any of those things. It's always crafting. Talk to us about the intentionality behind the way that you view that. I'm curious because I'm sure it'll reveal some of your inner thoughts about the craft, but what is it about that terminology that speaks to you and shows up in the way that you work?

Yeah, I think the reason I like that, I guess, image is There is— look, there— I'm not gonna say there's a right way to do sales, but there are best practices within sales. Um, but everyone's unique, to your point. And, you know, you think about, say, like woodworking as an example. There's a way to do woodworking. Like, there's a way to build a table, and you have to follow certain steps in order to produce something. But every artist is different, and everyone's going to build a slightly different table even with the same kind of general guidelines. So what I want to kind of portray within the term, you know, crafted sales is that you do need to focus on the process, you do need to focus on your skills, but to that end, you also need to understand who you are and what you bring from, you know, your strengths, your creativity, Um, just your skill set to, to really be successful within sales. So it's a combination of, you know, I guess it's art and science. I don't know. It, it's just bringing who you are to your sales work, and that work still requires dedicated effort, adherence to a process, um, and following best practices.

Yeah. And for all of you listeners, I'm gonna call it out right here, right now that Christie just revealed so many things that we've heard from so many different guests, and we all all here in all walks of life is that a lot of it starts with who are you? What is the way that you want to show up? And so, Christy, I love the fact that whether it comes to sales, whether it comes to something else, we can't forget that. Which kind of leads me to something that I always think is fascinating about sales, is that some people think that it's scripted. You and I were joking off air before we hit record today that none of our interview today is scripted. We love just seeing where it takes us. But sales, on the other hand, a lot of people are just like, give me a sales script, what am I supposed to say? And you just talked about how it should You know, there are the, the foundational elements of sales, but there are also the stylistic. The way that Grant Cardone sells is drastically different from the way that you and I sell. And so I'd love for you to talk about that sort of scripting, the foundational elements versus that stylistic. What are things that are universal that are good for us to follow? And what are some of those areas where you realize, hey, you don't need a script, like, do your thing here. You know your products and services. How do you balance that?

Yeah. So it depends on the conversation that you're having is what I would say. So there are instances in which you need to grab attention really quickly and really succinctly. And in those scenarios, say example, or for example, you're, um, leaving a voicemail or you're cold calling. If you get someone on the phone, you have to know exactly what you're gonna say, how you're going to hook them. You have to have a question right away to, you know, get them interested in what you want to say. Like, you have to be really intentional with those words. So to that end, I would say scripts can be really, really helpful because you just have to be really effective really quickly. But, you know, with product overviews, with demos, with, you know, other kind of more solution-focused pitches. I don't even really like that word anymore because it's, it's really about a conversation, right? I mean, you, you need to know your product, you need to know what you're selling, you need to be able to communicate its value, but it also has to be a back and forth conversation with a customer. So you can't just— like I said, you can't just show up and immediately start reading from a script or your PowerPoint slide notes or, you know, whatever you have in front of you to communicate your message. It's got to start with, hey, Mr. Customer, like, what are you experiencing today? What, what's working? What's not? Where do you want to go? And what's the gap that you need to cover to get to kind of your, your dream state, your ideal world? And so you have to start So many of your sales conversations with this really two-way dialogue as opposed to a one-way pitch slap, if that, if that kind of helps clarify.

Yeah. And I like the fact that you're using the term pitch slap because that is something that I think is so fascinating that we all have a tendency to do as entrepreneurs, because when we enter a sales conversation, we are worried for us. We are so nervous and uncomfortable with sales that we're thinking that the onus is on us, but you just shared with us. You shared real-life questions right there on the fly about the realities of it, which is solving their problems. Ultimately, that's what you have to be the most interested in. Which leads me to— I think that this is a fascinating thing to talk about. What are some of those big mistakes, Christy? You've seen people be really good at sales, people be really bad at sales. What are some of the mistakes that people make?

Oh gosh. Oh, that's a loaded question. Okay. Mistakes that I see people make. The most common is, I would say, jumping too quickly to talk about yourself and talk about your product or your solution, your service, before you fully understand where the customer's coming from, right? Like, we need to know on the customer side, what do, what do executives care about? What are their top priorities What are they talking about in board meetings? What are their big goals for the company for this year? Subsequently, what kind of projects or initiatives come out of those big priorities? That's step number 1, understand the big landscape. Once we know that, we can say, okay, of those projects and initiatives, you know, tell us about the current situation. What's going on today? Why is it bad? You know, What pains do you have? This kind of common discovery stuff. What, what hurts today in terms of your process or your current solution? What do you want in the future? You know, what's your kind of— what are your requirements for the perfect world, irrespective of if it's us as a vendor, you know, or service? What do you need? What do you want? And then how are we going to get you there? So All of that conversation, you're really not talking, right? You're letting them speak. You don't really start connecting all these dots with your product or service until after you understand this big picture. Now, I know sales isn't linear, right? So there may be— you might piece things together here and come over and start talking a little bit about your product, but then you go back. I get that. But I think too quickly I see sellers jump from Okay, we know they have a pain. Here's how we can solve it with our solution. The picture is much bigger than that, and we need to understand how we map to the highest level priority that executives care about. So I would say that's probably the biggest mistake I see people make. The other thing I would say is getting too technical. On your product or, you know, your solution without rolling it up to value. Like, what's the highest value that your, you know, your product provides to a customer as opposed to staying in these feature function kind of weeds? We've got to, we've got to bring it up to the highest level.

Yeah. As a visual person, I will say that I really like that visual that you just painted for us about connecting the dots. If we start viewing our job when it comes to sales is connecting the dots. Well, you got to get all the dots first, otherwise you're never going to be able to connect them. So I love that that's the direction that you took that in. And Christy, hearing the way that you think about sales and obviously talk about sales, it's interesting to me how you've already mentioned so many different elements. And I know you said it's not linear, but there are different stages of the sales flow. You talked about cold outreach, for example, whether it's cold calling, cold messaging, LinkedIn, whatever it may be. You talked about being actually on the phone with them and doing that sale. Obviously, a lot of us, when it comes to sales, we think about the close. I know from your work that you're also obsessed about onboarding, for example. With all of that said, it sounds to me like you view sales as a much bigger part than what most entrepreneurs probably allude to, which is the scary part of closing. But talk to us about that part of it and how it fits in in the greater thing, because it sounds like you're already thinking about the potential to close, but even more importantly, the potential to onboard as early as your initial outreach. How do all these different parts of the framework or the timeline fit in together? And then speaking of the close, Christie, how the heck do we close?

How do you close? Oh gosh. You know, the funny thing about closing is it takes— look, you're closing from your first conversation with a customer, right? Closing is, you know, we see it as a sales stage, like we're in these final negotiation agreements and then we flip it in our CRM to closed won or hopefully not closed lost. Um, but you are closing from day one. And I think if you're doing it well, you are building a consultative, positive relationship with your prospect or customer. Um, and that carries all the way through to the final sort of closing stage. Like sometimes you have to make a hard close. I get it. Like, it's not always just a quick— not quick, but an easy, you know, relational conversation where you're like, yeah, you know, we're going to get the red lines and, oh, Mr. Customer, you're going to be so happy. Yes, I am. I love your product. Like, it doesn't always go like that. But I think what's really important to remember is that you're setting the tone from day one, right? Even negotiation, like you are starting that from day one and how you approach your prospect or your customer. So to make it easier to close, I would say think about that when you first get on with a prospect on a phone call or on a, you know, Zoom and do a presentation. Like the way you set that tone from the very beginning impacts the way you close the deal.

Yeah, that gives us so much food for thought because it almost takes a lot of pressure off of us of thinking about, you know, and I don't know why I'm pulling on Grant Cardone as an example today. I've never used him as an example in particular, but you know, you always think of that like overly salesy energy. That he puts out about ABC, always be closing. And, and basically you're saying that, hey, actually you show up at all points. Like it's all part of the dance. There is not that one ultimate moment. It's not a Rocky movie where like it all coincides in the last 10 minutes of the movie. Is that it's one long dance. So I love that perspective.

Yeah. And I think it's because, you know, seller buyers today are so much more informed and they have so much information available to them that They've already, by the time you get a conversation with a prospect or customer, they've already done, they probably have already done a ton of research. They've already gone through a portion of your sales process, whether you know it or not, like they've looked things up, they've done their own discovery. They, they know what's out there. And so having this like hard close, I just don't think it happens in the same way anymore because there's just this information parity. So by the time you get to that closing, you know, or like the verbal win or the technical win or whatever, buyers pretty much know what they, what they want and need and who they're going to go with.

Yeah. I love that perspective, especially because throughout my twenties when I started my marketing agency, that was something that I learned early on is I always thought getting on sales calls was scary. And I heard in the marketplace more and more people, and today it's common practice where people call it a discovery call. And it kind of felt dirty to me because I was like, it's not a discovery call. Like, I'm getting on the phone to close this person. But the reality is exactly what you just said, is that they know it's a sales call, you know it's a sales call, they've done their homework, they know what they're showing up for. So it's not this big elaborate thing that you need to prepare for. It's more about discovering how you can meet their needs. So I love that perspective, Christie. I've got to ask you this though, because obviously we're talking about a topic that a lot of people are afraid of. But I know that one of your areas of expertise and brilliance is your ability to creatively craft these sales messages and positions and all of that. You wrote when we were doing our research about you, you wrote that you've once done a sales presentation wearing an inflatable dinosaur costume.

Yes.

Christy, talk to us about implementing or integrating creativity into the sales process.

This is something I'm really passionate about because I get— I personally get so many I get boring emails, prospecting emails sent to me, and I feel terrible. But you know what I do? I delete them. You got to stand out. There's way too much noise in the world today that you have to be unique and different in your communication and your approach. So yes, I, I mean, internally, you know, building sales enablement programs, you have to get the attention of your sellers. And I have loved a majority of the sellers I've worked with, but they are ADHD. They just don't pay attention. They want to be out selling. They don't have time for your training. They don't have time for what you need to say. And I don't blame them, right? Like, my goal is to be as efficient as possible in what I need to communicate or train on. So to that end, I try and at least make it fun so that it's engaging as well as informative. So that's where, yeah, I did a whole presentation at our last sales kickoff wearing an inflatable, um, I don't know, brontosaurus, maybe it was T-Rex, I'm not really sure, um, costume. I could hardly hear myself speak because the fan was like whirring in my ear the entire time. But yeah, and I've shown up to meetings in lobster costumes, um, I've produced music videos to communicate an idea or a, you know, new piece of collateral from marketing or something like that. But also, you know, on the external front, when you're, when you're prospecting, you can be personal and be unique and take a few risks if you see an opportunity. So for example, I was reaching out, I was actually helping with some prospecting, some outbound emails, I'm at my last company, and I reached out to someone who, he was like an IT director at a franchise organization. And it was a frozen custard organization. And I grew up in St. Louis. So frozen custard is a very big deal in St. Louis. And I made kind of an opening joke of, you know, hey, I'm not sure if you're gonna stand up to Ted Drewes frozen custard, which is what I was raised on. And, you know, I don't remember exactly what I said, but it was a little bit of a risk. He could have like been totally offended. But it was also something like, it could be a really fun hook to reel him in. He responded. Second email, I actually drove myself down to one of their restaurants. I got myself a frozen custard sundae thing, took a picture of it, and sent it along with my next follow-up email. So it was personal, it was unique. We had a great conversation. And I think just trying to find unique ways to be yourself and to be different in your sales communication, it will, it will take you far above and beyond just basic email templates or pitches or whatever.

Yes. I love that advice because it's advice that I for sure learned early on in my twenties, that all I can ever be is me. And I started using that to my advantage. And I love that you are waking listeners up to this and saying, use this, Christy. It seems like whether it's a corny joke, whether it's a rap parody that I know that you've done in presentations, it's just another way to stand out and capture that attention. And ultimately, let's face it, I feel like we forget, we lose sight of the fact that when we say terms like B2B sales, business-to-business sales, we forget that it's actually still human-to-human sales, like no matter what element of it. So I love the fact that you share that, Christy. As we come towards the end of this interview, I cannot let you go without also talking about your more broader love for business and entrepreneurship and the values that you bring to it and the reason why you and your husband in particular care about it, which obviously is freedom. You're one of us, the Entrepreneur to Entrepreneur podcast. We all share these things. I'd love for you to share some light or, or really shine a spotlight on how this plays into it, because I know it's so exciting for you to be running your own business as well as doing all the things that you're up to with your husband impacting so many other businesses and customers as well. Christy, what is it that drives you? What is it that's part of this entrepreneurial journey that makes you go, yes, we need to celebrate this, we need to be exceptional at it, and we need to keep leveraging this as a tool for freedom?

Yeah, I think the reason I ended up stepping out on my own last year to, to build this consulting group and to work alongside my husband, it does really come down to autonomy. There's, there's nothing wrong with working in corporate America as a W-2 employee, 9 to 5 every day. There's, there really isn't anything, right? Like anything wrong with that. I just, it wasn't for me anymore. I value my ability to choose, um, to choose who I work with, what I put out into the world, my, my creative freedom, That's all very important to me personally. But even beyond that, you know, part of the reason my husband and I are going out on this entrepreneurial journey is because we care about our community. We care about making an impact there. We, we love the idea that, you know, we've— within our portfolio, we can hire people in the Denver area and supply jobs and help grow people and and, you know, create leadership programs that really level up people in our community. So I think it's this idea of just carving your own path and, and pursuing that relentlessly. Like, there are days when it's very, very tough. Like, I can't tell you how many times I've looked at my husband and gone like, are we doing the right thing? Is this, is this even the path we should be on? This feels really hard. I don't want to do it anymore. I just want to coast. Like, there absolutely have those days, but I think at the end of it all, it's that pursuit of freedom, that autonomy, and the ability to really make an impact where we are that drives us.

Yeah, Christy, I so love and appreciate that you call out and, and really admit those things for all of us here today about, you know, the question of Is this what we really want to be doing? Is this what we should be doing? Because entrepreneurship is scary. And when I started this podcast all the way back in 2016, it's these conversations that I want to bring to other entrepreneurs. So I so appreciate entrepreneurs like you, Christy, who are willing to share those thoughts because it's something that we all go through. Christy, we could talk about all this stuff for days. You obviously love entrepreneurship, you love sales. But as we come towards the end of this interview, I always like to ask the super broad question for listeners' benefits, who they're sitting there saying, gosh, Christy, you totally transform the way that I view sales. I'm going to go back and reexamine my own inner approach to it about all the different touchpoints that we have. But Christie, tie it up in a nice little pretty bow for listeners. What's the one thing that you really think every entrepreneur would benefit from when it comes to honing their sales craft, when it comes to sitting down and reexamining the way that they view sales, the way that they do sales, and the way that they practice sales?

Identify what you're good at and what you're not good at and build up those deficiencies. You know, we, we tend to know our strengths, especially entrepreneurs, right? Like, we know what we're good at, we know what we set out to do. Um, it's maybe a little harder to figure out what we're not, not so good at, but I would say double down on that and really educate, grow, You know, find resources, you find mentors, find training, you know, whatever it is, just really take the time to pour back into yourself in the areas that you, that you do need to grow in. Be humble about it. You know, you've got to just continue to build yourself up in order to be better.

Yeah. Good advice there. And I think it gives listeners a ton of homework to go down and reexamine so much of this stuff. We talked about being yourself in sales, standing out, doing something different, also taking that pressure off of yourself. Closing is not one moment in time. It's the entire process. It is that dance. It is the connecting of the dots and figuring out what those dots are. So, Christie, you've shared so much with us here today. I know that listeners are going to be eager, especially because I feel like I've just been touting like different lines of your messaging from your website. Tell listeners where the heck they can go to learn more about you, your business, and everything that you're up to?

Yeah, so you can go onto my website, craftedsales.co, but honestly, the best place is just to find me on LinkedIn. I'm pretty active on there. Um, send me a direct message, connect with me. Um, yeah, that's, that's probably the easiest way to find me.

Yes. So listeners, as you already know, you can find those links wherever it is that you're tuning into today's episode. Christie's website is craftedsales.co. We'll be linking to that in the show description as well as just find Christy directly on LinkedIn. It's actually how we came across Christy's work. Just search Christy Laux on LinkedIn and you will find her. Add her. She's putting out awesome stuff there and it's always good to be connected with entrepreneurs doing good things. So Christy, thank you so much for coming on and sharing so much of you with our audience here today on the Wentrepreneur to Entrepreneur podcast.

Thanks, Brian. Appreciate it.

Thanks for listening to the Wantrepreneur to Entrepreneur podcast with your host, Brian Lofermento. For show notes and to get a free copy of Brian's book, visit us online at thewantrepreneurshow.com.