In this feasible episode, Christopher Filipiak, Owner of Christopher Filipiak LLC, shares strategies to stabilize your sales. If you struggle with inconsistent revenue or hiring salespeople, you won’t want to miss it.
You will discover:
– What systems are needed for a sales-ready organization
– How to shift your mindset to see structure as freedom
– Why mastering sales yourself ensures stable revenue growth
Episode Transcript
Scott Ritzheimer
Hello, hello and welcome. Welcome once again to the start, scale and succeed. Podcast, the only podcast that grows with you through all seven stages of your journey as a founder, and today we’ve got a big one, because if you’ve started a business, if you’ve had some success in sales, you’ve started building the team around you, one of the things that you’ll discover is that you now have to sell more to keep all of those people employed, and it puts this pressure on us as founders to continue to sell and grow while we’re managing and doing all these other things. And what we start to see is that doesn’t work real well. And we have months where it’s amazing, we have months where it’s terrible, and it’s this roller coaster of success and what feels like failure, and so to here with us today to tame that roller coaster, to bring in stable revenue that we can really scale and grow with is our guest today, Christopher Filipiak, who assists CEOs in excelling at their sales endeavors, leveraging his background in engineering, data analytics and fortune 100 consulting, he integrates strategy, execution and mindset transformation to build sales ready organizations capable of achieving consistent and profitable sales. Very important. His distinctive experience merges on merges an engineering Foundation, robust business principles and a strong emphasis on mindset delivering a holistic approach that comprehensively transforms sales organizations, and he’s here with us today. Christopher, welcome to the show. Glad to have you here.
Christopher Filipiak
Hey, Scott, it’s great to be here, and hello to the audience today. Thanks for tuning in and listening.
Scott Ritzheimer
Awesome, awesome. All right, so I’ve got what I think is a bit of a paradox, and I need your help with it. Maybe this will be helpful for some folks listening as well, but it seems to me that founders who are still like the leading sales rep for their team, right? Maybe they’ve got a couple people that are coming on, but ultimately, at the end of the day, they’re still driving things forward, not necessarily a problem. But folks at that stage tend to get there by like virtue of their visionary Ness, right? Like they can sell ice to an Eskimo. You know, they’re the most dangerous people to walk next to on the road, because you’ll end up buying something from them. They’re not sales people, but they’re so inspired by what they do that you can’t help but get excited about it. And and so that gift of seeing opportunity, seizing opportunity, the enthusiasm that they have around their ideas makes them at least effective enough to grow some successful businesses. But the problem here is when, when we start having to get more structured with it, the very same processes that they succeeded by not having and now need can become a stumbling block for them. So for those who who thrive on that, like winging it and making it up and they do their best work in that environment, how can they? How can they build the the structure that will really bring them the stable revenue that you help your clients achieve?
Christopher Filipiak
Yeah, it’s, it’s a is it an interesting question? Maybe it’s an interesting question. I think what you’re so, what you’re asking me is, how can a CEO or a visionary CEO who’s led based on their vision or sold based on their vision and their status transition to something that’s more structured, which seems Yeah, seems constraining to their to their vision, right? Is that that was
Scott Ritzheimer
Absolutely, yeah, yes, you said what I said in about a third of the words.
Christopher Filipiak
Yours had a lot more color and story, which is awesome. I think it’s mostly a mindset shift. Scott is. I think it comes down to understanding that the the what you were doing wasn’t actually creating as much freedom as you want, and it wasn’t allowing you to have the money and profit and the the structure that allows you to really create a purposeful and free life. So I think the first shift is really this mindset shift. Instead of going, Yeah, I just get to do what I want, and people are buying or not buying, but I don’t, it seemed like I’m having fun. I don’t know what’s really going on. And going, Oh, I get to have, I get to see structure as fun, or I get to see, you know, setting up my calendar really well as a tool or a vehicle to create a ton of freedom and the result that I want, not as something that’s limiting me or or hurting me or inhibiting who, the truth of who, who I am. So Right? I think that that’s the way. I think you mostly bring. In new information and new truths about what it actually means to be a business owner, and create some clarity on what it is you want and what the best causes are to create that for yourself. And I think when you make that shift, you’re gonna start to think about things differently, and you’re gonna see that your life actually has much more space for your vision and not so much confusion in what you’re currently doing. I think that’s going to feel real good. There is the truth is, is that we create based on our energy and our emotions and our activities, right? So it’s thoughts and action and your energy will trump whatever your skills are the majority of time. So that’s one of the reasons why that visionary founder who’s lit up about what they’re doing is gonna is gonna make progress regardless if they don’t have the right skill sets.
Scott Ritzheimer
So yeah, so one of the things that I’ve seen folks at this stage do is think that they feel like what you’re saying, that they feel a lack of freedom. And their thought is, well, if I can get somebody else to sell, then I don’t have to deal with this and and, you know, if they’re a good sales rep, they’ll just come in and be able to kind of, they don’t say this, but magically sell everything that we have. What’s wrong with the idea of just hiring a sales rep in and not dealing with any of this?
Christopher Filipiak
They fail the majority of the time, and it’s a very expensive mistake. You know, on average, founders hire and fire 3.25 sales people at a cost of upwards of, you know, or just over $400,000 as a 2025, right? So. And what’s worse, so that what’s what’s not even included in that cost, Scott, is that you as the founder or the CEO, go, Hey, I actually don’t need to do sales. Yes. So you take your foot off the gas. Of sales because you’ve hired someone and to staff a good sales team is going to take you 1218, 24, months. So you hire this person, you take your foot off the gas. They don’t. They don’t work out, right, which happens a lot, and we can talk about why that is, and how to actually set up a successful sales team so they don’t work out. You’ve taken your foot off the gas of sales, and everyone has a really bad day six to 12 months down the track. Yes, it’s okay, yes. So as a CEO, your number one responsibility is to drive the growth of revenue and profit for the firm right. And I think the easiest, most effective way to do that is to personally be involved in business development and sales like you’re in such a a sweet spot, easy place to make sales and drive revenue for the business, that any other strategy, almost like you can bring in other strategies, but any other strategy where you’re you’re moving away from sales or business development as a CEO of your business, I think is a is a mistake, right? Yeah, and yeah doesn’t mean you shouldn’t have help, or you shouldn’t set up systems and processes that enable you to sell really quickly and easily and really profitably at a large level, but when you surround yourself with that system and that set of processes, you’re going to have a lot of extra cash in your business that you can experiment and figure out what it actually takes to stand up a successful sales team.
Scott Ritzheimer
Yeah, yeah. That’s so true. To reinforce that point, not that point, not that you need it, because it was very well articulated. But there’s a client of mine who will not hire a first sales rep for a team unless they have a coach taking them through the process. Because of that, it just it. They, they had so many fail that they’re like, it’s not worth placing somebody because it’s just not going to work. Yeah. So let’s, let’s unpack that, though. So it’s one thing to say, hey, they, you know, they often fail. It’s another thing to say why that is, and even more importantly, what we can do differently. So let’s walk that through. Why do these fail so frequently when it’s such a pivotal transition that we need to be able to make?
Christopher Filipiak
Yeah, let me I’ll answer that. And let me just say, you know, one of the things that happens with founders, and this is one of the reason why sales people fail is because the CEO hasn’t mastered sales themselves, right? And they’re picking strategies based on their own fear or lack of confidence or overwhelm, instead of a place of cause and effect. So they’re, they’re going, Hey, I want to, I. Do this, right? Because I’m uncomfortable in sales, or I don’t like doing x piece of marketing or x piece of selling, right? Whatever that is. It could be anything. And they pick strategies, hiring sales people so they don’t have to do the inner work to try to bypass doing the inner work, yeah, and come to their own leveling up of their self worth, of their mastery of sales. So that’s one of the reasons why it fails, because energetically, they’re trying to get out of doing something that’s theirs, that’s yours to do, yeah? The other reason that initial salesperson fails is, is you got to understand that sales is a system of systems, like, I like to think of it as a race car team. So you need a right a fast car, you need a driver, you need a coach for the driver, you need a pick crew. So sales is a system of systems. And if you just hire an amazing driver, an amazing salesperson, and there’s no car, there’s no pit crew, there’s no coaching, it doesn’t matter. And in in sale, in a sales organization, that means that your your marketing is dialed in. You know who your market is. You know what their problem is. You have an offer that helps them solve that. You know how to message against that offer in sales. You know how to create and have conversations. You have the tools to lead and then under get the information and the data required to make decisions on your team has the right mindset, and you have all that, all of that manage in a well, in a well, put together project, and it’s one of the things that I help my clients with Scott is this idea of being a sales ready organization, and that basically is like looking at the business going, Hey, we want to make sure your mindset, your leadership, your marketing, your sales and your project management, When it comes to adding revenue to the business is dialed in. There’s nothing missing, and a sales person is just one part of that bigger system. The last piece on that is to understand that sales people are leveraged to scale something that’s working, but if there’s something fundamentally missing broking or needing improvement, bringing in a sales person to try to scale that up is not the right is not the right move, right? So that that’s, that’s one of the reasons. And it could be, it could also just be that you may not, you don’t have a good process for hiring and training and coaching and identifying top sales talent as as well. Like the business doesn’t have that competence.
Scott Ritzheimer
Yeah, right, right. It’s a skill set hiring those folks as well. So let’s break this down a little bit and maybe get it to a point where we can get some actionable steps today. So in terms of creating a sales ready organization. There’s a whole lot to that. Are there a set of steps or phases that you typically walk your clients through?
Christopher Filipiak
Yeah. So the first thing I do is we do a sales ready organization assessment to look at the organization and understand what they’re doing. Well, because you’re making money, you’re profitable, right? You have clients, you’re doing something, so we want to understand what’s actually driving and creating that profit and that revenue. But you look at that, and I actually have a self sales ready organization, self assessment, that is kind of a mini assessment that the audience, I’ll gift that to the audience, that they can take and I’ll score that, and they can understand how they stack up. But typically we’ll do a the the assessment, and then we’ll write a scaling roadmap. And I’ve done hundreds of assessments and roadmaps at this point, so I have a really good and with my engineering background, I can a lot of the biggest benefit is I can just tell people, Hey, you can stop doing this, this and this. Yes, we’ll do a lot of things that are wasteful, right? But they can’t see that, because it’s what’s comfortable for them. So I can go, Hey, this is what we need to do from a cause and effect standpoint, instead of just what’s comfortable for you. So I do that, and then we’ll typically build what like for me, I work specifically with helping CEOs succeed at their sales. Work like, that’s my sweet spot. That’s my niche. I don’t really do sales teams. I, you know, years back, there’s other companies that are much better at recruiting, staffing, coaching, training, sales people. My sweet spot is really helping support and lead, lead the CEO to make a lot of money and profit in their business really, really quickly, so that they. Can have some extra cash, but whether it’s the CEO or sales team, you need to have, you need to build the race car, you need to have some type of system that enables you to create and have sales conversations. Yeah. So that’s kind of the second phase. Once we have the roadmap, it’s like, okay, what are the conditions? What are the leadership, marketing mindset, sales and project management systems that we need to build so that you can hit whatever your revenue goals or revenue targets are?
Scott Ritzheimer
Yeah, yeah. What I like about that, and I get it like the temptation is so strong to try and skip a step, because we see step A, where we are right now. We see step c, where we’ve got sales people helping us, and we’re scaling, and it’s awesome. And it’s so tempting to skip this step B, which you keep coming back to, and that is that you have to develop a proficiency in this, right? You have to develop the ability to create stable revenue, not that you have to, but if you do the return on it is so high. If you can generate stable revenue, and you do that through a process with a car, the likelihood that someone else will be able to do it is exponentially higher. And so what would you say to someone who’s listening, and let’s be honest, most folks in this stage like they’re being pulled in 100 different directions, and burnout is like a real thing. We may not want to say that, but they’re tired. They’re worn out. How do you help folks to see the light at the end of that tunnel? Because it can feel like like you opened in the front end of this of adding system and process is actually making it harder. It’s making it more uncomfortable. How do you help folks to really get a vision for what it can look like when they have that process in place.
Christopher Filipiak
Well, I think, I think having some skill sets around burnout or stress or overwhelm is is important because that’s something that you’ve worked yourself into or learned yourself as a as kind of a default behavior. It’s not a natural state for for humans. So just recognize that, and I get it. I work with a lot of stressed out, overwhelmed, burnt out CEOs, and one of the things that we we coach around, is just understanding how to do that and create clarity on how they actually want to show up. You know, self trust, self love, efficient, right? Happy, feeling good, safe in their in their body, and that, that’s a real skill set to get your body to that state and move yourself out of, out of, you know, fear, worry, doubt, shame, guilt, stress, overwhelm, burnout, yeah, and then from there, you know, I don’t think setting up systems and structures are is actually very difficult, like, that’s a solved thing, so to speak. You just need some help doing it. So you can help. You know, you can use the sales ready organization framework, or you can use any sales process framework that you want. There’s a lot of lot of ones out there, but it’s really going, Hey, like, what is it you actually want? And then it’s just commit. I think it’s a commitment to being involved in sales. I don’t think getting out of sales is the goal, right? I think as you grow in your organization, you’re just going to do bigger and bigger deal sizes. You know, when I, when I was a w2, employee at a B to B, you know, consulting firm that CEO had been there for 20 years and was still doing huge, multi million dollar deals for that firm. You know, I work with 200 uh, $200 million consulting firm, and that CEO is still involved in in sales. And I’m not saying you’re going to be on the phones all day, but you’re going to spend some time doing relationship nurturing, yes, calling your best clients, and working on those million dollar, $10 million 100 million dollar deals like that’s that’s part of what the CEO needs to be, needs to be doing, in my opinion. And of course, you have other priorities, but I think if you master that skill of sales, that’s going to help you in not only adding revenue, but attracting the best partners, building the best team, right, having the best friendships and relationships. And it’s not, it’s not, it’s not about selling ice to Eskimos, right? And I a lot of people use that because it’s like, Eskimos don’t actually need, need ice, but it’s just understanding that you you are like, there’s just such a gift and such a personal journey in mastering sales, and it allows you to really have a skill set around creating what you want, whenever you want and need it. I think that that should be the the vision it should should be to. Hey, like, this is actually the company that I want, and a big part of that is developing a real competence and mastery for myself and for the business around sales.
Scott Ritzheimer
Yeah, so good, so good. Christopher, I’ve got one more question for you, and then I wanna make sure folks know how they can get in touch with you and take the self assessment as well. What would you say is the biggest secret you wish wasn’t a secret at all? What’s that one thing you wish everybody watching or listening to they knew?
Christopher Filipiak
Yeah, I would just say that to I think the secret is that sales is good. Money is good, right? I think there’s a lot of story around money and sales. And I, you know, I talk about this idea of sales as an expression of love, or sales as an act of love. And I think the biggest secret is that, in today’s world, sales and money is one of the main skill sets that you need. And we don’t. We don’t teach it in school, right? We don’t teach it you can’t, like I went to MBA school. There wasn’t even a course on sales, right in business school, right? And there was marketing and operations and HR and leadership and consulting and finance and all the things, but there wasn’t one course on on sales. And I think if you just just teach yourself that sales is good, is a good thing. Like, sales is a good thing to do to someone, right? Like, selling people is good. I think that’s a huge secret. You know, my mentor said to me, sales isn’t something that we do to someone, sales is something that we do for someone. That’s an expression of love. It’s an act of love. There’s and it’s how we create and interact as humans. So that that’s the secret I’d love your audience to take away today.
Scott Ritzheimer
Fantastic. Christopher, there’s some folks listening. It’s exactly what they need when they need it. How can they find more out about the work that you and your team do? And where can they get a copy of the assessment?
Christopher Filipiak
Yeah. So you can go to my website, christopherfilipiak.com, or find me on LinkedIn, and there’s an article, an article on my blog called, is your business sales ready? And the link to the assessment is in that article.
Scott Ritzheimer
Fantastic, Christopher. Thank you so much for being on the show today and sharing with us your time. It’s, I really, really appreciate it. It’s, it’s one of those episodes that it sounds so simple because it’s so true. And I couldn’t agree more, you mentioned this in the middle of the episode, but so much of this is about knowing what you don’t have to do. So if you’re looking for someone to come and help with your sales processes, help you as CEO, become a better sales leader and sales person, and you want to do that by not doing some things. This is a place to do it. I love that. And for those of you watching and listening, you know your time and attention mean the world to us, I hope you got as much out of this episode as I know I did, and I cannot wait to see you next time. Take care.
Contact Guest Name
Christopher Filipiak assists CEOs in excelling at their sales endeavors. Leveraging his background in engineering, data analytics, and Fortune 100 consulting, he integrates strategy, execution, and mindset transformation to build Sales Ready Organizations capable of achieving consistent and profitable sales. His distinctive experience merges an engineering foundation, robust business principles, and a strong emphasis on mindset, delivering a holistic approach that comprehensively transforms sales organizations.
Want to learn more about Christopher Filipiak’s work at Christopher Filipiak LLC? Check out his website at https://www.christopherfilipiak.com/ and find out if your organization is Sales-Ready at https://www.christopherfilipiak.com/blog/sales-ready