CUTTER CONSULTING GROUP

E193: Growth Through Sales with Sean Sheppard – Part 2 of 4

January 8, 2024


What challenges arise when the roles of creators and operators are not clearly defined?


This is the second segment of the conversation I had with Sean. 


In Part 2, Sean and I talk about:

  • Salespeople who need a built process vs. ones that can create the process
  • Self-awareness – what type of operator/founder/salesperson are you?
  • How most people (honestly) feel about change
  • Your #1 goal as a salesperson (and a company that provides a product/service)



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Sean’s Bio:

Sean is a serial entrepreneur VC and co-founder of GrowthX and GrowthX Academy, with three successful exits, who has successfully grown dozens of early-stage companies across a wide variety of products and markets. He was recently named the #2 Online Sales Influencer and contributor at The Huffington Post. He’s now committed to working with countries, companies, entrepreneurs and those who want to work with them on building startup ecosystems and developing the next generation of leaders for the innovation economy.


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  • Show Transcript

    Jason: Welcome back to the sales experience podcast and welcome to part two of my conversation with Sean Sheppard from the growth X and growth X Academy family of businesses out there changing the world via sales, which is really in alignment with how I feel about sales and the mission of this sales experience podcast. He is focused on doing it for startups early seed round type of companies who need help going from product idea into launching and generating income instead of just raising money. And you might be wondering why I have someone like that on the show for talking about sales. Make sure to catch all four parts of this conversation that he and I have and you will understand from front to back why I wanted to speak with them and the value that he has, which is literally in alignment with myself. So make sure to subscribe to the show so you can catch all the episodes here it is part 2. 


    Sean: And they can drive that functional learning that needs to happen in order to build something that people want because everybody just forgets you raise $1 million in this town. That’s 12 months of money that goes like that, especially if you’re selling B2B in a 12 to 18-month sales cycle. You don’t have enough money to do this. So you have to do it in the most practical and realistic approach possible. 


    Jason: And it’s so true in my experience as what you’re saying is that there are the ones who like to build and create from a sales, from scripting, from marketing, from just that whole process. And then there are the ones who just like to show up and do, and they just can’t handle anything that’s not already outlined or processed or something that doesn’t fit into what they’ve always done. So cause they’re not gonna mold to your process, they’re just going to bring what they’ve always done and it better work for you or not. And if it doesn’t, it’s your fault. Not to bash those salespeople. It’s just a fit for startup companies or wherever you’re at in your mature cycle. If you have no scripts, no process, no marketing, and you know you need somebody to bridge all those departments. Like you said, that’s one type of person versus here’s a process, here’s the playbook. Now get on the field and run with it. 


    Sean: That’s right. There’s a difference between creators and operators are like, you know, inventors, innovators, an operator, all three are very different. They all have their own specialty and it’s typically built into their DNA and that’s what I mean. It’s less about what background experience or skills or knowledge someone has and it has more to do with their characteristics and attributes. What is their nature? Do they get frustrated in a big company like I had a job once.


    Sean: That was it. It’s like people always ask me, you know how do I know if I’m an entrepreneur person, you don’t choose. It chooses you. 


    Jason: Right. Go get a job and see how that feels. 


    Sean: It pulls you in a direction. In its purest form. It doesn’t mean you can’t be an entrepreneur later. Of course you can, but it does require a change in behaviors. If you’re somebody who’s traditionally been an operator and you want to try and be an innovator, it requires a change in behaviors and thoughts, mostly thoughts which drive behaviors. And the same thing goes if you’re an inventor who wants to be an innovator or an operator, you have to change your thoughts and behaviors to get to that point. And that’s fine, but more often than not, we’re going to fall back on our lizard brain every time things get difficult because everybody’s got a plan as Mike Tyson said until you get punched in the mouth.


    Sean: And so that’s what happens. People say they’re going to do one thing and then the moment they get into the market, things don’t go well or they get seduced or pulled in a certain direction by people who express interest that have no ability to do business with them but have a willingness to suck up their time and resources. And those are the kinds of things that you see over and over again. So our focus is really on that dynamic that exists between taking something someplace new that is a learning process. The whole thing is a learning plan. Our entire market acceleration program and XP and I encourage everybody listening to this to go to growthx.com and sign up for it. The hashtag GX MX P newsletter. Every week we cover a different section of our, you know, I’d like to say world-renowned market acceleration program.


    Sean: It is now being licensed by accelerators, incubators, universities, governments, corporations, startups, grow stage companies and entrepreneurs all over the world. Because it’s all about that dynamic. How do you in a measurable way find the truth about where your product fits in the market, create a functional learning organization to pursue that truth in the leanest way possible and determine whether or not profitability can, and it should exist in a predictable, scalable way. And it’s all about those things. So that dynamic is very different. The attributes necessary to support it, the way to measure it, execute against it, and learn where that truth exists. All rides in that area. And so if you have a true entrepreneur on the product side, they’ll get it. They’ll understand that they don’t know what they don’t know about where the product that’s in the market. If it does it all, we may not know what to do about it and that’s great.


    Sean: So that’s the recognition of all right now I need somebody who does, but don’t go get that guy that comes from some big company that’s never taken something someplace new. I see it in big companies, small companies, and everywhere else. Cause that’s not about the stage of the company. It’s about the stage of the product in a market 


    Jason: And to the salespeople listening, right? And obviously managers and founders, but to those salespeople listening, it’s really about that self-awareness. It’s about knowing who you are and what you like to do, what you enjoy and what you’re best at that you can then bring to the market. Right? Like I realized that a long time ago about myself is that I really enjoy building it from the ground upsales, marketing processes, scripts, technology, all of that. I love fixing it when it’s broken, when it’s running smooth, I get bored and that’s not fun for me.


    Jason: And I want to move on to something else. Right? I am not a longterm operator. I’m not the kind of person that likes pulling a lever for 30 years, day in and day out. And that’s what I do. I like building great. I’ve even found in the past when I’ve stepped back and then I’ve fixed this habit, I’ve even found it where I’ll literally dive really deep to find more problems and or break something so that I can then fix it because that’s what I enjoy. I enjoy the creating and optimizing. And so for salespeople, it’s really key to know that because I’ve seen that what you’re saying is where we’ve hired somebody as a sales rep, tons of experience companies in early stage, it’s very flexible. Like what we do today might be different than what we do or call on or say tomorrow.


    Jason: And some people literally can’t handle that pace of change. And like you said, that ambiguity of what’s going to happen next week, we have no idea. We know what the vision is, right? So we’re married to that, but we don’t know what the strategy will be. 


    Sean: Seah, I mean there’s two things I want to, there’s two paths I want to take the conversation based on that. One is personal and professional development conversation for sales professionals, which I completely agree with. So that means for example, and now you’re getting me on my, you know, my growth X Academy soapbox, we launched growth X because most companies are failing because of markets and people not products. So we wanted to address it. We launched the Academy because nobody teaches professional selling. Okay. And nobody teaches it. The stage relevant selling of taking something someplace new and it’s very, very frustrating.


    Sean: There are over 6,000 institutions of higher learning purportedly in North America and less than a hundred even have a sales course. And most of those, God bless them, those people haven’t sold anything. They don’t know what they’re doing. Exactly. And so what ends up happening over half of college graduates end up in sales, customer facing related roles with no background knowledge or experience skills or behaviors necessary to support it. And what do you end up with? You end up with endemics 60% turnover in the industry. In the first five years, right? And that hasn’t changed. And who bears the responsibility and costs associated with that? Us the employers, right? Every year gal comes out with the same pole, come graduation time from all these college graduates graduating from these liberal arts colleges. And by the way, I’ve never seen a job posting that says seeking liberal artists. So from the schools saying, yeah, are your graduates prepared for the workforce and the rules?


    Sean: 8 and 10 say yes or 9 and 10 say yes. And then you ask the employers 8 and 10 or 9 and 10 disagree. There’s a giant gap there, right? And so now the Academy was designed to fill in a very focused and specific way to support our portfolio of investments as well as the community at large for all sorts of awesome people that want to transition from non-tech industry to High tech growth. They may come out of real estate or finance or retail or law or whatever, and they want to work in tech, but they don’t want to be a coder. I want to be an engineer. Great. So we’ve got a path in it and they can learn entrepreneurial selling and they can learn digital marketing, they can learn UX design thinking, it can even learn data science and some light programming to support data science in UX design in the Academy.


    Sean: And all of that comes from this fact that our educational system was born in the industrial revolution as a way to put people to work in factories. You died, do you know if he asleep like Rip Van Winkle 150 years ago and you woke up today and you looked around? The only thing that would look the same as the classroom, there’s a reason they use bells in the classroom to mimic factory whistles. There’s a reason they have programmatic learning moving from one subject to the next and they’ve got everybody lined up in desk rows and they go altogether. And the only thing, two people in a classroom having common is their age and location and that’s absurd. And that’s just so beyond the pale. I can’t even tell you that’s not preparing anybody for the innovation economy. No. The skills that are necessary to be successful in the innovation economy are number one, you need a mindset. You need a mindset that says, I want to be alert at all, not to know it all. We call it a growth mindset, okay? It means that you can learn anything and master anything.


    Jason: But also, you know, learn anything but also not, I’m guessing also not relying on knowledge, right? Because knowledge and information can now be found at your fingertips. It’s the wisdom to know what to do with create. 


    Sean: Yes. It’s a creativity of that. So you want to separate yourself in the age of AI, build your EI, your emotional intelligence. That’s the second thing behind mindset. Third is business activity. You can help anybody be successful. So to me in the role of sales is your job in this world is to help other people get what they want. Okay? If you help them get what they want, you will get what you want.


    Sean: And if you honestly believe that you can have everything that you want, but in order to do that, you need to know who these people are. You need to understand how they work in tech. You need to speak to them in a language they understand. Just cause we both speak English doesn’t mean we both speak finance or we both speak SAS. We both speak retail and we both speak HR. Okay? You can learn that stuff very quickly through business and market acumen. Understanding how business works and how you can contribute to it as the seller is your primary objective and then behind that you need to be able to communicate effectively. If you can’t articulate your value based on those prior things, having the great growth mindset where you’re ready to learn at all times. Strong emotional intelligence so that you can care about somebody before you know what to care about, that you can understand their business and how they run it and how you can contribute to it.


    Sean: That you can immediately adapt their taxonomy, their industry, vertical sector lingo and understand not just who they are, but who their customers are and how that drives everyone’s behavior and then ultimately articulate that in a way. It helps you get them what they want. Solve real problems for real customers in a measurable way and if you can do that, I don’t give a shit what industry or what sector. I don’t care what product or what market or any of those things. It doesn’t matter because everybody always asks me about this with MXP too. Is MXP your market acceleration program B2B or is it B to C or is it a marketplace saying as a technology only? No, it’s all of the above. It’s fundamentals. It’s H to H human to human cause until bots starts selling to bots and they don’t need us anymore, it’s still the process of one human interacting with another and trying to learn from that experience and so I that you call your podcast a sales experience for that very reason.


    Sean: You know what creates an optimal sales experience. I think it’s applying what I just alluded to, in a way. That does two things for customers and people always need to keep this in mind. The first thing is to create less work for people, not more every day. 


    Jason: Are you talking the sales person for the customer or you’re talking to the company for their salespeople? 


    Sean: No, I’m talking to the salesperson for the customer. Everything the company does for the salespeople should be in support of that. To me, every organization has an upside-down pyramid. Yup. Okay. At the or funnel. Think about it as a funnel. Okay. To me, everything’s a funnel. I learned that in college, hanging out with. Absolutely. Everything’s a funnel. At the top of the funnel is your customer’s customer. Okay. And then below that is your customer.


    Sean: And then below that is the people who face your customers, right? The people who find them. Right? The people who acquire them, sales and the people who keep and grow them. Customer service or customer success. And then everything else inside the business is underneath that and support of that. And at the bottom of the funnel is the executive and or investors and board and the people that support them. So everything that the company does internally needs to be driven by that experience. Does that make sense? So when I speak about this, I speak about it in terms of you need to go to market in a way that immediately creates less work and more value, not the other way around because what the problem is is we’re so heavily driven and focused on our own self and our own product and our own service.


    Sean: We often forget what kind of experience we need to create for our customers. That’s one of the reasons user experience design and design thinking is one of the critical components of that we teach in our entrepreneurial selling program as well as in the UX design program is because everybody wants that easy button that Apple provides you today, but they don’t understand, or Amazon, they don’t understand how hard and difficult that is. Amazon is the most valuable company in the world. They don’t make shit except all of us happy. 


    Jason: Alright. That’s it for part two. Again, make sure to go to cutterconsultinggroup.com/podcast where you can find the transcript, show notes, all of his links, catch Sean where he’s at online, his website, and of course, make sure to subscribe so you can catch apart for three tomorrow. And as always, keep in mind that everything in life is sales and people remember the experience you gave them.




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By Jason Cutter February 19, 2025
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By Jason Cutter February 18, 2025
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By Jason Cutter February 17, 2025
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By Jason Cutter February 13, 2025
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By Jason Cutter February 12, 2025
The Danger of Doing Too Much as a Sales Leader Alright – so maybe they don’t need to go 90. In true servant leadership mode, you would go way more than 10% of the way to your team. But you have to be careful, as a sales leader. The inclination might be to do it all for them. To help them close their sales. To make excuses for them to your leadership as to why they aren’t closing more sales. Especially considering the very high likelihood that you are a sales manager because you were a great salesperson in the role that you are now managing. And there is a slight chance that you are a player-coach…so you are leading and selling. This can make it really tough not to want to run out on the field to win the game each time. But that doesn’t scale. That doesn’t lead to increased results. You can only sell so much as one person. Creating a Culture of Ownership So, you need to have people on your team that are coming to you. What does that look like? The pinnacle is a salesperson who doesn’t close a deal, comes to you right away and asks for feedback. They want some critiques as to where they could have done things better, different that would have led to the desired result – a closed sale. That takes a healthy level of ego by a professional who has the ultimate growth mindset. They know there are always ways to improve. They want to improve. And they are willing to risk their ego (and the internal, protective, primal part of our brain that doesn’t want to risk our place in the tribe) by asking for feedback that could be negative. Whenever you can, encourage that type of response. Ensure that the team knows that the team itself, and you as their leader, is a safe space – where the goal is to improve, grow, win and that everything done to support each other is done in that mode. They truly have to feel safe to share their mistakes and to get support in learning how to do more, better. Feedback That Drives Growth Part of this takes team and individual meetings that are actually filled with positive support. That doesn’t mean it’s always positive, motivational fluff. It’s not even about the shallow strategy of the feedback sandwich. Its about being real, honest, and empathetic – meaning “I see you are here, I know you want to be there, I will help you get there – even if its hard and it means saying hard things.” It should never feel mean or abusive or like an attack. But you can give some really direct feedback that will sting that ego I mentioned, but the person will know the intent behind it. The second part is hiring this type of person. Hiring people for the team that wants to win, grow, succeed. And they know that you don’t get better by being coddled, sheltered, or protected. You want people who don’t like the thought of perpetually living safely in their comfort zone. And they are excited about the opportunity to be a part of a team that pushes everyone, empathetically, outside of their comfort zone. Are You Leading or Just Managing? If you find yourself as a leader having to push your team, or going to them most of the time, or most of the way mentally – then they see you as a manager not a leader. They see you as someone who manages them, pushes them, and wants them to do things they don’t want to do. I have written some blogs here that go into what your role should be – as a leader, not a manager. Pulling people along with you, inspiring people, and supporting yourself with a team of people who want to win. Not just those that want to show up, do as little as they can and hopefully go unnoticed (yet – complain about not making enough money and how the comp plan isn’t fair, or the leads are bad, or their schedule means they can’t be successful.) Make sure your team knows that they need to come to you – at least 51/49. They should be asking for help, guidance, training, feedback, and support more than you are having to push it down onto them.
By Jason Cutter February 3, 2025
If you have seen the movie Hitch, then you know the scene. Will Smith’s character (Hitch) is trying to coach Kevin James’ character (Albert) on how to finish out his upcoming first date. He is giving him pointers, one being that if his date fumbles with her keys at the door, it could mean she wants a kiss. So Hitch wants to see if Albert knows what to do – for a good night kiss. Hitch gives him the advice “you go 90 percent, and then wait for her to go 10%” which Albert then asks “wait for how long?” Hitch: “as long as it takes.” Albert leads in, Hitch is holding back to see if Albert will wait, and then Albert goes all the way and gives him a kiss. Hitch gets upset, and says “You go 90, I go 10 – you don’t go the whole 100%.” The Sales Analogy Kissing our prospective customers is not acceptable (just ask HR!). But the concept is the same. You don’t want to ever make 100% of the effort for your prospective customers. You don’t want to be the one who is doing all the work. Fundamentally, it is not good practice to want the deal more than the other person. When you go your 90, you need to wait – as long as it takes – for the prospect to go to their 10. And I would say that you want to go somewhere between 10-49, in reality. How Successful Sales Professionals Balance Effort Successful sales professionals know how far they have to go to meet the prospect where they are, while also knowing how much effort the prospect needs to put in to show they are committed. Where most salespeople get in trouble is they get desperate. They want the sale (kiss) more than the other person and they go the full 100%. Of course, persistence is important. And you won’t get what you don’t ask for (although…if you have followed me for any length of time, you will know I am very against having to ask for the sale). But you also have to ensure that your prospects actually want what you are selling. And they want it for their reasons and their motivations. They are driven to pursue your production option(s). They must go 10, 40, 60% of the way to you. The Pitfall of Chasing Your Prospect Just like courtship and relationships – if you find yourself chasing and one-sided-pursing the other person then it means you want it more than they do. It also means they own you. You are essentially begging them for the relationship – convincing, manipulating, begging, bribing, persuading your way forward. Which means they consciously and/or subconsciously know that they are in control. Because if they say no, you will keep pursuing and offering solutions. In sales – that looks like a salesperson who is calling, emailing, stalking a prospect – making offers, offering discounts and trials, and trying to find any way to make deal work. They are going 90-100% of the way for the prospect, not requiring them to go anywhere towards the agreement. This will end terribly. If they do decide to buy – taking the discount, free trial, taking the sale bait – they will not be happy (since they weren’t bought in for their reasons), they will look for reasons confirming why they didn’t really want to buy anyway, and they will know that they own you. Your company will have to convince them on a regular basis to stay in the relationship. The Right Balance for Customer Ownership You fundamentally need that prospective customer to come to you. Not 100% where you are just an Order Taker. But potentially 51% of the way – so they want it more than you. The more you can get them across that 50/50 threshold, the more they will be a satisfied customer. But remember – at 51/49 – they still need persuading, they still need to understand the value of your product for where they ultimately want to be in their life/business, and they still need your support. They lean in the right amount, you lean in the right amount = sales magic!
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