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 August 27, 2025
Most businesses struggle to grow their sales teams. At some point, they give up on looking for rock stars; they just need a team that shows up every day. In fact, research shows that 52% of sales leaders list recruiting as 'very challenging,' and average sales rep turnover hovers around 26% annually. That means for many leaders, the hiring process feels like a revolving door of wasted time, lost revenue, and constant stress. Here’s how to achieve scalable hiring results without having a massive hiring team and a huge job marketing budget. What Most Companies Do They need to hire salespeople. Maybe it’s one. Maybe it’s their very first salesperson. Maybe they need 10 more. So they: Write a job post about all the things the job involves and who they are looking for, and the type of experience they feel is important Put it on Indeed and/or LinkedIn They get hundreds and hundreds of applications They freak out – stressed at the thought of going through all those submissions They have someone on the team spend hours/days going through all the submissions. Have them call and email everyone whose resume fits what they think they want. A few people respond. So they call again, to ‘check in’ on the candidates to try and get more to respond. If that works, they have dozens and dozens of candidates ready for the first interview. Someone has to then take a week’s worth of time blocks away from their actual job to do first interviews. Most of the candidates don’t show up to the call/meeting. A few candidates make it through to the second interview. The boss or sales manager takes these. Two out of the three show up. Offers are sent to the two. One takes another job because the process took so long. The company ends up with one new hire The company repeats the process over and over again, feeling like the best they can do is one to two new hires after each complete cycle of hiring madness. And it is madness. It is also the definition of insanity – doing the same thing, running the same hiring process out of some playbook that no one can point to its origin or actual stats of success. Recent surveys confirm this frustration: more than half of leaders admit they lack an effective hiring process, and many acknowledge that their comp plans don’t even align with the results they want. The result? Slow hiring, bad hires, and retention issues that eat away at growth. Most companies struggle with filling their sales team, with both quantity and quality. They probably run the hiring process like they run their sales process. They default to old-school business thinking that the only way to hire is to just get experienced salespeople to join the team. But there is a better way. I have spent over 15 years being tasked with keeping teams filled with salespeople. Whether it was for inside sales in a call center environment or work from home, to retail environments, from consumer products and services to B2B, from within the United States to offshore, this framework works, even if you have failed in the past to try and scale your hiring efforts. In working with small and large teams, the key is the balance of quality and quantity. Humans will always surprise you. I have seen the ideal candidate – on paper – be completely ineffective in the role. I have seen reps with very little experience, whom we took a chance on, completely outsell their experienced co-workers. The experience of everything that goes into hiring over 800 salespeople, this framework is designed to help you succeed no matter the size of your hiring team. Here’s how to create a scalable hiring process that doesn’t require a large recruiting team and without losing your mind wasting time on candidates that aren’t a good fit. Step 1: Hire Traits, Not Just Resumes Did you know there are three different types of salespeople? The Newbie, The Entrepreneur, The Sales Veteran (email me, and I will send you the ebook that breaks them down). First, make sure you know what you need on the team, who you have the bandwidth to train, and if you need someone that follows your playbook (do you even have one?) pretty much exactly, or are you okay with them just ‘doing what they do best’ without much structure? Next, you need to figure out the mindset traits you find most successful. A business friend of mine, a long time ago, taught me: “Hire the smile, train the skill.” Given enough time and patience, you can teach anyone how to do anything. But it's really hard to teach someone a different mindset. Most people are who they are when they are applying to be a part of your company. Here is my list, in order, of mindsets that I know are successful for sales (in any sales role, any industry, any company): This aligns with broader studies: while past performance can matter, attitude and coachability are consistently ranked as stronger predictors of sustained success. Leaders who over-prioritize experience often miss the hidden talent right in front of them. Openness Curiosity Creativity Persistence Authenticity As I tell my clients, most leaders think they just need more reps who are ‘persistent’. They blame a lack of sales results on the team not asking for the sale enough or doing enough follow-up. The problem with biasing the screening process for persistence is that if you don’t care about the other traits, you will end up with a team full of persistent assholes who don’t listen to you or their prospects, don’t care to learn anything new, and don’t try to come up with new ways to move people to the close. They just see every prospect as a nail and sales is a giant hammer in their hand, where if they can just hit enough nails hard enough, they will win. [Don’t believe me? Ever heard the phrase ‘sales is just a numbers game’? That is this mindset in action.] The last part you want to define is what type of company culture you have and what personality is a good fit? Is it a fun environment? Does everyone like to joke around? Is it all serious and focused? Is it mission-driven? Do you actually have defined, stated core values that you care about? The answers to these questions will help you determine culture fit. One area that organizations will fall short in their selection process is ignoring culture fit and just wanting people with certain experiences on their resume or skills to help sell more widgets. If not careful, it can lead to bringing someone on board who might be an excellent, technical salesperson (meaning…technically they can do the job), but they are a not a good fit for the team. “The best reps don’t just sell your product — they sell it your way.” It’s not enough to just hire for experience; you need team players. Step 2: Treat Recruiting Like a Sales Funnel Now that you know who is open to bringing on board, what that winning combination could look like, it’s time to start building the hiring process. In sales, the initial key to success is attracting the right leads into your funnel. This is the job of marketing. Not just in the steps they take, but the messages they put out there to the world. Like fishing, putting out a hook with bait on it where the right fish that is interested will want to take that bait. Marketing should be doing the same thing for your revops. Your hiring team should be doing the same thing with the job posts and the hiring process. Your goal is to write a job post, like your marketing team writes their content, in a way that your ideal candidate would read it and say “holy crap, that is me!” Part 2 is to build in some hoops. One area that I see pretty much every organization fail at is building and managing candidate lead flow. They put a job post out there, get a shit ton of candidates, go from excited ( “We have so many candidates, we will definitely find all the reps we need!” ) to despair ( “How the hell are we going to get through all these resumes, and then what about all the interviews?” ). So many orgs are not ready for the flood of applicants. And did they even want that many applicants? If you haven’t noticed…recruiting is like sales. Well, to be specific, everything in life is sales, and selling, and persuasion. So building a recruiting process is like building a sales process. Sales teams think it would be great to be flooded with leads until it happens, and so much potential business falls through the cracks of inefficiencies and bandwidth limitations. This is why we want to put in a) hoops and b) templates for our hiring process. Let’s start with hoops. Think about it: in sales, 63% of managers admit their teams do a poor job managing the sales pipeline. If you can’t expect discipline in pipeline follow-up from a candidate during the hiring process, you certainly can’t expect it once they’re in the field. The hoops should be similar to what your prospects have to go through to become a customer. The logic is that your salespeople will run that process with their prospects, so you need to identify those sales reps who are naturally built for it. It’s similar to Alex Hormozi’s take on hiring – that what is more important than the years of experience someone has, is evaluating and selecting for traits like intelligence, work ethic, adaptability, and coachability. This is what we want our hoops to do – help the candidates show us what they are really made of. Some hoop examples: Do you require your sales team to use scripts? Yes, yes, yes…I know…salespeople shouldn’t use scripts…scripts are bad…scripts make everyone sound robotic…scripts are the problem. Bullshit. You are wrong if you think that. Alright…soap-box-moment over…back to scripts. If you require your reps to use scripts…let’s say for an intro, elevator pitch portion, compliance/disclosures – then one valuable hoop to put in place is to make your candidates memorize a short script in the hiring process. There are many ways to do it [email me, I can give you some examples of how, when, and what for this hoop], but it is an amazing filter for candidates. This is how you filter out the people who are not open/curious (remember, my top two sales success mindset traits above) – because they will decline your requirement to memorize the script. Or they will take the script, say they will work on it, and then disappear into the wind, never to be heard from again. And…that is the perfect result. I promise, no matter what fantastic story they spun on their resume or tried to present to you in the interview…their resistance to this step is all you need to know. Truly. The ones who say, “ Sure, sounds good, I will memorize this and get back to you, ” are the ones you want. Not because they are actually good at memorizing things – because I know I am terrible at it – but because they are willing to do it. A tiger can’t change its stripes. Is it a short sales cycle or a long one? If it is more than a one-call close, then you want to put hoops into your process that will help differentiate the short-term commitment versus long-term commitment people. Some salespeople out there are just too impatient to handle making follow-up calls, delays by stakeholders, and rejection after long sales cycles. They need immediate gratification. (and here is a contrarian thought…they are probably also single…because how someone is with work, they are in their life. If they can’t handle long sales cycles and long-term relationship building in a sales role, they probably aren’t very good at it in their personal life. And that’s okay…there is nothing wrong with that mode. The question is – is that what fits your sales cycle/length/mode? If you need reps who can do more than build enough rapport to sell someone something in the next 20 minutes before never seeing them again, then filter those people out by adding layers to your hiring process that extend the length. Now, I am not saying that if your sales cycle takes an average of six months, that your hiring process should do the same, but it should be relatively long. Definitely don’t interview people and then have them start the following Monday. Is there a lot of follow-up in your sales process? Do you expect your team to actually manage their pipeline of valuable leads to ensure they close? Then you want to build in a hoop that requires candidates to follow up with you. We want to test them on how well they will treat their future sales pipeline. If they won’t even follow up with you on their progress in the process, then they aren’t the type of salesperson who will follow up on their own leads. Or, they just don’t care that much about this job. Either way, this is a perfect filter to remove those candidates from your pipeline. If you want my ultimate filter process/scripting for this hoop – email me with the subject “ candidate follow up, ” and I will send you what I have done to successfully apply this filter. While that might look like a lot of hoops and processes to build out, it doesn’t take much to both eliminate the candidates who are not a good fit and allow the ones who are to raise their hand so you can pick them. Remember, no matter how desperate you may feel you are – needing to fill your sales team today, it’s never worth bringing on bad hires, especially in a sales role. The cost of their onboarding, training, combined with the cost to your leads (aka – the wake of revenue and reputation destruction that is caused by terrible sales reps speaking with your hard-earned, expensive leads is almost immeasurable) is not worth it. Fight the urge and bad business advice to just get butts in seats. And I guess that you are here reading this because you have already tried that mode and it failed. And with annual sales turnover costing companies millions, every wrong hire creates a hidden tax on growth that most leaders underestimate. Mads Faurholt-Jorgensen spoke about it in his TEDx Talk titled “ How To Master Recruiting ” with a focus on hidden talents over resumes. He called it the “whispering talents” – and in sales, we want that person who just automatically does the sales activities with the right mindset that fits your organization, sales process, and target customer type. TL;DR Most companies hire salespeople the same broken way: post a generic job, drown in resumes, waste hours interviewing, and end up with one shaky hire. It’s slow, costly, and sets teams up for turnover. The fix? Stop hiring based on resumes alone. Instead: Hire traits, not just experience (openness, curiosity, persistence, authenticity). Treat recruiting like a sales funnel by writing magnetic job posts, adding “hoops” that filter out the wrong candidates, and testing real-world behaviors like follow-up. This approach flips hiring from chaos into a scalable system—so you attract the right reps, faster, and avoid the expensive revolving door. In Part 2 of this series, I’ll show you exactly how I scaled this process to hire 50 salespeople without the chaos—complete with templates, filters, and lessons learned. Don’t miss it. And if you think that there might be some ways to improve your hiring process, contact us and we can do a free Hiring System Assessment to determine where the biggest impact can be made to help you fill your sales team.
By Jason Cutter February 26, 2025
How Can You Predict The Future Of Sales Ops? One of the keys to sales success is to be able to predict the future – what that other person is thinking, what they might say, what they will experience, how they will feel about the product/service. But what can you do – from a sales ops leadership perspective – to predict the future in masse of all the potential customers that will flow into and out of the sales process/funnel? That is a really tough one, but it is doable. Meeting Prospective Customers Where They Are The key is to always meet the prospective customers where they are and with the experience they hope to find. It’s a common theme now in these articles because it’s important AND widely disregarded – your potential customers do not care about you, your sales team, your company, your industry. They don’t care about your stats, your testimonials, your logos. They don’t care about your mission statement or your values. They only care about themselves. They also firmly believe that there is currently unlimited choice for any product/service, which means that everything in their mind is a commodity. Easily replaceable and interchangeable. Nothing (other than iPhones…which you can only get from Apple) is special to consumers unless they feel like it should be special. Are You Still Making It All About You? There is a good chance you are still running a marketing, sales funnel that is all about you. I bet if I looked at your company’s website that from the top down it’s all about you (the company). How great you are. What you do for people. What you have done for others. I bet if I tried to speak with your sales team, I will be made to go through your process whether I like it or not. Maybe fill out a form and wait for a response. Or made to call into a toll free number, even though I don’t want to talk to someone yet. Or made to use a chat widget on a site to get started. I bet when I speak with your sales team, 70-80% of the conversation will be about them, your company, and how amazing you all believe you are. This is all fair. No one starts a company to be mediocre. The goal is to provide value and make money. The missing piece, again like I said above, is no one cares about your goals. They only care about themselves. Predicting What Customers Want From The Sales Experience Back to your mission as sales ops leader – predict what massive amounts of prospective customers are going to want from the Sales Experience. It’s why I wrote about it last week and even offered up a book for free to help in any way that I can. To succeed at your mission, you have to stay ahead of the curve of what the public, and specifically – your buying demographic, psychographic, and valuegraphics, want from that experience. Key Questions To Shape The Sales Experience Do they want to call, text, email or chat? Probably all of them…so can you offer each one? (Don’t make someone decide if they want to go through your hoops…remove all the hoops) Do they need to see pricing online – should it be available and transparent? (In most cases, yes) What sales process will be ideal for moving the most people through the sales conversation to a successful outcome? (More discovery, empathy, active listening. More front-loaded about them, not you. Use the Authentic Persuasion Pathway as your model) Who are the decision makers? Is that individual going to decide or do they need to check with others for approval? (Set them up for success, and don’t force them to make a decision in the moment – you will just lose the potential sale) What type of follow up do they want and need until they make the buying decision? What type of post-purchase follow up would go above and beyond a) their expectations and b) what others in your industry do? If there is an ‘onboarding’ stage after the sale – how can you make that actually customer centric and successful? (It is rarely both) Can You Stay Ahead of the Curve? Remember – evolution is natural. The buying public is always evolving their desired sales experience. Can you predict the future of what they want so that when they encounter your company it matches what they were hoping to find – both in the experience and the solution to their need?
By Jason Cutter February 25, 2025
How do you, as a sales leader, help your team become Oracles that can predict the future? [make sure to read the Selling Effectiveness article this week https://go.sellingeffectiveness.com/LI.2.25.AM ] There are five ways to facilitate their Oracle-ness. Be Present in the Moment First, you have to get your salespeople to be in the moment. The challenge that most salespeople (and…humans, for that matter) experience is they are always thinking ahead. Salespeople default to thinking about what they will say next. The next part of their script or process. The next question they want to ask so they can get through discovery. The next part of the agreement they need to discuss and review. Their mind is too busy thinking about what they are going to say and do next, that they aren’t present. As weird as it sounds, if you want to predict the future you must be present. I have said this for decades: the moment you no longer need to think about what you are going to say/do next and can actually be present with your prospect and truly listen to what they say (and don’t say) – you will become a sales professional. Master Active Listening Second is Active Listening and paying closer attention. It’s actively listening…it’s taking what I mentioned above and putting into place. First step is to be present, second is to actually listen. For what they say. For what they aren’t saying. For changes in their tone. For when they are talking to someone on the side – who are they talking to, and is it about your sales conversation? If you sell in person, reading their body language and facial expressions. You must help them develop an almost sixth sense of listening (and yes, I know hearing is one of our senses…but this goes beyond hearing…it’s truly, deeply listening). Ask Better Questions Third, is to help them ask better questions. So many people in sales ask the discovery questions they are required to ask in order to check the discovery ‘box’. Or, they have done sales long enough they know all the answers, they think they know what everyone wants and why, so no reason to even ask questions. [Note – this type of salesperson thinks two dangerous things: 1 - everyone is the same and wants the same thing, 2 – people like to be sold to.] When your team asks better, deeper discovery questions with a focus on uncovering the what and the WHY, they will get better answers. Remember this – when you ask the right questions and you listen close enough, each prospect will tell you EXACTLY how to help them buy. Build Up Experience Fourth, build up experience. If you want to predict the future it comes from enough experience to know the probability of what will happen. For example, when I am in a season of commuting from home to an office, I am the type of person that can predict exactly what will happen on the freeway. Which lane is always faster around certain exits, which lanes always slow down, how much leaving five minutes later can make the drive suck a lot more. How do I know what will happen on a freeway with hundreds and hundreds of random people? Because of experience (and the fact that most people are just going through the motions in life so they become predictable). The more experience your team has with sales scenarios, they more they can predict the future. I generally see that it takes about six months for most people in a new sales role to have seen enough scenarios where they can start to know what will come next before it happens. Trust Intuition The fifth and final trait to help them with is intuition. One definition of intuition is “a thing that one knows or considers likely from instinctive feeling rather than conscious reasoning.” It’s that feeling you get when you know something, even if you cannot explain it. It’s what Malcom Gladwell wrote about in Blink! It’s what we do very well as humans, even if we don’t listen to it. The more you can help your team tune into their intuition and listen and trust it – the better they will do in helping persuade that other human. This goes back to the first suggestion – about being present. When your team trusts they know what to do and say next and they are mentally living in the moment with that prospective client, they can let their intuition guide them. Conclusion When I do trainings, public speaking, facilitating meetings, interviews, and sales – this is my main key to success. I trust and know that I have the experience to handle whatever comes my way in the present moment, while also knowing the destination I am heading towards. I can be present, let that experience and my intuition guide me instead of getting stuck in my head and worrying about what I will say next. Get your team to do some or all of these five steps – and they will become an amazing Oracle.
By Jason Cutter February 25, 2025
The Oracle’s Role in The Matrix If you have seen the Matrix movies, starring Keanu Reeves (as Neo), then you are familiar with an Oracle. In the movies, the Oracle knows what will happen. She has seen it, and it is predestined. In the Oracles mind there is no such thing as free will. In the first Matrix movie, Neo goes to visit her and knocks a vase off the shelf, and it hits the ground and breaks. Right before he hits it, she says “Don’t worry about the vase.” Neo says, “How did you know?” Then the Oracle responds with “What’s really going to bake your noodle later on, is would you still have broken it if I hadn’t said anything.” Becoming an Oracle in Sales Your mission as a sales professional is to be an Oracle for your prospects and clients. To know the future. Then be able to see around corners, as they say. Which means you know what is going to happen before it happens, because you have enough experience that you have become a psychic. You want to be able to predict, with amazing accuracy: What will happen next What will happen after that What issues will pop up What your prospect/client is thinking before they think it What concerns they might have before they have them Eliminating the Fear of the Unknown During your presentation/demo you want to set the expectation of what is going to occur next. Remember, humans fear the unknown. They want to avoid risk as much as possible. Your sales presentation is risky and dangerous and very unknown. They don’t know if you have good intentions or not. Are you going to persuade them? Are you going to try to manipulate them? Are you going to overcharge them? Will you actually care about what they need and want? Dealing with salespeople is so scary. Yet they still need and/or want something, so it’s the dangerous game they must mentally play. Guiding the Buyer Step by Step When you explain what you are going to do in part 1 of your process, and then what that part is done you let them know the plan for part 2, and so on – they will be at ease in the moment. They will feel like they have control over this portion, that there is an exit they can take if they don’t want to proceed. That level of control will help them accept the risk of part 1, and part 2, and part 3. Tell them what you will do. Do it. Tell them what you did. This will validate that you can be trusted. Predicting Thoughts and Feelings The next level is being able to predict what they will think and feel before they do. You can use this information in your presentation (without telling them what you are doing). You can also verbalize it, which could sound like “I am guessing from experience that you are probably wondering about _____, so let’s cover that right now.” Or “most people I speak with ask about _____.” They will think – wow this person knows what I am thinking, he/she is in my mind! And that’s a good thing. A really good thing. Conclusion The more they feel like you know what you are doing, know what they are thinking, know what they are afraid of – the more they trust you as a Guide. Because Guides only know what they know because they have helped other Heros successfully accomplish their journeys. Your mission as a sales professional: Become an Oracle.
By Jason Cutter February 19, 2025
What does it take to build the ideal Sales Experience? Why does it even matter? Maybe you think you already have one. You are a professional sales ops leader. You have put everything you can in place to help your salespeople sell more. You have optimized the processes so that your sales team can focus on one thing – selling. But I promise – even if you think all of that is true, it’s not. The Reality: No Perfect Sales Experience Exists I have never seen any company or team with the ‘ideal’ Sales Experience and operation. And to be honest – I have never built one successfully. Why would I admit that? Because the ideal Sales Experience is aspirational and business, teams, processes, and customer needs/desires are constantly changing. So as soon as you put new processes in place, something else needs to change and evolve. The Scalable Sales Success Iceberg In my Scalable Sales Success Iceberg – there are 24 categories that, when built out, create a scalable sales machine – where you can add in an input and get way more output. I would love to see companies have all 24 categories set up and running optimally. But that’s not even possible – because, as I mentioned, things are always changing. Focusing on the Biggest Levers Here is the key – to build the ideal Sales Experience takes focus on the biggest levers. The ones that, when pulled, create the biggest and best results. There are many processes and systems that you can put in place – but those are going to get you a few percentage points of improvement. Instead of putting it all in here, I want to make you a special offer. Email me at jason@sellingeffectiveness.com with your mailing address, and I will mail you the book that I co-wrote with Nick Glimsdahl called Reasons Not To Focus On The Sales Experience. It will be your starter guide, facilitating the creation of your ideal Sales Experience.
By Jason Cutter February 18, 2025
The Numbers Game Mentality is a Losing Strategy Sales is no longer a “numbers game.” You cannot succeed, long term, by focusing on volume of activity. Making a million dials, sending a million emails, knocking on a million doors (the first two are way easier than that last one) is a scorched earth strategy that will sink your business. You can’t out-dial a bad sales process. It will lead to even more bad online reviews. You can’t out-email a terrible sales funnel process that requires people to jump through poorly planned hoops. You can’t out-knock your way past slimy tactics and bad products/services. The Danger of the "Every No Gets Me Closer to a Yes" Mindset The whole “every no gets me one step closer to a yes” mentally is dangerous. That mindset and strategy assumes that it’s a numbers game. That the only thing that matters is finding the right person who will buy from you. Potentially, no matter what you even say – they are just ready to buy. Not only will this destroy any online reputation you have it will also wreak havoc on your team. It is the fastest and best way to burn out your team. It will lead to a revolving door or hiring, training, and quitting as people realize how unfun the game is you have built and how hard it is to be successful. It will also feel like a mismatch – very few people (and hopefully even less over time) are long-term excited about the business model of calling 500 people a day in hopes of making a few sales. If It’s Not a Numbers Game, Then What Is It? It’s quality over quantity. [Now…note – it does take a certain quantity of activity to fill a sales pipeline. So I am not saying that your sales team can just sit and wait for people to fall into their pipeline with money in hand.] It’s about the Sales Experience. It’s about your team ensuring that they are providing the right and best experience for that potential customer – in a way that sets them up to get into the buying mood and mode. All that matters is the Sales Experience. How can you support your team in terms of the quantity of activity to fill a pipeline, and then the quality of interaction that leads to sales? What Does an Ideal Sales Experience Look Like? What does that look like – the ideal Sales Experience? It’s when your team understands that the potential customer they are speaking with only cares about themselves. They don’t care about the salesperson, your company or the product. They are only focused on themselves. It’s when the Discovery/Empathy portion of the conversation is the most important part. Does your team realize that everything after Discovery – when done right – is just a presentation of the solution? It’s the fact that when you combine the parts of the Authentic Persuasion Pathway (Rapport + Empathy + Trust + Hope + Urgency) that the assumptive close is all you need. If your team is having to ask for the sale they are doing sales wrong. And don’t confuse earning the right to close with asking for the sale. The Sales Leader’s Role in Creating a World-Class Sales Experience Your job as a sales leader is to ensure your team understands that the only thing – above all else – is the sales experience they provide to each potential customer. That customer knows that they have the power and the feeling of unlimited choice. Which means they will decide who to give their money to based on the experience they have with buying from a company. How can you shift your team away from the numbers game mentality to actually providing a world class sales experience to each and every person they speak with?
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