E151: Being A Sales “Leader”

January 5, 2024


How can sales professionals transform into effective leaders to guide prospects to a successful sale?


Are you a leader of sales?

And I am not referring to a sales manager, team lead, VP or owner.


I am talking to you – the salesperson.

Your challenging role as a sales professional is to be a leader.


Of your prospects. To the finish line.

How can you be a sales rep and a leader? Check out this episode.



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  • Show Transcript

    Jason: On today’s episode, I want to talk about sales leadership. Welcome to the sales experience podcast. My name again is Jason Cutter. So glad that you’re listening and on this journey to help make your career in sales better. Your sales team’s life better and your prospects lives better while at the same time doing the right thing for you, for them achieving your goals, helping them get their goals, and so hopefully you’ve been enjoying the show. Make sure to subscribe if you’re not everywhere that podcasts are available. You can also connect with me on cutterconsultinggroup.com you can follow me on LinkedIn and now for today’s topic, what I wanted to talk about is leadership and sales. Now typically what happens is when people hear the term sales leader or leadership and sales, they’re thinking team lead, sales manager, sales coach, consultant, owner, all those people who are in leadership and leadership being a higher level.


    Jason: So somebody is higher up in the org chart or more experience or you know the person on the floor with tons of experience that’s kind of leading the charge every day or helping people feel better when they get down. If he gets some rejection from a prospect or a client that cancels or returns whatever you sold them, you know you’ve got the leader on the floor for the morale and then you’ve got the leaders that everyone thinks about. Now what my topic is for today and what I want to focus on and what I really want to shift for all of you listening who are sales professional salespeople in a sales role dealing directly with prospects, converting them into customers. Cause I want to talk about your role as a leader. Okay, so a lot of times sales people don’t see themselves as a leader and don’t embrace the leadership that is required to be a sales professional.


    Jason: Now let’s talk about leadership. Definition of leadership on a basic easy level is somebody who inspires others to follow them, right? There’s managers and then there’s leaders. Managers manage people tell them what to do. Delegate direct hold people accountable. Leaders on the other hand, they create a framework. They have a vision, they know where they’re going and they inspire other people to follow them, and that’s the big key managers, people who are in charge, people who are running things. Sometimes we’ll use manipulation to get people to do what they want, right, but sometimes it’s the carrot or the stick. There’s some kind of manipulation, whether it’s a forceful, harsh manipulation or it’s just a very subtle and kind of passive no matter what. That’s on the management side. A leader is somebody you want to follow a leader, whether it’s in the church or military or an organization or somebody like that where you encounter that person and you’re like, wherever they are going, I want to go as well.


    Jason: If you’ve gotten a job at an organization, as a salesperson, manager, leader, whatever that is, and you have come into contact with the ownership or you understand the culture and there’s a vision and the mission and core values, then that’s something that you want to be a part of at a deeper level. That’s a different feeling than when you go to work somewhere and it’s a job and you’re told what to do and you don’t really understand the mission and the vision. You don’t really care and you’re not understanding it. Last week I talked about marrying the vision and dating the strategy, right, and that’s about having a vision and knowing where you want to go and having everyone follow. Now it’s a salesperson. Your job is to be the leader of your prospect. Now, I know this sounds weird, rarely ever hear this topic or I’ve never seen anyone really talk about it, but your job as a sales professional is to be a leader and lead your prospects to the finish line, to the promised land of a solution for them.


    Jason: Now, a couple of weeks ago I talked about giving to give and making sure that you’re doing things for your prospects to help them get into a better place and not about you. It’s not about giving them to get, it’s not about pushing them to sell so you can get what you want. It’s about helping other people. When you act as a leader in your sales role with your prospects, it’s about getting them to follow you. Now, how do you get them to follow you, right? They have a problem. They have a need for your service or for your product or your idea, whatever it is that you’ve got. How would you get them to follow you? You’re the sales person. They’re the buyer. You should be directing them. You should be pushing them, should be moving them forward. Well, the key is to do what leaders do, which is to ask questions.


    Jason: It’s to build the framework. It’s to then find the issues that you want to solve instead of having a vision, right? I know that my vision is to help my prospects get from here to here. When they encounter you, when they talk to you on the phone or they meet you in person, wherever you’re at in your sales process, when that occurs, there’s a different energy that leaders have. There’s a different confidence that leaders have, and I’m not saying you have to be that charismatic leader, the one that has lots of stories. That seems to be the life of the party standing on tables. That’s not leadership. That’s a personality trait with highly charismatic extroverted people. I’m talking about leadership. There’s some amazing leaders out there in the world who are very quiet and very passive, but their energy and their power comes through in what they say and where they’re going and people just naturally want to follow them.


    Jason: And so your job as a sales professionals to do that same thing. It’s about building that framework, holding that space, and having your prospects come with you on the journey to the finish line with a closed sale. Now I know this might sound very woo, might sound very weird, like we’re just going to sit in a circle and you’re just gonna you know, chance and have your prospects follow you and you’re just going to talk about these theories and hope that they come with you and just grab their credit card and pay. Right? But no, that’s not what I’m talking about. I’m talking about actually being a leader and taking charge of the conversation and then having them follow you, like you know where you want to go so they’re going to follow you in it. And how do you do that? One of the best things to do, and this is some practical information so you know how to do it, is to focus on enrolling and not selling.


    Jason: Now, I’ve talked about this before on the show many, many times, but it’s about enrolling versus selling. When you’re selling something to somebody, you’re trying to persuade them and or manipulate them for your reasons, right? And remember, people don’t like to be sold to. They like to buy, they want to buy for their reasons. They don’t want to be sold to for your reasons. Even if you can see that what makes the most sense for them is very clear. You can’t push them into it or you’re going to have cancels. You’re in a buyer’s remorse. It’s not going to be as effective. So you need to make sure you’re enrolling. Now, what is enrolling? Like? Enrolling is kind of similar to the DMV. When you go there, they’re not trying to sell you anything. They’re just trying to help you. You have forms you need to fill out.


    Jason: They’re going to take your money. They’re going to process, you’re gonna move on. Now, if everyone treated everyone like the DMV does, that’s going to be terrible and no one’s going to want to follow you, right? That’s not a good leadership model, but you want to do is lead your people over it because of your passion and your desire to help them. That energy will come through. Now, here’s a good example as well. If you’ve ever known somebody or been in a relationship where somebody could make better decisions, right? Maybe eat healthier or workout more, you could tell them to work out more. You could tell them to eat healthier or you could just do it yourself and be that guiding post and that one that they want to follow and say, wait a second, it’s working for them. This seems to be good. I’m going to go down that same path.


    Jason: Now, how do you do that as a salesperson? That can be tough at times because you have usually a short window of which you’re trying to lead someone, but you have to make sure that they understand that you are very clear on the vision and the value of what your service or product does for people as well as how you will get there and the process and then what it’s going to feel like at the other end, right? Everybody is in things for themselves. What’s in it for me? Always got to keep that in mind that your prospect only cares about themselves. And so if you can set this framework of where you’re going, the vision and the destination, they will want to follow you there, especially when you put it in terms of what it’s going to feel like for them, what it’s gonna look like for them, and how their life is going to improve.


    Jason: Now keep in mind, it may sound like this only applies to people who are helping others, right? Get out of debt or deal with some personal issues, but that’s not true. The supplies business to business, business to consumer, whether you’re helping companies buy a new CRM or you’re helping an individual buy a car, all of that is about leadership and that vision that you have for them and then getting them to buy into that vision. But that’s enrolling, not selling. If you sell it too hard and you push it, it sounds like you’re trying to get people on board and it’s not going to come across the same. When you’re enrolling people and getting them to enroll in buy into the vision, then they are with you and you can lead them to the promised land. You can lead them across the finish line. Of course, with the caveat that it’s got to apply to them.


    Jason: They’ve, it’s gotta be a good solution. It’s gotta be something that takes care of their problems, their issues or helps them with a goal or a need that they have. But when you do that, when you enroll them into your vision for them with your product or solution as that vehicle that’s going to get them there, then you’re a sales leader. And sales leadership is all about getting people on board, having people follow you, and then also doing whatever it takes. And again, this goes into last week’s conversation about marrying the vision and dating the strategy is the strategy part is overcoming obstacles. How are you going to get there? Who needs to be involved and being very flexible in your sales while at the same time being very clear on what your vision is as the leader of that interaction of that transaction. If you find yourself talking to your prospects and you get done and you realize that you didn’t make the sale and they kind of walked all over you and they asked you lots of questions and they beat you up and they drove the process, you were not acting like a sales leader, you were not leading that conversation and directing it.


    Jason: Okay, and I’ve mentioned this analogy in the past, but think about the doctor example, go into a doctor’s office. They are leading the process now. They may entertain some of your questions. They may open the floor up to you to for your questions or concerns, but they are leading it the whole way they are driving it. And then based on their professionalism, based on how they’re handling things, and then based on their diagnosis and prescription, you want to follow them and their direction because you know it’s going to get you in a better place because you’ve trust them. They’ve built that trust with you as an authority and as somebody who cares about you and getting you there. That’s how that goes. That’s what that feels like. And that’s what you want to create for your prospects. So hopefully that helps. Remember, always focus on becoming a sales leader, that your prospects literally want to follow and will go with you because you know you’re there to help them and at the end they will be in a better place. So always focus on that, both in sales in life. Just like I say, 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 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?
By Jason Cutter February 17, 2025
The Abundance of Options Today we all have lots of options. While writing this I could speak into my phone and order whatever I want. I can get food delivered before I finish writing this article. I could get a TV delivered to my door before I wake up tomorrow. When someone wants to buy something, they are armed with as much information as they want to access. They can research, read reviews, and watch videos about a product or company. The Shift in Power to the Buyer Because of this, the power balance of sales has shifted away from the salesperson and company to the buyer. Knowledge is power – and they now have all the knowledge they want. With knowing that they have ultimate choice of what to buy (internet and globalization has led to the ability to order anything you want from anywhere…so you are no longer limited to the stores you can drive to and what they have on hand), it means that everything is a commodity in their minds. Nothing is unique or special. Everything is interchangeable. Does the Sales Experience Even Matter? So, this means the sales experience doesn’t matter anymore. There is no reason to put effort into the sales process, the conversations with potential customers. No value in spending time trying to ‘help’ people – since they just view products, salespeople, and companies as interchangeable. You are not special, so there is no benefit in caring. They will walk into your store, and they will decide what they want. They fill out your online for, and they decide if they answer when you call and how the call will go. They walk up to your event/booth, and they decide how the interaction will go and if they want to listen to your elevator pitch. They will let you know if they are interested in moving forward. They will let you know how they want to buy. So, like I said above, there is no real value anymore in the sales experience. Or could it actually be valuable? Is it possible that all that matters IS the sales experience? If people feel they have ultimate information and control of the buying process, how do they decide on what to buy and who to buy from? When I search on Amazon for a product type I have never purchased before, how do I pick? When I want to go shopping for garden supplies for the house, how do I pick where to go? When I need to buy a new fridge, who will I hand my money over to? The cheapest place with terrible service? The place with reasonable prices and great service? The Sales Experience Shapes the Decision I choose based on the sales experience that I will receive. With everything else being equal, I (and I believe most people) will select the place to shop at or the products to buy online based on the experience I receive. To me all that matters is the experience. While I am trying to buy something. Once I receive it – ensure it does what I need it to do. With the feeling of unlimited choices, it can actually be harder now to buy something that in the past. People get into analysis paralysis more often. Which means that for consumers to buy something new they need help. They need a professional salesperson. They need a sales experience that matches their expectations. They want a guide who will help them make the right decision for them, with an experience that goes above and beyond what more people receive any more when they walk into a store, call a company’s toll-free number, or visit a website and have to fill out a form. If you want to succeed in sales – the only thing that matters is the sales experience you provide.
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