CUTTER CONSULTING GROUP

E175: Doing Sales Automation Right with Shawn Finder – Part 4 of 4

January 8, 2024


How do you define a "right" question, and why is it different from any other question?


This is the fourth/final segment of the conversation I had with Shawn. 


In Part 4, Shawn and I talk about:

  • Shawn’s list of what it takes to be a successful sales rep
  • How Shawn recruits top performing sales pros
  • A very interesting cold outbounding script/strategy
  • Customizing your sales process for success



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Connect with Shawn on LinkedIn


Shawn’s Bio:

Shawn Finder has always been an entrepreneur at heart. At age 24, Shawn entered the entrepreneurial world after competing as one of Canada’s top-ranked tennis players. He started out importing packaging from the Orient and selling to top retailers in North America. However, knowing he always loved selling and list building, he founded ExchangeLeads in 2013 which helps his company build quality lists for outreaching new prospects. This was followed by his new venture Autoklose in 2017 that combines both sales engagement and list building all-in-one platform

Social Links:

LinkedIn: https://www.linkedin.com/in/shawnfinder/

Twitter@autoklose

Instagram@sfinds

Website: www.autoklose.com

B2B Sales Handbook: https://autoklose.com/books/b2bsales

673 Years of Sales Excellence
Book
https://autoklose.com/books/salesleaders


Books:

B2B Sales Handbook: 
https://autoklose.com/books/b2bsales

  • Show Transcript

    Jason: Welcome to the sales experience podcast. My name again is Jason Cutter. So glad you’re here. Before we dive into this, please make sure to subscribe, rate, review the show, share this with other people you know that helps so much with this podcast with getting the message out there and with helping other salespeople, other businesses, other companies do things in the right way which will then shift that landscape. Now we’re about to kick into part four my conversation with Shawn Finder. If you haven’t three previous parts, now obviously it’s going to be a standalone. We’re going through my questions where I actually asked him and he’s talking about the sales experience and what top reps do and what struggling reps don’t do. And then we also talk about the hiring process, but make sure you listen to those of the three sections cause it’s one continuous conversation, one take as we go through all of this and we had a good time, almost 50 minutes of conversation where at the end and we stopped recording, both of us were like, wow, I couldn’t believe it went by so smooth.


    Jason: So hopefully you’re enjoying this. And at the end Shawn will talk about his links and where you can find him and get in touch with him. So here you are part four, enjoy. 


    Shawn: So if you’re selling to a C level person versus a VP level or versus like a just a regular SDR for example, what’s going to make them tick is all different. So make sure you know their buyers personas. A sale does not stop once you pay, you have to know how to upgrade people down the road because as you add new features you might be adding different revenue streams. And lastly I would say like we talked about dating, ask the right questions and ask enough questions because you want to get to know that person at that company and as a prospect. 


    Jason: And I love that list, like all six of those things are a home run with that last one that you’re talking about with asking questions, how do you instill that or find that person? Right. This partly goes into one of the other question I would ask, which is recruiting and hiring, but you know, having that curiosity, how do you find that? How do you train that? How do you ensure that you’ve got someone on the team that’s going to do that for you? 


    Shawn: I always make sure there’s a, you know, here’s a handful of questions. You have to at least get three of these edge and every single call. So there’s five questions that will help you understand more about the person’s business. You know, Oh, are you, what are you currently have in your sales staff? Learn what they have because it also, it’ll lead to conversations where if they say, Oh, well, you know, we’re deciding between HubSpot and Salesforce and if you’re knowledgeable, you can actually come out now in consult and say, Hey, well, you know, I use HubSpot in the past and I liked Salesforce, but these are the differentiator. Now. You’ve also become a market leader and helping them decide on another product and they’re more likely to buy your product.


    Jason: Got it. So you serve up a list of questions and say each time, no matter what, ask at least three of these. Get at least three of these answers. And then do you have a quality control and audit process recordings? How do you ensure that it gets done? 


    Shawn: Everything is recorded and then it’s all saved to our CRM. 


    Jason: Perfect. Okay. So the second one that I would ask is how did you build this process? Like how did you come about this? I mean obviously I’m going to guess based on your own experience, but how did you create all of this with the team? 


    Shawn: So, uh, I would say there’s a few things. The first thing is trial and error. What we do is I’m a true believer in testing different things and testing things that you know, your competitors are doing, but testing new things all the time.


    Shawn: And then what you do is you eliminate the things that don’t work every quarter and you doubled down on the things that work. So that’s what we’ve tried with, you know, a just doing sales automation and then including calls and then including social. So once you get the process down path that’s working and getting those 16 demos a month, we doubled down on that. Another one. You know, learning that you can’t rely on one channel nowadays 10 years ago, you could now you have to have multiple channels inside of a sequence. Mechan includes social, it can be door to door knocking, mail, phone. You have to have at least two to three channels to be successful. Another one that really helped us build our sales experience and our process was every morning at eight 30 we have a 15 minute huddle with our AEs and every evening at three 45 we have a 15 minute with our SDRs.


    Shawn: So that 50 minutes is where we come on, we talk strategy, we talk some answers and kind of build that company so the AEs can hear what the SDRs are asking ya, STR to kind of hear what the AEs are asking. And lastly, every Monday on our Monday morning meeting, every person on my team must try something new. Now that could be anything new. It could be a new message, it could be a new cold top call tactic, it could be anything. But you have to present one new thing. And then if it works, we have other people replicated on the team.


    Jason: So what does that, what do you mean? What does that look like? Give me an example.


    Shawn: So one thing new might be, you know, for example, here’s what one of my team, they got a list of 15 people with the name Mike. Okay. And they did a video video and they said, hi Mike, I’m calling from ABC. Okay. Knowing that all those 15 people’s names were Mike, it looks like it’s personalized one-on-one who was actually sent to 15 different people with the name Mike in the same industry and it looked more personalized. So you know, somebody like that, that can be very, it can be like that. Or it could be there could be making a cold call saying, you know, Hey Jason, you know, this is a complete, this is completely a cold call, but I just need two minutes of your time. Instead of going into the script, kind of just letting them know this is a cold call. I want two minutes. So just trying different things and they come back and they tell us how that went. So every week they have to introduce one new thing


    Jason: And I’ll say in reverse order of as I’m listening and thinking about it, I love that tactic and that’s what I do with teams now and, and really believe in that, which is disclosing right away that this is a cold call. If you’re doing cold calls. I love using that technique and saying, Hey, I know this is a cold call. I know you weren’t expecting it, but if you could just give me 60 seconds, then I just want to ask you a few questions and learn more about your business. And if it’s a good fit, then we can schedule a different time to talk. Otherwise, you know, I’ll let you know and just sets that expectation for you know, what you’re really asking and you know, sure. Give 60 seconds and then that’s it. 100% and then I think it’s fascinating. And the reason why I asked for some examples is because on one side, you know, you’re talking about the system and having a process and a sales process that’s measured.


    Jason: And then balancing that with being innovative in the right ways and testing things, which sometimes is a scary balance with salespeople because they think they know a different way to do it or they want to do it a different way. And if they’re always trying new things and it’s not working, how do you know what’s not working? And it’s tough to have predictable results so that you no longer have a system, you just have like a kind of a free for all, uh, experiments going on. And so it’s interesting to hear you say that you encourage that on a regular basis and have them come up with ideas and then test them. And I’m guessing there’s some rules or some requirements as far as the framework within your process.


    Shawn: Oh, 100%. So there’s different frameworks inside each process. And obviously, you know, we don’t implement any of the new processes until they’re obviously tried, tested. But it just, I always like, you know, I find that the world is sales always evolving and if you keep doing the same thing all the time, you’re not going to look and explore different things. So it may even be, you know, a new thing might be you know, doing a video on LinkedIn, you just post to going and giving a sales type and seeing a big like just anything different to keep you always thinking and on your feet. I think it really works well because it also helps people kind of, you know, expand and grow as a salesperson.


    Jason: Well and I love that so much because in my experience, which you probably have had the same experience in all your years, is that the best salespeople are going to understand your framework. They’re going to understand the rules of the game and then they’re going to always be looking for ways to play the game better no matter what it is. Hopefully ethically and legally and within, you know, again the rules where we’re playing monopoly, but how do I play monopoly better and how do I strategize better? And so they’re doing that anyway. The top people are always doing like your whole example with the video card and the and the mic and making the videos and they seem custom but they’re not at that scale. And so the top reps are doing. And what I love the most about what you’re talking about, which is key for so many companies, is then taking what that one person is trying but sharing that with the group and so that everyone kind of knows it and then everyone can learn. Because what I generally see is the top sales reps are innovative and trying and experimenting, but nobody else knows it unless somebody shares. And then you have this one rep who’s winning but you know, nobody else is doing it that same way. And it could be something that’s awesome for everybody.


    Shawn: Yeah. And also, you know, it’s a little bit of fun because everyone in the group, every sales person kind of be like, who’s going to be the most creative this week? And it’s kind of like a fun thing for us on, on Monday meeting.


    Jason: So cool. So like on that note, moving forward, like let’s talk about both the top sales reps, the successful ones and the unsuccessful ones. What are the successful sales reps doing, you know that you’ve seen and what are the unsuccessful sales reps not doing or doing?


    Shawn: That’s a, a lot of this, we actually touched upon it because some of them you’re not little actually laughed up though. Top salespeople always ask the right questions and build relationships before they prospect. So it was try and build relationships, find something in common, find something they can talk about before they actually go in with a sales pitch. They always use a little bit of humor on our call. Actually our top sales guy, and we’ll tell you what he says, if he has a prospect that’s very close to closing on the call or the demo, he’ll at the end be like, okay, so a, should we call Rhonda and accounting and get this deal signed? And I’m not even telling you. Everybody laughs it call Rhonda and accounting. It’s just a funny thing could run into sounds like an account things name and every time, and I’ll tell you that the close rate on that is about 90% once he says, so what do you think? Should we call, call Rhonda and accounting and uh, and get this PandaDoc’s signed 80% of the to go like, yeah, we’re going to call Rhonda right now. And they laugh and they do it. They do it.


    Jason: I love it. I absolutely love it.


    Shawn: And the last one, we, I would say know the competitors and know the space. So I’m one of those people that I never put down my competitors and I teach people not to put down your competitors because sitting your competitors, there’s enough business in the world for everybody. And I think, you know, competitors might do things well, but you’ve got to find what you do better and what feature you might have better. So I think good sales people don’t have to put down their competitors were unsuccessful. Sales reps say, Oh well that company’s terrible, et cetera, and you shouldn’t use them. So that’s why I think I would say the four things that top sales people do and make them successful.


    Jason: And I’m so glad you brought up that about competition because I’ve seen that same thing where you know from an abundance standpoint you can talk about how great you are to solve that prospect’s problem. If you truly can, like if it’s a good fit. Like you said, not everyone is a good fit for everybody, but if it is truly a good fit, there’s no reason to make your sale at the detriment of some other business, you know, and putting them down versus you just know you have superior product 100% then the last one here, and I kind of asked it and I want to go more into it real quick, is when hiring salespeople, what had tributes are you looking for? With the standard caveat that we’ve all probably learned, which is salespeople, good ones are going to be selling you on the interview. And so you can’t always trust everything they’re going to tell you depending on how good they are in sales.


    Shawn: Yeah, so here’s the four things that I look at. Some people always ask why, but these are my four that I look on the resume. And then I look in the interview one. Have they played a competitive sport before? Has he or she been involved in a sport and even just as a, you know, in high school, university, anything? Have they played a sport? Two, are they outgoing, extrovert, personality three I like to kind of like, like money hungry, like you know, sales skill, you want to make more money. So they go to themselves, they’re not that type of salesperson that, okay, I want to hit my quota, then I’ll slow down because I’ve made my number and I’m going to have secure in my job. Any sales person that’s really successful always want to make more money. And the last one is, I actually look to see if they’ve ever worked at a bank.


    Jason: Okay. Explain that one.


    Shawn: Because banks, every bank that ever hired anybody for anything, they have a very, probably the best training that you can do. So if you’re gonna work at a bank, as a teller or a teller or doing calling for a bank, they’re going to teach you how to get on the phone and call. So when you get somebody that’s worked at a bank, you already have someone that had been trained on your, on someone else’s dollar. So your training will be a lot less than with if someone that did not work with me. I find the banks train the best people and that’s why I always actually look on resumes to see if people have any experience working in a bank.


    Jason: It’s so interesting. I’ve never heard of that felt. I’ve heard of the sports one. I’ve heard of people, you know, especially someone who comes from, let’s say like a background like yours where somebody has experience in sports, they understand the team, the competition, the drive, the effort, the sweat, the blood, the tears, like the nonstop relentlessness. Like I understand that and I’ve seen that so many times before. But the bank one is fascinating and makes total sense.


    Shawn: Banks spend so much money and time on training and they give you books and books. You have three months of training before you’re doing anything and if you’re on the calls, you’re making so many cold calls and practicing so much before you actually start the call. That ideally I always say let’s, I love somebody that’s worked in the bank because now my cost for training is one third. The cost would be if I had someone that never had any training.


    Jason: I love it. Well thank you for all that info and hopefully that helps. Some people listening to this, especially either they’re trying to get a job. So if you’ve been in sales and you worked at a bank and especially if you’re in the Toronto area, reach out to Shawn for sure. And on that note, Shawn, so where would be a good place? I’ll put all these notes, all these links in the show notes, but people listening, where’s a good place for people to find you? Find your business, you know all of that where, where’s the good place?


    Shawn: So if you want to reach out to me, you can email me at this shawn@autoklose.com LinkedIn. Find me on LinkedIn, follow me on LinkedIn. I’ll put a lot of content out there. I’m always on LinkedIn and obviously if you want to learn more about our product autoklose www.autoklose.com that’s autoclose with a K and uh. That should be good enough to start to get in touch with me.


    Jason: Yeah, if that doesn’t work, they’re not trying hard enough cause you’re, you’re all over the place and I love it and the stuff on LinkedIn is great and Shawn, thank you again for being here and talking about sales and relationship and all of these things that I appreciate very much and thank you. 


    Shawn: That was a lot of fun. Jason, thanks for having me. 


    Jason: Alright, and for everyone else listening, if you want to catch the transcript for this, and also all of Shawn’s links go to cutterconsultinggroup.com you can find the podcast episode on there. 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
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
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By Jason Cutter February 17, 2025
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By Jason Cutter February 13, 2025
The Balance of Effort in Sales The blogs this week have been about the other person going most of the way. Whether it’s a prospective customer and your salesperson, where the salesperson truly can’t want the deal or make most of it happen for that customer to truly be successful. On the path for that prospect to becoming a customer, they should go at least 51/49. Whether it’s your team and their manager, the manager can’t want the team to succeed more than the team actually wants it for themselves. It’s not scalable for the coach (manager) to run on the field every play to win the game for the salespeople. What about sales ops processes and systems? What about the tools available to the sales team and the ones that are classified as sales enablement? In a reversal of philosophy, I believe the sales ops processes should go 90, the team should only have to go 10. Why Do We Need Salespeople? Let’s start where it matters – what is the point of having salespeople? I know many owners question the need and desire to have salespeople. They are hard to manage, tough to deal with, always want more money (potentially for doing less work and closing less deals), and are very resistant to change. Of course, that is a generalization. Of course, there are salespeople who don’t check those boxes. However, having worked with a lot of teams in a lot of industries, that generalization isn’t completely wrong or unfair. So if there is even a small part of that which is accurate, why would we even mess with the messiness of having salespeople? Of needing to employ and manage humans? The Human Element in Sales We need them. That’s why. Even in 2025, AI and technology has not successfully replicated the requirements of sales – which is about helping a human (prospect/customer) make the right decision and move outside of their comfort zone to buy something new. It still takes your human (salesperson) to persuade that other human. It’s why I say all the time that its not B2B, B2C, Retail, SaaS, etc. – it’s H2H. Sure, people can buy something online or even in a store without speaking to someone. But if it’s a considered purchase where there are options and decisions to be considered – it still takes a human being involved. That means ultimately your human (salesperson) has one job, and one job only – persuade the right prospective humans to buy. Minimizing Distractions for Salespeople Everything outside of that mission, task, focus is a distraction that takes away from their highest and best use. Imagine if we had a surgeon who had to prep the room, prep the patient, schedule the surgery and meetings, and do all the parts of the surgery themselves. Nope – they show up for the surgery and do what they do best. Then they take off their gown, gloves, and walk away to get cleaned up and move on to the next thing. Your goal as a sales ops leader is to support the team with systems and processes that allow them to focus on the one thing you need them for. The human part. It would be amazing if they could show up, talk to people, and make sales happen. Of course, there is more that they (and any professional) need to do before, during, and after the sales conversation. But your goal is to minimize all that. Every hour that your salespeople aren’t selling or doing sales-related activities, they aren’t moving revenue forward. The Ultimate Goal of Sales Ops What processes can you put in place that go 90 percent of the way, where the salesperson can do the last 10 percent? An example would be building an email campaign that runs automatically, and when the right people reply, the salesperson gets involved in getting that person from email to phone call. Another example would be your CRM serving up people for the salesperson to call – leads or anyone in the sales pipeline flow – with all the backstory, research, data, intel needed for them to review it then take action. What can you put into place that takes away as much distraction and effort from your sales team such that they can focus on the one thing you need to focus on – other humans?
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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