E192: Growth Through Sales with Sean Sheppard – Part 1 of 4

January 8, 2024


What are the benefits of prioritizing revenue over fundraising in the early stages of a business?


Whether you are an aspiring founder, or seasoned sales professional – success comes from growth. The best, long term sustainable growth strategy is selling more and generating income (versus raising money). 


I had a chance to speak with Sean Sheppard, a serial entrepreneur, venture capital master and founder of GrowthX. We wind a conversational path from start up founders, to selling, to mindset, to human behavior. 


In Part 1, Sean and I talk about:

  • Selling as a Start Up Founder
  • A businesses goal is to make money
  • Having a clear message across marketing and sales


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Connect with Sean on LinkedIn


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 to the sales experience podcast. My name again is Jason cutter. On today’s episode I have Sean Sheppard. He is the co-founder of growth X and the growth X Academy. He is a contributor for Huffington post and has been for a long time a leading online sales influencer and is taking all of his experiences with building and selling businesses to help others start up their businesses and an ecosystem where he’s developing the next generation of leaders for this innovative economy that we’re now in going into this new decade. Sean, welcome to the sales experience podcast. 


    Sean: Hey, thanks for having me, Jason. I’m happy to be here. 


    Jason: Yeah, I’m really excited to have you on because of one thing that you’ve listed in your LinkedIn that really got my attention. I thought this would be a fun place to start our conversation where you said that your focus with growth X is to help entrepreneurs make money and not just raise money.


    Jason: And I thought this would be fascinating because obviously the basis of that takes some sales. And with the startup economy, Silicon Valley, there’s a lot of selling that goes on to fundraise, but it’s different when you’re actually selling something to generate money. So let’s start there. Tell me kind of how you get people to shift to that or what different skill does it take? The sell actual product or service versus fundraising? 


    Sean: Yeah, look, I’ve always been an aspiring sales professional at heart from day one. Yes. I’ve been a serial entrepreneur and a founder of five companies with three exits. Uh, very expensive learning experience. Growth X should be, I hope to be my last job and the legacy that I can leave behind. And we started growth X because as a founder I was always the sales founder. I’m the non tech founder as they like to say in a very derogatory sense in Silicon Valley.


    Sean: As if it’s a second class citizen status to be a non-tech found. But what I noticed and what I always had with me, it was great product-focused founders who would be wonderful partners. For me being the market focus side and I view any business through that prism of you’ve got a product side of your business and you’ve got a market side of your business and if you’re not paying equal attention to both, it doesn’t mean you’re going to fail, but you’re certainly not de-risking the opportunity because at the end of the day when you’re taking something someplace new, you have limited time, money and resources to find the truth about where your product or service or widget or software or whatever it is fits in the market. And what I found as a serial entrepreneur turned investor, turned frustrated investor because companies were failing.


    Sean: They were failing because they couldn’t build a market. And in the Valley in particular where there’s this very technology and developed technology focus and science focus, product focus, there is not enough emphasis. It has not been enough emphasis on sales. Traditionally product focus founders have always looked at sales as a commodity. And the reality is we now live in a different era. We live in what I call this age of, what we call it, growth X, this age of applied technology where it’s never been easier or cheaper to get a product or service to market. As a result, it’s also never been more difficult or expensive to get real traction for it in the market. So I think the pendulum is swung entirely in a different direction the other direction. And yet you still see 80% of founders focused 80% of their time on product in technology and staring at their screens as opposed to identifying problems and markets that they can solve really well and focus on solving the problem than delivering a product to serve that problem.


    Sean: And hopefully with the sense of the notion that there’s a bigger market behind that one, two or three early customers that you can validate that you can solve this problem for it. So as myself and my partner started to look at it, we were all angel investors. We saw that the problem was really not in product development, but in market development as we’d like to call it. It doesn’t matter what you build, if you can’t get somebody to buy it, it’s not a thing, right? It’s not dog food until a dog food eats it as they like to say. So we built our entire fund structure and model and approach around the idea of helping our companies make money, not raise money. And the focus in the Valley, especially in the startup world, is always very much focused at the accelerator and incubator level on raising money and people “celebrate the race.”


    Sean: And then what happens is, is they have that cold splash of water, that epiphany moment where let’s say that inflection point where they realize in their own mind and heart that, Oh shoot, I just raised $1 million. Now what do I do with it? When they hadn’t had any idea. Get customers, keep customers and grow customers. And that needs to be the emphasis because nothing happens until someone sells something and no one is typically able to sell something until somebody else recognizes a need. And people can’t recognize a need until they absolutely can articulate and identify a problem and gain mutual agreement on what that looks like and then explore different ways to solve it. And so you can reverse engineer your way into product-market fit if you’re focused on finding a market where there’s a problem that’s big enough that you can solve really well on a predictable, profitable, scalable way. And so our entire emphasis and focus the last six years at growth X has been on accelerating market development for great product development teams. 


    Jason: And there’s so much in what you just covered. I think what’s interesting is that a lot of stuff is started by that product, you know, developer creator in a field of dreams kind of a way, right? So if you build it, they will come and they just assume that something is so amazing. They hope it’s amazing, they hope people will want it because they think that people will want it or they realize that they built it for themselves. They think everyone else will. And yeah, it’s interesting what you say, how noisy things have become with, you know, there’s so many people creating so many things that are out there. Then costs even more and it’s harder to get awareness because it is so noisy and people being inundated with so much different stuff.


    Jason: Can you get that founder, that product focus founder to become a salesperson or is the best strategy to bring in a salesperson to offset that product-focused founder? 


    Sean: It depends, right? If it’s a solo founder then you don’t have much of a choice other than to get that person. In my view, I think the founding team needs to sell the first deals that get you through the learning curve and they have to demonstrate to me that they can do that before they’re even an investible company. And our thesis personally as seed stage investors looking for early customers and early revenue and a clear path to product market fit with the right kinds of, milestone driven, you know, activities. So if you’re a solo founder, you want to stay a solo founder, then you’ve got to demonstrate to me that you can close the first X number of customers, give you a statistically significant cohort, right?


    Sean: That says, okay, I think I’ve got a problem. I’ve figured out a way to solve it and here’s what I’ve learned from that. And then here are the unit economics support. The idea, this is a predictable, profitable, potentially predictable, profitable, scalable approach on a team level. If you have a founding team, there should absolutely be somebody of equal weight and importance and influence that is responsible for the market side of the business to work with the product side and they have to work together in a very iterative way. And that product person or product team has to respect that market developer’s role and the influence and importance of the market at large in the process of developing their product. And if they don’t, their chances of winning are reduced. And it’s typically a miserable experience for the team. Doesn’t mean you’re not going to win anyone with a product as sold, but it’s sure isn’t fun if you’re a market developer or an early sales founder, co-founder for sales hire in a startup.


    Jason: And I think that obviously continues on even as the company develops where that communication between sales and marketing and the product development team needs to stay together and be tight at some level, right? Not necessarily at sales rep as the organization gets bigger and developer individuals, but management needs to be communicating, bringing everyone together and making sure it’s one cohesive team. Because I’ve seen that so many times. I’m sure you have as well, where there’s kind of a two teams kind of battling each other. Product development wants to create this. Sales wants to just sell this and sell this hope and dream and then you know, can it actually be delivered on? 


    Sean: So yeah, there’s often a huge disconnect there. Look one of the things that we notice, look, 70% of funded startups seed stage, never get to an 8 round or breakeven. 70% in the Valley, 7 out of 10, 8 of the top 10 reasons why that happens have to do with markets and people not with products and technology.


    Sean: Only two of them have anything to do with the product or the tech itself or supply chain or anything about delivery. It’s all about whether or not your team can find the truth about where our product fits in the market, be functional learners and determine whether or not profitability exists in a market where people actually want something that you have to offer and the behaviors of the team are critical to that. So if they’re not behaving correctly and they’re not aligned from day one, it makes that a challenge. And one of the biggest problems that I see is we hire the wrong person at this stage. And that’s what I call stage relevance because my focus has always been on being the guy that takes something someplace new. It’s a very different dynamic, when you’re a stranger taking something strange to a bunch of other strangers.


    Sean: Then when you’re working in a big company with a brand name and marketing support, resources and money and a history and a clear book of business and support and all the resources you need to go ahead and operate and optimize something that’s already been standardized. But when you’re creating, it’s very different. So one of the classic mistakes I see, we started to make over and over again. I say go try it. Say they’re, say they’re building a SAS product in financial services and they’re going to go sell the big banks. The first thing they do is they go find some senior sales guy that’s been selling financial services into big banks at some big company for a lot of years and has a book of business. It’s very impressive. They have C-suite relationships at all the major players. So what happens first? Well, that person wants a big fat salary and unlimited PTO and health care and you know all these things that startups don’t have.


    Sean: Yeah. They want support. They want marketing materials and collateral. They want a clear, crisp message on a website. They want case studies, they want all this stuff that doesn’t exist. Right. And number one, they want that. Number two, most of them don’t have experience in creating those things. Number three, the team that they’re working for just wants them to close their relationships and convert those people into customers. Exactly. Meanwhile, so 6, 8, 12, 15, 18 months go by and there haven’t been any conversions or maybe there’s been one or two, but there hasn’t been enough to sustain the business to get to the next level and that person’s eaten up a shit ton of your, of your capital resources. They’re frustrated. The product team is frustrated because they love their product. They just think this shit should fly off the shelves.


    Sean: Why? I don’t know. Probably because they made it. They have some vision in their head that everybody’s going to want what they have and they’ve never sold anything either. And they certainly haven’t done it at this stage, which is very different than selling, as I said, in a mature environment. So those two expectations collide. You get a shit show. And it usually ends up sucking up the majority of the resources and killing companies and it happens well more than 50% of the time, more like 70 to 80% of the time. I see that. So my advice to those people is immediately don’t hire those people, make them advisors, give them a half a point or a quarter-point or a point, whatever you believe is necessary of equity. Put them on a schedule with that equity of typically a one year cliff and give them an opportunity to earn that equity by making introductions into key relationships and acting as a credible objective. Third-party advisor to their book of business, their Rolodex as well as to you and see if that works.


    Sean: And if that works, and then they’re willing to take on all the things that we talked about, which is half the salary, twice the upside on the equity side, have to build their own comp plan that meets the organizational investor objectives, convert and define these proofs of concept and then build out all the things necessary to get yourself to something that would just keep you on the field long enough to learn and get to that next milestone. Then you could have that conversation, but in the meantime, what you need is somebody who’s either won or failed at taking something someplace new and they can’t help themselves. They have to do it again. They embrace ambiguity, they love to create, they communicate beautifully across teams.


    Sean: They can talk to the humans in the marketplace and the engineers on their own team 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: Alright, everybody, that’s it for part one of my conversation with Sean Sheppard. Make sure to go to cutterconsultinggroup.com so you can find the transcripts, his links, and the show notes for this. We had an amazing conversation. For the rest of this, just a spoiler alert, please make sure to subscribe everywhere you can find podcasts, iTunes, Stitcher, Spotify. It’s also on SoundCloud, Google play. It’s on the cutter consulting group website if you want to listen to it or download it from 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 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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