E172: Doing Sales Automation Right with Shawn Finder – Part 1 of 4

January 8, 2024


What is the right balance between automation and personal engagement?


On this next 4-part series Shawn Finder, from AutoKlose and I talk about sales automation, finding the right amount to use without going full-auto (still need humans involved!), and the processes he has used with his teams to create success. 


In Part 1, Shawn and I talk about:

  • Living in the Canadian Silicon Valley
  • Dialing in the right amount and cadence of sales automation
  • Getting your SDR team to engage with prospects strategically
  • Why do prospects always answer when a manager calls?


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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: Hey, welcome to the sales experience podcast. My name is Jason Cutter. On today’s episode I have  Shawn Finder. He is the CEO of auto klose and that’s with a K at one point he was a top rank professional tennis player, traveling the world and then went on to be entrepreneurial and sales with his kind of destination has focused his path. And today he’s all about business and working with companies to help them with their sales process, their lead generation, all of that Shawn, welcome to the sales experience podcast.

    Shawn: Jason, happy to be here and can we for our conversation today. 


    Jason: Yeah. And thank you for being my second of season two, my second Canadian guests and my second guest from Toronto. So I’m super excited to expand the reach here and uh, you know, it’s fascinating how many like sales, business development type people I’m connecting with and finding that are, are in Canada.


    Shawn: Yeah, no, it’s funny. When I was at South North last week and I couldn’t believe all the SAS companies coming into Canada. You look 10 years ago, things have definitely changed and there are a lot of great things happening here in where I’m from. 


    Jason: Is that like just completely different side note off the topic of what I wanted to start with, but is Toronto kind of becoming, is it like a Canadian Silicon Valley? Do you guys have like a term for where you guys fit into a… 


    Shawn: I believe we are. I mean you know Toronto downtown is however you know a lot of startups are kind of now in Waterloo, which is about an hour from Toronto cause a Toronto real estate market is just through the roof. So a lot of companies can’t afford the office space in downtown Toronto city. Kind of been going to Waterloo, but I would say we are trying to be the next Silicon Valley, at least that’s an investor saying nowadays.


    Jason: Well and before prices in the Bay area, San Francisco Bay area, Silicon Valley became really expensive. That’s where everyone was at. Silicon Valley is South of San Francisco because San Francisco is expensive. And then just all of it became expensive so it didn’t matter. 


    Shawn: Oh, uh, I know I, you know, even anywhere within a half an hour of Toronto now is very expensive and you need at least two incomes to be affording it. 


    Jason: There you go. So where I want to talk about and kind of start our conversation with your, your experience, your focus kind of, you know, what you’re doing out there in the world of sales is you are another podcast and those sales related podcasts and you were talking about sales automation tools, which I think are important and they help companies in valuable ways. But what I found the most fascinating and really where I wanted to start was your concept and what you talked about is that companies are trying to automate too much and it seems like companies, everybody wants to automate everything in AI and they may say they don’t want robots to take over the world, but like everyone’s pushing that and they want to rely less on people.


    Jason: And then you’re coming across saying like, companies are actually trying to automate too much in the sales process. So let’s talk about that. 


    Shawn: Yeah, so you know, I just believe that, you know, nowadays people look at, you know, you can’t rely on one channel. So a lot of people are using you know, sales engagement tools, sales automation tools and thinking, okay, I’m going to plug and play, you know, press start campaign and it’s going to follow up and automate my followup. But you know, the problem nowadays is you have to have different channels inside any automation. So even if you are doing automation, you still need to get on the phone and make some calls. And ideally, which I like to tell people is you need to go on LinkedIn


    Shawn: and do some sort of social touches. Because if you’re not, then you’re going to miss out on really building that relationship with that prospect who once you build that relationship and you send that email number two, email three, they might say, Oh, I remember Jason liked or commented on my post on LinkedIn. Let me see what he wrote in the email. So you’re going to kind of interact and engage with different platforms right now and different channels to be successful I believe.


    Jason: Is there like in your experience, you know, for anyone listening to this, is there a right ratio or a formula? Everyone seems to have a formula for everything. Is there something that works well for that balance of automation and systems and then the relationship?


    Shawn: I mean, what I like to tell people is you’re going to test internally because you know somebody that is selling apples might be a different, you know, than someone selling software. So it all depends on your industry, who you’re selling to, you know, is the person that’s buying an introvert versus extrovert, is it a VP of sales versus just an STR? So I think you have to gear your messaging and your automation towards your salary. But you know, for me internally, what I find is, you know, I like to do like almost like a 14 by 14 where you’re doing 14 different touches. You know, a handful might be emailed, two to three might be, you know, calls in between that sequence. And the other one might be something that’s not tangible, which is just, you know, liking, endorsing, sharing, commenting, posting on some prospects post on LinkedIn where you’re not actually calling them or emailing them or you are getting your name in front of them. So I would say, you know, there’s not really any number, but it all depends on who you’re selling to.


    Jason: And so when we’re looking at this and this 14 by 14 is you know, what kind of scale of operation or better yet, like scale of sales goals or demo setting. Like what, where are we talking? Because that to me sounds like a lot of involvement, especially relative to a lot of companies and people I talked to where their SDR team is just powering through and just making a hundred phone calls a day and doing lots of outreach. Like where does that fit into kind of the goals of a company?


    Shawn: Yeah, so that would be at the SDR stage, but no. So what we’ve done is like you just said, however we do the phone call, but we try and do, you know, a hundred accounts. So we’ve tried in the past where you know, here’s a list, call cold call everyone. But now what we’ve done is we’ve really targeted, so for example, you know on this sprint for this two week 14 by 14 we’re going to focus on the transportation industry. On this sprint we’re going to do in every two weeks we add more accounts to their 14 by 14 they’ll remove the ones that are not interested or let’s continue to push them, you know, in our different columns in our CRM towards closer to trying to close a demo, which then goes to, you know, our AAE or what we call like is like a closer. So I would say the 14 by 14 is obviously an SDR role, but it really helps them find out a, who they want to prospect to. But B, put those 14 through different touches and not only automation so they can really get the best results from that prospect.


    Jason: And what’s the timeline for this? 14 by 14 do you have like a certain number of days or weeks that this has done over?


    Shawn: Yes. To be honest, it’s, it’s actually 14 touches in 14 days. Yeah. I would say at least 50% of those aren’t involving an email or a call. They’re involving some sort of social, it could be just adding them as a connection on LinkedIn as a touch. So you’ve just added them on LinkedIn, but that’s all you’ve done. That would be considered like one, but there’s 14 different things you have to do that we’ve planned out within 14 days. 


    Jason: And how much of that is the phone calls? 


    Shawn: I believe it would be about three. I think it’s three calls in the 14 days. And that’s expecting that you might call them and you know they’re not going to answer or you might have to leave a message. So they’re, you know, there’s always those variables that come into play as well.


    Jason: Sure. Well, and the reason why I asked that is because what I hear a lot in the marketplace of sales teams that I encounter or work with is that nobody wants to use the phone right there. Nobody’s answering the phone when they call or they’re just assuming, especially if it’s a B2B sale, especially if it’s SAS, they’re just assuming at the other end of the line are people who aren’t going to want to answer the phone. Right. And I think that’s important. Like you’ve got to have some phone calls in there. You can’t just completely give up totally on the phone. 


    Shawn: 100% to be honest, it was something that I, you know, about a few months ago, I sat down with my team even and I was like, okay, everyone was sending emails and I can tell it was almost like some of my rep reps in general just don’t want to make that color. It’s not like they’re, I mean they’re scared, they’re nervous, but the results that you’ll get from actually making those calls, I actually, I remember saying to somebody else saying to VP, I was like, listen, he’s like, I can’t get ahold of my tribe three, four times. Get on the phone. I’ll get on the phone, I’ll dial him right now. If I got on the phone, I’ll be able to talk to you. I actually called and got him on the phone. So I think you can’t eliminate phone, you’ll never be able to eliminate phone. You just have to be strategic on, you know, if you try them in the morning, one day you’ll try them, the African the next day, if they’re a C level person, you might want to try them like between seven 30 and nine or five to 6:00 PM he goes during the day like a CTO, CIO, you know, they’re running around, you know, burning fires. We’re throwing out fires all over the organization. Right. So I think if to be strategic on when you’re making those calls as well.


    Jason: Yeah, and I’ll tell you as a funny side note is every time I’ve ever done this or I’ve seen anyone do what you’re exactly talking about, which is a rep says, I can’t get ahold of them and not answering. It’s like, let me try. There’s something I don’t know. I don’t know if it’s just coincidence or luck every single time somebody else, especially higher up a manager calls somebody prospect or lead or client. They always answer.


    Shawn: Every time, every time, every time it happens. It happened a few days ago and I was just like, and I almost feel bad doing it cause I have to go back and be like, Hey, I’ll be like, I just called them and answered, why don’t you ain’t just like, Oh Hey, you starts getting nervous. He fits. He thinks he’s in trouble. But it’s, it just, you can’t eliminate the phone. And I think, you know, one thing we did early on was kind of did an activity to get people more even used to rejection, but give them some sort of activity on the phone that isn’t even selling a product. Just to get them on the phone. Familiar with hearing people’s voices and having those conversations.


    Jason: Yeah, it’s totally funny. And that side note, for anybody out there listening to this, that you’re in sales and you have prospect that’s not answering. You really want to talk to just have your manager call or the owner of your company, have them call 100% they will answer, you will look bad because they got it done in one phone call, but at least you got it done. So, and then you know what you’re talking about with just doing those activities where you make the phone calls and get with the phone and it’s not even a generational thing. Like a lot of times, and I mentioned this a lot on this show, is you know the finger pointing. Sometimes we’ll go to the millennials or younger where they’re not on the phone, they’re not using the phone, they’d rather text. But it’s for everybody. I mean I think everybody or most everybody has shifted away from using the phone or even wanting to answer the phone because they just know it’s going to be crap.


    Jason: And so everyone kind of projects that everywhere. But I remember one point early on for myself in my career, I had a telemarketing manager and what he used to do was to show everyone how it worked as telemarketing cold call, like business to consumer is he would literally just make a cold call and then even without the intention of getting that person transferred to the sales team, he would just have a conversation for as long as possible with this random person out of the blue to show everyone that you could just talk and he would sometimes talk to somebody cold for 2025 minutes about weather, about recipes, here’s just show the team. It’s like just, it’s just a person.


    Shawn: It’s, it’s funny you say that. So you know, one of the activities that we had, and I come up with different activities, but when we were, you know, when they were starting out, they weren’t, they’ve never been on the phone before. I actually had them call different companies and pretend that they were a restaurant and they wanted to send them corporate lunches and I wanted them to stay on the phone as long as you can to find out, Oh, who are you using for your corporate lunches when you bring stuff? Oh do you not have it? And they actually, so what we did was we actually kept track of how long their calls were, listened to the recordings after he gave them tips. But we’ll also do just random, we’ll just come up with a random thing once a week for three weeks and every week you’d have to do it. And it was like just a random activity we’d come up with, has nothing to do with our product or service, but just to get them used to a getting rejected on the phone cause we want them to get rejected enough. They realize not everyone you’re going to cause me to say yes, I want to buy your product or service. Yeah.


    Jason: Alright. That’s it for part one of my conversation with Shawn Finder. Make sure to go to cutterconsultinggroup.com/podcast or click on the podcast link on the front page and find this episode. You can find the transcript. You can also find Shaun’s links for him on LinkedIn as well as his website. And as always, remember 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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