E199: Technical Sales Mastery with Ian Peterman – Part 4 of 4

January 8, 2024


What characteristics or qualities define an ideal sales experience within your organization?


Are you selling a technical product or service? 


Do you struggle with being in the middle between your customer, engineer/product development, and marketing?


On this 4-part series, Ian Peterman joins me to talk about his experiences starting out as an engineer and moving into a consulting role. We talk about the challenges of technical-based sales and ensuring the best structure for success in moving prospects to customers. 


In Part 1, Ian and I talk about:

  • Engineers and Salespeople – can’t we all just get along?
  • Don’t Field of Dreams your product
  • Making sure the sales team is providing valuable feedback and suggestions
  • Sales – being the bridge between customers and engineers/designers


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Connect with Jason on LinkedIn

Connect with Ian on LinkedIn


Ian’s Bio:

Ian is an amazing entrepreneur, business owner, and an amazing individual. Ian grew up surrounded by design, engineering, accounting, and entrepreneurial people. Ian always had the desire to work for himself. After working as an engineer and designer for over a decade within startups and companies like HP, Adidas, Robot, and Nike, Ian founded the Peterman Design Firm. The firm has been named one of the top design and branding firms of 2019 by DesignRush, Clutch, The Manifest and Visual Objects.


Ian has been in the branding world for 7 years now running two different design firms. Social media isn’t a have to, it’s a get to and it’s a huge opportunity for brands to engage with people at all stages of their relationship to offer education, build trust, and share value. When done right, it’s an avenue for being seen, well understood, and garnering powerful loyalty with your ideal clients and customers.


Ian’s Links:

Website: http://www.petermanfirm.com

Facebook: https://www.facebook.com/PetermanFirm/

LinkedIn: https://www.linkedin.com/company/petermanfirm

Instagram: https://www.instagram.com/petermanfirm/

Twitter: https://twitter.com/PetermanFirm
Linked
In: https://www.linkedin.com/in/ianpeterman/

  • Show Transcript

    Jason: Welcome back to another episode of the sales experience podcast. Welcome to part four of Ian Peterman and I’s conversation about sales engineering, branding mostly about sales and engineering. We talk about niching, what you do and the sales experience, title, wide range of things, whether you’re a sales rep, a manager, owner, super interesting conversation. When you step back and look at it from any position, if you have experience in the realm of sales, especially with anything technical, sales and engineering, even sales and marketing where there are different stakeholders involved with a sale, then this is an important conversation. So if you haven’t checked it out, make sure you listen to parts one, two and three. Subscribe to the episodes and here you go. Here’s part four enjoy. 


    Ian: And I can knock to owners and the managers in the company that are wanting the project completed. And so my is kind of uh, odd turn because I got too broad and then narrowed it by just by changing the position of what I did. So I had technically still, you know, through my company, I offer product design, branding, marketing, all of these components. But they aren’t my personal specialty, my specialty is bringing them together. So it’s a journey. It’s always a journey getting there.


    Jason: Well, and I think that’s fascinating because I can totally visualize that and obviously it might be some salespeople listening to this and they’re like, what does this have to do with me? I mean you never know where your life is going to go and what you’re going to do and you know kind of what your focus is in your niches. But to hear your kind of journey, it’s very similar to mine and I can just imagine how you were doing everything and then narrowed it down, narrowed it down again and then, you know, cause I’ve done the same thing, which then broadens it because you realize you can do a lot of things and then bringing it back down together. But more from a higher level. And you know, for any owners out there listening to this and you’re thinking about what do you do with your sales team, what do you do with your product or service?


    Jason: You know, really focus on what that niche is and the niche within that niche, you know, and how many customers do you really need? What does that number look like? What does that universe, as they say from a marketing perspective, how many people out there would be your total addressable market? And then, you know, how do you serve them within that niche? So let me ask you this question. Now that you know what you know and you’re doing what you’re doing, you’re bringing all these people together, talking about the sales side, what does the ideal sales experience look like within an organization? You know, as a salesperson, but then also, you know, for the customer who’s looking at buying, like what have you seen? What is in your mind, what is the ideal sales experience look like?


    Ian: So in my mind, from the customer’s standpoint, the sales experience should be a very seamless and smooth process starting with, you know, the first time that they buy as a customer. You can hear about the company, you know, it’s making as a customer, I would want to see the same branding, the same messaging. You know, having a consistent feel through whatever the initial advertising, however you get me as a lead, right? Transitioning smoothly into actually talking to a rep, you know, talking to somebody in sales and then purchasing in continuing that journey down the road of actually using the product and things like that. Those when it’s not, when it’s disjointed and I’ll use you experienced, I just, Starbucks has a very, very good customer experience when you’re in their stores, right? It’s the exact same coffee. Every user experiences is great until you get to use their tech support for their app and as not as great.


    Ian: And so when you have those disjointing, you know, and especially in the sales process and you’re about to go spend money, especially if we’re talking about larger enterprise purchases, you know, we’re talking about tens hundred thousands of dollars being spent. You know, when you go through a process and you hit a disjointed piece where it jolts you and you get sent over to somebody else that doesn’t know you, doesn’t actually look at your information and starts talking to you, you know, things like that. That is the opposite of what you wine was smooth. You know, like you talked about the, when you had two people on your Skype call, all of a sudden it was very smooth and transition, you know, tech information and that tech support seamlessly joins in. From a salesperson point of view, it’s, to me it’s having the technical backup to make sure that I can actually talk to the customer, answer the customer’s questions, you know, have them on a Skype call with me, have an engineer sitting next to me so that I don’t look like an idiot.


    Ian: I can just say, Hey, this is, here’s a question and let them answer the technical side. It’s having them, whoever does the marketing and advertising and making sure that their sales copy is directing the correct people and giving them the right initial information. I’ve done a lot of work with companies that there, there’s a huge disjoint because marketing is off doing their own thing and they do. They run these lovely ads and they get leads and then they go to the sales team. The sales team started talking to them and they go, Oh, well this ad says this and we’re looking for this, and there’s some level, you know, it’s not a full like, Oh we don’t even sell that product. But there’s some level of disconnect between that initial contact that was through an ad or something like that. And then when sales takes over, they have a hurdle basically that they’re given to jump over before you can even actually have a sales conversation is you’re correcting misinformation that another department but out there, so it’s making sure that that whole process is smooth and you’re able to answer the questions, have the right information with you and actually close the sales smoothly.


    Jason: Yeah, I think that one is huge with what marketing is saying. That conversation then should be the same as what sales is saying engineering development. And then once somebody becomes a customer, account management, customer success, you know, customer service, tech support, all of that. Let’s, that’s why I’m a huge proponent of the sales experience being more than just sales. Right. And they, you know, big term is customer experience, but thinking about it even well before that person is a customer and looking at that whole journey of somebody going all the way through and how smooth is, cause you’re right that my example of the call with the two people on it literally just felt like one person, one organization, you know, the email afterwards, just a continuation of that. It didn’t, you know, there was one message that everyone was a part of, you know, from their website forward. And so I think that’s great advice.


    Ian: Yeah, it’s, so I was talking to somebody else about this and the way I consider a customer experience and journey, it starts from the second they first learn about your company till the second they are no longer your customer and that, you know, that whole process from entrance to exit, that’s their experience of your company. And that, you know, there’s on the backend, there’s some companies I’ve worked with that, that uh, the backend experience was bad enough so they could never recapture those customers. And so you know, not that sales is necessarily part of that, but account management, if your sales and account management, that’s definitely part of your job.


    Jason: Well and but a lot of it comes from like what you’re saying is the marketing’s got to have the same message as sales and they all have to set the right expectation for what the product or service does. If you’re a salesperson listening to this, keep in mind that your goal is to set the right expectation for the customer to be successful with your product or service longterm. Not just say whatever it takes to get the deal, but set the right expectation. If it’s a good fit, it will be a good fit. And here’s what I’ll tell you because I know this to be true for every product or service out there is not perfect. There is no perfect product or service in the world. There’s always some downside or some trade off, right? It’s never perfect. Like this might be the perfect solution except it’s going to be really expensive.


    Jason: So there’s going to be a trade off, right? It’s just not possible. You know, there’s always a, or a trade off or what somebody is going to see as kind of uh, negative, you know, it’s not always terrible. It could be minor salespeople like to gloss over those. They don’t want to mention those. And in fact, I think when it’s done right by a sales professional, they’re actually going to bring those things up relative to, you know, with the good and the bad relative to somebody’s situation. That’s going to be a customer pointing it out and setting the right expectation, right? Here’s what we do. But by the way, our program does it do this. So you’re going to want to make sure you keep this in mind when you’re using our software, right? For example, I’ve had many times where somebody has sold me some software saying it will do everything. I get into it and it doesn’t. And then it’s just terrible because the expectation was set for how amazingly perfect it was. But when in fact, you know nothing. Now everything’s got some kind of downside or other side to it.


    Ian: Well, and I think that instead of looking at as a downside, that could be this crippling thing to make you not make the sale. It’s, it really is an opportunity to educate and help your customer. You know, if you’re, if you’re the person that’s selling the product says, Hey, ours doesn’t do these three things, but you know, using a software integrates with these three programs over here that we’ll as together be able to take care of those needs that you might in eating those features. We can’t do that part, but we are a software connects to this other thing over here and you’ll get the whole package. You just be upfront with that. Then you’re not just selling people, you’re teaching them, you’re informing them and you’re consulting them a little bit on, you know, this is how we would recommend setting up your thing with using our product and then they’re going to buy from you because you’re helping them. You’re providing a product that does exactly what you say it does. Nothing more, nothing less, and you’ve given them a way to use their product. Even if they wanted a feature that you don’t have, if you give them another way to augment your product, basically it means engineering doesn’t have to come up with a new product and you can still make the sale.


    Jason: Right. Exactly. Well, and that’s 100% true because here’s what I know to be so true, which is every customer, every prospect out there who’s looking at buying something or is interacting with a salesperson is just waiting for the catch or waiting to uncover the, I always call it the gotcha, right? Like here’s all these good things, here’s this downside, right? So they’re always waiting or trying to figure that out. And the more transparent you can be as a salesperson to actually bring that out, when you’re in your sales process, you’ve talked about what it’s going to do for them, talk about what it’s not going to do. And then like you’re saying, provide a solution. Be a sales consultant, even in your role, no matter what your title is, and then help them understand, Hey, here’s what it won’t do and here’s my suggestion and here’s what we found customers are successful with, you know, integrating this with that or are using our tool or our physical product and here’s the ways to use it in these other aspects.


    Jason: When you do that and when you’re transparent, customers will actually appreciate it cause I go, okay, I knew there was going to be something, now we know what it is, now we’ve talked about it, I’m okay with that now I want to be a customer anyway instead of that being a surprise, right. Instead of that being an account management onboarding surprise that they find out and now they’re pissed and now they want to cancel or they’re not going to send you referrals. Right. Like I think that transparency is so huge and that’s where a lot of sales reps fail because they’re so afraid of losing the deal. That shouldn’t be a deal anyway. If that’s really like a stopping point.


    Ian: Right. Wellness, especially you say if you’re just pass, if you’re passing the pain to the next person in line, it’s still a pain.


    Jason: Yeah, and it’s just going to get worse, right? At some point it’s going to be so terrible, it’s just going to explode instead of managing it. It’s like the example, right? Like if your check engine light is on your car, if you can go deal with it right away, it’s okay. And then if it starts making noise because you’re procrastinating and then the noise gets worse and then now there’s like smoke or fumes come in. Like at some point it’s going to be so terrible. Like the problem is giant. If you solve it early, you can like, you know, get way ahead of it. Same thing in sales. You can get way ahead of something that might be negative to your prospect and set it up in the right way and set the right expectation. It won’t ever be a problem.


    Ian: Setting those expectations and you’re getting ahead of the Nos too because if you tell them all the reasons could say no to your product anyway, right up front, you just skipped the entire conversation of the masking you a whole bunch of questions to see if it’s a no. You’d say, well it’s going to be a no. If these, if you would need these things, we can’t help you. 


    Jason: Right. And usually that kind of conversation about the nos or the negatives are kind of a takeaway conversation we’ll usually get most people to then want to buy because they appreciate the honesty and it will also make them want it for the right reasons, especially if you’re telling them why they probably shouldn’t use it or you know the takeaway and not in a manipulative way. Just say, Hey, this might not be good for you and post you were like, wait, no, I want it. Let’s do it. You know, cause that’s opposite of what salespeople, there’s a lot of salespeople are just monologues pushing, coming up with these slick lines and closing people and trying to like force a man and Hey, if I can get you this, will you sign the contract today? Type of like high pressure stuff instead of just, you know, being a person, having a conversation, solving problems and moving people forward.


    Ian: Which is relationship. So yeah, that’s the reality is know like, and trust. It’s a thing. Yeah. And I think a lot of us forget those, Oh no, I can sell anybody anything. It’s fine. And we forget that. They don’t know us. They’re not going to buy right now. So it’s, yeah. 


    Jason: Well I think that’s a great place to stop, especially on the relationship side because where we started this conversation was about relationships between sales, engineering, marketing, bringing everyone together, kind of come full circle with the relationship being about all those parties and the customer, you know, the prospect turning into a customer for life, raving fan. You know, somebody who’s sending referrals.


    Jason: So that’s a great place to stop. Ian, what’s a, you know, where should people go online to find you? How do they get in touch with you? Like where’s a good place to, cause they want your help with like branding, engineering, sales or anything else you’re working on. Where should they go? 


    Ian: The best would be the main website, which is petermanfirm.com P E T E R M A N F I R M or you can always find me on LinkedIn and Twitter occasionally. Those are the best places to get me. 


    Jason: Perfect. And I will have all of that in the show notes for the episodes. Ian, thank you for being on the sales experience podcast and I appreciate you doing what you can for sales and engineering firms and bringing everyone together out there because I know what that feels like from both sides of the equation. And I appreciate anybody who’s trying to make that better for everybody. 


    Ian: Yeah, you as well. It’s good to meet other people trying to make that process better for everyone. That’s, you know, that’s my hope. 


    Jason: That’s my mission. You know, bring everybody we can. And it kind of shift the way sales is done and the way customers view sales. So yes, thank you. And for everyone listening, make sure to go to cutterconsultinggroup.com go to the website there. I’ll have the transcript from Ian and I’s conversation, all of Ian’s links as well. 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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