[E273] Tales of a new CRO, with Darryl Praill (Part 3)

January 17, 2024


Should salespeople deliver more productivity to get more leads so that they can increase profit?


Your sales team represents the structure of your company. Should they deliver more productivity to get more leads so that they can increase profit? 


There needs to be structure within an organization to guide salespeople on targeting their leads. Narrowing down to target prospects creates effective results that add value to their company.


Top salespeople may show leading performance, however, that does not necessarily mean they fit the team culture. With one person not being a team player or creating negative tension, this results in affecting the performance of the rest of the team. 


Having the mentality of being all in one team and supporting one another is part of the key to success. That is where training plays an important role for salespeople who need to improve their performance and grow their knowledge of selling. This combination of behaviors and actions in a sales team indicates back to the management team.



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Connect with Darryl on LinkedIn


Darryl’s Bio:
Darryl Praill is the Chief Revenue Officer at VanillaSoft, the industry’s most established Sales Engagement Platform. As an accomplished award-winning marketer, a Sales World Top 50 Keynote speaker, a 2020 top 10 SaaS Branding Expert, a Top 19 B2B Marketer to Watch in 2019, a social media influencer, a category-leading podcaster, and a serial entrepreneur. Darryl has raised almost $100 million in venture capital, acquired, merged and taken companies public, been hired and fired, and worked for companies of all sizes



Links:


• VanillaSoft

Twitterhttps://twitter.com/vanillasoft

LinkedInhttps://www.linkedin.com/company/vanillasoft/

Instagramhttps://www.instagram.com/vanillasoft/

Facebookhttps://www.facebook.com/vanillasoft/

 

• Darryl Praill

Twitterhttps://twitter.com/ohpinion8ted

LinkedInhttps://www.linkedin.com/in/darrylpraill/

  • Show Transcript

    Jason: This is part three of my conversation with Daryl Prail from Vanilla Soft. Please make sure to listen to part one and two. You're an aspiring CRO, you're a CEO of an organization, and you're struggling with the alignment between sales and marketing. This is the series for you from a revenue operation standpoint.


    Here you go. Part three, I will see you afterwards.


    Darryl: So now we have a whole ABM model going on. Invested in. Software. So we put it, we bought Terminus and then we bought salesforce. com. So we had a single source of record truth across the whole system and all the AEs are using salesforce. com before they just use Manila.


    So lots of technology, lots of overhaul. The purpose of doing ABM was still my AEs are not now being outbound driven. Now there's. Five plus 40 accounts. You're chasing junior. That's called outbound. You're going to actually target the accounts. You're going to know your value. You're going to map them all out and away you go.


    So getting them involved in creating those lists was huge to get buy in. So Long story short, we moved from an inbound to an outbound to do that. We went ABM to make ABM happen. We put in technology. We created supporting departments. We focus on training consistently on product and on selling. I actually brought in an outside sales trainer.


    We put together a three month steroid based training on sales skills. So they're having one on ones with every rep every single week, as well as with teams. We now average a minimum of five hours a week. Just in training, which we were never doing before. And so that's where we're at. That's a long answer, Jason.


    I apologize. But as you can see, I rolled that all out on day 30. And on day 30, I literally used the exact same way how it started. I called every single rep one on one and I spent 20 to 30 minutes with them again. And I said, okay, we talked a month ago. Here, we're fast forward a month. And I told them what I just told you.


    Same thing at the same speed. Here's what I uncovered. Here's what I learned. Do you think that's right? Yes, Daryl, that's right. Great. This is what we're doing. Ding ding. And this is your new role. Several people got promoted to become AEs. A few people got reduced because of the structure and change.


    And one of the feedback I got was, I'm so excited. I'm so thrilled. Like they were just jammed. They were just so pumped. They're like, we have a plan and it makes sense. And they were shocked. They were shocked at how much I shared with them and how in depth it was. Which that part surprised me that they were shocked because how else do you do it?


    We all need to be bought in. That's my first 30 days. Now we're in the middle of actually ripping out all the cadences and the processes and the tools and cleaning all the data. to make this all work. So we're in the middle of rolling out Salesforce. We're in the middle of making Terminus hum. So it's been a process, my friend, and I don't get sleep much anymore.


    Jason: I bet you don't. And one of the things that we talked about before this, that I think is important to add to that story. is essentially the reaction of the team when it was announced when you were going to be the CRO and you were now in charge of sales and it sounds like sales was a rudderless ship or there wasn't really much leadership over on sales there was awesome Daryl CMO and then all of a sudden CRO and what were people's thoughts or reactions to your face or Not to your face as far as what's maybe their concerns with you coming into that role.


    Darryl: So that's a good question. So were they rudderless? I wouldn't say they were rudderless before, but it's a fair point. What they were was they were perhaps misguided. So as they were clearly not hitting their targets, what they were doing was they were saying, we need to do more activity and more activity.


    Darryl, give me more leads. Give me more leads. Give me more leads. And they say, at one point you go dude. Do you know how many leads? We're making 150 calls a day! If more activity isn't getting you to hit your numbers, doing more activity isn't going to get you to hit your numbers, it's a bigger problem.


    So if you have that behavior going on in your organization, guys, FYI, you're not alone. Their reaction, I was actually really keen about that myself. The CEO and I had this conversation. I was curious how they would react. I expected them to do the old, a marketing guy? A marketing guy is going to be the CRO?


    He doesn't know jack crap about sales. A marketing guy? And for those who don't know me, I have been a VP of sales multiple times before. But by admission, I hadn't done the sales gig. And over a decade because I went all in on marketing, I eventually made a decision. I like marketing. So I have some sales experience, but it's been a long time instead.


    What I heard back and I always have to qualify it because the filter people will tell you what they want you to hear, right? What I heard back over and over again was we're not surprised. We're not surprised. It's you. It makes sense. It's you. And I think that's only because I'm so active. In the sales community, by nature, marketers are active in the industries where their prospects live.


    That's how they're doing their job. And I'm active in the sales community, whether it be on LinkedIn or at shows or what have you. And much of what I talk about is about problems that sales reps have. What do you, cold calling sucks, social selling, I don't get it. How do you handle objections?


    How do you do discovery? What's a one on one call look like? I have all this conversation all the time. And so this is the interesting part. When I have these conversations and I'm speaking to crowds or pining on places like LinkedIn or Twitter, it's only because I've talked to other people like Jason and Jason has said to me Darryl, here's what you need to know when it comes to doing discovery, blah, blah, blah, blah, blah.


    And I was like, really, Jason helped me understand this and he will educate me. And then it's forward a month. And all of a sudden I'm out there opining on how to do discovery. But if you're really savvy, you go back 30 days, you go. He's just parroting what Jason told him a month ago.


    Jason: One thing I've seen is that salespeople worry about only being able to win if they use manipulation, tricks, tactics, and hard closes.


    So they end up struggling to close deals, make their quota, or earn the kind of money that they want to make. If this sounds like your current situation, or maybe you wanna make more money in sales without feeling like you're selling, than my upcoming book called, selling with Authentic Persuasion will help.


    In it, I'm going to take you on a journey to transform from order taker to quota breaker. If you're ready to become an authentic persuader, crush your goals and create success in your sales career, then go to jasoncutter. com again, that's jasoncutter. com and pre order the book today. There's no new information if it helps.


    I'm never offended by that.


    Darryl: You got it. And so I expected the reps to say, yeah, we know he's busy, but he's a marketing guy. He doesn't really know anything. Because he's just parroting Jason all the time. And that didn't happen. In fact, I had a lot of excitement. And I think the reason I got the excitement, candidly, wasn't, it wasn't necessarily, they weren't necessarily questioning my skills, because they knew, it was explained to them from the get go, as CRO, that I will eventually, in a few months, I'll have a head of sales, and I'll have a head of marketing, and I'll be the CRO, true, the true CRO.


    So they understood that my skill set probably made sense in that kind of a structure. I think where they were excited was the energy. So clearly I have a reputation, which has been years in the making. I do have a style for better or for worse. My kids would say for worse, my wife would roll her eyes. But for some reason, many people like the style, which is a little more energetic, a little more bold, a little more audacious, a little more inappropriate.


    Some might argue, but it is a style and the sales reps were keen. And what it was, what I learned, this was a really interesting point was. They have felt like the whipping boy, if you will, for a long time because they were missing their numbers. So they felt like in me, because of the notoriety and the influence I have within the industry and within the company, that I was going to be their advocate.


    Which I am! And I remember getting on one call, it was a funny, early on in that first two week process. I was listening to this VP of sales say bullshit comments about why his reps don't have time to work in software. They're too busy closing deals. I'm not making this stuff up. And I started pushing back and I just I lost my cool, but I wasn't going to yell at the guy.


    I'm like, really? Help me understand this. And I started spilling facts. Gartner says this and Topol says this and how are you doing that and blah, blah, blah, blah. It was very fact based. It was very scientific. It was very logical. It was very best practice. It was very scientific. I was able to attribute all my reference points and you can see them go.


    Oh. And finally in the end, he was like, I don't know. I hear you're saying let's talk again next week. Okay, great. Got off the call and I was actually peeled. I was peeled. I'm like that guy, but waste my time, blah, blah, usual sales response. My sales rep, my account executive calls me up and he is.


    streets and I'm always so you gave it to him. He wa you just stood up and you that was eye opening for said yeah, he was rude. Everything I was as leader, a V. P. C. Level And he didn't have the answers and he knew he didn't have the answers. He goes, yeah, but he's now hanging up going, damn, I don't have the answer.


    Darryl's the guy vanilla soft knows what they're talking about. And that was an epiphany. It was like, okay, so not only did they want an advocate, my team. But they actually wanted somebody who could lead them in the battle and show them how to do that. And so I think that's why I've been blessed to have a team who has, once the full reorg was announced and they realized they still have their jobs, they appear to have embraced me.


    Now when we have, we had our sales meeting a couple hours ago, our weekly sales meeting. And there's a lot of laughter and a lot of trash talk, a lot of fun, a lot of hard questions, but it's a very different call from what it was even a month ago. So that's a good sign.


    Jason: And I think that advocate piece is important because one of the trends I see a lot is somebody moves up and or somebody's in a manager, VP, whatever role.


    And if there's a deal on the line or somebody's questioning something. To get the sale, they may throw their own team under the bus, which is terrible for the company. Unless if the rep did something incorrect or said something incorrect, that's one thing, right? But it's another one to try to save face by dismissing the person down the chain, if you will.


    And I've seen that a lot. And, of course, the team doesn't respect that. It's different when everyone realizes, Hey, the team needs to get stronger, but I'm still going to stand up to this person and tell them the truth, right? The customer's not always right.


    Darryl: What's interesting about what you say there, I'm not going to name names.


    When I was doing my assessment of the team, I observed I had a couple of individuals who were very talented. I would suggest they might have attributes of what you're alluding to. And I knew right away That was going to impact the culture that I wanted, which now puts me in a hard spot. Do I keep them?


    Because of their performance record, or do I replace them because of the culture fit and some stayed and some left. That was a huge consideration when I was doing the evaluation. Cause I can always teach you how to be smarter about the product or be more refined on the sales skill. But if you're wired to throw your teammates under the bus or to be passive aggressive.


    Or to play both sides against each other, that ain't gonna work on my team.


    Jason: No, and people can change, right? Anything is possible. Do they want to change? Will they change at the speed it's necessary? Is it healthy for the organization? A lot of companies aren't willing to do that, especially top performers who are usually Also, potentially very toxic and they're not willing to take that step backwards because they're afraid of what it might do.


    But you gotta protect the culture, right? And the group and make everyone feel safe and supported, highly accountable, right? It's not about cuddles and entitlements enabling everybody. It's about accountability and feeling safe and supported.


    Darryl: And it's tough because some of the decisions you make in these reorgs Are not just exactly what you're saying, because that's foundation, like you don't do that, you're screwed, you're gonna fail from the get go.


    Part of it is structural, like when I talk about going to an ABM structure, teams and verticals and the ratio of SDRs to AEs and all that stuff. But part of that as well was territory alignment. So when I actually had certain industries that were booming and, the number of reps I have there right now can't support the man and I have to actually break it up into smaller territories.


    That means I'm actually taking away territory from certain existing reps to do that realignment and that has proven problematic. And we're still working through some of those hiccups and some of those reps were saying but so that's my way of saying it may sound like we've got a plan here.


    Things are going rosy. It's not been without hiccups. And it's a process and it's a tough one, right? Because you want reps to do but you want reps who are hungry and chasing deals and they want to be king of the hill. You want that. So I continue to refine. Let's go with that.


    Jason: All right. That's it for part three. Again, you can find Daryl Prail everywhere online. Google him. You'll find him. And I will see you tomorrow for the final part of this conversation. That's it for another episode of the Sales Experience Podcast. Thank you so much for listening. If you find yourself on iTunes, can you leave the show a rating and a review?


    It helps other salespeople and sales leaders find the show, and please subscribe to the show and share episodes you find valuable with anyone you know in sales. Help me on my mission of changing the way sales is done. And if you're ready to work together, go to Jason cutter. com. Again, that's Jason cutter. com to find out how I can help you or your company create scalable sales success. I will see you on the next sales experience podcast episode and 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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