[E274] Tales of a new CRO, with Darryl Praill (Part 4)

January 17, 2024



Do you hold your team accountable based on company values?


Do you hold your team accountable based on company values? The behavior of your sales team is determined by your company’s mission and values. 


Aligning with teams in different apartments creates a seamless and effective approach to your business. This is where understanding the vision and goals to improve productivity is by contributing their strengths to tie results together. 


Technology plays an important role in today’s businesses. Taking the ability to analyze and track data can direct your business to additional strategies, but also help to further your process on current and future trends on how a salesperson is performing. 


Learn about what it takes to ensure that your company has a clear set of values for your team to make the right decisions, achieve company goals, and define your brand character.


Book your free Sales Power Call with Jason

Enroll in the Persuading Like A Professional Online Mini-Course

Download The Power of Authentic Persuasion ebook

Get help with your sales team

Connect with Jason on LinkedIn

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: Welcome back to the sales experience podcast. Welcome to part four. The final part of my conversation with Daryl Prill. If you have been following along and listen to all the episodes, we are going to wrap it up here with basically his tips, his suggestion on what a CRO actually what a CEO should do in bringing in a CRO and how to set that up.


    Lots of good value. Make sure to support him, his podcast, his work that he's doing in the sales and marketing community. And of course, subscribe to this show, share this with anyone, that's in a marketing role, a sales leadership role, a CRO, as well as CEOs who want to grow this. Please share this message.


    And of course, if they need help, if there's anyone you know out there that needs help, let me know. I would love to chat with them as well. Here you go. Part 4. Enjoy.


    Darryl: You want reps to do butt, butt, butt. You want reps who are hungry and chasing deals and they want to be king of the hill. You want that.


    I continue to refine.


    Jason: And that's what I'm always telling clients and various managers and owners I deal with is that theoretically, if you have a really good salesperson on your team, as long as they're aligned with your culture and their intentions, and it's a good fit for your values and the company's values, you've got to understand and appreciate.


    When they're pushing back, when they're selling you, when they're overcoming what they think are challenges or objections coming from management, because that's what you want, right? You don't want them to be an order taker pushover on the phone with prospects. And so you also can't expect them to not.


    Bring that into meetings and conversations when they want to try to get their way. They're a salesperson, right? You nailed it.


    Darryl: That's exactly it. And I remember having this conversation with my CEO and it was a really, we had many times to your point, I would use an abbreviated version.


    I would say to David, I would say, David, I need more Oracle reps. I need my reps to be more Oracle and he's you sure you want that? They're all I make. I know exactly what you're saying because it's a cultural thing, right? Because I'm using Oracle as a cliche. Maybe Oracle is much better now.


    But the Oracle I grew up with in the last 20 years is very cutthroat, very aggressive very type A. And push, push push, push. Because they're selling enterprise software. It's six and seven figure deals and eight figure deals sometimes for ERP, etc. So they're playing hard to win.


    And they will step on you if they view you as no longer adding value to go up one. It's a mix. I want more Oracle reps, but I want integrity and character. I'm not sure that mix exists, personally, but we're working it.


    Jason: And what you want is Oracle reps, integrity, doing the right thing, empathy, but also powerful closes who also just take your orders and run with them and don't push back on you.


    Darryl: And if you just heard what Jason just said, send your resume to me right now.


    Jason: Darryl at Vanilla Soft. com. Is that what it is? I'm listening. Please reach out to him. In thinking about all this and looking at this challenge that you have and this mission and kind of the fun part. Companies out there, one of the fundamental issues I see and because this started with the presentation that you were doing.


    Two marketers about aligning and that, classic sales versus marketing battle. And so I'm hoping their sales leaders, organizations, owners listening to this and they're inspired and going, okay, what we need is that let's evolve to a CRO who can tie everything together. Or even if it's not a chief revenue officer, it's a something revenue.


    Ops head at any scale.


    Darryl: I'll go one step further, right? Cause what you're saying is a thousand percent correct, but not every company is big enough or ready for a CRO, right? Fair enough. Okay. Some of you guys aren't going to I'm about to say, Mr. Or Ms. CEO, if you are big enough for a CRO, but you need alignment between your sales teams and your marketing teams.


    It's incumbent upon you to do that. You are the CRO, even though your title says CEO. Stop abdicating. Stop letting the kids try to figure it on their own. That's my harsh medicine for the day.


    Jason: And it's so true, right? Like people always ask me, how do you fix that? I said, it always starts at the top. And I think I've never thought about it that way, but the organizations where there is sales versus marketing is because the CEO has abdicated.


    They're off playing chief executive officer. And they're allowing the chips to fall where they may. And then everyone's egos and personal stuff and just people, humans being humans, gets in there and there's no mediator and there's no umbrella kind of leadership.


    Darryl: I get it. You look at president Trump, right?


    President Trump has this public state approach that he likes conflict in his leader. So when he's got his lieutenants, he wants them in the oval office to be scrapping over stuff. Okay, he's the CEO in that picture. That's his style. We can sit back and reflect and say, does that work? Personally, I believe scrapping in private is perfectly cool and acceptable.


    But once you open that door, we're all on the same team. We've determined the play we're about to execute. Nobody deviate from the playbook, right? That's why I point, if you don't have a CRO, it's up to the CEO to play that role to make sure that everybody's aligned. Because if you rely upon the sales leader or the marketing leader to come together on their own, chances are it's not going to happen.


    One will want to, most often. The other one Won't, or they'll want to, but on their terms, which are completely self serving, they're not looking for a compromise. They're not looking for a compromise. They're looking for I win, you lose. And that doesn't work out.


    Jason: One thing I've seen is that sales people 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 want to make more money in sales without feeling like you're selling, then 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 Jason cutter. com again, that's Jason cutter. com and pre order the book today. I had a Maya Conant on the show and she's a CRO.


    And one of the things that she brought up is that what happens like when she started out is. There was history right between sales and marketing a meeting a year ago. John didn't like Kim's idea and said something negative and hurt somebody's feelings. And now that baggage is there. And even if I want to be friends with you and align us, then something happens.


    Feelings get hurt. It creates a rift. And then nobody knows why that rift is there. It's just this feeling and this vibe. And sometimes bringing in something new can help because they don't have the history. They don't care. I don't care if somebody hurt your feelings a year ago. Like we have a mission.


    Let's be successful.


    Darryl: And that's also though why I created the RevOps team. Like we already had marketing ops and sales ops. I'll put them all together. And it was specifically so that we had data. So in your example. Maybe there's bad blood between two individuals a year ago, and no one knows how we got here, but here we are.


    We can either replace them, spot on. Sometimes those people are irreplaceable because of their tribal knowledge or what have you. Okay, no problem. It's like a child. Then what I need to do is I need to change their behavior, and I need to make sure, for some, it's a timeout. For others, it's corporal punishment.


    I'm going to, whatever. For others, it might be, I'm taking away your iPad. Who knows? The data that you get from the RevOps, eliminates the he said, she said, eliminates the interpretation. I can say, no, look at here is your leads that you've given sales, Mr. Head of Marketing. And I can tell you that the lead quality sucks or blah, blah.


    I can, here's the numbers, right? So you can point at sales all you want to, but you're not free here. You got problems. And then I can turn to sales and say, they don't feel gloating at marketing person over here. You're attrition, you're ramp time, whatever it might be. Here's the data. The data doesn't lie.


    So the data becomes the arbiter. And that's why I love having data. And I'm not smart enough to pull that data together, but I'm smart enough to get the people who are smart enough to pull that data together. Even to the point that they send me wonderful charts and everything. And most people would take the charts and they themselves would open it and peruse it.


    Yeah. I'm not that guy. It's in the charts and I say, okay, let's have a meeting. Walk me through the chart because I don't want to assume I know anything. I want to hear the story behind the numbers.


    Jason: They thought worthy of my seat. And that was the thing that Maya actually pointed out too, was. The data is important.


    It eliminates all that, right? It's no longer subjective. It's very objective. It's very direct, but then also her point, which was fascinating. And it's what you're talking about, too, which is the transparency of the data and the more live the data is, the less the data can be manipulated or stories being told or spun to protect somebody's position instead of here's the numbers.


    Now, Let's have an honest conversation so that everybody can win.


    Darryl: And that's part of the reason we are, we're implementing salesforce. com because we didn't really need it. My whole sales organization lives in vanilla soft and does a bang up job, but we have a federated tech stack. So sports got Zen desk, success has got churn zero.


    Accounting's got NetSuite, marketing's got HubSpot, sales has got vanilla soft. All right. You know what? I'm just gonna put salesforce. com across the top and everybody can plug in. And now I've got one. Holistic view and at the same time I can also log in and I can see, Oh, somebody's late on their payment or somebody's had 42 support calls.


    I wonder if they're not happy. Look, success is pointed. This guy's got a net promoter score of five. We should be doing something about this, that kind of stuff. So it was again. So we had a single record of truth that everybody can see for that wonderful word that Jason used.


    Jason: Final thought, final comment.


    What is the one thing you would want? Let's say a CEO who's going to put in a CRO position, right? So they're at that part. They've evolved. They're ready to go. They want to put in a CRO. What is the one? Because I'm sure you have 94. What is the one suggestion or tip or thing that they should know? To help that CRO position be successful, not just the person, but the position.


    Darryl: So if you're going to implement a CRO that has a heavy bias towards one discipline, sales, then don't put in a CRO. Because there's, make them the VP of sales. Because they're a default to what they know. Alright, I mentioned I've been a VP of sales, hadn't carried a bag in 10 years, so that's a bit of a risk.


    I know marketing, I'm in the sales community, I talk to sales leaders, I talk to industry analysts, I talk to the reps. I have pretty good ideas. No one person will ever be perfect. Clearly, I'm better marketing than I am in sales. But I've got enough of a balance, and I understand the process, both sides, that I can be Switzerland.


    I can be neutral. I can hold each team accountable and make sure this friction is gone. The challenge is, too many CEOs think they understand the craft. They think they understand marketing. If you talk to them, in their world, marketing is just press releases and great parties and trade shows. That's it.


    Or they think they understand sales, even though they themselves have never picked up a phone in their life to make a phone call. They actually do a cold call, right? You want somebody who's got foot in both camps, who is knowledgeable enough and experienced enough, or at least educated and informed enough.


    Know them minded enough to know what they don't know and get those answers before they make a decision. If they're going to default and bias to what they know, if they only bring one skill to the table, they should not be CRO. That means you have to really interrogate them, make sure you understand, do a great background check.


    That also means you need to be honest with yourself. If you think you know marketing, you think you know sales, but you've never picked up a phone, you've never actually done anything other than have your name appear in a quote in a press release, then you need to get outside experts to supplement your knowledge to vet the CRO candidate.


    And frankly, as a CEO, that's what you should be doing. The pressure's not on you to have all the answers. The pressure's on you to resource the answers and then to lead by example. So that's my advice.


    Jason: I love it. That's perfect. That's a great place for them to start and really makes sense. Especially the biased part.


    As far as where people can find you, I know the best place historically, except recently, has always been LinkedIn. Anybody that wants to find Daryl, it's Daryl Prail, P R A I L L. Go to LinkedIn. You were super active. You've taken a CRO mental hiatus because of how busy you've been. You've disappeared from there, but there's a lot of great content, especially if people want to go historically.


    Also, people can email you. Daryl. Prayle at VanillaSoft. com. Is there anywhere else where you're active right now? Any good resources?


    Darryl: I'm active on Twitter, too. You can go to my own website, DarylPrayle. com. The simplest method? Just go to Google, type in Prayle, and you'll find every location that I've ever been at.


    You'll also find a Prayle from Alberta, Canada, who apparently killed her mother. No relationship to me, but it's a great story. So it's a win.


    Jason: There we go. Lots of good stuff. And you're in Canada as well. And so it makes sure it's the Canadian press. Something about that. I don't know. You got it. Yeah.


    Darryl, thanks for being on the show again, coming back and with some new information, new kind of experience. Super excited to see what you do, but thanks for being on the show.


    Darryl: Jason Cutter, killing it in the hallways. Thank you, sir.


    Jason: 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 jasoncutter. com. Again, that's jasoncutter. 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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