[E283] Leading As A CRO, with Christine Bottagaro (Part 3)

January 17, 2024


How do you ensure that your compensation plan is aligned with the goals of your organization?


You can’t just dust off an old compensation plan. To boost productivity, you have to speed up on modern trends and align your comp plan to what you want your salespeople to achieve.


Start with what you want to achieve. And make sure your comp plan recognizes that. You want to make sure that you’re rewarding the behavior that the organization wants. It can get complex if you have cross product. And that’s where you want to make sure if it’s a team effort that the team is rewarded when the team succeeds.


Be intentional and proactive. Here’s the comp plan – here’s how you will win – here’s what we want you to focus on. It’s not hand holding. But it’s partnering. It’s collaboration.


It is about putting value on their performance and concrete contribution.


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Connect with Christine on LinkedIn


Christine’s Bio

A challenge-seeker, Christine loves tech, focusing on building storylines, high-performing teams, and pipeline through Sales and Marketing functions. Happiest when collaborating, innovating, and delivering, Christine marries strategy with execution. Christine’s leadership roles at Sybase, SAP, Rally, Rogue Wave, and Kapost give her deep experience in tech go-to-markets, customer connections, and acquisitions.


Links
:

Linkedin – www.linkedin.com/in/christinebottagaro
Website 
– https://resurface.io 

  • Show Transcript

    Jason: Welcome back to the sales experience podcast. My name again is Jason Cutter. This is part three of my conversation with Christine Bottagaro. And if you didn't catch it, make sure to listen to the first two parts because it'll make a lot more sense, obviously, but we're going to keep on talking about sales reps, compensation plans.


    Just everything from that perspective of the Chief Revenue Officer role, which I think is very important for bringing everyone together and for alignment on the team, for the team, for the company, and for the customers. So here you go. Part three. Enjoy.


    Christine: All of those things. And that's why, again, it led me closer and closer to the edge of sales to say, how does this big machine work from quotas and comp through the marketing engine through to closed one and retention?


    Jason: Have you found a ideal type of compensation plan for a sales rep because you could go really complex and like telephone book manual with lots of rules or super short.


    Christine: I have to say I haven't seen that many Jason where I found the perfect one. And again, I would say you start with what you want to achieve and it can be even within a business year.


    It doesn't have to be like, this is our corporate goal for the next millennial. But For this year, what do we want to have happen if it's organic growth and you better make sure that your comp recognizes that I think where it can get complex and where I've seen businesses make bad decisions is If you have cross product and if you're trying to do something where Jason, I want you to have quota for yes, your core product, but also if you sell this other stuff and you can handle that with spiffs and some one off, but shared quotas, they can get complex.


    But where I've seen mistakes made is when people. And it could be on the CFO side, they get really parsimonious with the comp. And that's where you want to make sure, if it's a team effort, that the team is rewarded when the team succeeds. And there's this, I don't want to double comp, and that kind of mentality, I think, is fair.


    But you really have to, again, say, what do we want to have happen? If we want to cross sell into our user base, we have to make sure the mechanics support that. And if an SC is A sales engineer or somebody on the tech side is very involved. Are they being comped accordingly? Or are they going to focus on install base because that's their comp plan?


    So I think you can make it overly complex is one mistake. And the other is being a little bit short sighted in terms of paying for good thing to pay for it. And then maybe in a year after you've got that growth, then you revisit. Or you say, this quarter, we're going to double comp on X and Y. Wow, weird how it happens, right?


    And then at the end of the quarter, you revisit it. And say, you know what, that was too expensive. Our cost of acquisition was too high. Let's talk about what that looks like to dial it down. Or give all of that quota to a SDR, BVR, ISR, something else.


    Jason: No, that's a great point, Christina, and I know because I've seen so many comp plans and dealt with them, that there is that balance between complex, the complexity that's usually because you're trying to cover all the loopholes or steer the behavior in a certain way.


    And salespeople are very creative. Most humans are very creative, but salespeople are very creative. So you got to be careful where you put the money and then where you put the consequences and you got to outline all that. So you can get really deep and really in the weeds and making it also really easy for them to figure out how much did they make.


    That's one of the things that most successful teams will do. It's like I closed a deal. I just made X, right? Not I have to go into this formula and then I have to consult with this team. And then we have to run this program to tell me how much I might make.


    Christine: I learned this from one of my previous sales partners.


    And he said, there's the Denny's day that happens right after you hand out comp plans. And I never heard of this. I was like, what are you talking about? And he said, you give out your comp plans. And that's another thing is often I've seen those delayed. If you're starting the year, you better have those ready.


    It can't be three months down the road. But anyway. That's a separate topic. The reps will go to Denny's and get that big pot of coffee and sit there and figure out how they're going to make their quota with what they have. Can I make it just on renewals? Can I make it just on this? That's the Denny's exercise.


    And so I think you have to be cognizant of that. And again, go to what behavior do you want them to have? And at the end of it, maybe that Denny's exercise is exactly what you want the organization to do. Which is I need to go find new business or we need to retain customers. Great, but just make sure that those two are in line.


    Jason: And I have rolled out many a comp plan and what I have got into the habit of doing is exactly what you're saying, but facilitating it intentionally and proactively, which is here's the comp plan. Here's how I see that you can win. And here's what we want you to focus on. And this is to the whole team based on your pipeline, based on your activities, based on what you've been doing.


    If you do this, and this. You will win in this way. And this is what it will look like if you're already doing X, here's what it's going to be like in the new comp plan, focus on this, or you have options, like you said, you have renewals, you have this here's the different ways to win.


    Here's what I would do for all of these. Cause my brain goes into sales mode. My brain goes into loophole finding mode, which makes me good at building the comp plan, but then also helping them win. It's here's the rules to monopoly. And here's what I would do if I wanted to win the game.


    Christine: I love the, it's not handholding, but again, it's partnering.


    I want to make sure that my manager, that my sales team is in lockstep with what I'm thinking. So using the whiteboard behind you and just saying, how are we going to get there? And I love one on one and think about it too, Jason. I wonder if you couldn't do like team, get all your AEs together and then you get some sharing.


    And then you get maybe some good behaviors that come out that's actually, if I bring in these four and that, somebody's yeah, okay, I got four, I can target. So the power of working through that instead of here's your comp plan, go get your pot of coffee and come back with your numbers, right?


    I love that partnership, that collaboration, that's pretty powerful.


    Jason: And I also really always want my reps and teams to know that I know the loopholes. I know what they're going to try. I know what they're thinking. I know what I've already plugged. I know what we're watching in the reports now because we've built those as new metrics.


    And don't try it, right? Raising kids, don't try it. Like we'll already, we'll know. I'll know don't and not to control them, but just to help them win. It's don't try to go over here. Here's the way we want you to go. If everyone goes this direction, we're all going to win.


    Christine: I also think it will expose the motivation behind the reps.


    And as you and I were talking about, I think it was a couple of weeks back, but the people that are going to be like. If I just make my number, I'm good. Like I'm close to retirement. I don't want to pick on that group of people, but that's a personal experience. Instead of the people who are like, what is it going to take for me to hit accelerator?


    And then how do I get there? And I think through that exercise, Jason, as you outlined, you will identify the people who are going to try to hit their accelerators or the people that are like, okay, I'm good with this quota. And again, just understanding that maybe that's okay. Or maybe you want to put that person in a role that's more on the maintenance side or something like, I think you'll see the sales rep in a different way.


    They'll show up differently.


    Jason: And you put them where they want to be if you have space in your organization. If you need account management or renewals or some kind of maintenance where it's like it's not hunting, it's more farming. Then if you have the capacity, that's great. Put them there, build that team around them.


    It's valuable. It's generating revenue. Hunters, killers do a terrible job at account management because they want the next big thing and they don't want a long term relationship necessarily like some of the people I'm thinking like they want short term. Yeah. And so just build it to win.


    Christine: Yeah, exactly.


    And that's part of the DNA, right? Is that In interviews. That's one trick I think that we have is sales and marketing people interview very well, and we all have our success stories and things. And then when they show up to work, it can look differently. So how do you find a way for them to be successful?


    Finding that rep that's willing to do the cold calls, finding the rep that only wants to go out and hunt and see people face to face and putting them in a way, in a place that they can win at that,


    Jason: speaking of which, because that was, this is one area I want to talk about with salespeople in particular.


    How have you found a way to identify that through the interview process? Because good salespeople are mediocre and good salespeople are good at selling themselves in interviews if nothing else.


    Christine: Yeah, it's true. And I think I'm always one for detail. And so people will use these platitudes or these generalities around I did this and that.


    It's okay, tell me exactly how you made that happen. And then I'm pretty. Quick to figure out how involved they were, or it doesn't, that's not necessarily a good thing, or they were smart enough to say, then I knew I had to bring in my tech team. I was out of my element, but I wanted to make sure that we kept the ball rolling, blah, blah, blah.


    So can you give me the details behind what happened? Or were you a little bit on the sidelines of that? How often did you talk to this customer? What did you find was the compelling event? What did you understand about their business before that first call? So I tend to hone in when somebody says.


    Yeah, I got 38 percent growth in one quarter. I'm like, okay, walk me through that. Where did those leads come from? How did you manage that? Were you working with this team? And then through the details, you understand the level of involvement, their expertise, the value that they brought and what that customer interaction truly looks like.


    And I always have them do an exercise too. And this is true on the marketing side is whatever the role is. You're going to present or you're going to write a paper or you're going to write some code like there is an exercise that's going to be germane to the business, but will help me understand how you approach a problem or an issue or a challenge and then how you're going to work through it and that you can tell a lot from those things.


    But then at the end of the day, you hope for the best and. Sometimes you don't win. There have been some bad hires on my book. And I think one of the bigger mistakes I made Jason early on is to think that I could coach somebody through that because I'd always built high performing teams from like interns and people who are, I don't know, pharmacists, right?


    Like coming from all walks of life and I could build them up, but you spend a lot of cycles on that. And at some point you're sacrificing the business and your own credibility. And I realized I was serving myself with the storyline of being that really great coach and development person versus what I really needed to deliver to the business.


    And so finding that balance was a good learning for me.


    Jason: I can totally relate to that. And I think there's so many leaders out there that if you, because I attribute it to myself of being always optimistic, always glasses half full, always seeing the best in people, even if they can't see it in themselves.


    Which makes somebody a good coach and a good leader because you just see it and you want to encourage it. But balancing that with if they don't believe it or they're not going to put in the effort. And I'm the only one working in this relationship and seeing this possibility. That's where I've learned to draw the line and cut it off.


    Which is, I know you can do this. I'm going to give you coaching. Here's your action steps. Come back when you're ready and we'll get to the next step. Or here's a book. I recommend you read it. Let me know when you've read it. And I check in a few weeks later and they're like, no, I haven't read it yet. It's okay, that's all I need to know.


    Like my work is done here because you don't want to do the effort.


    Christine: Yeah. It's tricky.


    Jason: Are you in the fire fast or fire slow?


    Christine: I think I'm leaning towards fire fast. But to your point, I want to make sure that there's a fit. Have we put somebody in a role where they cannot be successful? Have we taken somebody who's a great sales rep and made them a manager and then expect them to be a great manager?


    Have we done the reverse and taken a manager and made them go out and hit the streets and they're not really comfortable with that. So some of it can be a bad decision on the organization's part, but I think you get signals pretty quickly. And when people are unhappy and that's the thing is it always feels like it's put upon like you can either turn somebody or not.


    But the reality is that if they're not doing a great job, they don't feel good about it. Have that conversation. That's a Jason. No, I know you'd be a stellar. You never Bob. Yeah. You never know. That's true. Hey Bob, this really feels like a struggle lately. Tell me what's going on. And because I think we have to make a change and have that real conversation and you never know, maybe there's something on the personal side.


    Like I would want to be empathetic and Hey, take some time. We'll backfill or you know what? I really love the sales ops. I want to move into that. I'm like then let's talk about that. So yeah, I think. Maybe a little faster to conversation, maybe not as fast to pull the paperwork.


    Jason: All right. That's it for part three.


    And as always, I will see you tomorrow for the final part of my conversation with Christine Baragaro. And if you haven't yet, make sure to look her up on LinkedIn, or you can go to resurface. io and I will catch you tomorrow. 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 sales people and sales leaders find the show and please subscribe to the show and share episodes you find valuable with anyone, 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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