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Published on:

31st Jan 2025

7 Ways to Master Sales as a Founder-CEO

As the former Managing Director of the US Chamber of Commerce and a CEO for investor groups, I've helped numerous IT companies scale their sales, and I’ve been through this journey myself. I’ve learned these 7 keys through hard-fought experience, so watch and take control now!

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Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green.

About Ray:

→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.

→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.

→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com

→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.

→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com

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Follow Ray on:

YouTube | LinkedIn | Facebook | Twitter | Instagram

Transcript
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Speaker 1

Being the CEO in your business, and the chief rainmaker like the main salesperson is really hard. I've done it myself. You're spinning all the plates. You know the strategy you've got managing the team. Everything falls to you, and you're responsible for generating all the cash that's necessary to pay for all the other stuff that you're managing. Believe me, I've done it, and I know how hard it is.

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Speaker 1

But if you don't prioritize the actual process that you're going through and generating cash, frankly, like your business is going to plateau. But worse, it's also really easy to end up in founder led sales hell, which is that dreaded place like right between. I've got enough activity. I got enough sales stuff to do every single day that I'm overwhelmed.

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Speaker 1

Right? I feel spread too thin. There's shit still slipping through the cracks. I know that I'm not doing it incredibly well, but I'm not generating enough in terms of results that I feel comfortable going in hiring somebody else full time to do this for me. And so you end up in this valley where you're doing everything, and you don't even see a path to being able to hand this off to somebody else.

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Speaker 1

But there is really good news done right. Founder led sales is the best way to build a systematized and scalable sales system. So what I'm gonna do in this video is just breakdown. Real briefly. Why it's important for you as a founder to run this process from the get go, and then how to do this to make it a lot easier on yourself, and how to set yourself up to be replaced when you get this flywheel turning.

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Speaker 1

Let's dive in. Hey. What's up? I'm Ray green, former managing director of the US Chamber of Commerce and CEO for investor Groups Leading Turnarounds. Now the founder of MSB Sales Partners, where we help companies scale sales. And I have not just worked with a bunch of companies that are a bunch of founders who have gone through this process of leading sales at the get go until you get into, you know, seven mid seven figures and need to start building out that sales team and that revenue engine.

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Speaker 1

But I've also done it myself in multiple companies where I've started the company. I've gone through the initial process of, you know, figuring out the prospecting piece and the lead gen piece and the sales piece and the closing piece, and eventually hiring a salesperson or in some cases, breaking that process down. And hiring a different SDR on the front end and then later a closer.

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Speaker 1

So I've gone through it, and I legitimately know how tough it can be, because there's virtually no more important function in your business than sales. Right? Like cash is oxygen to your company. And if you don't have cash coming in the door, you're going to die. So it's a it's a pretty critical function, but it's also got a lot of functions associated with it that don't always feel important in the moment.

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Speaker 1

You know, like a hospital's administrative. This feels like follow up. Or is that person really going to buy anything? So we let things slip through the cracks, particularly when you have all these other issues. Right. Like maybe have some client emergencies, maybe you have, you know, some operations issues, maybe you have some internal team issues. And so those things are like on fire and you're like, okay, this can get tabled, this can get tabled.

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Speaker 1

And what happens is sales eventually becomes like kind of relegated to I'll do that when I have time, which is the death knell to to growth or at least aggressive growth in a, in a company, which is what you want. The thing about founder led sales is, yeah, it keeps cash coming in the door. That much is obvious, but it actually serves three really important functions.

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Speaker 1

And this is why it's important to do this process from the get go. The first is sales calls are the best research and development that you are going to get in your business. When you sit down and you talk to prospects and you see the body language that they have, you hear how they respond to the things that you're saying.

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Speaker 1

You hear the questions that they ask, you hear the objections that they have and how they respond to certain rebuttals and what they're thinking and how they describe their problems, and how to describe their pains and how they describe themselves and where they're at in the situation. There's no better tool for you to understand your customer than sitting down and selling them yourself.

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Speaker 1

So sales is a research and development tool. Protip turn on the record button of every damn sales call that you run, because those transcripts are going to be a goldmine later in in marketing strategy and messaging and positioning. But we're not going to do that now too. Is that by running these sales calls, you're actually establishing the the systems that that you're going to eventually hand off to somebody.

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Speaker 1

Right? Because you've got to get really efficient with this. And we're going to talk about how to do that. But you've got to get really efficient with how you do your prospecting and how you do your sales calls and how you do your sales follow up because you don't have ten hours a day to focus just on sales activity.

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Speaker 1

So you're going to get fairly systematized. That's a good thing because those checklists that you create, those tools that you create, those processes that you create, that automation, that you create all the things that you're creating for yourself to be really efficient is what you're going to hand off to somebody when you actually hire them. So you want to run this at the beginning so that you can build those systems and be able to hand them off and ensure that the person that you're going to bring on board at some point is actually set up for success.

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Speaker 1

The third reason you want to run sales initially is because you've got to learn the fundamentals, like whether you like it or not, like a lot, if you're a technical founder, you're running an IT company and you're like, listen, I you know what DNS and tufa and VPN mean? Well, I know what SQL and MQ are like. We speak different languages.

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Speaker 1

I completely get it. If you eventually want to replace yourself, you're not going to be able to go to market and say, I just need a salesperson and then cross your fingers and hope that the person that you hire is the right person. Do you need a full cycle sales? Well, somebody that does prospecting in sales, do you need an SDR?

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Speaker 1

Do you need a closer and an 80? What what do they need? Like what are their responsibilities? How are you going to train them? Who are you looking for? What do they need to be good at? Those are the things that you've got to understand and listen. You don't have to become Jordan Belfort and The Wolf of Wall Street in order for this to be successful, but you've got to understand the fundamentals of the role if you're going to find the right person and if you're going to know that they're doing a good job.

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Speaker 1

I recently talked to an 18 business that's had somebody on staff for two years and they haven't closed, but just a few deals and they're going, yeah, but I'm not really sure I don't I mean yeah, there's no sales but isn't you know, the list isn't good is it. The process is a good is it the, the plans and the pricing.

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Speaker 1

Is it all these other things. Well, you would know that if you had gone through this process yourself. But it is easy to get really overwhelmed and it's easy to get trapped in what I like. What I was talking about, like founder led sales. Hell, right. Like that value where you're like, damn, I'm doing this all. But it's not enough to get me to the other side.

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Speaker 1

So how do you do founder led sales efficiently so that you do drive the sales. You do build the systems, and you do get to a point where you can bring somebody else on to replace you. There's seven things that I've found that have really helped me manage the business and manage revenue generation in being a rainmaker. So I'm going to break this down for you real quick so that they can help you do the same thing.

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Speaker 1

First thing is, you've got to prioritize the the high impact sales activities. All sales activity is not created equal. There are different parts in the process that are more important than others. And that part actually changes as you go on. So for example, really early on, you know, there's there's probably some lead generation, there's, there's some prospecting, there's some outreach, there's some, you know, maybe you're, you're sending out the emails, maybe you're knocking on doors, maybe you're making phone calls, whatever it is that you're doing to generate leads on the front end when you don't have any leads, that's going to be the most important thing that you can do.

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Speaker 1

So you're going to prioritize the front end of the sales pipeline and all the activity that happens there. So you can actually get some deals in the door as those deals start to come in, the door, the priorities will start to shift. Why? Because, well, if I got ten leads and I ran five sales calls, three of them are in follow up right now.

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Speaker 1

Well, those three are actually closer to the buying pocket and closer to the money. Then started getting a new late. So that would be more important to me than trying to go get a new league, because what's the point of getting new leads if you're now not moving them through the system and following up with them effectively? So you're going to start to look at what's closest to the money and where's the highest ROI on my time.

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Speaker 1

Look at the activities are going to have the highest likelihood of producing a result for you. I'm going to talk to one leads. Before I talk to cold leads. I'm going to talk to people already in the pipeline before I try to get more people in the pipeline. And the goal really is move your focus and move your allocation of time, which is the most precious asset that you have to the area that's going to have the highest leverage and the highest likelihood of producing cash for you.

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Speaker 1

Number two, time block your sales activity. Even if you can only dedicate 45 minutes a day when you're running a business. I know this first hand you. If you have a block of time that frees up. It's amazing at how quickly that shit fills up, right? Like it's almost like you don't want to tell someone like, hey, I've got like a couple hours here.

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Speaker 1

And the soon as you say it out loud, it's like, oh, shit. Like, here it goes. All the fire start popping up, right? So you've got to get stuff on your calendar, because that's what's going to create the space for you to actually run the activities that you need to run, whatever that is. It does that in two ways.

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Speaker 1

One, it being on the calendar is a reminder for you. You're gonna look at your calendar. You're going to see it every single day. All right. I've got to run this activity. It's on my calendar, go to is and blocks out the other space because it keeps somebody else or something else from booking that time. So when I say time block, I mean put it on the calendar, turn that appointment to busy.

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Speaker 1

Don't keep it available. Like don't keep don't don't do one of these. Well it's on the calendar but it's available so the automated calendars can still like actually overwrite it because I know how that works. And it just gets punted and punted and punted and punted because the number of things that you need to do as a business owner, as a CEO, is always going to exceed the amount of time that you have in a day.

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Speaker 1

Just the way it is. Your to do list is never done. As a CEO, there's always going to be more activity that's in there. So you've got to look at it and say, how am I going to prioritize what the most important activities are for me? Well, sales equals cash. Cash equals oxygen. That seems pretty important. That should go on your calendar.

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Speaker 1

If you want to know how the business is going to look six months from now, 12 months from now, you only need to look at two things where you're spending your money and where you're spending your time, right? The third thing is simplify your lead generation, like simplify the activities and the processes that are actually creating the new leads, the new opportunities that you have coming into your system.

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Speaker 1

And what I mean by that is if you're doing, for example, like LinkedIn is a is a play for you that you're using as a, as a client acquisition platform. You know, when you're sending 30 connection requests a week or whatever that number as well. You can do that manually, right? Or you can set up some automation on the back end that sends those invites out.

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Speaker 1

It doesn't have to do your conversations. It doesn't have to pretend to to be. You don't have to write out a 14 message sequence, but you can fairly easily automate at least the connection request, right? Like so. You can get that piece going and then you take over for the people that actually accept the connection request, which is going to be half the number of people.

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Speaker 1

So now you've cut out a step that you have to do entirely, and you've cut the amount of people that you're talking to down and have the same outcome, same output is actually going to be occurring. So just look at your process and the different steps that you're taking. If you need to do a time audit like actually audit what you're doing and take a look at it after a couple of weeks and go, you know, there's some pretty simple ways to automate that email sequence or that workflow.

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Speaker 1

One thing that I found that actually helps me a lot is I just create a checklist, right? Like every I get a checklist shows up every single day and it says these are the activities now, the checklist changes now based on one where we're at in the process. And then two, maybe I find, okay, this activity is not working as well as this activity.

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Speaker 1

So I'm gonna go ahead and take this one off. The checklist shows up every single day. You know, it's a task or an activity that I need to do every single day. And it's going to pop up in a recurring basis. I'm going to go through and knock those things out. I actually have it prioritized by the highest impact things at the top, down to the lowest impact things to the bottom.

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Speaker 1

How those low impact things should still be, things that are still valuable, like if there are no impact, things are really low impact things. They shouldn't be there, but they're lower than the top priority. Meaning, if I went and hired somebody who had ten hours a day to do this, other doing those activities that I'm seeing right now are low activities, but a lot of it is based on the prioritization process that we're looking at now.

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Speaker 1

Those are the types of things that you're actually going to create. You're gonna hand to somebody else, right? You're gonna look at them and say, hey, we've we've been running this checklist here you go. Like, here's the checklist to start with. And of course, their list should be longer because they have more capacity and more available time.

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Speaker 1

So you're going to add to that list. But they have some basic systems and processes to help you get more out of them. Right. Like more output out of the person that you're eventually going to have to do this. So simplify the process to maximize your output today and the ROI down on your time, but also to create maximum leverage for the person that comes in and starts running those activities for you.

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Speaker 1

The goal here is balancing efficiency with effectiveness, right? Like the only the only caveat to all of this is you don't want to get so efficient on the front end that it's no longer effective. You don't want to start automating stuff before you know what actually works, or you don't want to start automating things like messaging or responses or, you know, any of that kind of stuff before you're like, hey, does does that messaging even work where you can get the efficiency and lose as little of the effectiveness in that process or in that step as possible?

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Speaker 1

Right. The fourth thing is leverage asynchronous selling. And what I mean by that is when we think of selling, a lot of times we think of, hey, I've got you know, actually, you know, get on a sales call and I'm going to talk to somebody. And, you know, depending on what you're selling and where you're selling and how you're selling and all that.

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Speaker 1

So some of that may be may be the case, but there's always an opportunity to create some asynchronous selling or pre-selling in your process. So think about reusable assets. Right. Like what are the things that as I'm going through this process, I can create those and say, hey, you know, I've I've reply to this email roughly the same way about four times.

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Speaker 1

Let me just go in and create a template, save it here. Or, you know, maybe you run a webinar and then you use that webinar over and over and over and over again in other parts of your sales process. Maybe you think about there's some some ways to add resources or add content or add steps to your booking funnel that allow you to get more efficient and effective in your in your sales process that that maybe that's, you know, questions in, you know, the form that they're filling out.

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Speaker 1

Maybe that's after they fill that out, they get some an email sequence or they get some content that you've strategically picked to handle some of the most common objections. There's all kinds of ways that you can evaluate your process and say, what are some strategic ways that we can insert some asynchronous tools that mean I have to do less?

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Speaker 1

I mean, that may mean, you know, using loom and or Vanguard or whatever it is that you want to use, like a video tool to do personalized messages that don't require getting on a call. Right. The fifth thing that you can do to make your life a hell of a lot easier, and founder led sales is just streamline your sales process.

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Speaker 1

And what I mean by that is take a minute to define, generally speaking, what are the stages that people go through when they're buying stuff from you? I'm not trying to give you an assignment or task here. That's like, all right, I'm going to sit here for days and weeks and, you know, try to iron out like this process and put it into a, you know, big, pretty board and then not do anything with it.

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Speaker 1

I don't know, like this is about understanding the basic steps or the phases or the journey that people go through when they're buying your stuff. That is important for a couple of reasons. First is that'll allow you to actually prioritize who's most important. So say, say you've got your CRM and you choose to say we're going to label people for lead in.

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Speaker 1

Like that's anybody that comes in the door, right? Like from marketing, any opt ins, anyone from content, whatever. Like this, like this. Just lead. And then there's an interest category. Like they've done something to indicate some degree of interest. So you've got lead in, which is, you know, basically anybody that comes in the door okay. Like get all everything that marketing produces gets pulled into this list.

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Speaker 1

They start it at lead and then there's interest. All right. Like what's interest you had you know, a constructive positive conversation with them on on sell by chat or they expressed some degree or took some, you know, even small action to indicate that they had some intent to move forward with your company and potentially buying something at some point.

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Speaker 1

So there's a little bit of interest. All right. Cool. Then there's, you know, qualified. All right. Are they okay. So I'll just get your intro. Doesn't mean we actually sell to you. So are they in the vertical that you sell to. Are they in the geography or the demographic or whoever it is that you break down your target market?

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Speaker 1

Do they fit that market? Okay. Well then that's great. Like a little bit of interest and they're qualified. Now let's say sales qualified and sales qualified is hey there's a buying opportunity right. Like they've not just like taken a step in terms of getting a lead magnet. Like they've actually in some way, shape or form raise their hand.

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Speaker 1

They've they've booked a call. They've told the salesperson, yes, I want to I want to hop in that call. Yes, I want to do an assessment. Yes, I want to like something. So there's some sales, qualified opportunities. Then there's the actual process okay. Now they're in discovery. Now they're at the assessment phase. Now they're at the proposal phase.

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Speaker 1

So those are your stages. Why do I care about that. Well because when somebody is over here and they're at the proposal stage, I'm going to prioritize my time because they are closest to the money. They are the closest thing to if I move this forward, the probability or the likelihood that they become a sale or that results in cash in the door is higher than somebody who's just a lead in.

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Speaker 1

I don't know if they're interested. I don't know if they're qualified. I don't know if they have any intent whatsoever or they're not in the sales process. So as a founder, I'm going to say this thing helps me prioritize my time. The other thing that this does is it gives you the opportunity to create some some simple playbooks, right?

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Speaker 1

For each stage at that. At the discovery stage, do you have a framework that you pull up that you're you're running your calls? Do you have something at proposal? Do you have some some templates that you can use there. So you can start to create playbooks and, you know, checklists and things that you want are things that you're already doing that each of these stages.

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Speaker 1

So when you bring somebody in now you can do the same thing. You can sit down with them and say, hey, let's look at these opportunities. These are the highest priority. And are you following the playbook? Are you following a checklist? Are you using the tools? The sixth thing that you want to do is outsource the administrative tasks, okay.

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Speaker 1

In every sales process at every level, like from, from, you know, BDR up to, you know, enterprise level, like enterprise level salespeople, there are tasks along the way that are around that activity that aren't necessarily essential for the sales person to do, especially if the sales person is also the CEO. You run a sales call and you know you set the follow up for, you know, two days from now and you say, you know what?

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Speaker 1

Hey, hey, I'm glad you're interested. This is awesome. Why don't we go ahead and book a call for Tuesday? What I'll do in the meantime is I'll send you a follow up. I'll send you the, you know, two answers to the questions that you had. And I'll send you a couple of the testimonials that we have from people that are in your industry.

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Speaker 1

I'll get that over to you within the hour. Go ahead and take a look at that. And then I'll send the calendar invite, to make sure that that's, headed over to you and I'll do XYZ either. Now, do you have to do all of those things? Probably not. They don't know if you sent that. I mean, if it's coming from your inbox, that's not an essential activity for you to do.

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Speaker 1

Now, if it requires you writing the email, okay. Like if that requires a lot of custom work, okay. But I would definitely look for ways to systematize and templates that there will be some of those tasks that you've got to do, but not all of them. You want to look at this and say, what are the things that actually require me to do?

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Speaker 1

I mean, I need to show up to the call. Got it? Either. Do I need to send the email? Can we create some templates to do that? Can I can I create an automation on my call? I've got an AI note taker and after that call it listens for the action items and then sends those action items to my sales coordinator or my sales admin.

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Speaker 1

Right. And and he or she starts to execute those tasks and lets me know what, what questions they have. Right? And then when they're done, they just add the task back into the, you know, CRM layer and send me like, okay, cool. Like all done. I'm like, you're you're set. There's a lot of ways to do this, frankly.

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Speaker 1

I mean, you can leverage, you know, a junior salesperson, you can leverage a VA, you can leverage AI and automation. But if it's administrative, it's probably not something that you have to be doing. And there's probably a way to get that off of your plate to free up more of your time, to either do more, higher leverage sales activity, to get more revenue in the door or to to run the business.

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Speaker 1

All right. Number seven actually saved the best for last, because I think that this is probably the highest leverage thing that you can do in founder lead sales focus just on high value accounts closing a small deal basically requires the same amount of time, the same amount of resources, the same amount of everything in your business for a lower return.

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Speaker 1

Now, if you just said, you know what we're going to do, we're going to increase our minimum, right? Like instead of ten workstations as an I.T company, we're going to say 20, like we're just going to go up one level. You don't have to, you know, to say, listen, like we're only selling fortune 500, you know, think you have to go from here to there.

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Speaker 1

But you can say, let me just move this up a little bit because I'm still going to run the same activities. I'm still going to invest the same amount of time. I'm still going to have the same amount of time on that sales call. It's still going to require the same follow up after that call. It's probably going to require the same number of calls.

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Speaker 1

The difference is the return on that time is significantly larger. The return on that time is significantly larger. If you focus on smaller deals, you just crusher margin not just your financial margin, but the margin on your time, the margin on your head space, the margin on your focus because you have to meet a higher volume level to get to the same number.

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Speaker 1

Now, here's the other thing about high value accounts is because you need fewer of them to hit your revenue goal, you have to support fewer of them, which is a benefit all the way through the company that your team has to manage fewer people. They can give better quality. You probably need fewer people to support them. And bonus, bigger clients tend to be better clients.

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Speaker 1

They're arguably more sophisticated as a as a business. They have more budget, and the impact of your services on their budget is actually smaller. So you have all these other things that come with picking high value accounts. But the biggest one, for the purposes of this video is that you're going to get maximum output per unit of input that you're putting into your business.

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Speaker 1

So there you have it. Seven things that have helped me transition from founder led sales, where I'm basically doing everything to having the systems and the processes and the tools and resources that are necessary to hire somebody that can actually replace myself and get the knowledge that I need about the process and the systems and my market to know who do I need to hire, what kind of sales person, and what do they need to be good at?

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Speaker 1

Because you know what? I just did it and I know. So I hope this has been helpful. If it has, subscribe to the channel for more business tips. And just a heads up, we do have a an MSP sales toolbox where we have resources like playbooks and forecast models and questions to ask salespeople when you're, you know, interviewing them.

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Speaker 1

If you want access to that entire toolbox, that's absolutely free. You can the links in the, should be in the description below. Feel free to hop over and grab that. I'm usually adding stuff to it like every 2 or 3 weeks. At this rate, it's already about that. No strings attached. Otherwise, audios.

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About the Podcast

Repeatable Revenue
A podcast for MSPs and B2B business owners who want to scale sales.

Repeatable Revenue is hosted by Ray J. Green, an investor, entrepreneur, and strategic growth advisor to MSPs and B2B businesses. He's led national small business for the U.S. Chamber of Commerce, run turnarounds as a CEO for private equity groups, and advised 100s of MSPs and B2B businesses on how to build sales teams and scale sales from Cabo, where he now lives with his family.

This podcast is a collection of interviews, lessons learned, and other infotainment to help you build your business... and the best version of yourself.