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Published on:

11th Jul 2025

Not Good at Sales? Neither Was I (MSP Game-Changer)

Shy, introverted, and autistic - I bombed my first sales interview selling knockoff perfume. But I went on to never miss a sales target for 3 consecutive years and built a 20-year career helping MSPs scale from $5M to $50M+.

If you're a technical founder who thinks you're "not cut out for sales," this video will change everything.

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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

00;00;00;00 - 00;00;02;24

Speaker 1

Have you ever met somebody who was just born to sell?

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charisma. They're magnetic. They know what to say. Smooth talker. They can sell. I used to ask him, I was right.

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that's not me.

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going to tell you why that's a good thing. Especially if

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you're a fairly technical type of founder.

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Speaker 1

Like a lot of the MSPs that I work with. I'll share why that's a good thing for you.

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Speaker 1

Hey what's up? I'm Ray green, founder of MSP Sales Partners where we help IT company scale sales. And

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Speaker 1

my background, my career has basically been sales for over 20 years.

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I

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started as an individual contributor. I went to manager, I went to an exact

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became managing director, leading, you know, multiple sales divisions

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was a turnaround. CEO focused on driving sales. And

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almost all of my content is about sales. So a lot of people think that sales came naturally for me,

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Nothing could be further from the truth. In fact,

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I'm generally very shy, very introverted. I like networking events, things like that. I can do, but small talks never been super easy for me.

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and just earlier this year, I actually discovered I have a high functioning autism. Right. And which which actually puts a lot of things into, into perspective, specifically around sales for me and, and how I got into it and how I managed to get good at it

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Speaker 1

And when I think back to

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how I got going in sales and how I really figured out

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how to do it effectively and how to

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word things and how to message things in the right systems to build.

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I rewind the clock and I give you this a little bit of context,

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you know, over over 20 years ago picture, you know, shy, introverted, autistic,

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kid with not a ton of sales experience, no real sales experience to speak of.

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my first sales job was like selling knock off perfume in a California parking lot. And when I showed up for my paycheck for the first time,

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they were gone. Like the place was empty, right? So that's that's the extent of my sales experience at this time.

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I wanted to be a lawyer.

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I actually wanted to, to be a lobbyist.

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And I, you know, I'm living in Texas at the time,

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the U.S. Chamber of Commerce, who's the world's largest lobbyist by by spending. Anyway, is has a job like for for fundraising. And I'm like, hey, this is this is phenomenal. Like, I actually want to get into to politics. This is a foot in the door. I can,

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you know, just do this stupid sales thing.

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Speaker 1

I just plug my nose and do the stupid sales thing until I can get into the into the lobbying side of things. So let me go try to get this job right. Like. And it was a pretty rare opportunity because we're in, you know, the middle of the country were the national organization. And I'm like, all right, so really excited.

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I want to go in, I want this job.

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Speaker 1

And I get there and I bomb the interview like it is. It is bad, right? Like even even when I miss some social cues periodically. Like this is one where you're like

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Speaker 1

this, I know this isn't going well,

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right? I didn't know how to sell a pen. I didn't know how to answer any of the sales questions.

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I don't know how to,

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respond to any of the the objections or any of the stuff that we did was just not good.

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we're actually walking out as his name was. Larry was a, consultant for for the chamber at the time. We're walking out to the door, which I assumed was going to be the last time I walked through the door.

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Speaker 1

And because the interview is based universally terrible, we start talking politics, right? And I just light up, right? Like it's because at the time, my intense focus at that time was was all politics, right? For many, many years, I was just I was into it. I was passionate about it.

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Speaker 1

So as soon as we started talking politics, I just lit up and I'm, you know, I'm talking facts, I'm talking figures and, you know, commentators and different opinions and this and that as we're walking and he goes,

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Speaker 1

you think you could do that on the phone

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Speaker 1

You know, and I was I probably sounded much more confident than I really was because I wasn't actually sure.

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I really wanted the job and said, yeah, yeah, I'm pretty sure I can.

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So we walked back to the office and I'm like, dude, I'm getting this. I'm getting a chance here. So we go back, basically set the start date, and next thing I know, I've got my first real life big boy sales job.

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I know the product really well, right. Like I, I've read I've bookshelves full of books. I'm you know, up on current events. I know the numbers. I know as much as you can know as a, as a regular person, as a lay person in politics.

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I know the product that I'm selling like we're, you know, at the time we're selling more advocacy based stuff and I know nothing about sales.

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Speaker 1

Right. So I'm actually I pick the cubicle furthest in the office away from everybody, because I don't want everyone to hear how bad I'm going to suck. And like, so I my voice is low and, you know, I'm I could even on my first practice calls, I'm like, God, I hope nobody can hear this. This is because I know it's terrible.

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Person on the other side of the phone knows it's terrible

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But I had this motivation, like I had this drive because I needed this job in order to get the job that I really wanted. So I had to figure this out. I had to find a way to break through. And this is where

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Speaker 1

while sales wasn't my natural ability, I was born with, Liam Neeson would say like a very particular set of skills.

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Right? Like there are there are some strengths that I have

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that have served me really well over the years and in sales in particular.

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And one of those is the ability to see patterns in people and what and what we're doing in build systems.

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part of the reason for that, I'm sure, is because that's how I've basically managed to live my life, right, like and function the way that I do.

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Speaker 1

Like, I'm constantly like building little mini systems and shit like that.

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Speaker 1

that's exactly what I did. Right. Like, so as I, as I started, I went, I sought out the top performers, and thankfully one of the one of the top performers there was, Charles very generous, like, you know, here's your script. Would do any coaching, would do, you know, would get feedback, would like actually like a great, great leader in terms of sales.

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But I would listen to the calls and I would ignore what, like the people

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weren't getting the results that I wanted to get. Just ignore that completely. Right.

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And I start, you know, taking the tools and what's working for other people and just start implementing it.

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And I'm listening very carefully, like, okay, well, at this time we're changing this and we're kind of changing how we say this or we're changing how we're doing this.

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you know, like, and during this time, there's actually a management transition where a new VP came in who was much more effective at at training and at coaching.

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Speaker 1

Well, it took me a minute to ramp up, right? But once I ramped up, I, I never missed

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a goal. A monthly target in three consecutive years as an individual contributor. Every single month,

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boo boo boo

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every month would start over and I'd go through the same little stress factor like, oh my gosh, I'm not going to hit it.

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And I'd figure out what I needed to do to get there. And every single month I

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was one of the only two people to do that.

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I was a top five performer. I was a multiple Presidents Club Award winner.

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I did that by learning sales, like I didn't I didn't go into sales with this with the skill set.

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Right. Like I had to learn my product.

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Then I had to learn how to sell. I had to learn how to deliver a script.

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I had to learn how to leverage tonality one way or the other. I

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had to learn all of these things and stack these skills over time,

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did well as an individual contributor, then got promoted into management and as a manager, then executive, then managing director.

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Speaker 1

I was I was there for ten years. You know, running in a from a management executive management standpoint

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and never missed an annual target,

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like none of the strategic goals that I was given in a decade. Now

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that's through

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economic differences.

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Speaker 1

That's through political transitions. That's through, you know, I mean, you can just imagine the gamut if you are in the world of politics or you're in the world of current events, or you're in the world of advocacy,

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Speaker 1

the ebbs and flows and things that happen and, you know, shitty candidates, great candidates, you know, momentum one way, momentum the other way,

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And we hit our number every fucking year,

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Then I did it as a CEO. I've done it as a consultant. I'm doing it now as an entrepreneur.

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All sales related. And the reason I tell you this isn't isn't a brag, right? Like the reason I tell you this is because

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Speaker 1

sales is a learned skill for some people who just come naturally.

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You know what? Like in some ways, I'm I'm jealous of that. But in many ways I'm not.

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if it comes naturally, you oftentimes never learn the system. You

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never you never really learn why something is working. You

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Speaker 1

never really learn why something isn't working. And it actually makes it more difficult to systematize and scale something like that, because I've had some exceptional, like unicorn level salespeople work for me and I'm like, damn, like, okay, now we need to we need to bottle this up and, you know, replicate it.

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Speaker 1

And when it comes to that

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that person's like,

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I'm just being me, right? I'm just doing what I, what I do. I don't know what I'm doing.

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Speaker 1

when you have to learn it and you have to take it on as a skill and you have to practice it and break it down into components and go, okay, well, now you know why it works.

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now you can look at it almost the same way that you look at your tech stack. Like you can look at it, understand it, know why it's working when it's not, start to diagnose it.

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Speaker 1

And that was the benefit for me of not naturally being good at sales and frankly, wanting to do something else so bad that I was going to learn this dumb sales thing along the way.

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just to do that.

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Speaker 1

I am so glad that I took the time to learn it. I'm so glad that I was basically forced into it because it is not just a business skill, although it

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Speaker 1

is an incredibly lucrative business skill.

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Speaker 1

Like if you can learn one, this is the one because you don't starve. If you have sales, you can fix almost any problem, so long as you have cash, so long as you know how to sell something, so long as you have revenue coming in the door, you have resources to fix other problems.

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Speaker 1

so sales as a business skill, I think it's hard to match.

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but for me, learning to sell went way beyond the sales as a business skill. It went way beyond the ability to persuade someone for the reason that I want them to, in order to get my commission right, like it was.

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Speaker 1

Once you understand the psychology, once you understand how to position something not you understand how to word something. Once you understand

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Speaker 1

how people read things, how people think, and you spend a lot of time figuring that out so that you can sell more effectively, it makes you better in virtually every aspect of life.

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makes you better in relationships,

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it makes you better in parenting.

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sure as hell makes you better at rebuttals. When your kids give you objections to to asking them to to do shit, right?

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Speaker 1

But you think about it and you go, wow, we are selling all the time,

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right? Like we're selling somebody on an idea. We're selling somebody on who we are.

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We're selling somebody on getting that next thing for the house.

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and knowing how to sell just makes you a better relator.

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Speaker 1

if you are somebody who finds yourself more technical, more introverted, more a little on the shy side or on the analytical side, and you've ever told yourself,

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Speaker 1

I'm not cut out for sales, for sales isn't for me. Then as long as you recognize that that's a limiting belief of yours that that's that like that's that's something that you tell yourself.

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Speaker 1

And you can choose to think differently because I am living proof of the fact that sales is a learnable skill.

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is something that can be taught.

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Speaker 1

It is something that can be learned. It will take a little bit of work, but if you are actually somebody who is more analytical, there are going to be strengths that you bring to sales, that somebody who is naturally charismatic and magnetic and smooth talking isn't going to bring.

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Speaker 1

So the limitation is not real. It's something that you tell yourself. And had I not had a motivation bigger than the effort that was required to go through that, I don't know if I would have done it frankly. Right. Like but I wanted to be in politics so bad and I didn't have very many routes into it. Like I didn't have family in politics, I didn't have money, I didn't have education, I didn't have like the pedigree.

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Speaker 1

I was like, hey, looks like money is the way to do it. So in hindsight,

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Speaker 1

So that's one thing. If you tell yourself that recognize it's a story.

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Speaker 1

the second reason I share it is you may find that in hiring and building your team sales, of course, but anywhere else for that matter, sometimes there's going to be an outlier.

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Speaker 1

Sometimes there's going to be a candidate. There you go. I don't know,

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Speaker 1

on paper they don't check all the boxes. Right? But my gut, my intuition says, hey, maybe this person is coachable, right? Like maybe based on how they're responding to to not knowing this thing,

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Speaker 1

or maybe they're coachable.

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Speaker 1

Maybe they just really believe in what we're selling or what we're doing, or they have some bigger mission or other driven some other way that is going to, allow them to bring more discretionary effort and more energy than anybody else.

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Speaker 1

Maybe that's going to help them. Maybe

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Speaker 1

they have

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Speaker 1

a superpower that ends up, you know, turning into a strength. Right? Like for for me, it was like building systems. Right. And the ability to do that helped me as an individual contributor in sales, but then also helped me scale teams, because that's just how I saw the world, just how I, how I work.

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Speaker 1

So that's why I share it so that it's a like one, an internal piece and then two, if you're recruiting, you're thinking about building a team. Listen, like there's going to be things that you look for. There's going to be experience and characteristics and skills and certifications and things like that, like the standard stuff.

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Speaker 1

But there are going to be people that may not fit that mold that,

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Speaker 1

if you don't take a shot on them, you may be missing the person that leads you into the next, you know, 10 or 15

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Speaker 1

years of, of growth or whatever it is that you're hiring for. So, hopefully these lessons have been helpful for you or you've taken something from it.

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Speaker 1

If you have, feel free to jump on my email list. We actually, I send an email every single week on largely sales and business growth.

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Speaker 1

Or if you're an MSP or an IT company specifically, you can actually check out MSP Sales toolbox.com and get access to our toolbox that we put resources in every single month. You've got templates, we've got playbooks, we've got forecasting models like different things that we've used in sales and sales management, and we drop them in there.

00;13;29;35 - 00;13;35;49

Speaker 1

It's new resources all the time. And you have access for absolute free, if you just go to MSP sales toolbox.com. So.

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Speaker 1

thanks for watching. I'll see you the next video. Adios.

00;13;39;58 - 00;13;44;30

Unknown

You.

Show artwork for Repeatable Revenue

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.