The Sales IQ Podcast

Secure Bigger Deals By Going High Early, with Jamal Reimer

June 15, 2022
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The Sales IQ Podcast

Join us as host of the show Luigi Prestinenzi talks to thought leaders from around the globe about the art and science of sales and marketing, personal development, and the mindset required to sell more everyday. Luigi is a master of creating pipeline and breaking down targets, he specializes in helping sales professionals build the mindset to achieve greatness and #bethebestyoucanbe.

Imagine you've lined up one of the largest deals of your career. What's your first move?

In this episode Luigi is joined by Jamal Reimer, Sales Coach and Author of Mega Sales Secrets. Luigi and Jamal discuss how to navigate a challenging selling environment, why you should be a 'heliskier' not a 'mountaineer,' and the two abilities critical to closing mega deals.

🔗 LINKS

Connect with Jamal on LinkedIn. Find his book Mega Sales Secrets here. His website is here.

Connect with Luigi on LinkedIn.

Learn to sell at your best in any buying environment. Explore the Create Pipeline course from Sales IQ Global here.

Luigi Prestinenzi
CEO & Co-Founder @ Sales IQ + Host @ Sales IQ Podcast
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Jamal Reimer
Author, Mega Deal Secrets
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[00:00:00] Luigi Prestinenzi: By the Sales IQ Network, this is the Sales IQ Podcast. I'm your host, Luigi Prestinenzi, and each week we'll be going on a journey that will inspire you, motivate you, and help you be the best sales professional you can be. Our focus will be on mindset, tactics, and the strategies that will enable you to create more pipeline, and win more deals. 

Welcome to the Sales IQ podcast. I'm excited for what will be an incredible episode. As this week we are talking about how to land the big deal, how to land the strategic monster that will completely transform your pipeline. This is a topic that I was absolutely obsessed with earlier in my career. I always wanted to.

Bigger deals. I was always chasing the bigger deals. I landed bigger. I'm like not big enough. I need to get a bigger one, a million, a 5 million, a 10 million. And I was pretty fortunate that I was able to win some large opportunities in my career. Now, this week's guess is gonna talk about, you know, how, what he did to land some absolutely massive opportunities in his career, right? So this is gonna be a great episode.

But if you're not, you know, working on those multimillion dollar accounts, Don't, you know, switch off now and, and go back to what you're doing, right? Because there's actually a lot of takeaways. There's gonna be a lot of takeaways on how you can apply some of these principles to different size of deals that you know, and this is the great thing.

This is what I love about selling, right. Is some of the concepts we think only are there for. Bigger opportunities or, you know, concepts that you'd use in say smaller opportunities to say, look, that's actually not applicable to large ones. You can absolutely contextualize them to the different opportunities you're working on. So there's a lot of content in here. There's gonna be a lot of takeaways that you can implement immediately, some actionable items that you can implement immediately.

But I do wanna address something because as you probably know, but I'm not a big fan of the news. I don't really watch much news. I just keep my eye on kind of some of the business news, some of the you know, financial information coming out, just in case there's information about clients. I wanna make sure I've got my finger on the pulse, but you can't now hide from the fact that there is so much negative talk about the economy, right? People being laid off economic downturn, interest rates going up and you know what, it's just dooms day out there, but.

If you're working in sales, you cannot have that viewpoint of doomsday. You can't have that negative view on the world because it will impact your performance. Now, one thing that COVID did teach us is that even during real difficult times moments of adversity, we were able to stand up. Be counted and make a magic happen.

And even if the market starts to be, get a bit difficult, the reality is it's a great opportunity for you. And I'm gonna record an episode next week around how to capitalize on the opportunity. That's about to, you know, that that's in front of us right now. Right. But just wanna quickly sort of talk about and discuss that before I get into this week's episode, because there are so many things that we simply cannot control.

But again, this is why listening to podcasts. Focusing on self development is critical during these times, you know, of times of adversity, because. If you're finding it a little bit difficult, then it doesn't necessarily mean you can't meet the targets that you've set for yourself. It just means you've gotta go a little bit deeper.

You've gotta assess your ICP further. You've gotta look at your by persona. You've gotta change your narrative. You've gotta be proactive and then you've gotta increase your temper. You've gotta increase the level of prospecting that you're doing so that you can build more pipeline coverage so that when a deal does.

Because things will happen. I just had one happen to me this week. Right, right. At the point in the end, I was pretty much guaranteed the deal. They said, look, we've actually hold everything. We're just putting everything on hold because we just wanna see what happens in the next three months. Now, if I didn't have another five or six deals sitting behind that, I'd be like, fuck stressing out.

But the reality is I've got other deals sitting behind that. So I've gone right. Completely understand where you're coming from, trying to work through it with them. But I'm not gonna put any pressure on them right now. Right. Because for me, I'm not relying on that opportunity.

So as we embark on this next period of of of life of the world, like 2022, all of a sudden there's another particular crisis that we're working through. Our mindset is gonna be crucial. That's gonna help us really work through some of those challenges. So make sure you tune into the next episode, which I'll be talking a little bit about how you can capitalize during moments of adversity, how you can turn a negative into a, into a massive positive.

[00:04:36] Sponsor: This podcast is brought to you by the Create Pipeline program from Sales IQ Global. This program will equip you with the skills, tools, and confidence to run an outbound strategy so you can generate more qualified opportunities and close more deals. Hear what Ellis from DocuSign has been able to achieve since joining the program and our incredible community.

"So, my name's Ellis, I work at DocuSign as an ABR. And the reason I started Sales IQ was because I really needed that guidance and that training to make sure that the outreach that I was doing was hitting the nail on the head. So I was lucky enough to start the program early on in this role and since then I've been pretty successful and last quarter I finished on a 185%. So I've seen some huge results by adopting the principles."

Our next cohort is starting soon. So to learn more, go to www.salesiqglobal.com, or if you have a team of sellers, talk to us about our in-house offering. Control your pipeline, control your destiny, with Sales IQ.

[00:05:40] Luigi Prestinenzi: But let's get back to this week's episode talking about big deals. So this is great because Jamal reer who's joining us for this week's episode has a lot of experience working in this space. He's worked for, you know, some, some pretty large organizations in his career. And he's been an author of, you know, mega. Secrets. It's a book. He does a bit of investments in his side worked at Oracle, you know, a huge organization putting some massive deals together.

So he's gonna bring that practitioner type of theory to the table and provide some insight into what he did to land some of those big deals. And it would also love that if you are loving these episodes, give us a, like, give us a rating. Share with your network, what you love about this podcast, because we would love to get more listeners.

We, I absolutely thank you. You know how grateful I am for you joining me every week and giving me a platform to share some of my ideas to, to share some of the guests and just to give my viewpoint on the world of selling. So I just wanna say, you know, if you do have people that you think might benefit from listening to this podcast, let them know, but also hit me up.

Send me a message on LinkedIn. Tell me what you love about this show. Also if you haven't subscribed to our community, please jump in and subscribe. We've had some incredible guests presenting in the last couple of weeks and it's only gonna get better. So look, get your pen out, enjoy what this episode's about to bring, because Jamal's gonna bring it.

You're gonna learn stuff and it's will help you in your quest of being the very best sales professional you can be.

Welcome to the show, Jamal.

[00:07:14] Jamal Reimer: Hey, thanks for having Luigi.

[00:07:15] Luigi Prestinenzi: Yeah, pretty excited, mate. We're talking about a topic that I've been a bit obsessed with over a number of years, right? Winning big deals.

So I can't wait to dive into this topic and really deconstruct what it takes to win big deals and what sellers can do to create more opportunities in their pipeline with more Sable opportunities as well. But before we get into that topic, I would love to learn a bit more about you and. You started in the wacky world of sales.

[00:07:43] Jamal Reimer: I mean, if, if you want the origin story, it goes back to university where I in, in high school, my family lived in Southern Africa. Yeah. And at that time the government in South Africa was under duress from the rest of the world because of apartheid. And the currency, the ran dropped about 25% of its original value.

And so my family's savings and income was in no way gonna help me in university. And I found myself a freshman, a first year on the university of North Carolina chapel hill with basically $300 to my name and long story short. I was approached by a teammate. I was on the fencing team about a summer job and it turned out to be selling books door to door.

Yep. And that was my first experience with, with selling was selling educational books. Far from home 80 hours a week, 13 weeks. A summer. Yeah. That's where it began.

[00:08:45] Luigi Prestinenzi: And you, you fell in love with it, or it was something that you just did as a, just to make some cash?

[00:08:50] Jamal Reimer: The first year. I absolutely hated it. After, after working 80 hours a week, every week, 13 weeks of the summer, I came home with $2,200, which is like, you know, less than minimum wage for sure.

And you know, door to door is like the hardest type of sales there is. And. My self esteem was shot, you know it was, it was a terrible experience that I was extremely frightened of and it was exactly because I was so frightened of. that I came back to do it again. Because I just couldn't let there be something out there in the world that scared me that much without like trying to conquer it.

Yeah. And over the next several summers I improved, I just kept getting better. And the way that I got better was I would just follow another student who was doing better than I was. Mm. And I would either model or adapt what they did to fit my personality and what was becoming my selling style.

And then by the end of the five summers of doing that, I was, I don't know, one of the top five sellers in the company. And I had recruited a team of nine people. So I learned about management as well. I was able to leave it with my head high.

[00:09:57] Luigi Prestinenzi: Yeah. Fantastic. That's a pretty cool story, right. Because I know for having done door to door myself, it can be a very, very brutal job, especially when you're working commission only.

Right. And you're getting knocked backs and people aren't answering a door and they, they even look out the, the window and then they just completely ignore you. Right. So you've gotta build that level of resilience. So it's really interesting to see that you didn't let it stop you, you kind. Embraced it and we're able to master it, which is just goes to demonstrate why you've been able to achieve some, some of the success you have in your career.

We'd love, obviously we're talking today about the big deal frameworks, right? Of moving from that transactional door to door sales process. When did you start to really find your way working on strategic sales opportunities?

[00:10:46] Jamal Reimer: So for the first. Decade of my career. I was a mediocre seller. And it was during that first decade that I was fired twice in a row for under performance.

Yeah. And somehow some way at the end of that decade, I, I wound up with a position with an individual contributor position at Oracle. It's a big, big brand. Mm. And A couple of years into it, three years into it, I was basically brought into an opportunity. It was a, a fairly significant customer. It was like $10 million run rate for a three year deal, which is, which is significant.

Yeah. But they, they were very dissatisfied and there was lots of attrition on the services team on the account and, you know, they were shopping for another vendor. So it was an, it was an existing customer. And under the tutelage or mentorship of my head of sales and my head of services, you know, both these guys were like 20 year veterans in our space.

It was pharmaceutical technology, you know, and they had been there and they just seen everything and done it, done it all over a nine month period. We did so many things differently and recreated A different commercial model, an operational model, a governance model to the point where this dissatisfied $10 million customer renewed for $50 million.

And it was through that experience that I was kind of shown the light about what it takes to have these, you know, super large deals. Yeah. How to bring 'em over the line.

[00:12:31] Luigi Prestinenzi: And so that opportunity, when you were able to take a dissatisfied customer work with your kind of in-house gurus, so to speak, to really build that out and turn it around to a $50 mil op sort of talk to me about how you then created your framework to win more of those type of accounts.

[00:12:53] Jamal Reimer: So many sales, methodologies, or frameworks despite everyone's best efforts, turn out to look quite complex. Yeah. There's several steps. It's like a, like a, like a train with lots of cars behind. I try to keep mine as simple as possible. And it, and it oversimplifies things by a long shot because long large deals are long deals.

They take a typically they take quite a long time in a lot of twists and turns and they look more like a novel than a framework or a methodology. But if I was gonna describe it, I've, I've started to use this term, the two mountain model. So, if you can just think about if, if we were standing at a whiteboard and I drew a big capital M on the whiteboard and those, you know, the, the peak of the S were, are these two mountains and in the middle is this kind of valley.

It's like a journey of going left to right across that whiteboard mm-hmm and mm. And I don't know if I would call it unique, but I would definitely say underappreciated. Is the whole concept of getting very high, very quickly in an organization like at the beginning of a sales cycle. And I think culturally, so many sellers me included for the first decade of my, you know, plus of my selling career.

We, we kind of come into a new opportunity with this mentality that we have to start at the bottom of the mountain. and walk up the whole mountain. We see ourselves as mountaineers, right? We're taking every step ourselves. We are the seller, right? So we're going from the bottom through the worker worker bees on the shop floor, up toward middle management.

And ultimately we want to get to senior stakeholders that have budget and decision making power and, and projects that matter that we can. and that's where most of us live, but, and in, in that kind of framework or that culture we're getting knocked down or held back by those lower stakeholders all the time.

And we waste weeks or months kind of sparring or pleading with them. Yeah. To sponsor us higher in the organiz. and what I've learned both through the experiences that I've had with doing large deals. And now talking with others who have done really large deals is there's a few common threads. The big one is how laser focused.

Yeah. Big deal sellers are on getting very high, very quickly. . So if you, if you, if you're looking at this whiteboard, you see this big M the, and the, the first part of the M is that first mountain that's that represents getting to power quickly. Yeah. But most sellers. Lack the skills or confidence to really go high very quickly.

Mm. And what I say is that, you know, big deal, people don't see themselves as mountaineers walking or climbing up this mountain. They see themselves as Hellis skiers and they just go leverage a helicopter. Yeah. That takes 'em to the top of the mountain in 10 minutes, then they're skiing down the other side most of the day.

[00:16:12] Luigi Prestinenzi: Yeah. I love the concept.

[00:16:13] Jamal Reimer: You know, the, the helicopter is just an analogy for. People who already ha people who we have access to who already have peer status, peer business status with the senior people we're trying to get to. Yeah. And so the big, the biggest, the, the biggest target for that in my world is our, my own executives.

So I use my CEO or the, the C-suite or the senior vice presidents. And I'll, I'll map them to senior people within my accounts. And whether I'm in the room or not, doesn't matter. Now, two peers, two senior business peers are having a serious business conversation with, with no introductions being made, no lower people saying yes or no giving access.

It's. It, it it's, it's a serious business conversation very quickly.

[00:17:05] Luigi Prestinenzi: But you, and this is, this is great. And I love, I actually love that analogy, right. Because if I look back on my career and I have, you know, I was obsessed with winning strategic ops and I've done a couple of you know, one 10 mill deal, one just shy of 20.

And if I look back, you're absolutely right. If I look at that mountain framework, I was able to get to the top of the mountain very quickly. And they became my executive sponsor. Right. If you look, take the Miller Hyman concept, for example, they became my strategic advocate very early on. So we didn't have to go through the process of getting a project manager or a divisional manager.

It was actually somebody that had the seat at the table. Right. Which was, which was why we were able to progress it so quickly. But I just wanted to go back a step because you mentioned, you know, having that peer to peer engagement, which I absolutely agree with. Right. We can't be elevating if we're not at the same level or not thinking at that level.

Right. Just would love for you to share how you went about building your commercial acumen and understanding of the C-suite that allowed you to elevate the conversation and have those peer tope conversations.

[00:18:19] Jamal Reimer: Not, not to plug it too hard, but I wrote a book. And in this book, it tells the story of the first big deal that I did, that I had all these revelations, right.

The first there, all these firsts for me. And in the book, I tell this short story where ex that, that points exactly to your, your comment. It was, it was early in this, this one deal that I was talking about going from 10 to 50 million, it was early. And I had my VP of sales on my right, my VP of services on my left and across the conference room table was the, the executive sponsor for the project, from the customer.

And we were going through our, you know, little ideas here. Hey, we could discount the software here. We can put an onshore team instead of the offshore or vice versa to either increase the quality or, you know, change stuff around. And the customer stakeholder just put his hands up and he's like, guys, guys, guys just plain talk.

Right? He's just guys, guys, guy. This is not about. A discount here or there, or moving a team around here or there. This is about how we steward the most important IP of this company and those long pause. And I just kind of sat back and thought about that. And then the conversation started again in, in, in a different tone, on a different topic.

And it was a, it was a, it was a what an aha moment, you know he had just stripped away all our sales process, all our you know, our preconceived ideas about what commercial or, or sales conversations were like. And he, and he just, you know, reduced it to its essence and raised its level of importance in simple, clear everyday language.

Mm. And it struck me in a way that it still strikes me today, the high. And I, I noticed this more and more, the higher I get in any organization, the simpler the conversation becomes. Yeah. Partially because executives simply don't have the bandwidth or mandate to get into details. Yeah. Partly because I think the most effective communication is, is minimalistic.

Yeah. And so I just started to learn that language. And as I learned that language, I started to gain confidence because it's actually easier and more intuitive than what we find at the middle layer of our own organizations, of the customer organizations. All the know-it-alls are at the middle tier. And they're using all the jargon and they're, they got the complex spreadsheets and they got the, you know, crazy architectural diagrams and they're just doing everything they can to show how much they know.

Yep. And when you rise above all of that, what really matters is much less, it's much more simple and much more powerful.

[00:21:29] Luigi Prestinenzi: This is, this is actually really great advice, right. Because I think. For a lot of sellers, they can get stuck. They can get stuck in those tactical conversations. And you're absolutely right when you've gotta elevate and talk the language of leaders you really like at that level, if they're gonna be spending a mil 5, 10, 50 in your case, that's not just a basic transaction that needs to take place.

There's some sort of significant outcome that they're working towards. Right. And if we don't elevate that and if we don't really think and talk in their language, there's a disconnect and that's when we get delegated down or potentially we are just seen as another vendor, who's trying to push some sort of transaction.

So would love to dive deep in a little bit deeper into your mountain framework. you know, taking too much of the concepts from the book. Right. Cause we make sure we pub, we, we, we, we put the show notes of where people can buy your book, but when it comes back to that mountain framework, what are some of the other elements that sellers must be considering when trying to land larger accounts?

[00:22:35] Jamal Reimer: So there's the, there's, there's a whole world of topics and subtopics within working with executives. There's the language we use. There is the there's something that I call the, the mega deal premise. Then the mega deal premise kind of straddles two big topics.

One is how to work with executives. The other is the how to create that value story. Yeah. And at the, at the heart of that's something called the, the C level insight, you know, we talk a lot about insights. Now. We used to ask a lot of questions. There was consultative selling and there was spin selling, you know, there's all these questions based frameworks.

Yep. And we've moved. We've moved on from there into, I think we're kind of in this era of insight selling. Mm. Everybody knows that the, the, the buyer cycle has changed and the internet has freed information and 50 to 70% of decisions are made before the first interaction with the seller. Mm. And so, Insights play a huge role because it's the way that we, that we command attention from our audience is giving some impactful new information to them.

Yeah. But there are insights at different levels. You can, you can have a, a shop floor insight. Yeah. Yep. That's not terribly deep, but it would, it would really help the one guy who's the busing button push. , you can have a middle tier insight, which can help a manager. Who's got a team of 15 players. Yeah. Or you could have a C level insight, which could impact an entire organization entire enterprise.

So we as sellers need to figure out which, which insight are we sharing with? Which audience. it's not gonna land very well. If we share a, a shop floor insight with an executive. Hmm. So the level of research, the level of due diligence, the level of engagement with customers to dig into their problems, what they've tried, you know, where in the data stream, where in the, in the business process are the bottlenecks, et cetera.

You know, it's really hunting for needles in, in the haystack. Yeah. To the extent that we do that, we're able to discover more impactful insights. so that's the second one. Obvi the first big one is working with executives. Yeah. The second one is that value story. That is a very front loaded process. And then it becomes a hypothesis that is, that is there to be proven.

And then, then that turns into some kind of evaluation. so I could go on and on, but those are like three really key, key areas of doing these larger deals.

[00:25:36] Luigi Prestinenzi: Yeah. I love that. And I, but, but you know what? I think the framework that you've just shared can be applied across any opportunity, right? In the B2B space.

I'm not talking transactional stuff. Right. I'm talking. Cause what you've shared is absolutely great. If you don't have that point of view, then you're not creating any value and you're not AB and you're not. Able to open the conversation about what change could look like because often when you're selling bigger deals, what I've learned is they're not buying current state, they're buying a future state, they're buying change, right?

They're if it's a system, it doesn't matter what it is. They're trying to move from here. We are today, and this is where we need to go tomorrow. And I've seen some interesting stats about how many organizations. Maintain the status quo because they couldn't get consensus. There was, you know, a lack of alignment in, in the buying committee.

And again, I think this just comes back to that initial premise around what is that point of view that you're bringing to the table to allow people to really talk about? Well, this is a hypothesis that we're discussing now, how do we get consensus around bringing this to life? Right. And that, that leads me to my next question.

What are some of the strategies that you've, that you have used when you have had multiple people cuz in a strategic account of that size? I can only imagine there's multiple buying people or multiple people in the buying committee. What's a strategy that you've used to actually get alignment, engagement and consensus.

[00:27:02] Jamal Reimer: Well the first thing I do is I ask to be on the buying committee.

[00:27:05] Luigi Prestinenzi: Yeah. okay. Yeah.

[00:27:08] Jamal Reimer: And I I've been successful a few times, but the way that we negotiate that is when, when, when you're with a, when you, when you can establish a certain level of credibility, either as an SME or as, you know general business Strat strategist or somebody who knows a market well, Or product area.

Well, once you establish a certain light of cred credibility, then the next thing is that, well, gee, we're a buying committee. You can't, we can't, you know, let you in behind the curtains. And so I said, well, just let, let me attend the, some of the meetings or the first part of the meetings, and then I'll leave.

And then you guys can talk about money and competitors and all that kind of stuff. And, and oftentimes they go for it. Hmm. so, you know, a lot of sellers don't even think about asking for that, you know, so, and, and you know, the rationale for that is, look, you, you, maybe you wanna do it with me. You might wanna do it with others too, but I think.

if you ask your own people about my stuff, they'll be able to ask, answer the first line of questions. But when you get to that second or third line of questions, they're not gonna be able to answer. I will. Yep. So it's just gonna speed up your knowledge gathering data, gathering to speak with me directly and let me be a part of that.

[00:28:27] Luigi Prestinenzi: Yeah. But that's a mess, you know what? I love that, cuz you're right. Like. They're basically putting a level of trust in you to help them make decisions that they don't have the capability potentially to make themselves. Right. And if you're not in the room, if you, if you haven't got a seat at the table, you're not able to really strategically partner and help them arrive at that point of decision.

So getting into that and I, I call it the seat at the table. I love it. You know, I, I actually love that concept of actually. Explaining why you should be there. So I think that's amazing. And I just wanna, because I know that we're coming to to an end and mate, I, I could actually talk to you for hours mate, on this subject, cuz I've got so many things that have so many questions that are popping up, but I just wanna make sure for our listeners, you know, we've got the mountain framework.

It's absolutely crucial getting to the top of that mountain as soon as we can, but making sure that we're speaking peer to peer, the language of leaders. And also bringing a, a point of view that allows you to have a hypothesis to discuss change around and then getting yourself in the buying committee is fundamental to ensure that you're helping them get consensus and alignment.

I think, I think, you know, those points there. It's just amazing for people to hear Jamal. So I really wanna thank you for, for sharing that with regards to kind of where people can find you, mate, what's the best way for people to be able to connect with you engage with you and, and, and, and get some of your content.

[00:29:51] Jamal Reimer: I'm, I'm pretty active on LinkedIn. So I'm, you know, you can, I'm sure you'll just put my LinkedIn, you know, URL in, in the show notes. That's one. I, I do other things. I have a masterclass, which is a 10 week experience where, where I not only teach, but we work on deals together in a small group environment. And, you know, I do the other, the speaking and consulting and all that stuff. And for that, it's just Jamal reimer.com.

[00:30:19] Luigi Prestinenzi: Okay, awesome. We'll make sure we put that in the show notes and for our Sales IQ community, we could have Jamal attend one of our sessions to really talk about you know, really how to land those big deals and go a bit deeper than, than what we've got in this podcast.

So I just wanna say, mate, thank you very much. I, I do value content that you share on LinkedIn. I think it's great. You, you really get, you get me thinking a little bit different. And so you're always creating value. So I wanna say thanks for the contribution you make to our community. We need, especially now as we're on, we've spoke about this before the show in the green room.

We're on an Eve of, of what he's looking like to be a bit of a recession, and we're seeing this across multiple markets. But for most sellers, we know that the one great thing about what we do. Is, if we focus on what we can't control, we can sell ourselves out of any challenging environment. So I just wanna say, thanks for being a guest in the Sales IQ podcast.

[00:31:11] Jamal Reimer: Thanks for having Luigi. It was awesome.

[00:31:14] Credits: This show has been recorded remotely produced by Sales IQ Global, audio editing and music production by Stefan Malliate. Show notes by Victoria Mathieson and graphic design by Julie Marshall. Don't forget to leave a rating and review on your podcast player. And if you want to find more about the programs that we offer at Sales IQ, head to www.salesiqglobal.com

This episode was digitally transcribed.

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