Sales Hustle is now Sales Transformation
Oct. 11, 2021

#169 S2 Episode 38 - From Working At A Research Firm To Sales Enablement At Challenger with Michael Randazzo

On this episode of the Sales Transformation Podcast with Michael Randazzo, VP go to market strategy and enablement at Challenger, knowledgeable guy, and an expert on implementing organizational sales transformations.

On this episode Michael talks to Collin about the way the Challenger approaches sales differently than any other type of seller out there. Not only that, the two vibe about how sales transformation is similar to how the Challenger works as well. Want to know more? Listen now to find out!


01:01 How Michael started to where he started and where he's at today

05:29 What are the key seller profiles that the research has uncovered in Challenger

11:15 Transformations are hard and here's why it's the same for transforming yourself into a Challenger

16:54 How to think and act like a Challenger

22:01 How to connect with Michael and learn more about Challenger 


05:55 "The 'Challenger' just kinda looks at the world a little bit differently and they seek to educate customers about problems that they don't realize exist in their business. So they're kind of the inverse of some of the other profiles we found, the 'Problem Solver', for example, who takes a consultative approach in figuring out what's going on in a customer's business because they don't know yet."

09:38 "The thing that a 'Challenger' does better than anyone else is they don't lead with their products and solutions. They lead with customer problems and in particular problems that the customer either has overlooking, or under-appreciating, or just completely missed. And they seek to have a dialogue around what that problem is actually doing ... then they lead back to the product or the solution."

17:37 "To be an elite seller, to have this sort of challenger mindset, you really need to think about being in your prospect's shoes. Like what's going to make them be motivated to take the next action and who are they more likely to go with." 

19:38 "You might notice if that CIO is much more open to sharing information that they're likely not sharing with other reps because you've shown up and demonstrated to done the leg work to get to know them. You've built that instant credibility and with just a couple of simple questions, unlocked information that's probably not available to your competitors."

20:27 "The most common misconception to be a 'Challenger' seller you just have to be a great, innate, natural-born seller. It's actually more about sweat equity, it's about whether or not you're willing to put into work, the preparation, and do the leg work before you show up in the conversation."

Learn more about Michael in the links below:

If you enjoy the Sales Transformation Podcast, please subscribe, share, and send us your feedback. Please make sure to rate us and leave a review on Apple. 

Learn more about Collin in the link below: 

Also, you can join our community by checking out If you're a sales professional looking to take your career to greater heights, please visit us at and set a call with Collin and Chris. 

Looking to start your own Podcats? Book a FREE strategy call. 🚀


[00:00:00] In the world of sales, you either sink or swim or breakthrough to the next level. My name's Colin Mitchell. And this is sales transformation, a new kind of sales show designed to bring you through the epic life-changing moments of elite sellers. So you can experience your own sales transformation.

[00:00:24] All right. Welcome to another episode of sales transformation as always. I've got a fantastic guest for you today. I'm going to be talking with Mike Randazzo. He is the VP go to market and enablement over at challenger. They wrote a book. Uh, they have a sales methodology that many people are familiar with and use.

[00:00:45] And we're going to dig into his experience and talk about some of the awesome work that he's doing over there at challenger. Mike, welcome to the. Thanks for having me call and looking forward to speaking. Yeah, man. We've been, uh, I feel like I've been saying this [00:00:59] a lot lately, but for whatever reason, the last couple of guests, uh, have been guests that I've been wanting to have on for awhile.

[00:01:06] And we had some scheduling conflicts and then we kind of did a little bit of planning, uh, which I'm glad we did. And so now we're finally making it happen. So I'm pretty pumped up absolute. Me too. So give us the, uh, give us the whole story here. And where did it all start for you? Where, where was your, uh, first sales job?

[00:01:24] What were you doing? And then let's take it there. Cause I know there's going to be a lot to unpack versus where you started and where you're at today and, and tons of learning lessons in there as well. So my first sales gig, I actually just celebrated a. Uh, what's a strange anniversary. The September 15th, 2008, I started as an SDR for a company called CEB corporate executive board.

[00:01:46] And we'll get into them in a little bit, but September 15th, 2008 was actually a, um, uh, a day that sort of has gone down in infamy. That's the day that Lehman brothers [00:01:58] actually filed for bankruptcy and they sort of became. Kind of the first visible domino to fall and what would then become the great recession, the financial crisis of 2008, 2009.

[00:02:09] So yeah, heck of a way, uh, to start a sales career, heck of a day to start a sales career, I should say, well, I, when you were sitting there telling me that I was like, man, I wish I knew my likes sales anniversary date and had it nailed and buttoned up, like, like Mike there. Um, and then, you know, you had something else that happened that day, that, that made it pretty memorable.

[00:02:33] So yeah, kind of an interesting time to be getting into sales. What sort of challenges did you run into with the financial state of the country at that time? And what were you. Well, look, I think the thing that happened, you know, coincidentally on that day, when I started in sales was the world of selling changed.

[00:02:52] Um, I think you got to a point with complexity that that sort of reached a new [00:02:57] height in that economic disruption and the backdrop here. I think there's actually like a silver lining to all this of course is, you know, starting a career in a tumultuous and uncertain time is, uh, is not great, but it, it makes you, it gives you some level of.

[00:03:11] In terms of pursuing, um, growth in your career and success in your career. And what was interesting is this company that I was working for again, um, corporate executive board CV, big research company, um, so best practice research across all corporate functions, their sales and marketing practice at the time was really digging into what this new complex and recessionary environment was doing to sales professionals, um, how it was impacting the way they sold.

[00:03:40] Um, going out in serving and assessing thousands and thousands and thousands of B2B reps to figure out what the high performers are actually doing to achieve success in a really difficult and complex. And it all turned out that, you know, ultimately there were different profiles of sales professionals.

[00:03:55] You [00:03:56] could neatly sort of categorize them by their approach, by their behaviors, by the skills that they exhibited. Um, and that's actually where challenger was born. So this idea that the challenger sales rep, if you will, uh, is more likely to be a high performer than the other. For rep profiles that we uncovered in that research.

[00:04:13] I won't get into the whole thing now, but if you've read the book, the challenger sale, that research turned into a book, the book turned into a company and that's where I, where I work today. Uh, so CB, uh, gave me a great start at a strange time. Um, but luckily down the hall, uh, you know, uh, the proverbial hall, uh, we had, uh, something burned there that had actually helped transform the world of B2B selling.

[00:04:38] Yeah. Yeah. Wow. What a, what a story? You didn't know what you were signing up for? I didn't know. I mean, what I was selling was, you know, big research company. I was selling research, research subscriptions and consulting programs for, um, to, to HR executive. And it wasn't until a few years [00:04:55] later, after doing that role after, you know, SDR role account management roles, client success roles, um, moving into this world of challenger several years later, once it had already established a reputation and then you start to see and get involved in, and, and in my roles as a consultant and an engagement manager being involved in the transformations that are happening across organizations who are, are implementing the challenge or idea.

[00:05:20] That's why I was really excited to talk to you today. Like there was definitely a personal transformation from me from day one as an SDR to, you know, uh, years later as an account manager, as a consultant with a revenue target. Um, and it all fell in line with the things that we were teaching and training and ultimately implementing within client organizations around the world.

[00:05:38] So, yeah. Yeah. Wow. So tell me, uh, for maybe people who haven't read the book, like, what are the kind of, you know, key, different seller profiles that this research. Yeah. So of course you've [00:05:54] got your challenger, right? And the challenger is sort of the, the it's the punchline. Of course we named the book after it at the time that was a, that was a controversial name actually.

[00:06:02] Um, because the defining characteristic of the challenger is not so much pushy, aggressive, you know, used car salesman type of a profile that that can be a common message. The challenger just kind of looks at the world a little bit differently and they seek to educate customers about problems that they don't realize exists in their business.

[00:06:21] So they're kind of the inverse of, of some of the other profiles that we found the problem solver, for example, who takes. Sort of consultative approach to figuring out like what's going on in a customer's business. Cause they don't know yet. And so the question is always like, Hey, what keeps you up at night?

[00:06:36] Um, and that can actually backfire for a lot of sales professionals because that problem that keeps you up at night, that's articulated by the customer could be. The surface level thing that the customer just wants the seller to hear so that they can move on with the next step in the demo, for example, or it can be like a [00:06:53] problem that's completely outside of the realm of, of what you are here to provide as a solutions provider.

[00:06:58] And it goes nowhere. So there's the problem solver. There's the relationship builder, which is exactly what it sounds like. Right. Building rapport, having pleasant conversations and trying to sell on relationship alone. Um, and then there's the hard worker and the hard worker is really sort of, uh, they're, they're going to put in the discretionary effort.

[00:07:16] Um, and, and finally, there's the, uh, we, we have some fun with this one. The lone Wolf, the lone Wolf is exactly who you're envisioning right now. There is a lone Wolf on every team in every organization. You may be. Um, but the funny part is long wolves can be pretty successful. It just turns out that when their luck runs out within a certain organization, because they're marching to the beat of a different drummer or not following the process they're doing, what's worked for them until it stops working and they need to go and find somewhere else to try their own process.

[00:07:44] So at the end of the day, when we advise heads of sales in terms of, Hey, what do you do with all these profiles that exist across your team? The point [00:07:52] really is look for places where you can. Leverage the skills and behaviors that challengers tend to exhibit that are disproportionately likely to lead to high performance and be predictive of high performance.

[00:08:04] You can absolutely have. High-performing hard workers and problem-solvers and relationship builders and lone wolves. It's actually just much more likely than in a complex selling environment. Um, that challenger profile, uh, is going to be a high performer relative to those peers. So that's kinda like the, the, the first finding of that book in a nutshell, and kind of where the name came.

[00:08:24] Yeah. Yeah, yeah, no, I love it. Um, in, and if you haven't yet picked up the book, I think that's a good place for people to start and. And so what I hear you're saying is like, there's these different personas of sellers, right? And the key takeaway is that the challenger is typically going to be your high performers.

[00:08:43] Not everybody can be a challenger, right? Like a team is going to be made up of all of these different personas, but knowing what they are [00:08:51] and having that level of awareness and trying to get them to maybe exhibit some of the challenger profiles. You know, skillsets or characteristics, um, is going to, you know, increase in, in, in, you know, your team performance overall.

[00:09:04] Right. It's exactly right. And you know, there are certain people who you'd look at some of your top performers in an organization. If you're leading. Uh, sales organization, if you're managing a team or if you're on a team and you kind of get a sense for who these people are around you, your colleagues and your peers, and, and you you've read the book and you have an idea of who the challengers are, who the lone wolves are, who the, the relationship builders are.

[00:09:27] The point is not, you know, Hey, everybody must become challenging. The point is as a research company, At our core, we re we really are just seeking to continuously keep our finger on the pulse of what those high performers are doing and doing differently. Um, and then see if we can find ways to help enable the rest of the organization to take some of those things and implement them in their day to day and [00:09:50] execute at a higher level.

[00:09:51] And that's, that's really the point what it all comes down to is the thing that a challenger does better than anyone else as they, they don't lead with their products and solutions. They lead with customer problems and, and in particular problems that the customer either as overlooking or under appreciating, or just completely missed, and they seek to have a dialogue around what that problem actually is doing and what it's causing in their business.

[00:10:17] Then they lead back to the product or the solution. Right. And that's opposite of what most corporate farmers tend to do sort of naturally. Yeah. Yeah. Because you know, people are comfortable with talking about their product or even just going to here, you know, here's, you know, here's the solution, here's the desired state.

[00:10:35] Here's where we can bring you. Right. And just leading with that because it's what they know. And it's, you know, a little bit. Dis, you know, it's a little bit uncomfortable, um, to, you know, ask better questions and be curious. And, and in, in, I [00:10:49] like to consider myself a challenger myself, because I think the best way to build trust and rapport with your prospects is by making them think about something they hadn't considered or even challenged their own thinking a little bit.

[00:10:59] And so, you know, I'm not saying you go out and say, you know, you're wrong and I'm right. Because that's not going to get you very far, but you can be very tactful to just, you know, tell your prospect like, Hey, you know, have you maybe considered this? Or like, Hey, that sounds like a good start, but what about this?

[00:11:14] How does that sound? And so there's tactful ways to get them to think outside of, or what I like to say, challenge their thinking. Well, and you make a really good point, right? Being tactful, being sort of diplomatic in your approach to this. And if you think about the bigger picture theme that we're talking about here, transformations.

[00:11:33] Transformations are hard, right? People revert back to comfortable behaviors because new approaches are difficult and I'll be the first to admit. Challenger is not an easy transformation to make. Like there's a reason why. Folks who have, [00:11:48] you know, let's, let's cut, let's say mastered the challenger approach over a number of years or are on the path to at see disproportionate successes because it is truly a differentiated motion.

[00:11:59] Um, and customers pick up on that and they value it and it ultimately leads to longer term loyalty in those relationships, but it's not easy to make that transition. And so there's a lot that individual sales professionals can do to start on that path. Thinking about the things that you just mentioned there, Colin, but there's also a lot that organizations need to do to, to help support and enable this motion.

[00:12:20] If, um, they, they decided it's the right model, the rights, um, sort of approach for their team to take to the market. Yeah. And how can, let's say, let's say you're a seller and you're one of those other personas that you've mentioned. Right. And that's just part of your personality, your, your characteristics, your comfort zone.

[00:12:43] How do you start to adopt some of these [00:12:47] characteristics of like the challenger persona that are going to contribute to being a top performer or a top 1%, or rather than maybe just an average. Yeah, I, you can, you can take baby steps for sure. Uh, what's really funny is like people who are listening, who know of challenger, they probably know of this whole idea of teach tailor, take control and build constructive tension.

[00:13:10] These are sort of the core four, uh, behaviors or characteristics or attributes, the things that that challenges do particularly well and under. Each of those four clean, you know, forties. And there's a, there's a reason why they all have T in them. Right. It's easy to remember, it's marketable, but, um, there are several drivers, there are several tactics and activities and skillsets underneath each one.

[00:13:32] So, so I would, I would recommend like take baby steps and just think about what. What are the steps in your motion? What's the process that you follow today? It may be a formal process. It may be an informal process and may be something that your company makes you follow. It's maybe [00:13:46] something that you've tweaked on your own because you've been given some autonomy.

[00:13:49] Yeah. What are the critical sort of leverage points? What are the moments across that process where you really need to show up? These moments tend to be the inflection points and the, and the difference makers between, uh, qualified opportunities that ultimately turn into pipeline that ultimately turn into bookings versus those that fizzle out at some point or end up, you know, deferring or, and no decision land, or closed loss to a competitor.

[00:14:14] But map out those map out those steps and, and you'll probably find some sequence of events or moments that look something like, you know, reaching out in and outbound, um, manner and scheduling meetings cold. Right? How are you doing so first that would be, how do you do that? You know, are you, are you showing up and talking about who you are, what you do, how long you've been around all the other companies you work with, all the other companies.

[00:14:39] Um, or are you doing the opposite? Are you leading with hypothesis about a problem that might exist [00:14:45] in your customer's business? Because you've observed it in other businesses like theirs, right? That would be the first sort of baby step towards flipping from, you know, a relationship builder, product centric, outreach to an insight led, um, sort of question-based uh, if you will, uh, approach now there's a big difference between the insight led approach and the question based approach.

[00:15:06] I mentioned it before. If you're showing up to a call on your first question is what's keeping you up at night. You're you're falling into, I think a trap that sort of gets part of the way to what we're talking about. Right. But not all the way there. So, so that might be the second step. Like when you show up on that call, what are you doing?

[00:15:22] Are you running right to a demo? Are you asking questions when you're asking questions? Are they open-ended questions or are they closed ended questions? Right? What, what are you learning in that conversation that might give you a foothold or. To teach a customer something new about their business. So first steps are simple when you're scheduling those meetings, how are you doing it?

[00:15:43] Are you leading with [00:15:44] yourself or are you leading with a customer problem? And when you get on those first meetings, are you asking high gain questions that get the customer sit back and think, you know, I've never really considered that. Which leads to two, a dollar or is it simple? Yes. Or no response questions that ultimately don't really get you anywhere.

[00:16:00] And then we run right to the demo and maybe we get the second meeting. Maybe we don't like, those are those, those first couple of moments in your process where you can sit and sit and say, what would a challenger do here versus, you know, what might a relationship builder, um, do here? And then of course, there's everything you get into beyond there.

[00:16:16] And when it, when it comes to. Uh, putting proposals together and managing complex stakeholder groups, negotiations, working with procurement and finance, like there's a whole set of different behaviors that challenges exhibit that, you know, we probably don't have time to go through all of them today, but, uh, think about those baby steps in, in terms of how you schedule those first calls and how you show up in those first.

[00:16:37] Yeah, no, those are some great baby steps that people could take. Um, you [00:16:43] know, and I love, you know, starting from the very top of the process there of, you know, how are you prospecting, right? Like, are you. Posing a question that's value added. That's peaking their interest to get them to have a conversation in the first place.

[00:16:57] And then how are you showing up on those first calls, which is so important, right? So your example, you know, are you asking what keeps you up at night? Are you asking good open-ended questions? And the thing that I love most about how you framed that is are you asking open-ended questions that are putting you in a position to educate your prospect about something in their business now?

[00:17:19] Asking questions to see if they have budget or authority or to line up the next meeting or to get them in your funnel, but asking questions to really challenge their thinking, making them consider something they hadn't thought of or educate them on something that they are not aware of. Um, which is a huge difference.

[00:17:36] And most people are not showing up that way. In initial sales calls. I can tell you right now, I've been on [00:17:42] both ends people pitch and want to sell me things all the time. And, and I love just sitting back and examining that sometimes. Um, but you know, you really gotta think of when you're, you know, to be an elite seller, to be, you know, have this sort of challenge challenger mindset.

[00:18:01] You really need to think about your pro being in your prospect shoes. Like what's going to make them be motivated to take the next action. Right. And who are they more likely to go with? Probably somebody who taught them something. They didn't know. Wasn't just a yes man or woman with everything that they said, you know, and, and, and, and basically provide.

[00:18:22] You know, value and not just treated them like a transaction to get to the next step of the sales, the process. Well, and if I might just point to something you said, which I think is just critically important, putting yourself in your customer's shoes, this is, this is what really differentiates the challenger approach, uh, from the rest.

[00:18:40] [00:18:41] This is what really turns a core performer into a high performer. It's it's actually preparation. It's research. It's building hypothesis. It's gathering information before you show up in that call by putting yourself in your customer's shoes so that when you're showing up, you already know probably 80% of the way, uh, what that customer truly does care about.

[00:19:03] And here's the kicker. When you start asking questions and you start stating your hypotheses, something that's really important. I think often overlooked in these initial calls is as just articulating what you've already. In an effort to build credibility, because if I can go in and say, Hey, look, I'm not you.

[00:19:18] I have not led an it function at a fortune 500 company for 20 years. Like you have, however, I speak with three or four others. Well, just like you every single day. This is what I'm hearing lately, based on the research I've done on you and your company, I'd hypothesize that you're probably trying to accomplish XYZ this year.

[00:19:38] What most other [00:19:40] CEOs miss is blank. Right? And that's your lead into an insight. Then you turn that into a question say, now I couldn't have possibly gotten all that. Right. What did I miss? What did I miss? What, what can you help me fill in here in terms of what's going on at your company? You might notice that, that CIO, if you, if you take that approach is actually much more open to sharing information that they're, they're likely not sharing with other reps because you've shown up and demonstrated that you've done the legwork to get to know them.

[00:20:08] You've built that instant credibility. You've just with a couple of simple questions, unlocked information. That's probably not available to your competitor. Absolutely. And I love kind of like getting that validation confirming and making sure you didn't miss anything, which is, which is a missed opportunity by a lot of sellers, because so often the notes that go into the CRM are the assumptions and perceptions of things that sellers came to based on what was said.

[00:20:37] Uh, and [00:20:39] by not following up with additional questions or validating what they think they heard. Yeah, it's it's the most common misconception is to be a challenger seller. You just have to be a great innate natural born seller. Um, it's actually more about sweat equity. It's about whether or not you're willing to put in the work, the preparation and, and do the legwork before you show up in the conversation that prep helps you show up in the conversation, whether you're a natural public speaker presenter, it doesn't matter.

[00:21:08] Yeah. And, and I love what you said too, is like, you know, we kind of went, okay, prospecting showing that first call and we could go through the whole sales process, but we we'd have to do a part two for that. Um, let's go. And, and, but I, what I love is that what you said is, is, you know, just think about like, what would a challenger do, right?

[00:21:27] Like, so even just the awareness of asking your. That question at each stage of, you know, following up after the discovery or, you know, getting to next steps or [00:21:38] proposal and negotiation or whatever the case is, whatever stage you're at, questioning yourself, like what you should do would be a good way to start to have a level of awareness of maybe, you know, approaching things a little bit differently than how you have in the past.

[00:21:52] Absolutely. Mike, it's been awesome having you on, um, we covered a ton of value here. I think we, I think we are going to have to have you back for part two. Let's do for, yeah, man, I think, I think it would be good. And we can, we can go, you know, further down the sales process, uh, on part two. So stay tuned for part two with Mike.

[00:22:13] Uh, we're definitely gonna make that happen and. Just let everybody know here, how they can connect with you, find out about what you guys are doing or what links are we going to include in the show notes for them to get into your, yeah, so obviously feel free to reach out to me directly on LinkedIn. If you ever have any questions or ideas to bounce, uh, related to challenger Michael Randazzo, [00:22:37] uh, on LinkedIn, um, I would say, uh, the best place to kind of consume.

[00:22:43] The tactical advice that sort of, we're sort of teeing up here today in this conversation. Um, we've got a monthly webinar and podcast series called winning the challenger sale. You can go to challenger Inc com slash events slash winning the challenger sale. Check around the website for, for our podcast and, and recordings and everything.

[00:23:04] Um, but, uh, that's where we really take, you know, if you've got your foundational understanding of what challenger is all about from the book, how do we actually apply those ideas and concepts to the day to day? Um, because ultimately it's all about execution from one call to the next, from one day to the next.

[00:23:20] And so simple tactical practical frameworks for getting stuff done, uh, in a really complex environment. That's what we're all about. So check us out. Awesome. We'll drop the links there in the show notes, everyone. I've you enjoy today's episode. Please write us a review, share the show [00:23:36] with your friends. It really does help us out.

[00:23:38] And as always, we're listening for your feedback. Hey, you stuck around that tells me you're serious about your own sales transformation. If you're tired of doing things the old way and want to get started in your journey with other people on the same path. Head over to sales, and crush your numbers on your leaderboard.

[00:23:56] Yeah. It's free sales Send me a DM with your best pitch and mention this ad. And I might even give you free access to our best templates.