The Transaction

Solving the Go-To-Market Skills Crisis in B2B Sales with Chris Orlob, CEO of pclub - Ep 64
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Chris Orlob: [00:00:00] We are in an era of a Go-To-Market skills crisis. Where reps and sellers are drowning in technology, but starving for skills and skill capacity. And skill capacity is dangerously low across the profession.

The bar for what we need is also getting higher. When the complexity of your go-to-market motion

goes from here to here,

but your skill capacity stays the same,

you've got this deficit that starts to look like this.

Skill capacity is what to do, why to do it , and how to do it so that you're building judgment.

Assuming you have the basics of your Go-To-Market strategy down, skill capacity and increasing that is now like a top three lever for you to pull as a Chief Revenue Officer. I think the right way to do it is to introduce a skill transformation loop into how you transform your sales team. So in other words,

is training a process or an event?

Matt Amundson: How's Newport Beach?

Chris Orlob: It doesn't suck.

Matt Amundson: No,

Chris Orlob: It's pretty good. I, uh, I took my kids to the, walked across the streets to the, [00:01:00] to the beach at the end of the workday a couple nights ago. I'm gonna play pickleball in Laguna tonight against my son. It's, it's pretty fun.

Matt Amundson: I'm still, yeah, Craig, well, Craig doesn't live here, but Craig is currently in, so am I currently still in Foster City?

Chris Orlob: Yeah, I'll probably may be making a trip back in the next few weeks 'cause my son really wants to go. 'cause he's still got such a good group of friends out in Foster City

Matt Amundson: right, well, tell you what, nothing has changed.

Craig Rosenberg: Tell him

Chris Orlob: except for there's no fireworks. They didn't do the firework show on the 4th of

Matt Amundson: Well, that's because they're redoing the, uh, the youth center. The teen center or whatever they call it.

Craig Rosenberg: Wait. Foster? No Foster. Did they do a drone show or anything,

Matt Amundson: No, no shows of any kind. No fun here.

Craig Rosenberg: oh. Um,

Matt Amundson: cigs and no fireworks,

Craig Rosenberg: God it.

Matt Amundson: no ripping darts, no blowing a finger off.

​[00:02:00]

Craig Rosenberg: So, uh, how many times has Orlob been on?

Matt Amundson: This is number three. If I'm no.

Sam Guertin: Well, I guess in, in total, yeah. I guess you would say three.

Matt Amundson: Oh

Craig Rosenberg: yeah, man. Uh, we really appreciate You're the best guest, dude. I, I just, you're well, oh, sorry. Everyone else that we've said, you're the best guest, but you're, you're all, you're, you're, uh, you're up there.

Matt Amundson: And your

face, Albro

Craig Rosenberg: Oh man,

Chris Orlob: I appreciate pissed.

Craig Rosenberg: He's gonna be pissed. He's at eight though, right? Or he

Sam Guertin: at a

Craig Rosenberg: at eight. Yeah. we just realized like, hey man, like when we have a good guest who's willing to share, we're gonna, we, there's no, we, we don't need to always mix it up. We gotta bring back the, [00:03:00] the stalwarts and you're one of 'em. All right, so, um, let's start Chris Orlob multi. Episode guest and like literally one of the greatest guys to listen to of all time. By the way, Matt, we did a workshop with him, like people were going nuts.

It was awesome for the portfolio.

Matt Amundson: Yeah, this is my surprise face.

Craig Rosenberg: Well, dude, I mean, you never respond to Mark's emails. So

that's why. I'm gonna.

Alright, so, all right, so let's start with this. So

An Instructive B2B Sales Story: How to Interact with Procurement Leaders
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Craig Rosenberg: Chris, let's kick this show off with a bang. Uh, tell us, um, give us a story, man. Something, uh, selling story. Let's go.

Chris Orlob: Do you want entertaining or do you want instructive?

Craig Rosenberg: Well

Matt Amundson: Entertaining.

Craig Rosenberg: entertain

Chris Orlob: All right. Because I've got a somewhat entertaining one, but it's not exactly instructive and well, I guess it

Matt Amundson: it could be what not to do.

Chris Orlob: Yeah, it's that kind of instructive.

Craig Rosenberg: Those are the bad.

Chris Orlob: So, uh, [00:04:00] I really hope I don't get in trouble for sharing this story,

Matt Amundson: You will be

Chris Orlob: here we go.

So we, we had, um, we had a new customer join us in June, um, over here at P Club. And it was a good size deal. I'm not gonna tell you guys exactly, but it was like close to close to a six figure deal.

And I had a little bit of heartburn over this deal because my AE had forecasted it like. With a high degree of certainty in May and May came and went and you know, there were a few blocking and tackling errors that we had MA made.

So it slipped in June and we finally got through those blocking and tackling errors and they introduced us to procurement. By the way, at this point, my face is on several dartboards in procurement offices across America. I'm certain of it, it's absolutely the case. Um, but I joined the call with my AE this [00:05:00] procurement guy who was, who was a nice guy, but he's a procurement guy and they're motivated to, you know, their, their, their incentives are at odds with a salesperson's incentives, let's just put it that way.

And so he comes in and he says, Hey, we're, you know, we're basically got ready to go forward this, or with this, I just have one problem. And I said, what's that? And he said, we got 40,000 bucks. Now keep in mind what we were asking for was pretty close to a hundred thousand. And I wasn't really in the mood to be like reckoned with that day.

Matt Amundson: Uh oh. Uh oh.

Chris Orlob: And I didn't like, I didn't say anything mean, but I was just kind of like, well, you know, that's, that's a significant gap. Um, compared to what we're asking. And so what do you do? What do you think we do about that? Because your sales team and your SVP of sales wants to move forward with this, and there are some significant problems in the business that we're solving for.

I don't know if you're aware of those. And he goes, it's 40,000 bucks. And I said, then we can't do it. And I think he was surprised that I [00:06:00] said We can't do it. I think he thought I was going to like, make some sort of concession and, and I, to his point, I don't think I phrased it in the nicest way. I probably could have been slightly more socially intelligent or emotionally intelligent or whatever.

Um, but we ended the call and it was like, okay, I guess we're not doing a deal. And so I shot an email to the SVP of sales and he called me shortly after. He was like, Hey, heard you were pretty mean to the procurement guy.

Matt Amundson: Ooh.

Chris Orlob: And I was like, it was actually like a parent child situation where like in kind of a nice way.

I was like, no, he was mean to me

Craig Rosenberg: No way. Thank you. Yes.

Chris Orlob: and this is kind of how the conversation went. And I was like. I'll make up a name. We'll say his name was Drew, right? The SVP of sales. I was like, drew, I'm only trying to defend what I [00:07:00] think is fair, right? Like, I'm not going to drop my price now, now. And anyways, like it ended up getting to the point where he's like, I want you to write an apology email to my procurement guy. And I told him, I'm like, and I, I was like, are we going to be able to move forward if I do this? And he was like, yes, I'm the decision maker. I'm the budget holder. And then I was like, okay, are we going to be able to move forward if I do this at the price that I think is fair?

Matt Amundson: Yeah.

Chris Orlob: And he was like, yes. So I wrote a apology LA letter to the procurement guy and it was signed within a couple days.

That's my latest story when it comes to selling.

Matt Amundson: Wow.

Chris Orlob: So not crazy, but uh.

Craig Rosenberg: No, I I've never, I've never been put in time out before and it was, it was humbling.

dude, he was mean to me is an incredible line.

Chris Orlob: I mean, that's not what I.

Craig Rosenberg: Yeah, I, is that not in the best [00:08:00] practices?

Matt Amundson: Oh God. Put that in the objection handling. Uh.

Craig Rosenberg: Okay. I,

Craig & The Case of The Bloody-Eyed Business Meeting
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Craig Rosenberg: you know what? I've been dying because now that I got you guys, I, I'm gonna get your guys' reaction on how, how, how I played this, and then you guys, if you have any others. Have you heard, have I told you the bloody eyeball story, Matt? No. Oh, I have, oh. Wow.

Matt Amundson: I I

Craig Rosenberg: So, so I had a, we had a big sales call on a Monday.

It was like, remember the days where we'd have to be in the room with like 10 people boardroom to like get the deal done and do your presentation and all that stuff. But I had gone to Reno with my brother who hadn't seen in a long time, and yeah. And I hadn't drank enough water is my excuse, but like I lost, I mean, I not, not my money, my.

Whatever I had eaten that day, let's just say all over the hotel room. I mean, I could not stop throwing up for [00:09:00] like 14 hours and I burst vessels in my eyeball to the point where it was totally red.

Matt Amundson: Mm-hmm. Demonic.

Craig Rosenberg: Demonic. And so I'm like, oh my God. Actually, at the time I wasn't even thinking about it.

I was just, we were driving home and my brother goes, bro, what the hell? And I'm just like, what? I look at him, I'm like, oh my God, geez. And I didn't even look at my schedule. The next day. I, I had no idea. But then I wake up the next morning getting ready to go and I'm like, oh my God, I got this huge sales call.

So I get in there, there's 10 people in the room, and I start to present and everyone. I could see they're like going, oh my God, what is going on? Right? And, uh, so I stop presenting and I just go, okay guys, let's just get the elephant in the room out on the table. I have a bloody eyeball. And they're, and the woman who's amazing, uh, still friend to this day [00:10:00] goes, are you okay?

And I said yes. I don't even feel it. I just had, I was sick this weekend and I, I burst, I, um, blood vessels in my eye and I mean, literally, I just see people just go, phew. Like they're relieved. They're not, uh, doing it out outwardly, but they're, they're relieved because they were sitting there, I was presenting like 15 minutes and they just couldn't take it anymore, like the bloody eyeball.

So, um. I'll give you the outcome. The outcome is we won the deal. The point I normally make on that is like in, uh, we called it the elephant in the room play, which is like, if something is patently obvious, you can't hide it. You just gotta get it out on the table and bring it out on the table. So, bloody eyeball story, did I play that correctly?

Not just 'cause I got the deal because I, I think the deal was pretty, this is sort of perfunctory meeting, but uh, if you have a bloody eyeball. Did I do the right thing? Chris?

Chris Orlob: I [00:11:00] think so. But you also could have like really played the role up if you wanted to and just like come across as the crazy person. You may have not closed the deal, but I wonder what would've happened if you, you know, like kind of intentionally twitched every now and then, or something like that.

Craig Rosenberg: Jesus Christ

Matt Amundson: if you said, Hey,

Chris Orlob: close the deal outta fear. They're like, I think if we don't sign this thing, we might all be in trouble. So

Craig Rosenberg: Oh, like the oh real fomo. Like the world's coming to an end, right?

Matt Amundson: you could have, and maybe, maybe you could have said, Hey guys, I'm gonna, I know the schedule for 90 minutes. I'm gonna have to cut it a little short. I've got a meeting with a priest after this.

Craig Rosenberg: Those are all great plays. Yeah. I mean, but basically you guys are suggesting, like there's this play here where like not just the bloody eyeball, but potentially like I just show up to a sales call on like a Viking costume, or I could have taken the bloody eyeball, walked in like a walking dead zombie.

And just like, guys, the end of the [00:12:00] world's coming. I like this.

Matt Amundson: the end is nine Yeah. I've been dying to ask Chris's take on my bloody eyeball story. He just, he, he threw me for a loop saying, go with it. That, that would've been amazing. Just sort of like. Yeah, I love it. All right, cool. All right, so, uh, let's do this, Chris.

What's Going on In The World of Sales
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Craig Rosenberg: What's happening in the world of sales? Like, give us three things, one thing, two things. Whatever it is that we need to know that works in today's environment. Um, and, and I can't wait for this,

Chris Orlob: well, I, I have a pretty, um, well developed and further developing take unlike what's going on in the world of sales right now. And the one liner I would say is we are in an era of a Go-To-Market skills crisis where reps and sellers and customer facing people are drowning in technology, but starving for skills and skill, capacity and skill capacity is [00:13:00] dangerously low across the profession. And there's actually a few like trigger events that made all of this happen. Let's first one was like the ZIRP era, 2021. 2022. Uh, budgets were loose. People were buying money was cheap. And so sellers, you know, your requirement for success was a decent product and a pulse, and so you didn't have to be all that good.

And so that softness, you know, they were then thrown into like a sudden jolt where the economy shifted overnight. Decisions are made way up here. Um, they're scrutinized. Buying committees are bigger and more risk averse, and because we didn't, we went through an era where we didn't need skill capacity, skill capacity was deteriorating all along and decaying all along

we just didn't notice it until the emperor's clothes were off because the shore dried up, and so that's one big thing is like compared to what we need, skill capacity, all time low. [00:14:00] The second thing that has exacerbated this is remote work, and I'm not even like an advocate against remote work. My company is a hundred percent remote today, but I'm just calling it for what it is, where you have a younger generation.

Of account executive typically, right? Like most AEs these days, particularly in SaaS and technology, like mid to late twenties, they entered the workforce in the ZIRP economy and now they're in this new economy that demands greater skill capacity, and yet they've all been remote. And so their ability to rapidly build their skills has been really, really limited.

And then the third thing is just the abundance of AI and tooling and, and the ease of efficiency in some cases at the expense of effectiveness. And so when you look across basically the entire Go-To-Market profession compared to what's needed, there's a big deficit of skill capacity. [00:15:00] And I think a lot of sales leaders have been a little bit burned in fixing it because they have confused sales process.

With skill capacity, the solution has been process, and process is fine, but the definition of process is it stops at what to do. Here's what to do. MEDDIC, MEDDPICC great examples, right? Go do this. Go get the med, the metric, the economic buyer, the decision criteria, et cetera. Skill capacity though is a different thing than process.

Skill capacity doesn't stop at what to do. Skill capacity is what to do, why to do it and how to do it so that you're building judgment and reps can have audible ready, rich business conversations that create value for, for buyers and customers. So that kind of trend of like, we went from an era that was basically led by economic tailwinds to one that now demands significant skill capacity, and yet [00:16:00] we're pretty low as a profession

when it comes to that measurement, if that's what we want to call it, that's the biggest thing I've been noticing lately.

Craig Rosenberg: Okay. You know what's interesting? We just did, uh, some Go-To-Market benchmark research, and one thing we found was especially, uh, when you're selling AI that win rates are down. And I know everyone talked about from ZIRP to now, but like now it's like, we're in a new now. And, um, what you're, what you're talking about, um, it really resonates with me 'cause we have, what you see is this uber competitive market very. Confusing and being able to sell, uh, is an Im, it's an imperative here, unless you have like a killer PLG play. Like, and, uh, and so what, what you're saying is, well, we're going into this issue, this hyper competitive issue without the skills in order to be [00:17:00] successful. and, and the second thing that really resonated with me is like, AI is there to enhance what you figured out is great. It doesn't, it's not gonna come with great. It's like all the automation that you need to. So I, I'm in favor of automation, but not until you figure out what great looks like and how you could support Great. that, that's the thing is that the AI is not the solution to the skills gap.

It could help maintain it, but like we have to, we have to determine from a uniquely human perspective what actually is gonna work.

Chris Orlob: it actually just dramatically exposes the skill gap because it puts reps in a position where if they were very good they could, you know, they, they, they would be closing like crazy, but it puts them in more situations that expose the la the, the low skill capacity we've been talking about. And so to answer your question, you posed earlier about [00:18:00] like, what are you seeing, what are people focused on?

What's working? I'm seeing skill, capacity and the growth of skill, capacity becoming one of the most important levers. Um, and going from almost like a, a nice to have perk to somewhat existential depending on how you look at it, right? Because if you look at the Chief Revenue Officer, the commonality between all of them right now is they, for the last several years have been asked to do more with less, right?

We've exited the growth at all cost era. We've exited the era where my strategy for growing revenue is headcount driven, and now it's about getting more out of the team that I have. And so if revenue per rep is one of the biggest metrics of success in today's economy. Well, what's your levers for driving that?

It's not just skill capacity, right? It's, it's tight ICP targeting it's product market fit, but assuming you have like the basics of your Go-To-Market strategy, down skill capacity and increasing that is now like a top three lever for you to pull [00:19:00] as a Chief Revenue Officer, now on the other side, so, so that's what makes it existential for the business.

What makes it existential for the rep, is we're in a tough job economy where sales leaders now, because they're trying to get more with less, are only hiring the best of the best, right? So if, if there's not an abundance of open head count, they're going to pick the people who already have high skill capacity if they can.

And so reps who have not taken their professional development seriously and haven't accelerated their own skillset in some way. They, they're more exposed to some of this AI disruption than people who are very good, regardless of whether the economy is good with them.

Matt Amundson: Yeah.

Craig Rosenberg: Man. You

know what's funny, Matt? You, this was your original. This honestly, like I've been, we've been, how long have we been doing the pod? Two years.

Matt Amundson: 17 years, I think.

Craig Rosenberg: We have, [00:20:00] we haven't gone back to Matt's thing has always been, uh, I'm gonna speak for you. Just 'cause you were, that was the thing. You used to always pound your fist on the table.

I've made you move away 'cause we've had all this AI stuff, but like you used to say no, you like we have. A selling problem, you know? And like I, right, that was like your thing. But for a long time it's like, dude, you, we gotta, these guys the,

Matt Amundson: a lot of salespeople mad at me. Got a lot of salespeople mad at me, but, uh, yeah, I did. Um, but the thing is, is like, you know, when I began my career in SaaS, it was at Marketo and, you know, Bill and, and Patrick and those guys, and, and, and, and Ray, you know, they, they trained the shit out of our reps. It was constant.

It was, you know, it was an hour of enablement every week. And that enablement, yeah, it included like, here's some new marketing programs and here's new product releases and here's how to talk about that. But it was like. [00:21:00] Here's how to run a first call. Here's how to improve the, the quality of the way you qualify.

Here's pricing negotiation. Here's how to, you know, tie, you know, benefits to problems in the organization. Here's how to make a business case, right? Like, and those are things that I feel like, you know, when I see modern sales organizations like their enablement is always. Here's this new product, or we're gonna be at Dreamforce this week.

And it's like, it's a lot of, I mean, that stuff is important. I'm not saying it's not, but it's like

it's, yeah, it's fluffy compared to like, what do you do when you're in Chris's situation and your buyer has agreed to a deal and the procurement team comes in and says, I don't give a shit. What? You know, drew said. We we're only giving you 40 grand for this. You know, like I can tell you, 99.9% of the sales reps that I've worked with over the course of the last couple years would [00:22:00] not know how to handle that situation. They'd get it solved 'cause they'd take it to the CRO or they'd take it to our C uh, somebody would help them solve that problem, but on their feet, they'd be like, dude, I don't know what to do here.

Chris Orlob: Totally.

Craig Rosenberg: but how should we think about it, Chris? Like it, because you're saying, I mean, are you saying across the board we have a skill pro like every, or, or should we be thinking about it incrementally or like what's the, or where are the biggest areas where you see pain or, you know what I mean? Like I, I want to like turn this into, I think. I think we agree, but like, what, what, what should we do? Like how should we approach

Chris Orlob: well there, there are a few philosophies that I, that I think are helpful to start moving the needle fir. First of all, I think it is pretty widespread the, these days. I think it's pretty rare for me to come across a sales organization. Where the Chief Revenue Officer feels like things are buttoned up from a skill capacity, they, they exist.

I'm not saying they're not there, but it's just rare and it's, it's very. It's very surprising when I have [00:23:00] a conversation that goes that way. Um, so one of the things to realize, um, this isn't actionable, but it'll give you the right mindset to action on it, is just making that first distinction between process and skill capacity, right?

Are we directing our team on what to do, which is a good start, but if it stops at stops there, it's not skill capacity. We've gotta do the what, why, and how. The second mistake I make is we like to make a distinction between skill depth and skill breadth, right? So breadth. That's the multitude of skills that it takes to be successful in a given role.

Right. So if you're a typical SaaS ae, that might be discovery, multithreading, champion development, running great demos, running a closing motion, negotiating, et cetera. That's the breadth of skills you need. Depth is getting really good and really deep at one of those skills. And what I've found is sales organizations who are trying to build skill capacity, they [00:24:00] do a a, a common error that's driven by instant gratification, which is they try to tackle breadth.

Before depth. They'll roll out a training program that touches on every topic, and as a result, they go a mile wide and an inch deep. And the reps have no lasting change. They were dabbled with Multithreading, they were dabbled with discovery, dabbled with demos, dabbled with this, that, and that. And they walk out of it with nothing that lasts.

And what I found is the sales organizations that truly wake up. A year from now, two years from now, to a completely different sales organization, a formidably, excellent sales organization. They go deep before they go wide. They say over the next 60 days or 90 days, we are going to master the discovery craft.

Matt Amundson: Mm-hmm.

Chris Orlob: when we feel good about that, we're going to stack the next still skill, multi-threading, whatever, and we're gonna build this [00:25:00] portfolio of mastered skills over time that stack on top of each other instead of let's try to do a little bit of everything and hopes it solve and hope it solves our problem entirely a quarter from now.

Meanwhile, all they've done is motion without accomplishment.

Craig Rosenberg: Hmm. Motion without accomplishment. I'm gonna get that t-shirt made. I love that. So, That's the name. That's the name of my next album.

yeah, I, I, I told actually that everything you just said. A hundred percent resonates with me. How do you figure out where to start though? Like should you just go like left to right, like the first step in the sales process or like what?

What do you do?

Discovery is the Fundamental Sales Skill That Reps Need to Learn
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Chris Orlob: I, I think it can be unique to the selling environment, right? What, what are the skills that matter for our unique selling environment? Where's the biggest gap of all of those? What do we think is gonna be the biggest unlock, right? Often that's gonna be discovery, because discovery is what I would call a threshold skill, meaning you almost [00:26:00] can't be good at the other skills until you're good at discovery.

That's not to undervalue the other skills. They're separate skills from discovery. They're very different. Being great at discovery is not going to make you automatically great at demos, for example, but it's kind of impossible to be great at a demo or a business case or negotiating and defending price with value if you haven't first uncovered and developed everything you need to be able to do those things.

So I think the answer is, it depends. If I was to give a canned answer that's maybe applicable 60 or 70% of the time, it's probably discovery.

Craig Rosenberg: I agree. That was a setup. I mean, like, you know if, yeah, well, no, but like, I remember in the days when we used to do this, someone would say, well, we need help with negotiation. And it's like, we would go in there and discovery was the

problem. They'd say, we're doing a terrible demo. It's like, well, discovery was the pro, you don't even know what to talk about in the demo, bro.

And so I get that and, and so it totally resonates. [00:27:00] What's discovery like the, well, first of all, I'm gonna tell you this. Uh, from what I could tell from people buying stuff, and Matt tells me all the time, they don't do discovery at all or very well. So like, you know, like they're jumping into tech demo outta the gate, and even if they ask us a question, I'm not even sure that it feels like it's sticking.

Like it, it doesn't, it almost was like on a list of things to ask, but not really meaningful. So like, what, where are we with discovery in this world? And like, how, how should we approach it?

Chris Orlob: Well, the, the first thing I want to talk about or, or just like preempt. Is I'm not attacking sellers when I say everything I'm about to say or everything I have said. In fact, like it's not their fault, right? Like most of them are mid to late twenties. Like I said, they've entered the work workforce within the last five years.

The economy fell out through from under them like few generations have had to deal with. And nobody has guided them. Nobody's given them the playbook. So, so that's my, that's my preamble to everything I'm about to say. [00:28:00] Um, when I look at the status quo of discovery across. The AE profession there, there's usually a couple thresholds.

Number one is no discovery, right? It, it's just not being done. I actually don't think that's the most common one. Like I, I'll give some credit where credits due. I, I don't think that's, you know, that's maybe 20% or something like that. I think the most common is the next two buckets. The next bucket being qualification but not discovery.

Right? I'm gonna ask the three or four questions that tell me whether this person's a technical fit for what I sell rather than a business conversation. The next layer after that is a business conversation, but it's a checklist. It's, I'm gonna ask you five pain oriented questions that feel generic and come across that way to the buyer.

And those first three buckets between no discovery. Qualification, but not discovery. And then a checklist oriented discovery. I, I would estimate that's 80% of B2B sales organizations today, 20% are fluid [00:29:00] and can have insightful problem solving oriented conversations that aren't just about extracting information for you as a seller, but are about having a conversation that helps your buyer solidify priorities and crystallize the problem and what have you.

Matt Amundson: Yeah.

Yeah. with that, Matt?

I do. I do. And, and one of the things that, like I find when I'm being sold to nowadays and, and not that much 'cause I'm not really buying much, but is I'm being qualified more than anyone's doing any real discovery. And what that means is it's like really easy for me as a buyer to walk away from the deal or just say like, eh, now's not the right time.

Let's check back in down the road. Is uh, which is just me being nice, is, um. If they can't build a case for me of how they're gonna solve my problem, I don't really wanna buy it. I just don't wanna buy it. Like I'm just, I'm, why would I be [00:30:00] enthusiastic about it? Right? Like I always think about like the pain of implementation and enablement, how many cycles I'm gonna have to spend, bring something on board.

Adoption, transformation, enablement for anybody else in the organization who's gonna use it or read the reports that it's spitting out whatever. I'm just like, ah, that's a hassle. If it's not solving a big problem for me. And we can, we can sort of build that case together. Like, I just don't care. So like, usually what I find is I'll hop on this call and they're like, oh, how many employees, like, uh, roughly what's your revenue?

You don't have to tell me exactly, but is it here? Is it here? Is it here? Um, you know, what are your plans for the next six months? It's not like, you know. What metric are you trying to impact? How valuable

is that to your organization? What does that mean for sales? You know, what does that mean for sales now?

What does it mean for sales six months from now when it, or a year from now when it comes to renewal, enablement, upsell, like all that stuff. Like nobody is having that conversation with me. And that was the thing [00:31:00] where like, you know, because I started my career where I started my career, I just thought that that was just a thing that everyone did.

Right. Like that was just a part of it and I was just, you know, the, the further I get away from Marketo, the further, you know, I, I really value the sales leaders that we had in that organization. 'cause they were just so a plus.

Craig Rosenberg: What about Chris? I want to ask you about that. We've had a couple guests on that have, I would say they're more AI centric, but they make a really key point as we think about discovery, which is one of the best things we could train these and, and young reps on is business acumen, like, so that the, yeah.

So, because there could be an, there's an interpretation issue often if, if they're going through their checklist. Uh, do you, do you believe that is, that that's a true statement that

Chris Orlob: Uh, well, it's not just true, but I think the need for it is expanding, just like the need for skill capacity is expanding. We're almost building a backlog [00:32:00] of debt. When it comes both to both skill, capacity and business acumen. And, and what I mean by that is we've already talked about the things that have set the stage right?

Like there, there was the ZIRP era and the transition there. There's the fact that we've all gone remote. The the workforce is younger for AEs, typically, those have set the stage. At the same time though, companies are becoming more complex in their Go-To-Market motions, right? There's a need to become multi-product and become a platform.

Competition is increasing in most categories, and that makes the go-to market motion more complex. And when the complexity of your go-to-market motion, you know, goes from here to here, but your business acumen and or skill capacity stays the same, you've got this deficit that starts to look like this.

Matt Amundson: Yeah.

Chris Orlob: So we didn't just get tossed into this world where it's like low scale capacity, low business acumen compared to what we need the bar for what we need is also getting higher across many [00:33:00] categories.

Matt Amundson: Yeah,

Craig Rosenberg: That is so true. I, uh. I, I every, I, I hate to, I want to be more, um, I

Matt Amundson: you wanna back on

Craig Rosenberg: you more. I know, but I can't. He always nails it. That's why I love this guy. I, I just, I love your stuff. Um, so I think that makes total sense. I want to, I'm kind of moving down the line in all the experiences I have.

How B2B Companies Should be Approaching Discovery and the Buying Process in Today's Market
---

Craig Rosenberg: So, but, but like for discovery, we talked about this with you before. There's so. Do we, are we back to how, how long should we take for discovery and how do we get that? Because the buyer wants to see product more and more, or is, I don't know if that's true, but early. I think that's true, right? That the, I mean, they, they want the, the demo is actually a byproduct of what the buyer wants typically.

So we've talked about this before, but now we're in this. Frankly, from the last time we talked to you, we, a lot has changed [00:34:00] and the, it's gotten even more competitive and more confusing. So, uh, is, is it optimal to spend an hour just doing discovery or is this a stupid way to be thinking about it? Like, how deep do you want sellers to

Chris Orlob: Yeah, I, I think it, I'm gonna give you a concrete answer, but I'm gonna start with the abstract, which is, it depends on the buyer's stage in the buyer's journey, as well as the role that they're wanting or expecting from you as a seller. So, I'll give you a couple of concrete examples. If they're coming inbound, they've solidified their problem.

They, they, they, they know what they want. They have high urgency. You doing an hour of discovery before and, and insisting that you don't show the the product. Big mistake. You can do both though, right? You can play a game of tug of war where you can say something like, you know what you want more than most people I talk to, which is great.

Um, that, that tells me you probably have a well-defined problem. You've probably had meetings about [00:35:00] this internally. And now you wanna see a solution. And so how about we play a game of tug of war? How about I show you a couple things that map back to what I think you're going to want. And in exchange for me doing that, I ask you a couple questions about what's going on in your world.

And we just play that loop throughout to increase our mutual understanding of each other. I, I've used that talk track a hundred times approximately. Guess how many times I've received pushback on that? Zero.

Craig Rosenberg: Oh, I was gonna go with a small number.

Chris Orlob: Yeah. I mean,

Craig Rosenberg: is the smallest number.

Chris Orlob: yeah. Never they're, they're like, that's the exact kind of conversation I wanna have.

Now there's another type of buyer who demands to see the product, but is not far enough in the buyer's journey. Like the the first person I mentioned. Now, why do they demand to see the product even though that even though they're not really there yet, they're not in solution mode because they don't see the seller as a credible thought partner.

They, they [00:36:00] don't see a discovery conversation with the person I'm talking to as being productive. And so sometimes when people demand to see the product prematurely, it's not a sign that they're like at the bottom of the funnel. It's the sign that they are saying without saying, like, without being explicit. I'm going to diagnose my own issue. I don't trust you to diagnose my issue, so show me what you have so that I can mentally map back to my own problems, and you're just going to be there to inform me while I do this myself. Now, if you happen to be high acumen, high business acumen, able to deliver insight, able to ask very good questions, those same buyers that they're surprisingly devoid of wanting to immediately see the product.

They want to engage with a conversa in a conversation with you because now they see you as credible. But that bar is up here now and as a professional, we're, we're about right here.

Craig Rosenberg: Interesting. All right. I love that. All right. Can I keep going down the line, [00:37:00] Matt?

Matt Amundson: You're, you're allowed to. Yeah.

Craig Rosenberg: Okay. What's the biggest issue? Uh, I, I, I'm saying it in a negative, but you always twist it in a positive 'cause you're a good guy. the demo. Uh, like, well, we could ask Matt what he thinks the biggest issues are with de, but like, what, what's the, where are we stubbing our toe today on the demo, and what should we do differently about it?

Chris Orlob: Matt, do you wanna answer first or do you want me to?

Matt Amundson: Yeah, so what I've seen. Uh, change the most, uh, now is in addition to getting into the product faster, we, I also get to some kind of se, se, se whatever we're calling the technical component of selling faster. And so, like, it is not unusual for me to go to a first call, be maybe handed off by a BDR, although I usually request demos.

So like they're usually not there. [00:38:00] Uh. Meet a salesperson who talks for four and a half minutes, immediately be punted over to another person who then will take me through the demo, and then at the end I get a salesperson who says, so what do you wanna do next? Right, like, I mean, just the worst of the worst types of sales, uh, uh, execution is what I see on more, more often than not.

And I'm not saying that to be an asshole. I'm just saying it because it's my own anecdotal personal experience. I think that's the thing that bugs me is that like I'm on a call, there's two people on the call, there's another person who, you know, they do the sort of lazy podcaster thing, which is like someone's.

Presenting and I'm talking or responding, and they're in the back going, mm, Mm-hmm. Mm-hmm. And I know it's fucking bullshit, right? Like, I know that they're not hearing me for what I'm saying at all. Like, they're like, mm mm Oh, foster City. Yep. [00:39:00] Mm mm mm-hmm. Oh, Marketo, huh? Yeah. Mm. I'm just like, What What does that even mean? So like.

Craig Rosenberg: is the mm mean?

Matt Amundson: Yeah. And I do that on this podcast and I'm always like, God, you're a lazy podcaster. But like, uh, um, like that's the thing. I just, what is that guy's value or that gal's value? Like what, what is their role on this call like, and, and, and how have we gone from, you know, sellers who could, you know, pre.

Predate BDRs, right? Sellers who could prospect Sellers, who could sell sellers, who could demo sellers, who could negotiate. Like we're chunking out all the skillset. And I'm not saying that like there's no place for sales architects or whatnot, 'cause there are, but like where does the modern AE begin and end?

It feels like that's like their portion of the sales cycle is like really truncated at the beginning and then it comes back on strong at the end. F as a buyer, I, I'm just like, who am I talking [00:40:00] to today? I can't remember everybody's name.

Craig Rosenberg: Hmm. I, I've seen that dynamic get even more accentuated with AI solutions.

Chris Orlob: Be because sellers, um, you know, they, they can't explain how AI works. And so like, I've even seen, seen many motions where se aren't pulled in, but product managers are

pulled in to like the first or second call. And that's just another example of like skill debt, right?

Like knowledge for what you're selling has gone up dramatically. Ai, lots of every SaaS solution on the planet it feels like at this point has some aspect of AI and sellers don't know how to talk about it. And so they, they pull in somebody else. The other thing I'll say about demos, I don't, I don't think this is particularly new.

I think it's gotten worse for all the reasons we've, we've already talked about in some of the trends, but, uh, most demos that I experience are point and click feature tours rather than, earlier you shared X, Y, Z problem was happening in your [00:41:00] organization and it was creating these negative impacts and you were dealing with it because of X.

Here's how we address that. Right, that that's simple, but like now the posture of a demo is about solving your problem rather than let me show you how all this works and how cool it's.

Matt Amundson: yeah.

Craig Rosenberg: That. Yeah. I love that. Um, alright, so we don't have much time because I wrote down that I was gonna ask you this, so I'm, if I stump you, that'll be great. Oh yeah. I, okay. First of

Matt Amundson: we've gone to the game show portion of the podcast. I

like this.

Craig Rosenberg: F. Okay. Sam, do you mind capturing the sounds that matches made? The, oh,

Matt Amundson: Yeah. And a super

cut.

Craig Rosenberg: a different, different than Mm, right?

Mm-hmm. Mm-hmm. Yeah. Yeah. Um, so who's the best rep you've seen over the last two years and what was so remarkable about that? We can learn from them.

Chris Orlob: Over the last two years.

Craig Rosenberg: don't know. I made up that timeframe that, that part of the [00:42:00] question I could not figure out, but I, I just want someone, an example. You're, you're just one thing about you, man.

I know you, you talk, you part you like, you learn as much. Selling shit and training these folks is like anybody, but I just like give, I just want like this rep that you're like, you know what? I love this about

Chris Orlob: Yeah. Um, it's actually one of my reps. He's the, the top rep at P Club. He's an ae and what makes him so great? Is he can sell category visions, not just transact products, right? So like everything we've been talking about with like the transition from Zer to this new era and scale capacity being dangerously low and all that kind of stuff, he has the acumen to be able to educate buyers on all of that during his sales calls when he's selling P club.

And it's really rare for an account executive to do, right, like even great account executives. It's, I'm gonna diagnose your problem, I'm gonna offer a solution. And that's that [00:43:00] he, Ryan tidbits, he changes how buyers think and feel about the problem at hand. Kind of like in the way that we've been having this conversation today.

And it's a very real or very rare skillset I've seen across account executives,

Craig Rosenberg: That you went with the uh, the in-house. Do you want to tell us his name? We she, he, geez, he

Matt Amundson: did.

Ryan tidbits.

Chris Orlob: brain.

Craig Rosenberg: tidbits. Oh, I

Matt Amundson: No, not tidbits. I love this guy. I wanna meet Ryan.

Chris Orlob: Oh, he, he is,

Craig Rosenberg: say his name.

Chris Orlob: he, oh, the, well, the other, his name's Ryan Tibbits. Yeah. The other thing that's really great about him is sometimes as a sales leader, you coach and it's like you're talking to a wall. You're like, thi, this rep is not gonna implement anything I talked about Ryan is like the definition of speed when it comes to acting on coaching.

Anytime I'm on, I'm on a call with him. We, we'll hang back for 15 minutes, not because I'm a nice person or I want to develop him, although I [00:44:00] hope those are true, but because it is a very high ROI, 15 minutes for me, I'll say, you know, we'll, we'll have a 15 minute coaching conversation. At the end of it, I'll give him one new direction to go work on next call.

It's implemented. That's rare.

Craig Rosenberg: And what's this guy's name again? No, I'm just kidding. Sorry. That was, dude, I can't believe I did that. I did the lazy rep thing or podcaster thing. Okay. That was great.

Why B2B Sales Leaders Need to Implement a Skill Transformation Loop Into Their Teams' Training
---

Craig Rosenberg: Okay, last one that, um, so I, the skill, we have the skill gap problem. When we address it, obviously we buy P club, but like I what. So you were saying like, let's go deep on, let's say discovery.

We do it over X amount of time. What, how do we do this? So we, we get trained on it. Create a methodology, I'm sorry, we create a methodology for our business. Train them, listen to their calls or practice or like what, how would you recommend we go,

Chris Orlob: [00:45:00] Well, I,

Craig Rosenberg: go deep.

Chris Orlob: I, I think the right way to do it is to introduce a skill transformation loop. Into how you transform your sales team, right? So in other words, is training a process or an event? Because most people treat it as an event, right? We're going to cram everybody into a zoom room, we're gonna teach 'em. It's an adrenaline shot to the arm. Everybody's hair is standing up by the end of it, and three weeks later, nobody, not only is nobody doing anything, they have no recollection of even being there. Okay? That's like typical sales training, a skill transformation loop. Is a multi-step process that you repeat.

It starts with diagnosing the issue, training the reps, entering a practice environment, having the reps intentionally apply it in a real environment, reviewing it, reinforcing it, measuring the results, and then looping that in a never ending way that leads to formidable sales excellence. And so the, that was kind of a complicated way of answering the question.

The short way of answering the question [00:46:00] is transitioning from sales training. Which is an event to skill transformation, which is a process, event versus process.

Craig Rosenberg: but, and then, but like, I hate to, this is not an advertisement for P Club, but do you diagnose or do you train the sales leaders to diagnose on their own? Or how, how should they do that?

Chris Orlob: Well, you, you don't need P Club to do it, right? You can, you, you can do it yourself. Um, we do it for companies, um, at the start. We both have trained enablement practitioners who do it. Um, one of the things we have coming down the pike is AI based skill intelligence, where we connect to Gong and, um, nooks and, and Orum and Salesforce and use

tons of data to be able to benchmark your sales organization against the skills that matter to you. So, so that's another way that, uh, we plan on delivering against it. But, you know, P Club just makes it really easy. Um, you can do all of these things in house if you want it to.

Craig Rosenberg: Yeah. Okay. [00:47:00] And then, uh, it's an infinite, like we're, we're, we're always so even though, because we're talking about depth versus breadth, there are other areas we're gonna have to go train against all these areas that we dug in on. So like. Um, we're, but we're still, we never leave the sort of the loop on our training for discovery or demo or, you know, whatever it

Chris Orlob: And, and new skills crop up, right? Like if, if you taught your SDRs three years ago on how to do cold email copywriting before ChatGPT and AI were tools of the trade to do that. Well, they have a need for an updated skillset now. And, and I'm not saying how do we rely on ChatGPT to do our job or anything like that, but there is a new tool belt that people have and so.

S sales train or sales skills. Some of them are timeless, some of them are evergreen. Some of them move with the market though. And if you want to future proof your organization, it does have to keep, you know, you have to keep doing this [00:48:00] on a continuous loop if you want to be the best.

Craig Rosenberg: Matt, do you want to be the best

Matt Amundson: Uh, usually,

Craig Rosenberg: usually? I like that.

Matt Amundson: yeah. I don't wanna be the best at bad marketing though.

Craig Rosenberg: You know, I gotta tell you, uh, Chris, I. I asked you, every time I talk to you, I have you go through discovery and demo. Uh, your, your general philosophy has remained the same. Uh, I do see you adjusting with the market. That's why I should have said at the start, Hey, I'm gonna ask you this again. Uh, but like, I, I, uh, I, one of the things I appreciate you is I get.

Like where you're trying to get folks to, I know there's, you know, as the market continues to evolve, you'll make, you know, slight changes to the ways that they need to play it. But I, I always understand where you're trying to take things and so that's why I love having you on the show. I like having you [00:49:00] trying to expose people I know to the stuff that you're doing.

So I just, I really appreciate it and, um, it was awesome.

Chris Orlob: I appreciate y'all having me on.

Matt Amundson: What a great Who.

Craig Rosenberg: Yeah, it's always a good one with this guy. Speaking of other people at P club though, so we had Kristen on, uh, should we have her on again? Is there someone

Chris Orlob: Absolutely. You should. She's a Well, she,

Craig Rosenberg: well, she was so, yeah, she was so prepared. She, I don't think she was ready for me.

Um, and, and

my zaniness No, that's a good point. But I, no, but if I, maybe I'll try the bloody eyeball play that you guys

are talking with her, she. But she's so organized in her thoughts, like you, I don't know if you train them on it or you screen for it,

Chris Orlob: That's not me. That's all her. Yeah.

Craig Rosenberg: her, her thought organization was like extraordinary.

Like it was, yeah, just the way she thinks about things in like groups of three or four, like bullets and like, uh, sequentially sort of delivering, you know, what she's talking about. Amazing [00:50:00] stuff. So. All right, we will have her on again because we are now reminded how good you guys are over there. So, um, thanks again bro.

Appreciate

it

Chris Orlob: thanks

Matt Amundson: Have a great weekend.

Thanks for joining us for another episode of the Transaction, Craig, and I really appreciate the fact that you've listened all the way to the end. What are you actually doing here? For show notes and other episodes, please visit us@thetransactionpod.com, like and subscribe on Spotify, apple Podcast or any other place you get your podcast from.

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