The Transaction

Craig Rosenberg: [00:00:00] I'm fat, I'm gray. I mean, it

Sam Guertin: say that again, now that we're recording.

Matt Amundson: Yeah, you hit record at the perfect time.

Craig Rosenberg: Oh, jeez. It says that I'm fat, I'm gray. Look at, look at Chris just coming in hot. Love this guy.

Chris Orlob: How are you guys doing?

Matt Amundson: Oh man, great now.

Craig Rosenberg: I know, and actually, we are saying that truthfully. We are very happy to see you. Um,

Chris Orlob: happy to see you guys too.

Craig Rosenberg: So I had this guy at Topo, uh, named Tom, and he used to insist that he would start every business workshop. So let's say there's. You know, [00:01:00] 20 executives, you know, director up in a room getting ready to do some go to market workshop.

And he'd make everyone in their intros go around the room and say the first concert they went to. And it was so cringy, but it was amazing. It worked great. All right, so let's go around the horn. First concert, Sam.

Sam Guertin: Three doors down

Craig Rosenberg: Uh, if that's a concert, I mean, was this like at Disneyland in Frontierland or something? What the hell is he

Sam Guertin: I have not been to a lot of

concerts so

Craig Rosenberg: Okay, well, that, yeah, you're no fun.

Orlob, how about your first concert?

Chris Orlob: I was 16 years old and somehow my parents let me go to Motley Crue.

Craig Rosenberg: Oh, I might come close to you. Wait till you hear mine. All right, Matt, yours? That's awesome, by the way. Wait, was that Dr. I don't know, I don't know how old you are. Was that like the Dr. Feelgood tour?

Chris Orlob: No, this was like, this is when they came out with like their latest album. I think it was called like Saints of Los Angeles, but it was like the one. They must've come [00:02:00] out with it in like 2009 or something like that. So it wasn't, it wasn't Dr. Feelgood. I mean, I'm sure they played Dr. Feelgood, but it wasn't that tour.

Craig Rosenberg: Okay. saw them perform at the draft

Sam Guertin: last year That was the best

Craig Rosenberg: Matt,

Chris Orlob: He's always drunk. Like he's, everybody in that band is like good live, except for Vince. He's just like shit faces entire time. And you can't understand that.

Matt Amundson: right, Craig. Technically, my first concert was 1985 at Cal Lutheran University in Thousand Oaks, California.

Craig Rosenberg: where are we going?

Matt Amundson: I saw, I saw Raffi, uh, doing, doing Baby Beluga tour. Just incredible stuff. Uh, my first like real concert though, is I, I went to the, I went to the Warped Tour in 1994, I want to say at Cal State Dominguez Hills and saw one of the last live performances by the, the actual, uh, Sublime Band, not like, Hey, we've replaced, [00:03:00] uh, The, the, the lead singer, uh, and I'll, no doubt was performing and, uh, it was, it was amazing.

It was a lot, it was more of a punk show, but, uh, but those, those, those folks were still big or were not quite big yet.

Craig Rosenberg: That's actually pretty good. So mine was, this will age me based on what you get. The, actually the insight here is that I'm significantly older than you guys. My first concert was in sixth grade. Judas Priest Defenders of the Faith Tour at the Cow Palace with my dad and my buddy Siobhan Chakori. Unbelievable. My poor dad who isn't, he's not one of those dads that even listened to the Beatles. This guy had season tickets to the San Francisco Opera and Symphony for like 40 years. So like this was Taking one for the team. It was amazing Um, all right, so that that's I just had to ask you guys. I I literally was just Thinking about that the other day.

I think I we brought it up, you know, [00:04:00] maybe at dinner the other night I don't know like I just want to throw that out there. Okay, so Chris I just want to say this Like dude, when we did the show with you, it was so unreal that like, , we just, we wanted to bring you back and it was just that good.

And so I'm just that when Matt was like, we're really, now his day is better that you're here, he was serious. Now, I don't know what was happening in the rest of his day, but like, it's, it's that exciting. So I don't, I'm just going to say on the intro. We talked about this last time. So, you know, by the way, I didn't know you're at Insight Sales.

When you were at Gong and you were doing all of that content, like that's Matt and I still marvel at that. We still tell stories about that because that was like the start of this run where you were just in my face all the time, telling me things that were not typically talked about in the market.

Right. So, you know, in your days at Gong, when you were first listening to recordings and first, you know, sort of. Looking at sales in a different way was when we [00:05:00] all, at least Matt and I got really exposed to you. And now, uh, with P Club, which is a online sales learning platform with a library of content, it's gotta be amazing because your LinkedIn action right now, man, is

Matt Amundson: Yep. She

Craig Rosenberg: So, uh, I just want everyone to welcome Chris Orloff. To the new show, the transaction. Chris, welcome to the transaction.

Chris Orlob: I'm happy to be here. If I, am I right in seeing that you guys talked to one of my old bosses recently. Kelly, right? Was she on here?

Matt Amundson: Yeah.

Craig Rosenberg: Inaugural. Yeah,

Chris Orlob: and we got to talk to her.

Craig Rosenberg: that was awesome. You know, cause she's doing the culture driven sales stuff. So she had like a, you know, a thought process that allowed the story to like move in a really compelling way as she was talking and use examples. Like unbelievable. So good. Um, all right, well that was not, we did [00:06:00] not.

necessarily make that connection when we had her on. So now that we have, boom, look at that. We got the some Gong alumni going. So, Let's start with this because we started with this last time. I don't know if this has changed for you, but as you know, what we like to do is, uh, say what, like, are there things that the market thinks are true or best practices or a way of doing things?

And actually they're wrong. They should be thinking about it in a different way. And, and, you know, you answered it for us last time. I don't know if your answer's changed, but we'd love to hear it. So

Chris Orlob: What did are you at on that right now?

can't remember what I said last time. What did I

say last time? asked, you actually said it's not, you know, we sort of presented it as being surprising and you said, well, it's not really surprising.

Craig Rosenberg: And, um, you know, you were sort of locked in on, I think it was just kind of value building and, and some like really, um, sort of foundational stuff that you, you know, you said, look, I'm not going to surprise you with this. We [00:07:00] just got to do better in terms of, you know, uh, assembling value on behalf of the customer.

So that's kind of where you sort of lost. I'd like to. You know, it was a perfect lead in last time. I don't know. I mean, it's been four months.

Chris Orlob: I'll give you one. It's not really sales related. It's

Matt Amundson: Ooh. Okay.

Chris Orlob: And I'm like the world's

least qualified marketer of all time, but I still have strong opinions about it. Um, I I feel like everybody is like anti gated content. And I'm actually not like, I'm pretty bullish on like putting like cheat sheets and stuff behind like an email squeeze page.

Now it depends on your business, but like here at pclub we have a B2C2B motion where we get a lot of like individual contributors signing up with their credit cards and that springboards to B2B And because we have that motion, our email list is like a license to print money. And so for us, it makes a ton of sense.

And I get shit from people all the time being like, [00:08:00] dude, just ungate it. Right. Like I'll share like our 39 questions, cheat sheet or whatever on LinkedIn. And I'm like, I'm, I'm hated, but I'm getting richer because of this. So you just keep going to say, you know, you say your thing, but I'm going to do my thing.

And so that's one of my things is like, I do think it makes sense to ungate, um, content in some situations, but everybody's so dogmatic about it. And has like this one size fits all, like you should never do it. And I disagree with that.

Craig Rosenberg: Wow. Matt, come on, dude. You get

Matt Amundson: I like it a lot. I'm

Craig Rosenberg: Now you're just buttering up to

Matt Amundson: I'm not, I'm not, I'm not. Let me give it, let, let,

Craig Rosenberg: Yeah, you are. This

Chris Orlob: Now he's going to slam me just to like, make sure

Matt Amundson: no, no, no, no, no, no. I think, uh, so, so one of the things that I always go back to is like at Marketo, we gated almost everything. Right. And like, it was just a lead machine and just to know who these people were was great. And I understand the value and the [00:09:00] experience that you can create by ungating assets.

And I think that there's definitely assets that you want to ungate, but I do agree with Chris. It's like, I think that there's been an over rotation towards ungate everything, let people, you know, consume whatever they want to consume. But like, I mean, there's been a whole slew of new, uh, MQs from Gartner.

Like I haven't downloaded one of those that wasn't gated. And my expectation was, yeah, of course this is gated. Somebody just paid a shitload of money to license this asset. Like you better make your money back from it. And then I think, you know, because I do so much production on our content at, at Census, I'm like, Yeah, man, like if I just spent 10 hours writing this and getting it designed and polished up I'm going to want to actually know the people that are engaging with it now It's different depending upon like what channels you're pushing people towards it because if you know who they are then what's the point of gating it just

Chris Orlob: And like, how, where is it in the funnel? Cause if it's like total top of funnel, then you [00:10:00] probably, and like, you're trying to like get a lot of exposure. You probably don't want to get it. You probably want to release something that has like a. I don't want to say viral effect, but it's shared between people.

But there's some sort of call to action in that ungated piece of content that leads somebody to gated. And, uh, I think it's especially true for startups, right? Like if you're doing 100 million a year, you can afford to not gate content because you already have a predictable goal. Pipeline machine, probably.

But if you're a startup and especially if you're bootstrapping, like you need leads, that is the lifeblood of your business. And if you're just like posting some, you know, free course on the internet, hoping that. You'll generate some sort of goodwill six years from now because you did that. And then they'll buy.

You're not going to be here six years from now for them to

Matt Amundson: Yeah a lot a lot of truth to that. Yeah

Craig Rosenberg: Honestly, I'm, uh, here. So number one is, uh, this [00:11:00] comes from Chris who offers insane value ungated via LinkedIn. So like the difference is a startup that creates their seminal piece. Has to release it in the wild. You guys, they can't gate it because there's not enough trusted value. So like, actually Chris can get away with gates because dude, we get a daily feed from you or your team.

The, uh, God, was that the multi threading one? I can't wait to talk to you about that. Oh my God. That was so good. I printed that one, but like, that's not exactly like we just, uh, okay. Here's what I agree with. Uh, there's no one size fits all. It depends on where you are in the funnel. I think what I'm hearing from you guys though is like cheat sheets, tools, value add down the line after you've delivered literally daily value to the market.

That makes sense to me. I would not, by the way, startups, I agree [00:12:00] that they're life bud is leads, but they're not going to get them right now. I mean, it's really hard. The market is so convoluted that like you do have to establish yourself for free wherever it is in prior LinkedIn. Um, and you have to have that.

content be the flow through to something more valuable? In my opinion, though, what you said, so initially we said 39 point dots. I'm like, Oh no, if it's 39 tips. Give it for free. If it's a checklist that you can use and it actually, in many ways that is worth money. There's ROI in what you just described as that content piece.

Then you can ask for that currency, which is their email. But like, I don't know. The other thing too is like when we were gating everything, Matt, and everyone was down, you know, you and I just talked about this, like the, in my opinion, the fallacy of digital fatigue is like, there is, Obvious, there's just a adversity in the market for bad content like [00:13:00] four years ago.

You could do The five reasons to dot, dot, dot webinar and get 400

Matt Amundson: Yeah,

Craig Rosenberg: You can't anymore, right? You, that one, you got to give for free. You have to really think about the value you're driving in a Gartner report is a great example of something you have to get. There's monetary value tools, those things there is, there's actual ROI in that piece.

So I don't know that

Chris Orlob: Let me add some extra nuance. What I am not saying is you should get everything emphatically. Not saying that what I am saying. is you should create so much overwhelming free value that it spreads through your market like a wildfire. But once you've got that wildfire, put something up, you know, dingle something for them to pop their email in.

Craig Rosenberg: Okay. We're all in it. Then I

Matt Amundson: Yeah. And then I think, I think the thing that people make a mistake on is if they have their 40 tips or 39 tips or whatever, [00:14:00] they drive someone to a landing page and then they just gate it and it's just like a form fill, like put the first six there. Right. Like, let's see if somebody is like, Oh yeah, this is actually valuable.

Great. Like I'll fill out my email address to get the other 33.

Craig Rosenberg: Yeah. I love it. Okay, that was so there you go, Chris, you've already surprised us with the topic you

Matt Amundson: I'm so, I'm shocked. It's amazing.

Craig Rosenberg: I mean, it's funny. So, uh, so actually, so I do, I mentioned the multi threading piece and I believe that this was one of your folks who did the research on this. I forget her name.

Chris Orlob: Kristen.

Kristen Conner. it was beautiful.

Craig Rosenberg: But can you talk about it for, so multi threading now is, you know how in B2B we get the topic du jour, and then when you dig in, there's all these different like, Like the definitions of what they're talking about. Um, and it seemed like that was one of the things that you were debunking and as you were talking about it.

Um, and so I'd [00:15:00] love to hear more about like, you know, what's working, like what is multi threading, what's working, what's not working, like, how should we be thinking about it? It's definitely something I hear about all the time. So

Chris Orlob: Well, I'll get, yeah, I'll give you a few tips, but keep in mind, Kristen Conner is the expert when it comes to multithreading, but

Craig Rosenberg: You know, we will have Kristen.

Chris Orlob: I'm doing my job of writing on other people's coattails, but hopefully I'm giving them enough, enough credit here to, to get some value out of it. Um, she did, she did a course with us, um, at P club called multithreading masterclass.

And, uh, the way it starts out is she sells you on the idea of multithreading, which according to Gong. Who can track different state, you know, stakeholders in a sales cycle. You're 34 percent more likely to win a deal if you are multi threaded compared to single threaded, which is when you're only talking to one person.

Right. That's, that's gone data. And so that's kind of an easy. Um, tweak that you can make to your sales process if you're consistently single threaded, but most salespeople [00:16:00] go about it wrong, right? The distinction she makes is there's random acts of multi threading, which is just, I want to expand my footprint and we're not really thinking tactically or strategically about it.

And then there's strategic multi threading, which is what is the right blend of people that I want to put together. In order, knowing that if I pull the wrong person in, even though I'm multithreaded, it might be bad for my deal. And if I quote unquote attack these people, that's not the right, that's not what I was trying to say.

If I approach these people in the wrong order, that can also be bad for my deal. So I'll give you an example. Early in the Gong days, like 2017, uh, we had it in our mind that sales ops was where we should start our sales cycle with because Gong, we perceived ourselves to be a data play and that turned out to be the wrong multi threading strategy.

We would start those deals and then they would gatekeep us and it was a nightmare. [00:17:00] Now what we ended up doing is Still looping in sales ops later on in the deal, but not until we've built like a significant, powerful, loud champion out of the VP of sales. And then we would suggest how sales ops be involved, which was helping us run a pilot.

Because now if they start to like kind of weasel in and box us in, we can just give the VP of sales a call. And so there's both like who should be involved, who shouldn't be involved, and in what order do we start talking to them. And it's always going to be a little bit different based on your sales motion and the market you're selling to.

Craig Rosenberg: the, um, um, as you guys were looking at it, so like if you were, but is multi, there was this part to it, which is like, as we talk about multi threading, we are. Engaging ourselves, like we, we is, is part of the goal. Like when you look at great sellers today, [00:18:00] are they engaging one on one with the different threads?

Like, are they marketing to others? Like how, because that, that's often the challenge, right? Which is like, depending on the, how many threads let's call it. Uh, getting to everyone, if that's the required, you know, cause you're, you're, you're studying this stuff, uh, to get to them all is very difficult. I don't know what you'd say to that.

Chris Orlob: I'll give, I'll give you a few tips, like very tactical ways to get multi threading right. One is, and most of these come from Kristen. One is multi threading starts before your first discovery call. So if you get a new discovery call booked, especially if they came to you, your best move before that call happens is to find three other people in that account that you think you're going to want to get in contact with.

And start providing value to them in a very light way on like LinkedIn, like by commenting on your, their post or something, just making yourself visible to them. [00:19:00] Um, and letting them know, right, if you have a conversation, like in a LinkedIn thread that you're going to be talking to their colleague and I'll be sure to keep you in the loop.

Right. That's it. Then when you start the discovery call. Your biggest risk of an inbound discovery call, like somebody who came to you, is because they came to you, they're now Hmm. you, right? If you like try to ask them like, who else should be involved? And they're like, just me, I'm the decision maker.

So instead, if you've already kind of fanned out in a light way, you start the discovery call preempting that from ever happening. Where you're like, just so you know, um, you know, we've, we're in contact with a couple other people in your organization. Some people in my, in my company are in contact with a couple other people and I'm happy to keep you in the loop with how those threads are going, but let's put that aside, let's just have a conversation.

You and I, that is a really subtle way to prevent somebody from being like, don't reach out to my colleagues because you started it and you already made the point that we are in contact, right? So that's another one. Um, [00:20:00] the other point that Kristen makes is. And this is like gold if you're not doing it.

She said, it's not multi threading, it's single threading with multiple people. And so the mistake that she, yeah, the mistake that

Craig Rosenberg: That's a quote of the century.

Chris Orlob: Yeah, like so the mistake that she talks about is like most reps think they're multi threaded if they get on a group demo, right? Pretend this podcast was a group demo.

I'm demoing all of you. Awesome! I'm multi threaded with three powerful people, but you're not really. They just agreed to attend one meeting with all of them there. And so the rep is usually gonna send a follow up email with every person cc'd and nobody responds. Because they see that everybody else has cc'd and they're just relying on somebody else to take it.

Whereas great reps will pick out each one of you, send an individual meeting, and try to have a one on one meeting after. And that's what she means by, it's not multi threading, it's [00:21:00] not a group meeting. Although that's fine if you start that way. It is fanning out and having single threads with multiple people throughout the organization.

That's

Craig Rosenberg: Chris, I'm just going to trigger Matt for a sec. I don't know if you know this, but Matt has a clapper and when he's very excited, he does the clapper. And that was, He, there you

Matt Amundson: he made his first point and I was like, can I shoehorn it in here? But then he kept rolling.

So I was like,

I didn't want to slow him down.

Chris Orlob: true.

Craig Rosenberg: Yeah, it's hard to hear the clap if you're, you know, if we don't isolate the conversation, you know, sometimes it's hard to hear the clap. So I actually appreciate you letting it all manifest itself. And then I think it works

great. Um, well, any, Matt, any thoughts or questions real quick? Cause I, what,

look at that guy.

Matt Amundson: yes, definitely. So.

Craig Rosenberg: because

Matt Amundson: so I think one of the things that I've seen as a big mistake a lot of salespeople make is they think that they're multi threading because the buyer is bringing in multiple [00:22:00] people and they're like, no, no, I'm multi threaded. I did a call and there was like six people on the call, but they don't.

Keep the conversation going separately with those other people. They just either wait for them to come to the next thing or they're like, okay, well they all came there. So I add them all to Salesforce. So like when we're, when we're doing deal review, it's like, oh yeah, yeah. There's eight people involved in this deal.

When the reality is, is there's one person driving the deal, one person gatekeeping you from everybody. And there's six or seven other people that showed up to one meeting, but you don't really have a conversation going with them.

Chris Orlob: Yeah. You essentially had like a webinar with like a group of people and you're chalking it up to being multi threaded. Part of the point of multi threading is to be able to have off the record conversations and ask like, Hey, like, you know, here's how I'm, if you find somebody who's like advocating for your deal, here's how I'm approaching this.

Who's the most influential in this? Who's not, and what advice do you have for [00:23:00] me? And you can't have those conversations in a group meeting. You can't be like, so the sense I get is Craig is not that

Matt Amundson: Yeah.

Chris Orlob: Is that right? Right. Obviously that's not going to work in a group meeting, but like, you can have that one on one conversation if you've built rapport with somebody in a one to

Matt Amundson: So, so,

Chris Orlob: Right. Like we, we did a demo with a company like two weeks ago, it was supposed to be with their VP of enablement. And unexpectedly she invited like 15 sales leaders, which was terrifying. But like, you can't say, we can't say we're multi threaded with 15 people. We're still single threaded with that one head of

Matt Amundson: in situations like that, do you feel comfortable recommending people to start having one on one conversations with those people? Cause as long as the, the, the sort of the prospect or the, uh, whomever is actually driving it is introducing those people, would you say that it's now fair game to, Hey, look, like Craig brought Chris to this call and I, I haven't talked to Chris, but I just did a [00:24:00] presentation for him.

Like, would it be okay to reach out to Chris afterwards and say, Hey, what do you, what are your thoughts? And you know, what, like, what's getting you motivated about this project?

Chris Orlob: Yeah. One of the ways, like if I find myself in a situation like that, one of the tactics I will use to increase my odds of getting introduced. When we're like talking about a challenge, I'll say, who else is impacted in the organization and how are they impacted? And when your buyer spends a few minutes waxing poetically about how Craig is impacted and then, and only then do you make an ask by saying, well, it sounds like Craig is like pretty concerned with this challenge and it impacts his day to day.

Feels like it would be fair to loop him in. It's a lot harder for them to say no, because they just spent a few minutes selling you on just how impacted Craig is. So it's, it's almost incongruent if they're like, Oh no, I know Craig is impacted, but it doesn't make sense for you to talk to him. And so it doesn't work, you know, nothing in sales works every time, but I would estimate [00:25:00] you just added like a 50 percent improvement to your odds of getting introduced to whoever you're trying to.

Craig Rosenberg: it. I, uh, the off the record conversation, you made me think of, uh. You know, at Topo we were doing a deal with a company and they, it was, uh, it, the scope was across the go to market and they had the sales leader, the, the CMO and the sales ops person, and they get on and literally they, they're like, we're the three Musketeers we beat all the time.

This is, I mean, they, I'm not sure, but I think they had their arms around each other on the call. Sales rep, first instinct is, you know, I got this, I've got the whole buying team here. They love it. They work together. I can imagine the forecast call. He comes back. He's like, guys, I had all three decision makers on the call, but he did right thing.

He said, do you guys mind? I, he said some [00:26:00] things specifically that I thought were really interesting and we have some data that might help. If you guys don't mind, I'd like to reach out to you guys individually and talk through. You know, I forget, you know, the sales leader talked about sales process and show you some of the tools, whatever.

So we do the three off the record calls. I'm just going to call it that from now on. Cause I love it. It literally, the first call we get on is sales ops. And he's like, Oh my God, how horrible is that CMO guy? The three Musketeers was a false. That was, it was like, it was like false branding, man. I was like, Oh my God.

And then the CMO just starts tearing into sales. I'm like, Oh my word. The off the record thing. That's all I could think about there where we had a bunch of pieces we had to pick back up. And by the way, what we decided to do there was actually start in one function. Cause. Had we left the first call as it were, we would have said, great, we've got this big deal.

Then when we met with them individually, we realized, no, we don't. And like, [00:27:00] let's just go to one place. Now we had to try to bet who is most powerful and going to make it. We bet wrong. Um, but, uh, it ended, you know, in the end, it ended up working out, but yeah, we just said, we're going to start marketing.

Just because we want to know that. So anyway, just a fun anecdote to the three musketeers was a false flag. All right. I got, I got one for you though. I've been dying to ask you. I'm going to combine two things, but you know, you can uncouple them or however you want to do it. So like in today's SaaS sales, Like, what about the pitch or the sales presentation?

Like, are those things, like, what do the best reps do for either of those? Like, and when do they come into play? I, I can't wait to hear your reaction to this. I've been dying to ask you.

Chris Orlob: we talking about like a sales demo?

Craig Rosenberg: No, I'm talking about six PowerPoint slides on the [00:28:00] company, et cetera. Is that dead? Are we going

Chris Orlob: No, I I don't think it's dead, but I have a lot to say about like what good looks like and when you should do it. Um, so.

Craig Rosenberg: Boom. Yeah, I I think the company-oriented sales deck is dead. I don't think it was ever super alive to be fair. Like, I mean, it's almost just a way to add content to an agenda that you don't otherwise know what to do with.

Chris Orlob: To me, the right use of a, of a call deck is when you book a meeting with an outbound buyer. Right. They didn't come to you and you start that discovery call, hammering them with a bunch of questions. It tends to

not go very well. Cause they're like, dude, like you reached out to me and now you're like pummeling me with all these questions.

And you practically have like a light shining in my face. Like I'm being interrogated. Like, just show me your product. How about we start with that? Which is like every sales reps nightmare, right? That's not how you want those meetings to go. [00:29:00] And so my suggestion for call decks. is I call it a discovery prompter where you get in a meeting room with an outbound buyer and you basically say, look, I have a lot I want to learn about your company.

But my guess is you didn't show up to this meeting, thrilled at the idea of me asking you 20 questions right off the bat. So how about we spend the first 10 minutes walking you through some of the challenges that we solve so that you have context. And maybe even a success story or two. And then we can use that conversation to springboard what's going on in your world.

And they almost always like exhale with relief. They're like, thank God I'm not going to be pummeled with questions. And then your deck has almost nothing to do with the company. It is a pain oriented, oriented narrative where you're walking them through the challenges that you solve in the market. In such a way where they can see themselves in the story. And if you're talking to the right [00:30:00] ICP, and if you've got that deck like really well tuned and it strikes a chord, and then you end it by saying, anyway, enough about us and the problems we solve. Tell me what's going on in your world. And you strike a chord, it's, they'll like unload, right? They're like, that's exactly what's going on in my company.

And let me show you how this is, um, playing out, right? The principle behind this, that, uh, a mentor of mine taught me like a decade ago is he said, if you can articulate a buyer's problem and pain better than they can themselves, like it's a page of their diary, They will automatically now trust you and want to engage in a discovery conversation with you.

So that's how I think about call decks. It's a little bit different than like a sales presentation or a demo, but that's how I

use [00:31:00] yeah. It's interesting that you brought that up because you recently had a post on LinkedIn about how to apply that same logic to prospecting. And I was like, this is the best differentiated prospecting email I've heard of in forever. And, you know, we've sort of entered into what I refer to as kind of a dark ages of sales development, which is like, you know, people are either just kind of Spraying and praying like they were, you know, forever ago, or they're using really outdated tactics.

Matt Amundson: I mean, like, I can't. Like the number of fourth emails I get where it's like pick an option and the fourth one is you've been eaten by an alligator It's like it's outrageous how much I see [00:32:00] that that that junk so um, just like trying to to to show some level of empathy like I know what you're going through or at least like we work with companies that are going through this problem and That could be something that's affecting you, right?

Like not that language, but, but just trying to get into your buyer's mindset a little bit as opposed to doing the like What's keeping you up at night? Leading with uh, this is what's keeping people like you up at night. We know it We've been solving it for other businesses. Maybe that sounds like yours.

Maybe it doesn't if it doesn't god bless you're on your way But if it does it might be worth a conversation

Chris Orlob: Totally. Yeah. I mean, some of

the best. No, go ahead, Craig.

Craig Rosenberg: Oh, I just, I, I, I hate to say that I did miss this one. This, so this was a prospecting email that Chris was

Matt Amundson: Mm hmm. Yeah

Craig Rosenberg: and it, and, and I get the gist. We're, we're leading with empathy. [00:33:00] We, uh, and, uh, at, at least a impression that we understand their

business in some way or their

industry. Okay.

Chris Orlob: Some of the best prospecting messages don't even like talk about the product or what you do or even its benefits. It's just like a very well articulated grasp of the challenges They're probably going through and we've been able to help a bunch of other companies solve this Is it worth a chat to see if it's is this challenge worth a live chat and that's it

Craig Rosenberg: Okay. Got it. And what you're doing though, I mean, are those, is that from specific company research? So I'm looking at where Matt's census and I'm writing it deliberately for them based on what I know about them. Or is that coming from a place of like at least market understanding where you've got sort of a grab bag of things?

What does that look

Chris Orlob: I think it's both. So let's, let's see if we can like voiceover an example. It's not going to be as good because like, I'm, you know, [00:34:00] just going off the cuff, but let's say I'm selling to like, selling P Club to like a VP of sales who runs like a mid market SaaS company. And the email would say something like, Hey Craig, I'm curious to learn more about your sales organization.

I talk to a lot of like Series-C VPs And one of the challenges they share with me is it was the go-go days in 2021, and their reps did not need any selling skills. Your product was probably flying off the shelf because the economy was so hot. Now we've transitioned into new market conditions where reps are struggling with uncovering deep business pain.

They're struggling to get multi threaded. They're struggling to defend a price through great negotiation strategies. I won't go into too much detail, but we've helped, you know, six other companies in your space increase bookings by 30%. Curious if upskilling your team is something that you would want to talk with us about.

So like, had nothing to do with pClub. We're not talking about a learning platform. Or our [00:35:00] online courses. It's like, here's the challenge. Every other VP of sales in tech is going on right now. Their win rates are suffering. It's due to these skill gaps. And those skill gaps are really specific in language that a SaaS VP uses. By the way, we've helped a bunch of other companies. Here's the result Do you want to talk about.

it

Craig Rosenberg: That was awesome. You know, one thing though, I think is really important here because I do think that there is still a bad email under that. Um, sort of methodology, which is when they just lead with benefit, you know, like, or, or they lead with, uh, sort of statistics that are all patently obvious, right?

So like an example in our space is seriously, you cannot bring up that the buyer 60 percent down the buying cycle anymore. And why am I bringing that up? Because what Chris did was he took things that anybody could say. But he made the recency. There was [00:36:00] this understanding of what's happening now, which was the 2021 to now transition.

Just that sentence alone earned credibility because that's where you get the head nods. Right. Because I mean, shoot, like guys, like it's sales tech, like the, you know, the sort of the issues that are happening. You have every vendor using that sort of pain, trying to amuse it to their advantage, but when you add the elements that Chris did.

That changes the game there. That shows a real understanding of what's happening in the market. And it was one sentence

Matt Amundson: yeah

Craig Rosenberg: what I mean? That was a beautiful, uh, that was the beauty of that for me, by the way, that, that is, and by the way, I have deep regrets on advice. I gave someone about four months ago after hearing that, damn it. Um, so I love that and I do, I agree with Matt, those, those things kind of went together. Okay, the, [00:37:00] the, you did mention, um, I wanted to go back. We spent a lot of time on the demo last time. So, uh, it seems like in SaaS, the demo on the first call is happening no matter what. Is that true? Right.

Chris Orlob: I think it's happening more often, but I think there are some sales motion. Like I don't demo on our first call, but it also aligns with what the buyer wants. Right. I'm it's, I'm not like trying to hold it back or anything.

Craig Rosenberg: Because like the old school folks from my generation, like, Oh no, you don't demo until you've put them through like, you know, Guantanamo Bay type of interrogation. Right. Um, and last time you had some really good tips, which is how you incorporate both, but it does seem like, well, it's so for my 20 something inside sales reps in a more of a velocity motion, even into a mid market motion, they got to show product out of the gate. Is that, I mean, do we, I mean, we're all, yeah.

Chris Orlob: At least like a team.

Craig Rosenberg: Right. Right. [00:38:00] Absolutely. So, um, so if I were going to, and you brought, I'm making you repeat from the last show, but it was so powerful because this is still really important to incorporate the learnings that we need to have in order to be successful down the line in the sales process, in a scenario where we're getting pushed to bring product forward.

And, uh, the ability to create value out of that. Uh, you know, what, what are your, like, what do you see in the best reps doing in that scenario and like, what can we learn from it?

Chris Orlob: I think there's a handful of things. I think that entire situation needs to start with expectation setting, right? High velocity buyer comes to you. The first thing out of your mouth during that discovery call is acknowledging the fact that they probably want to see the product, right? So like if I'm setting an agenda, it's like, it looks like you requested a demo on our website.

I want to make sure you walk out of this meeting informed on our product, more so than you walked in. And so we'll definitely [00:39:00] reserve some time to go over some of it. If it's okay with you though, I would like to make that part of our agenda really crisp for your situation. And so maybe we spend the first 10 or 15 minutes going over what motivated you to reach out to begin with.

And then I can make sure I'm informing you on the right pieces of what we do. Does that sound fair? And most buyers are going to agree with it because you're calling it out. At the beginning, you're saying, we'll get to that. And most reps don't do that. They just launch into discovery. They might even intend to show a demo later, but because they never gave the buyer the expectation that I'm going to show you something, the buyer can't read their mind.

They're just getting asked all these questions. And like the third question, then they go, dude, like I requested a demo. Can you just show me your product? And it creates all this unnecessary friction that you could get ahead of just by framing the call in the right way and setting the right expectations.

Craig Rosenberg: I knew you were going to make my day. That's great. Isn't it funny how with all the, you know, like how, you know, that [00:40:00] is very specific and in many ways tactical, right? It is this. Specific piece of a call, but it's strategic in that it will move needles for these guys like big ones. Yeah I mean, it's

Chris Orlob: The alternative is you don't do it. You ask two questions. The buyer's like, go F yourself. Just show me your product. And now you're just throwing spaghetti at the wall and hoping something sticks and they go dark on you and the deal's dead and you have no control.

Craig Rosenberg: Yeah for sure But like matt you like to see the product on the first call

right as a buyer or no?

Matt Amundson: I think it's rare that I haven't seen a product before i've gotten on a first call

Craig Rosenberg: Oh, that's that's a good point. Yeah

Matt Amundson: to

I

mean, just

in this day and age with the technology, with how much people put product out in front, uh, I mean, it's unlikely that you can't just get on YouTube and like watch a demo of whatever product you're thinking about before you even get on the call.

So like what you want is like, Hey, I have a tech stack that looks like this. Show me how it all integrates, I guess. And like, then show me whatever I didn't see [00:41:00] on that call. But you know, it's, it's interesting. Cause I was a part of a couple of companies that just had, Awesome, awesome sales culture, right?

Both Marketo and TIBCO were just awesome at it. And they never, and I, look, I understand it was a long time ago, but like they never, ever did a demo on a first call. And the thing that I will say is they did a really good job of setting the stage, the way is sort of unfurled here, which is like, Hey, like.

I'm going to tell you what's going to happen on this call. So like, I don't just like start peppering you with questions and immediately turn you off. And they made people understand the value of why they weren't seeing a demo on the first call. So were there people who are like, fuck off, show me the product?

Yeah, there were, but that's like less than 1 percent of the interactions that those sales teams had with their prospects because they did such a good job of sort of Laying out what that process would look like and that's something that I really really don't see out in market right now Is you know, it just it's [00:42:00] it's like still operating as a flywheel even when I know it's not a flywheel Right, like because I know what the market conditions are, but you show up And like in some cases the AEs are like taking the approach like, I mean I got like 30 other people that are lining up to buy this thing so like I gotta crank through this really fast, you've got to answer some questions for me or whatever and it's just kind of like, oh man, like that process just sucks.

Chris Orlob: We'll see that you made a good point, which is like, if you're going to do a pure discovery call and not show any product. Then you need to run that call and even name the call in a way that's buyer beneficial, not seller oriented, right? In fact, you probably don't even want to call it a discovery call.

So like our first two steps in our sales process at P Club is our first call is what we call a skill analysis. Discovery call, right? Like we're looking for skill gaps. Um, and then the second call is content mapping, where we walk them through our platform and show them what specific learning programs would [00:43:00] attack those skill gaps and our buyers actually, like, I've never gotten this like discovery fatigue because our buyers value going through that skill analysis with us.

Because they exit that call, uh, regularly sharing how we helped them crystallize their thinking on like what skill gaps they need to attack in their organization. And we just put that out on the first call, right? Like when we're setting it up, we say usually what we do from here is we try to get clear on two things.

Number one is what are the various skill gaps that you're seeing? And I'm happy to share some of the skill gaps we see in the market. And then number two, if we solve those skill gaps, what business outcome would be positively affected so that we know we're building a business case in advance? What that helps us do is in the second call, we can then walk you through in detail how we would attack the skill gaps that we align on in this call.

And I've never had any pushback, but it's because I made it about them and their benefit, not, hey, I have to. answer my BANT questions because I have a pipeline review on Monday. And so you're not getting out of this thing alive, [00:44:00] baby.

Craig Rosenberg: Yeah, that, you know, by the way, there, you know, one of the things that, uh, that we tried to do at Topo was separate discovery from qualification because, uh, there was way too, you brought up Bant, there was way too much intermingling there. So we said, look, here's how we're going to talk about things. Bant is whether you should do work on the deal.

I'm sorry. Qualification is whether you should work on the deal. Discovery is how, uh, how you will win the deal. Now, I know that's very vendor centric, but just go with it because, um, you know, oftentimes that experience also gets broken, which is that discovery is banter medic. And in that actually is also a turnoff, right?

Where like, um, the reality is, uh, in a, an analysis, a skill analysis, or whatever that might be. We're, we're talking about what's happening in their [00:45:00] business and understanding, you know, in your case, it's a gap analysis. Actually, I guess in most cases, a gap, or you could say like a use case and try to figure out what they're trying to solve or whatever that might, um, you know, I think that's really important.

I would just say this, like, if I take what Chris said before, like we're, we're trying to help the buyer. We want to do the, we want to facilitate the journey they want. In my opinion, most buyers today want to see product out of the gate and it's not their fault. It's our fault as the vendors. We've made the world so cloudy on what's what and who's who they just, there's this part of their overcoming their, you know, their massive indecision is to feel comfortable along the way.

You know, it just proves that the UX, you know, and what you're showing out of the game makes a huge difference. So that's why I like what you're talking about, which is in some cases, Look, that's what the buyer is wants and expects. In some cases, it's not, you know, I [00:46:00] once ran a panel with some Fortune 500 IT folks and they just said, no, you have to do discovery, man.

You will waste my time if you don't. I actually want you to because I have been pitched products that have nothing to do with my life and it's, I need that time back. So like, you know, I think it depends, right?

Chris Orlob: Well, you also don't know what you don't know as a buyer sometimes. And like, I've been in that experience where I'm like, I kind of want you asking me a few questions to make sure this even applies to like what I'm trying to accomplish. Instead of like running me through something. The other thing you said, which is really insightful.

Um, it reminded me of a lesson that I learned from one of our course authors. His name is Brett Baldwin. He teaches a course on how to access power. And he said, you can't ask about process until you first created value, meaning like they're buying process. Right. Like if you start a discovery call and you're like, so who's going to be, um, you know, involved in [00:47:00] this decision and where's funding and you're leading with that before you've had like the hefty business conversation about like what's going on in your world, you know, what's the negative impact and like helping them solve it, you have that conversation first, hopefully you can get some sort of. And then once you've started to give them value and showed them how like you can solve the problem, then like, you have every right to start asking some of those questions. Like, what steps are you going to need to take from here? But most sales people will start with those and it's, it's, Dude, I don't even know if I want to pursue this.

I'm just trying to flesh out my problem and whether or not you can solve it.

Craig Rosenberg: Yeah. Love it. Now, Matt, just so you know, Chris, in the background while you're talking, I, you said, I said something really insightful. My hope was that Matt would go to the clapper on that and he's, he denied it. Uh, Matt,

Matt Amundson: It's not clap worthy. [00:48:00] Yeah.

Craig Rosenberg: You mentioned negotiation. I have multiple flavors here, Chris, of things that I hear. So one is, uh, we're still faced with competitors, and especially in SaaS that are willing to drop their pants to get the deal, right? Big time. And I'm talking like, not like chipping away at it.

I'm talking, there's all these different companies at different points of the life cycle and how they, you know, how they're doing it. Tackle negotiation is often I'll go as low as I can to win the deal, right? That's one. Two, these are all tied together. I'm just giving you all the use cases that come in on this.

Two is like, how do we maintain price integrity or like our ACVs are falling or whatever that might be like, you know, what can we do differently? Oftentimes they assume that's negotiation. In my opinion, oftentimes it has to do upfront because they can't articulate the value to the Customer when we're talking about that specific deal.

Okay. [00:49:00] Uh, that's two. And then it, so those are two sort of classic use cases for me. The other though is a little different and maybe we park it for another time, which is, um, there's so many nicks and cuts of the blade now, like in this buying process. So even if you've been, if you've multi threaded effectively, there's shadow folks, there's these, Bumps in the buying cycle, like Ted Purcell, we had him on the show.

He said, the biggest thing I could tell you right now is buyers think they know how to buy, and they don't. It's the buyer, right? And, and that is the other thing where they're getting sort of, uh, you know, when they think they're in the final throws of everything and they're getting, you know, particularly from finance, but let, I mean, look, there's many other use cases where they get, you know, sort of arrows shot in their back when they're not looking.

I don't know if that's in the negotiation phase. But that is when it's happening. So anyway, I just threw a bunch of use cases at you. You talked about it. [00:50:00] It's a topic that I'm really intrigued by and I don't know how you approach it. And I would love to hear your take.

Chris Orlob: Yeah. Um, I think people who teach negotiation are a little too nice these days because like almost every negotiation training talks about like We got to create like a win win and we want to make sure like your counterpart like feels good and all this kind of stuff. And like, I'm not saying no to those things, but I'm like, have you, have you ever negotiated with procurement before?

Like, have you been in a situation like that? Because they are not playing the game that you're teaching my dude. I can tell you that right now. Um, so the first thing that comes to mind, and this is kind of utopian. But if you can get three things done early in the sales cycle, negotiation tends to go a lot better.

Number one is quantifying the value in a way that your champions agree on, right? So we just closed a deal with a big, uh, SaaS company that everybody would recognize, and we spent the first half of [00:51:00] the sales cycle getting them to estimate how much ARR is at stake. If we make good on our promises, which was like between four to five million bucks, right?

So that was check and as soon as I got thrown in with procurement, I like I just kept pointing to that I'm like we're we're arguing over thirty thousand dollars, but like Your VP of enterprise, your VP of mid market, your VP of enablement have all agreed that there's five million dollars at stake here.

So this just feels a little off to me. So that's one, is like months before you're negotiating, getting the business case like rock solid. The second thing, uh, is, and this one is more utopian SaaS Products just are not well differentiated. But if you can find a way to establish your differentiation throughout the first half of the sales cycle in a way where your most powerful champions value it, now procurement can't do their other play, which is, if you can't meet our price, we're gonna go fill a bunch of competitive bids.[00:52:00]

They can do that, but if you know that your champion or champions want what you have because you provide something unique that nobody else does, You can be willing to walk away. You can say, you're more than welcome to do that. It's not going to change the price at which we can sell this. All that's going to do is delay the start date.

And we've agreed through the business case that that's worth about 400, 000 a month. So if we want to play that game, we're welcome to. And then the third thing, and this is almost like an outcome of the first two, is finding a powerful champion who's willing to spend some of their political capital. So the same deal I'm talking to you guys about, where I was, you know, going face to face with procurement, I actually got to the point where I thought we were going to lose the deal because we wouldn't come down any further, and they were like, we might have to go field a bunch of competitive bids.

And so I texted my champion. I'm like, Hey man, here's where we are. I don't think we're going to get this done. And an hour later he responds and he's like, Hey, I just talked to procurement. They're sending, check your email. [00:53:00] They're asking for the order for him at the price that you, you want it. And Wow. Look at this closer. Oh man.

you can get those three things then like sure there's a bunch of negotiation tactics that happen in the moment of negotiation But like if you don't have at least some of those three things it almost doesn't matter how tactical you are with negotiation Because they're gonna go. Hey, we found somebody who does exactly what you do Our VPs don't care about which product we choose and they're only 200 bucks a year and you're a thousand. I, there is no slick one liner or question or silver bullet I can do in that moment to convince somebody to pay five times the price.

Matt Amundson: God dang.

Craig Rosenberg: Oh, there it is. Bring it back on. Good. All right. That was the, uh, I was hoping that would be like the perfect end of like, uh, of content [00:54:00] pieces. And it was so, uh, but dude, honestly, if I could, I would invite you every week. Because I learned something every time. And, um, and that's, what's so amazing about you.

But look, by the way, Sam, we should put the, a couple of the referenced LinkedIn posts in the show notes. Um, and I say that only because I love budgeting show

Matt Amundson: Yeah, it's a fun, fun, fun phrase, yeah. Uh, the thing that I'll say is like, at the very least, if You know, if, if you're not following Chris, just start by following Chris right now, because he gives so much good free information. I think like I commented yesterday, I was like, I was trying to make the like Miracle on 34th Street reference because I was like, yeah, every time Chris posts an AE, uh, hits their quota or gets closer to hitting quota.

Chris Orlob: I think that's a,

it's a wonderful life. That's not Miracle on

Craig Rosenberg: Oh,

burn! Yes, thank you, Chris. I'm gonna clap. I mean, I got nothing. I mean,

Chris Orlob: I watch that [00:55:00] every Christmas Eve for like the first 20 years of my life and I never want to see it again because my parents made me

Matt Amundson: yeah, but it's true. Every time you post a AE gets their wings, man.

Chris Orlob: it. Oh, I love that. I love that. I love that. Yeah, man, you're doing right by the world, man. It's just great, all the stuff that you're doing. And it's, there's nothing better than having you on the show. So I personally really appreciate it. We've, we've got a, a new pod, The Transaction. You did help us talk to everyone about driving transactions and you covered marketing

Craig Rosenberg: too, which I thought was surprising

Chris Orlob: the most unqualified, unwarranted way, like not a marketer at all. And I shouldn't be the one talking about it, but I still have opinions about it. So

Craig Rosenberg: By the way, 50 percent of great market. I mean, 50 percent of marketers, the great ones always want to listen to the people outside their inside baseball to get their takes on what's happening. Cause that's, that's where the truth lies. [00:56:00] So, um, everyone, I just, you know, again, we can't, we can't keep thanking Chris.

We're just going to have to end the show because it was awesome. And this was the transaction.

Chris Orlob: thanks y'all.

[00:57:00]