The Transaction

TT - 057 - Jake Dunlap - Full Episode
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Jake Dunlap: [00:00:00] stop asking the question, what's our AI go to market strategy? It's not the right question.

the goal are the outcomes,

not the activities.

Outbound never ends, you cannot take a project based mindset to outbound,

Find your one bottleneck. Deploy gen ai there. So simplify, simplify, simplify. sales leaders, executives, listen to me. You have to learn this yourself. You cannot outsource this through rev ops.

This is a foundational shift in how we solve problems as human beings.

You gotta have fun, man. Sales is fun.

Craig Rosenberg: Jake, how you been buddy?

Jake Dunlap: I am good, man. How are

you?

Craig Rosenberg: good. Just like, uh, you, ready for this?

Both my cars got stolen outta my driveway a week ago. Why? It's not, it's crazy.

Matt Amundson: get it Gone in 60 seconds. Graphic for this

Craig Rosenberg: They found

Jake Dunlap: Unbelievable.

Craig Rosenberg: one. Uh, I have to go get it

Matt Amundson: was it The

Port of Long Port of Long Beach.

Craig Rosenberg: No.

Jake Dunlap: I cannot, I just keep thinking of the other guys. If [00:01:00] you guys know the scene where his car gets

Matt Amundson: Yeah,

Craig Rosenberg: actually,

Jake Dunlap: we found your

Matt Amundson: Turned it into

a

Jake Dunlap: Oh yeah. Here's a note from dirty Mike and the boys. Yeah.

Oh, the old soup kitchen. to me about it. 'cause I was saying, you know, in California it's a 73% recovery rate on stolen cars. Right? uh. He's like, yeah, I mean like, I don't know. I remember a buddy was talking about how the bums were having sex in the car, and I'm just like, bro, that's a movie.

Craig Rosenberg: Like I know you're old, but like

Jake Dunlap: Yeah, exactly.

Craig Rosenberg: a story you actually heard with the other guys, right? Like I just going to. Lay that out there for you. But truthfully, like that is what they look for now, is like, buddy's car got jacked and then he, they found it with a gun in the glove compartment, and then they gotta total it.

You know, like, it's, it, so, we'll see. I don't know what it's gonna look like. praying the baseball stuff's in there. Everyone's like, it's gone, you know, whatever. But, um, it's, uh, the biggest thing is the paperwork. [00:02:00] the biggest thing is I didn't, I run my cars into the ground? I drove a fricking Toyota Camry 2005 until that thing I got rid of it only because my kids who at the time were like eight were asking me to drop them off two blocks away from school.

'cause they didn't wanna be seen with it. anyway.

​

Craig Rosenberg: all right. So, uh, this is gonna be fun because, Uh, here's the thing on Jake, Matt.

Matt Amundson: Oh, I know Jake.

Craig Rosenberg: no, I know, but this is why I think he's the one an interesting guest is because, so Jake, I'm gonna give you a little context then I'm gonna tell you why you're on the show and introduce, use that as my intro is, [00:03:00] we started the show because Matt and I were working.

He, he was at scale. He was my first DIRI think one or two, him and Sidney Sloan. Oh, she beat you. Yeah, maybe by a couple weeks. So, um, and we were sitting there talking to folks and like we just looked at each other. We're like, holy shit. the past playbook is dead. It's gone and we gotta figure this thing out. So we started the show so we can go interview people. I think over the last six months, it's like. Change is true change or die situation. And so like, it's been interesting for us as we've sort of, you know, uh, you know, we, we look for guests and want to have conversations with folks you are an interesting one because you've been through all the wars and now are like one step ahead. On AI and, and like doing things that are amazing. He did a event for us, Sam, which like clear that like he's [00:04:00] more than one step ahead. And so like, but for everyone here, like Jake has been around for a long time doing, I. these iterations of, consulting that the market needed, and now we're in this new space over the last six months and going forward where that has fully changed.

And so for the OGs like Jake, if they don't evolve, they're, they're gonna

go by the wayside.

Jake Dunlap: A hundred

percent.

Craig Rosenberg: is, is two steps ahead. Um, and he also is a sharer, which I've always appreciated about him. He's always one to. talk about, well, frankly, everything, anything. And so like you were, um. You were a target after you and I did this like panel or something and I was like, I just

remember, I was like, holy shit,

Jake Dunlap: yeah, God, that was a while ago.

Craig Rosenberg: you. I got on. I'm like, dude, like I'm, I'm the old man. I, if

Jake comes in just like

Jake Dunlap: What's this guy up to?

Craig Rosenberg: alignment, we're screwed. And uh, you know, I was like, oh no. Jake's on the AI thing. Faster than I think at the time you were ahead of [00:05:00] everyone and now it's like it's on. so that's why we couldn't wait to talk to you, man. We wanna learn from you. So audience, this

is our guy,

Jake

Jake Dunlap: Pumped.

Craig Rosenberg: He is like one of, he's famous for all his years, but he will be uber famous now because he is like, as I said, way ahead of the game. So Jake, thanks for coming on the show, bro.

Jake Dunlap: Hey, I appreciate that man. We'll see. We will wait and see. I mean, hopefully this all, everything pans out. Um, but I'm excited for the conversation and yeah, it's been, it's been a minute. It's good to see Matt too, man. I've seen you in a minute. dude,

I probably haven't talked

to you in like, God, it's like years, man.

Craig Rosenberg: Well, Matt was fully on the, he was fully on the circuit. Right. He's like a pre covid man. Like a lot of us, you know, it takes, it's been weird sort of coming back from that. You, he, you get that a lot, you know? No, and not just Matt but me. It's like, there was, like, before Covid, we all, everyone in the game saw each other every month. Basically Right. With events or webinars or [00:06:00] whatever, that just kind of slowed down. So, um, yeah. I'm glad you guys were reconnected. So. Here's how we do the show. So we got two sections. So section one is the, is is a Matt Amundson innovation. we just ask you for, any fun, heartwarming, exciting go to market stories that you want to tell us.

Just, you know, we like to get the stories out front. then the second part we kind of maed a little bit, which is like, we'd just like to hear from you, like one to three things in go to market that work today. In today's market, and that's it. I mean, we ask questions as you talk, but

otherwise

Jake Dunlap: of course.

Craig Rosenberg: force of the show.

So let's

start with

Jake Dunlap: Cool.

Craig Rosenberg: And now I told a story about my cars getting jacked, but, um, let's say you'll have to try to, that's, that's a

baseline for you buddy.

Jake Dunlap: you need one of those LifeLock things. Remember LifeLock back in the day, it was like this like crowbar thing you

put like in your steering wheel. I don't, do they still

make LifeLock? I don't know if that's a thing anymore.

Craig Rosenberg: were

they

called?

Jake Dunlap: No, it's probably

not. LifeLock. [00:07:00] Yeah. that's your identity. But you? know what I'm talking about.

What was that called? It was like a

thing. It had a

key in The club.

Yes, The club exactly.

Craig Rosenberg: because now everyone has a nice car, but back then I remember we would all, like you would walk. I lived on Oak and Masonic. You would walk down the street. Everyone had to park in the street and it was like Toyotas whatever, parked on the street.

Everyone had a club

Matt Amundson: Yeah, on the Tercel. the club. Shout out on the cel. '

Craig Rosenberg: cause everyone makes a big deal. But even back then, your car was getting robbed every three

weeks and you

know,

they're

Jake Dunlap: Uh.

Craig Rosenberg: So anyway. All right Jake, so we'd love, so let's start with a, like, just, we'd love to hear, go-to-market stories and, and we take 'em in any flavor. But obviously we hope the moral of the story is something we can learn from.

Jake Dunlap: you know, for those of you, I don't know, I run a revenue performance consulting company. Um, have been doing it for 12 plus years. And so I get a chance to work with hundreds of companies every [00:08:00] year and CEOs, CROs, everything in between. And you know, I think for me, over the last.

Hmm. I feel like the last six months has really been around Jake. Like got like, we know we need to get on board with generative AI and we just, there's so much noise in the market and what is actually gonna move the needle. and I think it's really easy for people to get overwhelmed. And so one that kind of comes top of mind. A client we worked with private equity company. That company, uh, actually ended up exiting about three weeks ago. long story short, you know, field led org, kind of old school and you know, technology adoption, et cetera, and, you know, but came with like an open mind of. Look, here's what our teams are doing.

Like what can we do to fix the bottlenecks? And this client, uh, what we did is they sold multiple SKUs, right? So they had, you know, a customer's working on this thing. What are the two or three other things that they're working on? And the reps would have to kind of consistently go. And [00:09:00] find and search through this details, you know, what's this SKU versus that one.

And what we were able to do is partner with them and build a assistant for the, the field team. And again, especially field reps, like not known for like high

technology adoption.

and we basically, you know, loaded it up with the SKUs, put in and place our custom instructions and. Now, you know, the team literally says, Hey, this is what they're doing.

What are the top three things I should be talking to 'em about? And it's saving them, you know, like three to four hours a week per rep. And so that, those are the things that get me excited right now is just like, you know, we've got another client we just implemented assistant for around prep and research. And you know, it's like the old way is like I go to Google, I go to LinkedIn, I do this, and the feedback is like, Jake literally we're saving 20 to 30% of all the time we did research, et cetera. So a lot of the use cases I've been really excited about have been around ai. And then the other one is outbound. Which might be a little bit of a wild card, right? I think everyone is like, oh my God, outbound's dead, or [00:10:00] whatever you say, but it's really not. I actually feel like for our clients, like the bar is super low because everyone is just trying to automate everything. And so it's like, Hey, if instead we automate the prep and research, we do some of that, but then the reps actually know how to do the customizations that are relevant to like. You know, I always talk about it's not the industry, it's a sub-industry. So if you can put together snippets that say, I know what a VP of operations, not in manufacturing, not in industrial manufacturing, but heavy equipment manufacturing and I can talk to them about trends and pressures. Competitive, you know, pressures they're probably feeling as well. It's working like people still take meetings if you can be relevant and we had a client kid, you not, we started with them in January, uh, between Q4 and Q1, I think maybe 20 SDRs, 100. New meetings

above Q4. And so I feel like outbound, like the bar is so stupid low that if you just go back to being relevant and, and allowing your teams to turn their brain on, and we had, we had another success story at the end of last [00:11:00] year's, like we AE based teams 60 AEs.

Nobody wanted to prospect. We put in place a plan, did 44% better best month of the year, 44% better than their average. And I think a lot of that is just getting back to what, what's working. And also to setting clear expectations. I think a lot of companies we come into do more stuff. It's like, no, like you gotta have like

realistic targets

and things people can achieve and then set them up for success.

but I think those are a couple, man, and that's a long, I know it's like a long-winded double answer, but I think those are kind of the, like the use cases that are popping out for me right now.

Craig Rosenberg: All right, well let's start there then. Uh, so one is, it seems like, and Matt actually has done a ton setting this up too, one of the best use cases that everyone can do right now,

Matt Amundson: Yeah.

Craig Rosenberg: but I, I know there's work to be done, is account contact research. that a true statement or

true or false?

Jake Dunlap: The, the, the basic, the basic research is not. [00:12:00] Is not defensible, right? Like anybody can do basic research. I think what what we are seeing provide real value is, you know, and again, like this is where a lot of these technologies just don't have the context, right? Like, they're like, here's account research.

It's like, well, if you've been a sales leader, like, you know, this is what actually matters. And so I would say it's, it's, it's understanding the right type of research that you can automate.

And get in front of them, or at least set up a custom GBT where they can query it and just say, Hey, gimme a link, and it does it. Um, which is like a good kind of V one for a lot of people. So yes, the a hundred percent, the very first thing that you should look to for generative ai, where are the little tasks? My people are doing prep and research, and how can I get them that information, not only faster, but with 3, 4, 5 x quality.

Craig Rosenberg: gonna say it's better too. Like Matt. Matt. Anyway, go ahead

Matt Amundson: the thing that I often hear though from reps who are sort of, well, I'm gonna experiment with philanthropic or I'm gonna experiment with open ai, is. [00:13:00] They often don't understand the right prompt to use and so they get hung up and like, yeah, I get a little bit of research but this isn't really what I'm looking for.

And I think if like you wanna make that a part of your actual process, then as an organization you gotta think a little bit more deeply about it. Which is to say like, you gotta train the AI a little bit. They have to understand like. What your company's value prop is why a company would want to adopt a technology like yours. Otherwise, you get these really bland, generic answers that like, you might as well just came up with on your own. So one of the things like, uh, we had Matt Heinz on the show a couple of weeks ago. I think his episode went up. Yeah, Sam, his episode

Sam Guertin: Today.

Matt Amundson: Yep. And one of the things he was like, he was saying was, Hey, like, you know, why wouldn't someone just go out and create like, uh, AI agents of their buying committee, so that they can, you know, sort of flash, you know, new marketing materials, new sales decks, new website in [00:14:00] front of it. And I was like, oh, challenge accepted. So I went out and so I. know, just in my spare time. And what I realized was like if I just ran that stuff through like a blank. or GPT or whatever, like it would give me just, oh, this website looks good. It clearly explains your value prop. But if I ran it through these four, you know, kind of buying committee AI agents that I created, it would say, is what I like. This is what doesn't make sense to me and this is what you're missing. And it was so much more valuable because I

fed it.

Jake Dunlap: Mm-hmm. does. I fed it all the persona research that we had done and documented so that it knew who the buyers were. It knew what we did. It knew what our primary value props were and what we were trying to sell.

Matt Amundson: I think if you just kind of approach a blank GPT, you're gonna get back in a lot of cases, especially with open ai, you get back. Positive feedback. Oh, your website's good. It's well designed it, or it, you know, [00:15:00] articulates your value, props well. But if it thinks about it through the lens of your buyer, and if you train it to think about it through the lens of your buyer, it actually gives you really good feedback. Now, I tend to not pay attention to what it likes. I, I tend to pay attention to what it says is missing. And there's good information that you get from that, like. Hey, this could really use social proof. This could really use, uh,

some quantifiable metrics behind what you're saying. This sounds like marketing hyperbole and isn't really saying much, that's so valuable to me because, you know, the alternative to that is I. Can I get 10 or 20 of my customers in a room and show 'em and then collect their feedback? And are they willing to be real with me? Are they just trying to get off the phone? How engaged are they?

Jake Dunlap: Yep.

Matt Amundson: super powerful and I think that applies to that same level of sales research, which is. it knows what your target buyer wants, if it knows what it is that you sell, if it seen successful outcomes in the past and you've fed it that either through transcripts of phone calls or whatever, [00:16:00] then it can start to actually give you real answers based upon your business as opposed to just generic answers based on any business.

Jake Dunlap: Yeah, that's exactly right. I mean, that's why, look, we've created like, I think, what up to like 15, um, custom GPTs, right? When the custom GPTs are basically, we use the custom instructions and knowledge documents on the backend to say, this is what somebody who's analyzing an annual report is gonna want to know.

Here's our persona. This is what we do. And now like the annual port summarizer one we built is insane. It literally says, gimme the link or gimme the PDF Done. And it literally, this is work that if you're in enterprise sales, you, you can feel this pain. It would take you like three or four hours.

To do it right and be like, okay, is this relevant? And it can triangulate. And so, you know, we've got discovery call, prep discovery call trainer, help me book a meeting with like, and the future is, look pro, you're, you're candidly today just to, to call this out. Prompting is, is not what any rep should be doing now

because I can build agents now, [00:17:00] now I'll, I'll give you the exception. I can build agents for almost every primary, you know, competitive, oh my God, competitive deal winner now has gotten insane. Like, battle cards are dead.

Dead. Like I can now build a custom battle card for every single selling scenario based on trends for the prospect. You're going against, you're trying to reach, you know, Hey, where should you concede?

It'll tell you like, look, dude. Don't try to say you're better at this. Like they have

10 years of this on you.

And so the agents like that's kind of this next iteration prompting is V one. Most of you're too young to remember. We used to have to prompt software, like you used to plug, like put in this thing called a floppy disc or you'd had MS.

Dos and it said, uh, and it was like this blinking thing with like a forward slash you just have to prompt computers to run things and that's kind of where most people are still. But the reality is like custom GPTs are the first set like, you know, kind of set of software and then we can, you know, we'll get into automations and what's possible for certain GPTs that you can, you know, you don't even, you can just run it in the background.

Like we built a [00:18:00] ChatGPT Salesforce, like the first like kind of native integration where you add a contact says run, and we run four of our agents behind the scenes and just

populates the record.

Then you don't even need to

think about prompting as a part of this. So there's just a lot of evolution for a lot of Com people listening.

I don't want you to like your head to start to spin. Craig, you hit on the head look for the research based activities and prep. Those are the ones that you can build agents around the fastest. And ime, I, I promise you, within a week, your team is gonna say, oh yeah, I, you know, what I wanna do is go back to, uh, Googling and searching LinkedIn profiles and like, maybe I had 10 minutes to like look at things and my prep sucks, to being like, oh my God.

I literally, it said, give me a link. It gave me a link. And this is the

best prep I've ever seen.

Craig Rosenberg: Uh, there's a second part to it. one is I think it's interesting that, um, basically are, are doing similar usages. Um, Matt's doing it from the marketing side, [00:19:00] And I know Jake, you help with the marketing side too, and

then, you know, and the sales side. So that's the breadth is really interesting. and then, but here's the other thing I think we should talk about. The business reason. And I think it's a lead into what you just said for the second story, Jake is like, you have to do research now. Because remember, one of the things was you could do research, it was bad, but you could, uh. and, and you were likely better if you were trying to get into five accounts. Like you, you just had to do it. But if you were, you know, someone who had a hundred accounts of territory, many of them just did a cursory glance because you could, there's been a moment in time here where you didn't have to do as much research, right? So we have this combination of things, which is actually, it's better and faster than ever before. If you don't, you're not likely to be relevant enough to get in the door and to be able to sell some shit.

Those both things go

together at the same time.

Jake Dunlap: They

always, have though, right? Like, that's, that's all [00:20:00] that's, it's like, it's kind of

always right. It was a little easier. But look, what is the point of sales is if it, if the point of sales was just information giving, guess what? You wouldn't make commission, right? The point of sales has always been, Hey, I care about this industry that I, I serve. I want to help these people make a great decision. And I happen to think that we've got a pretty good product that can help a lot of people, right? But I feel like, you know, it's like we're, we need to go back to like 2014 pre-sales engagement platforms, right? And say, guys, the sales engagement platforms were never meant to hit Send All Ever.

Literally, some of them didn't use to have that feature. I think it was SalesLoft. SalesLoft. used to literally not allow you to hit Send all, and then it was like, okay, maybe a little send all, and then it was like, oh crap. What did we do? Right. So you're hitting it on the

head, Craig? Yeah.

Craig Rosenberg: if you just take like Matt, um, you know, on his, uh, I think it's a breakthrough for, you're talking specifically about [00:21:00] webpages or any kind of content, Matt, is that kind of the idea that

Okay.

Matt Amundson: basically what I threw down to the marketing team is you are, you're not allowed to use AI to create your content anymore. Because you can smell that stuff coming from a mile away,

Craig Rosenberg: Right,

Jake Dunlap: Mm mm.

Matt Amundson: a customer of Jake's. but what you should do is you should use AI to be critical of the work that you create because it's a really, really good editor.

Craig Rosenberg: right, right.

Matt Amundson: you're gone.

Craig Rosenberg: No, no. I'm here. Sorry. I just, I had something I was looking for in my pockets and I knew it would be distracting.

Matt Amundson: Okay.

Craig Rosenberg: I'm was the key for, It was the key for, his

Matt Amundson: It's a key

Craig Rosenberg: Okay. So you actually, I remember this shit because Jake, when we were on that panel, he was like, you were actually sarcastic. This was, by the way, this is a compliment.

So do not get, do not

take this the wrong way. No, I don't. Yeah, it takes a a little bit.

And he was, banging his fist [00:22:00] on the table. He was like, actually, none of this is different. This is what you were supposed to do in the first place. Right? So I'm summarizing you, Jake. Um, and so, but I love, because I do feel like marketing on the website or in the content, um, there, there's use case marketing that's happened in the past, but generally speaking, we haven't been able to try to capture. The buying committee in a, in a credible way. I mean, even if you did, focus groups or whatever, it's still, you still ended up with something pretty broad and probably not relevant or interesting. So I think that's, better, and it's how you should do it. Right. So both things coming together.

but Jake, my point is yes, it's always been better and I Yeah, I, I totally agree. Except right now things are crazy competitive, and if you're generic, you're fucked, you Right.

Is that true? [00:23:00] I don't disagree, man. Yeah, I don't disagree. I don't disagree at all, but, but,

Jake Dunlap: I think, I think it's like the, here's what I see. I feel like honestly, we're in like a bizaro world. Like we are in this bizaro world where leaders cannot un anchor from activities. It absolutely is insane. And by the way, you know, um, I'm not saying that certain funds or other people don't put this pressure to say, well guys, this was the recipe Aaron Ross taught us. There's, it's

this. And, and, and, and,

what I want to call out though is like, just so any of you who are managing your teams by volume, like let, I'm just gonna make a very simple analogy.

You can take it or leave it. When predictable revenue was written. Okay, keep in mind over like based on data from over 20 years ago, every activity, okay, was a high quality activity. Back then, we really only had the phone and a little bit of email, and every single touchpoint was what customized. There was no this.

[00:24:00] So therefore, when you have a homogenous data set where everything is the same custom, you can start to make some leading indicators that this activity equals a meeting. Fast forward to today. You're asking a rep to connect on LinkedIn, send all on this, write a message on LinkedIn, do this thing. Not all activities are the same, so therefore your activity data is dirty and, and therefore is not a leading predictor of meetings because it's not a homogenous data set.

It is all over, and some of these things are nurturing and other things, so. Again, like a lot of this is like, you have to start to realize, and the bizarro part to me is guys, the goal are the outcomes,

not the, not the activities. It's like, you know, we use this concept called meaningful conversations, which is, and fine if you don't want to, measured, like purely just meetings book, but it's like, did you connect And one person responded with, let me get you to Craig.

He's the right person. Or, yeah, this is interesting. Let's catch up. Like, you know, leading indicators of outcomes I think is where, where the future is, is [00:25:00] not. Activity based tracking. And I, but I do feel like, look, you know what? tracking activities is easy.

it's real easy. And that's why we we're not unch anchoring from it, even though the results are like, you know, down the tube.

Craig Rosenberg: Matt, you were agreeing.

Matt Amundson: I did agree with Jake there. Yeah, it is easy.

Jake Dunlap: Okay, good. That's good.

Craig Rosenberg: on

that part

Jake Dunlap: Well, it's more, it's a lot more fun if like, there's a good conversation. You know what I mean? Like it's, everyone's like, oh, I agree. Like, Hey, I, I like that. Mix it up a little.

Craig Rosenberg: back 'cause when you first started talking, uh, Matt was agreeing initially with, do you guys track activities?

Matt Amundson: We do, uh, too much. Right? Like, and this is one of the things that I'm trying to break our BDR team out of. Like, I don't give a shit that you made 500 phone calls this week. In fact, like, I think that that sucks. I don't want your job to suck. One of the, you know, when I rewind the clock all the way back to when I started in tech and was A BDR, I love the challenge

Craig Rosenberg: The challenge of.

Matt Amundson: Putting it all together [00:26:00] and making it work and being thoughtful around like, what are the parts of the Marketo platform that people would actually wanna buy and cause them to become a customer? There was so much to it, right? Like, could I lean

Craig Rosenberg: Yeah.

Matt Amundson: that was meaningful for them and like, could I show them something that was gonna get them interested enough to want to talk to a salesperson? Now it's just kind of

Craig Rosenberg: Now.

Matt Amundson: ugh. Like let me just send this to as many people as possible, whether it's they're using a sales engagement platform, a power dialer, automated InMails, uh. Products. It's just volume, volume, volume, volume, volume. And then tracking BDR volumes on a dashboard

Dashboard,

oh, we made, you know, 1500 fewer phone calls last week.

And you're just like, guys, this is not getting us anywhere. We should be thoughtful about our approach. I don't

Craig Rosenberg: I

Matt Amundson: I'm, I'm in a zone where I'm kind of like, should we just get rid of outreach? Like should we pair back on all these things that do automation? Could, should we get rid of a power dialer? Yes. Our activity [00:27:00] metrics will suffer. Our activity metrics will look shitty, but like do we get more meetings as a result? Like are we better off not putting a list into a machine that's gonna automate our calling or automate our emails and just say, Hey, you got 20 accounts this week. Turn it into, you know, five meetings, it's better off.

You're better doing that than saying, Hey, make you know, 3000 activities and turn it into two meetings.

Jake Dunlap: well we also that it doesn't allow people to play to their strengths. Look,

if Susan can go send 20 customized videos a day and crush it, then amazing. And if Rick is really good, and again, I'm not here, here's what I'd say. There's a time and a place for activities, right? It and early in your career.

So it's not like zero or a hundred. You know, but I'm saying if you can manage to outcomes, but here's what I would say is like, these tools were meant to help. And I think if you can, if we can get back to that concept of like, maybe step one is just turn off the send all function on outreach.

Right. Turn it off. Just turn it off and, and [00:28:00] instead again. But what the, the issue I see though is we're just not training the SDRs or BDRs or even AEs on what are the trends in the industry like? I think back to back in the day, you know, gosh, like 20 2006, I just started at a company and I got a binder, I swear to you, was like this thick of like industry trends around talent acquisition and like we had to learn it and like, hey, if you're meeting with a manufacturing company, you better read. What these trends are, right? And so I do feel like part of this is on the companies that we have to just realize you have to still keep investing in people and, and let the people, to your point, Matt, like let them think like, Hey, these templates we know work. So Jake, you work your magic in here and if you break it, amazing, let's take that data and let's spread the love. So I, it's, it's this kind of combination of tracking, but not trying to templatize, you know, and, and I

think part of this is though, is this kind of co, this covid generate, like, I feel very unfortunate [00:29:00] for anybody who joined sales in 2019. They have not had the ability to learn from peers really, really quickly. You know, they're disconnected, they're not learning as fast. Like for all of us, we were on the floor, like you hear, oh man, I'm gonna take that. Oh, that's good. Now let me do that. And so we've got a whole generation of sellers right now with five, six years of experience that have been taught to just execute templates.

And then we wonder why they're not, you know, we didn't really teach them much. We're like, just do med pick. Just do med pick and just, uh, and just send this email and that will

solve everything. It's this crazy med med pick is like, is has been taking over. And I'm like, guys, do you know Med Pick Med was invented in 1996? The internet wasn't even a thing. There was one decision that, that's a whole other like debate we can get into, but

these are the conversations that we're having around how to modernize your your GTM process.

Craig Rosenberg: it. All right, so if, so help me on this is, those were some pretty successful outbound stories and most of the stories we hear are not, [00:30:00] I know. That's why you brought it up, right? Like it, and, so if you were building a, an outbound team. Today, you don't have to get, I know you have some proprietary thi, but

like, generally, like what No man, I'll give it all away.

the steps. Like what,

how do you build it to be successful today?

Jake Dunlap: I think there's a few core elements that I think will be absolutely critical, and I'm gonna, I'm gonna kind of work it backward. The first is mindset. Outbound is the

same as your Google AdWords or any of the things that you're doing.

It never ends, so you cannot take a. Project based mindset to outbound, which is what probably 90% of companies do. They say, we're gonna redo our cadences, and we're gonna

write 20. And I'm like, 20. How do you know it's not 200? How do you know it's not six? So step one is, and I talk about this in my book, it, it's the four C, which is continual optimization. And so you have to have the mindset that I'm gonna need somebody at my firm, assuming that we're gonna be scaling to like a decent amount of, [00:31:00] you know, amount of accounts we're working. Where this isn't a part-time job of an SDR manager and a rev ops leader who, and, and we're basing all of our cadences on opinions like, nope.

The same way that your, your marketing team that's spending $200,000 a month on Google, you're spending 200,000 a month on SDRs. The goal is the same. Generate meetings. Guess what marketing does? They hire someone who tweaks the dials 24 7, who doesn't think about opinions. You need that person for your outbound. Number

one, you cannot be buyer behavior's evolving. What messaging works you need to optimize that faster. We had a client, when we plugged in our kind of performance pulse tool, they had a sequence that had three emails, 63,000 sends, 39 replies. And when we, everybody laughs and then we plug it into their instance and they're like, uh uh wait, that one was 20,000 with four replies. And you're like, yeah, you can't do that anymore. So you gotta be smart early and build this mindset of like, we are never done. We are always going to be optimizing outbound performance [00:32:00] and what works. So I think like mindset is first, and then two is again, we have to invest in teaching the people who are the actual buyers.

And I know that that sounds cliche, but like, look, you know, I'll, I'll give you an example. I, I, when I ran a sales team, this is years ago, we, we sold into operations. I happened to have a buddy who was a VP at McKesson. I took my team to his, his production facility. This is what a VP of operations does.

This is what they do. And I feel like if you, if sellers, and this is for all of you out there, sellers, over the next three or four years, it's gonna get hard. And the reason it's gonna get harder, buyers are not gonna wanna talk to anybody who can't add incremental value, not a little more value, incremental value, because everything else I can get from ai. And from groups that I'm a part of. And so sellers, we have to train them on what do these people do? What actually are their issues? And then [00:33:00] train salespeople in the mindset of your job is to help these people with the three or four problems that we solve for. And in that way, when I'm training them to do outbound, they can say, oh, okay, this person, they do this. So, uh, let me try this little customization. And like what we do. So I think it really, like if you do those two things, and I think you can use an outreach or a SalesLoft or a Gong or whatever, um, but I think if you do those things, you're gonna be successful because I really feel like the bar is so low right now. There's all kinds of crazy plays we can get into around, you know, customized podcasts and things like that. But those are the foundations is training the team what the persona actually does and the trends that that person, what are the pressures that person faces and how we solve those pressures. And man, if you invest there, you're training people how to think. And I feel like we are, we for a long time have been saying, you know, just follow a template. So if you train 'em how to think so they can connect and you have an idea of like, we're gonna continuously learn and optimize. I, I think that you're gonna be, you know, you should be [00:34:00] successful. Obviously there's the messaging and how tight is your ICP and all that stuff.

But, you know, I think those two are ones that I hone in on.

Sam Guertin: Did you say customized podcasts? Yes.

Craig Rosenberg: Oh,

damnit. I was Sorry. I, yeah. Yeah, yeah.

do I

do that because, is Yeah. Dude.

following, but yeah, dude,

Jake Dunlap: Oh ha. No, man. Wait till.

Craig Rosenberg: up. I mean,

what No, dude, let me, well let me tell you the play. Literally, we're like, this is alpha play, right? Again, I go back to like, pattern disrupts the other thing. So if you guys haven't messed with Notebook LM yet, um, go check it out. It's a Google product. It's called Notebook lm. Just how it sounds, um, with Notebook lm, um, we did this for, um, we're basically running prospecting plays with it. So imagine what I can do is, and I can upload like your LinkedIn profile links about your company, links of like, uh, like industry trends, a link to my website. And I can say, I want you to create a podcast that for this [00:35:00] person it's about Craig and Craig I'll, you know what I'll do, Craig and Matt, I'll make personalized podcasts for you. It takes like 10 or 15 minutes and it says, look, I want you to talk about the pressures that this person in this type of role is facing. Talk a little bit about his background and why he's, why he's uniquely positioned to take advantage of this. And then toward the end of the podcast, I want you to start to talk about why we are the logical solution for someone like Matt to help him to solve the, the industry pressure challenges. And then Notebook LM in the matter of like 45 seconds, creates this very, very realistic podcast that's anywhere from like seven to 12 minutes long. Um, and

Jake Dunlap: now imagine if your BDR team just sent out 25 of those a day versus email, call, email, email, LinkedIn, et cetera. So that's what we're testing. And then we'll talk about like, uh, customized white papers too.

So with the chat GPT oh three model with deep research, I can write an eight page white paper with 25 sided sources that are about trends in Matt's world over the next three to four years based on his industry and things that he needs to know as a, you know, a vp, you know, and then [00:36:00] triangulate that, you know, with how we solve.

And so if I send you. You know, a customized, uh, white paper that's about your business and shows that I understand it and then I send you a customized podcast that also does that. You're taking the meeting,

like you're taking the meeting. Like it's, so that would be the third thing maybe I didn't ask the outbound.

It's like, guys, be clever. Be clever, be interesting. So,

Matt Amundson: Be different.

Jake Dunlap: yeah, and it is fun.

It's

a lot more fun.

Notebook, lm, go check it out. If you aren't already, you're

gonna get the, the

AI is getting so good,

Craig Rosenberg: yeah,

I,

Jake Dunlap: so

good.

Craig Rosenberg: dude, why don't you lead with that story? That was insane.

Matt Amundson: Yeah. Uh. Because most people can't handle it, man. most people are not. They're like, Jake, it's not a volume activity. I do

Jake Dunlap: not know how to forecast this or tell my, tell my, my board. My board will yell at me if volume activity drops. So I gotta keep volume up, you know? that's why

Craig Rosenberg: The,

uh,

Jake Dunlap: when you're ready, you're

ready, Yeah.

Craig Rosenberg: that's a great [00:37:00] idea.

Matt Amundson: Let me get your opinion,

Jake, just because I think, Steel. Yes.

Like Anthropic is headed in a, they sort of made an announcement, I think it was like late last week, and they're headed in a interesting direction and actually was chatting with a friend of mine who was like, oh yeah, you know, I'm working with this company.

They love Anthropic. They love it because, you know, it's different and they're, they're taking things in different directions and say, open AI is. They made the announcement that they were gonna start integrating with business tools, and I think a lot of them, for the most part right now, are sort of like back office, although I think they might have a HubSpot integration. How are you feeling about like the encroachment of. GPTs into your actual business tools, and do you think that there is like a future there where we could be OpenAI or we could be using Claude to start asking questions and make connections between all of our different business tools that, you know, that might help us, you know, in various ways, whether we've had [00:38:00] previous conversations or whether it's like, hey, it looked like the last five customers that we just closed for these reasons, et cetera.

Jake Dunlap: I know for a fact OpenAI is in beta with, uh, direct Salesforce integration as well

too. So like, this is not a, this is a when, not if.

Um, scenario again, I think that again, here, here's this interesting world that we're living in. This is, these are all great insights, right? I'm talking about being able to give someone the best prep or best insights, et cetera. You know, the, the, the reps that are gonna make it, and you know, a lot won't candidly, are the reps that actually understand what the heck this thing's putting out, man. And so it doesn't absolve you from learning. It, you know, there, there parroting parroting back. AI will, could maybe get you that meeting, but then you have to get on the call. And so I'm all for, you know, these automations again, we've built some et cetera. Um, but it does not take away the fact that you have to then tr okay, well what does that [00:39:00] mean? So this company says that they would make money doing a, B, C, Hey John, what does that actually mean? Can you teach that to me? Can you tell me about it?

You know, a a a really fun thing to do is. After you do kind of the discovery call prep, GPT, you say, Hey, create a 15 question trivia game in real time to teach me this company's industry.

And it's like, that's how you learn it. And so I'm, I'm all for this, but we have to remember we are dealing with humans.

We are not neo from the matrix where you

plug it in. And I know kung fu. And I think that is what we're actually expecting from people is that if we, if we spoon feed them the, the play. We still have to train people. And so I,

I, that, that is critical. And if you're a seller, you cannot afford to just be rep number, you know, whatever.

Like you have to invest, you know, like you have to invest in learning, actually learning this stuff too.

Matt Amundson: I, I wanna

Craig Rosenberg: I,

Matt Amundson: a

Craig Rosenberg: yeah,

Matt Amundson: real quick. Uh, I know that this

Craig Rosenberg: can.

Matt Amundson: no, go ahead, Craig. You go?

Craig Rosenberg: [00:40:00] Well, I, before you ask the question, I just wanna point out

Matt Amundson: Yeah.

Craig Rosenberg: that Jake has brought this up twice. It's because, Matt, you're not picking it up. just kidding. No, that was a joke. I just saw you looking at me. I I was like, I just tried to break it up. No, that's, that's not why, but it is, it's, it's really important.

And actually that hasn't changed. 'cause I, you know, when we had Topo, I remember we'd go in and they'd say, well, these guys need to do research. And I, there was one sales leader who is running the SDRs. He's like, well, I'm training him how to look at a. S one or not s you know, the, the investor,

Matt Amundson: K. Yeah.

Craig Rosenberg: 10 K. Sorry,

I lost my,

Jake Dunlap: Yeah. Yep.

Yep.

Craig Rosenberg: like, but bro, if they don't know, right, if they don't have the baseline, that's like, that's actually a waste of time. And going to continue to be bad content. So I really think it's important, like I think it's always been important if they don't [00:41:00] understand, as you said, that one of the reasons for me, there was a bunch of reasons why I was attracted to account-based, it wasn't because of the applications or shiny objects was if you focus on a certain type of. Company and a certain type of people in the company, then everyone has a better baseline of what to talk about and could read something from, uh, the chat GPT or whatever, and actually do something with it actually be creative. 'cause you can't, unless you learn it and like, um, it, so anyway, I just thought that was a good point and I actually just reiterated what Jake said. So I'm sorry Matt. I,

Matt Amundson: you're

Craig Rosenberg: that was. Am I? Oh, thanks, man. As you were,

Matt Amundson: yeah. It was an

Craig Rosenberg: I wanted to make a point, you know, I felt like, you know, I, you know, I could contribute there. Matt,

um, what was your question?

Jake Dunlap: did. You did.

Matt Amundson: Well,

I wanted to use the sort of like classic transaction question here, which is like.

Craig Rosenberg: Oh, there he is.

Matt Amundson: [00:42:00] are like, you know, you're working with lots of companies and my, my guess is many of them have tried, they've tried to implement somewhat of an AI strategy. What is it that they're

What is

it they're getting?

I. to, come to you?

And I'm guessing you're probably hearing the similar, similar stories over and over again.

Craig Rosenberg: Wait, this is a,

transaction classic It

you went with.

Matt Amundson: Yeah.

Jake Dunlap: yeah.

Craig Rosenberg: God. I love it, Jake.

Jake Dunlap: Is this a go? Is

this a

Craig Rosenberg: Well, no, it, we tried to move away from it. He keeps bringing us back in. This was the per, that was the

perfect time for the

Jake Dunlap: Well, I think

it's a really good point. I think It's a great. point because, you know, a, a lot of people will listen and, and say, oh yeah, that sounds like me. Uh, okay, I'll, I'll start a little higher level then I'll try to get pretty tactical. Um, I think there's a couple of, of, of issues. One, it teams do not know what the hell is possible and because they don't know what's possible, it, it teams cannot keep up. They are not up to speed. I cannot tell you how many companies, um, you know, it's like, [00:43:00] well it we're banning chat, GBT, that's my absolute favorite one. Right? And it's because in April of 2023, lemme just give you guys a history line around how dumb this is. In April of 2023, chat, GBT could not access the internet without a plugin.

You couldn't do PDFs. It's like a little baby, it's like five months old. Somebody uploaded Samsung's board minutes and you know, it says, do not do this at the time. And somebody was able to reverse engineer and find like a couple of lines from it. And now because of that, the IT world says, oh my God, chat GBT isn't safe.

My friends, guess what? They fixed that

like, it very clearly calls out when you're using the teams edition or other editions. Like no information is shared back with the model. No like nothing, no conversations are shared back with the model. And so I think part of this is, is executives. Are not staying up to pace the way that they need to and they're trusting an IT team that is not capable of comprehending what generative AI is possible.

And I'm not saying every IT team, I've seen some teams that are way out there and doing really cool stuff, but I do [00:44:00] feel like IT teams are also struggling. Like it's like imagine your IT teams before the internet and, and how capable were they of understanding how each individual role at your company should deploy the internet if they had never seen it before. Probably not very capable.

Right. In 96, I looked this up, they did create roles called chief internet Officer and what are companies doing? I'm okay on the product side to have an AI officer, but people are creating a chief AI officer. It's like guys, AI is a role by role use case by use case deployment. So that is the, that kind of combination of issues is really where I think most companies are getting paralyzed. Um, even if it is telling them, you know, a, B, C, stop asking the question, what's our, what's our AI go to market strategy? It's not the right question. AI is like the internet. It says, Hey, for our content marketing team, what are the three ways they should be using it for our BDRs?

What are the top two ways that they're that, that we're gonna

deploy a chat, either assistant or an advanced model. And so [00:45:00] simplify. We already talked about this, the first use case, my friends, you don't ignore all the other cool stuff. I ignore all that prep and research. All of you should be using generative AI to pull in interesting insights, whether in an agent form or automatically. To help your team do basic things, and it doesn't advocate them from learning those things, but that to me is, is why companies aren't doing it one a lot. I'd say at least probably 70% mad of the conversations I have that it gets involved. I, I'm just, I'm like, this is just wrong.

Like you are, you, you do not obviously comprehend what is possible and two, for the rest of the people that are like, we want to do something. Is they're not trying to solve a bottleneck. They're looking at the qua. They're, they're trying to instead like, what's the bottleneck in your rev org Boom. That's where we're gonna deploy Gen AI a little bit for this role and this role. Great. Now, [00:46:00] where's the bottleneck? Great book called The Goal. Shout out to the goal. Uh, if you have not read it, it's about the theory of constraints. Find your one bottleneck. Deploy gen ai. There. So simplify, simplify, simplify. Don't worry about all the other cool use cases. Write 'em down on a piece of paper. Go through your own existential crisis about what does this mean for you and your life later. But find your bottleneck and just start there. And Matt, those are the companies that we're seeing are, are making choices. Like that case study I kind of gave upfront, it was like, okay, forget all the other AI stuff. Our reps are spending too much time trying to identify the next obs skew. Amazing. Let's just fix that. So that, those are the things that I think the other kind of cautionary tale is sales leaders, executives, listen to me. You have to learn this yourself. You cannot outsource this through rev ops.

This is a foundational shift in how we solve problems as human beings. This is not another tech. We've actually abridged it.

We don't say people process technology anymore. We say people process AI and technology.

[00:47:00] AI is not a technology. It is. It's like saying Google's a technology.

It's a shift in, in going and solving problems in a, in a completely different way than we are used to. So if you can get over those two humps, you can realize that your IT team may be, operating from a knowledge deficit and it's your responsibility as an executive to learn this stuff.

You can't outsource it. And two, you pick the bottleneck. You, you will be successful whether you, you know, you do it on your own or, or whatnot. But that, that's the winning

combination.

Matt Amundson: Shit.

Craig Rosenberg: was a great answer. Yeah. You son of a bitch. God dammit. That was good. Yeah. Um, that, that's definitely, that, that's going to be a social shared, uh, piece, man that was passionate as well.

Matt Amundson: Yeah.

Craig Rosenberg: I love it. And, um, I think that's right. I actually think, uh, that makes a ton of sense. I, I have. Watched like Matt, you know, Matt's the perfect example. He's still in the seat and you know, he was telling you that it's the same thing, like he [00:48:00] did it, he's doing it, he's actually doing it on the side. When we just did our summit, it was like we had, I. Sales leaders and marketing leaders. Right. And all of them were the leaders.

You know, they were doing it because they, they were, as you said, AI is a, a way you work now, not, not necessarily a technology. And I think that's, I think that's a great point. Uh, I think it's a masterful point. How's that?

What do you think? Yeah, I Ooh. I like, I like that. I

Jake Dunlap: like that.

Craig Rosenberg: to use a different word every week, Matt.

Um, so, uh,

yeah, Today's. Yeah. Well, you should have

Jake Dunlap: told us in the beginning we could have all worked in. You know, at some point, You

know, that's what we used to do on the sales floor. Did you guys ever do that? Where like, if you're like, again, this is about having fun with it, I remember being on the floor and we'd be like, all right man, bet I'm about to work.

Abraham Lincoln and John Wilkes booth into this pitch. And I'd get on the phone and I'd be like, you know how it is, John? It's like, you know, like Abraham Lincoln and the conflict with John Wilkes booth. And so, [00:49:00] alright. Anyway, like we would, we

would, We would give each other words to. I love To try To work out. You gotta have fun, man. Sales is fun. Like, never forget that. Like that's why a lot of this stuff, like to me why it's so exciting is like, man, I would loved to have had half of this stuff and then I could have just like been smarter, faster, and, but you still have to have fun with it. There's a lot of rejection and things too. But Yeah.

that just reminded me of, of like

those, those days.

Craig Rosenberg: that. And that was great. And let me throw this to you guys. So for my next events coming up. Here's what I'm gonna tell the presenters. So, Jake, you've done one. Matt's done one for me. I'm gonna give you f How many words do you think is the max to have to squeeze in? Three

or five? Can I do five?

Jake Dunlap: Oh, this is like, this is like a name that tune. Uh, five. Five. I think I could get five in. Yeah, I could get five in. Matt's like I could

do six.

Craig Rosenberg: you present

Jake Dunlap: Yeah.

Craig Rosenberg: of my things, even if you're doing 15 minutes or an hour, you have to get, you're gonna do this presentation and you have to find a way to get these five words

in. [00:50:00] Wouldn't that be fun?

Jake Dunlap: I kind of prefer that honestly. Yeah, like I, I would actually prefer that.

I think just to

spice it

up a little bit, like this is

like little Easter

eggs. Little Easter eggs you can pick up on.

Craig Rosenberg: them off considerably and that is actually also enjoyable.

So, um,

Jake Dunlap: Yeah, yeah, for sure.

Craig Rosenberg: before or a

Matt Amundson: No,

after. No, no. You let the No, you definitely don't. And you're like, why did that dude say Abraham Lincoln so

Jake Dunlap: many times? Like, why was it all his references to, to like Civil War period history, right? Like, and then I'm like, oh, he had to work in

Matt Amundson: How do

we

make

Jake Dunlap: the Getty. Yeah. He used the word Fortnite.

You know, like it was a Getty

Bird's address or something like that, you know?

Sam Guertin: to that. Huh?

Matt Amundson: There we go.

Craig Rosenberg: See that now? Now I've got a,

Matt Amundson: fun.

Craig Rosenberg: I have a

practical idea and It is that, see, you're having fun, you're laughing. That's what, that's what sales is about. Like, and, and all this stuff is just if, if we can remember that, have [00:51:00] fun. It's about connecting with buyers that that's how you're gonna future proof your job. All this stuff just makes us better at, at those things at the end of the day. And you know, the sellers that figure that out will be the ones that continue to win.

Boom. Let's do it. That was great.

Matt Amundson: that was a

Craig Rosenberg: All right. Well, Jake, yeah. Yeah, I mean, dude, that was a really good show. We didn't

even do the formal Good. normally do, so thanks for doing this, man. That, that was the, uh, was the transaction personified. Thank you.

Jake Dunlap: Good man. I'm glad there was, uh, there's some value, uh, out of it as well

too. And, you know, I, I do what I can. It was.

Craig Rosenberg: have even remotely come close to

that,

even if Yeah, he the get Forget the Getty Bird's address. Yes. There you go. I like that.

[00:52:00]