The Transaction

TT - 074 - James Kaikis
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James Kaikis: [00:00:00] But it was that moment where I actually realized like, man, this AI thing is [00:00:05] real.

James Kaikis: we have lost sight in B2B SaaS of who matters.

James Kaikis: I just don't think companies actually give a shit about [00:00:10] their customers

James Kaikis: Companies that I considered working at two years ago have been commoditized overnight. [00:00:15] Like they're literally non-existent.

James Kaikis: trust and value are the ultimate [00:00:20] currency and this next wave of B2B SaaS.

James Kaikis: the world of BDRs, AEs ES [00:00:25] essays, PS, CS support AM is fundamentally broken [00:00:30] for a strong majority of businesses.

James Kaikis: This is the first time that I could really remember that we are at a level [00:00:35] playing field. We're all kind of learning on the fly right now.

James Kaikis: If you aren't going from zero [00:00:40] to one right now, you won't have a job in the next couple of years. I don't think people realize the [00:00:45] severity of that. If they're not taking the leap and jumping in, there's not gonna be a [00:00:50] job for you.

Matt Amundson: Craig, that's a great haircut. You look wonderful today.

Craig Rosenberg: You know, normally, [00:00:55] uh, you, uh, what you'll say is, [00:01:00] um, what's remarkable about me is that my hair grows so fast.

Matt Amundson: [00:01:05] It is fast growing. Are, are you taking some kind of daily multivitamin? [00:01:10] It's good for celery production.

Craig Rosenberg: Oh, man, [00:01:15] I, yeah, no, I'm not, it's wild because I'm kind of bald, but my hair [00:01:20] grows really fast. The hair that I do have grows really fast.

Matt Amundson: it's great.

Craig Rosenberg: [00:01:25] Yeah. Is this, is this what you guys would like to dig in on today? Is there a way to

James Kaikis: I,[00:01:30]

Matt Amundson: why

Matt Amundson: we brought James on.

James Kaikis: I was actually hoping we could talk about Craig's glasses because [00:01:35] I've never met a man with more colored glasses in my entire, entire

Matt Amundson: Can't say. You can't say [00:01:40] colored anymore,

James Kaikis: Oh, so

Craig Rosenberg: Hey, by the way, by the way. Yeah, and speaking of [00:01:45] which, I just got my eyes checked. I have to go to a new, like a higher, [00:01:50] more, a more intense lens. So that means a whole new slew of glasses.

Matt Amundson: Wow.

Sam Guertin: [00:01:55] Oh, let's go.

James Kaikis: Anytime I ever see a video of Craig, my first thing is like, what color is the [00:02:00] glasses? Like, it's like a game that I play every time I see Craig on camera. It's, it's [00:02:05] fantastic.

Craig Rosenberg: You guys see why I got him on the show. I mean, shit, you know.

​

Craig Rosenberg: [00:02:10] [00:02:15] [00:02:20] [00:02:25] [00:02:30] so it feels like today, this week was a, a, a [00:02:35] busy, like a, there was a lot of intensity in this week for everyone in the world. I, it [00:02:40] was wild. No. Is that dumb? Um, [00:02:45] so.

Matt Amundson: particular to you, Craig, or.

Craig Rosenberg: [00:02:50] Jesus Christ. What kind of show is this, man? [00:02:55] I love it. Well, Matt, um, I'd love to discuss, [00:03:00] um, no, I,

Matt Amundson: government shutdown, huh? That's what our, our listeners wanna [00:03:05] hear.

Craig Rosenberg: Let's do it, man. Let's do it. gerrymandering conversation. That'd be great.

Sam Guertin: [00:03:10] Yeah.

Craig Rosenberg: yeah. Yeah. I love it. The, um, all right, so today's guest I [00:03:15] was trying to remember, so I met you through Doug Landis.

James Kaikis: you did meet me through, [00:03:20] yeah. Doug

Craig Rosenberg: Yes.

Craig Rosenberg: Fucking Landis. Yeah. Yeah, that guy. We gotta get that guy back [00:03:25] on the

Matt Amundson: back. Get him back on.

Craig Rosenberg: I told him and then I never, I [00:03:30] gotta follow up. Yeah. Lemme write

James Kaikis: actually, I'm actually catching up with Doug next week, so,

Matt Amundson: tell him

Matt Amundson: we want him [00:03:35] back.

James Kaikis: I'll let him know. I'll let him know. Doug. So, Doug and I have known each other from Pre-Sales [00:03:40] Collective 'cause I would bring him on to like, talk about the profession and the role and like from a VC [00:03:45] perspective. And then when I had left, uh, pre-sales collective and took some time off.

James Kaikis: I was [00:03:50] talking to him about a couple different things that I was thinking of doing, and he's like, you gotta talk to Craig Rosenberg. Like [00:03:55] Craig, like built Topo. He sold it to Gardner. Like there's a really good opportunity there. [00:04:00] And I had my meeting with, with Craig and from my, from my recollection, Craig is [00:04:05] like, you went into that meeting of like, all right, this topo competitive like [00:04:10] idea is the right idea, and then all of a sudden I threw you a curve ball that told you I'm thinking about start my [00:04:15] own business or going to test box as the CRO [00:04:20] after this company pivoted.

James Kaikis: And, and Craig was like, oh shit. Like that is like the one of the best [00:04:25] career moves ever. You started the pre-sales collective, you know, the demo automation category. [00:04:30] Yeah. You need to go to that company. And so that's, that's my recollection of the story of how I got to know [00:04:35] Craig.

Craig Rosenberg: That is amazing, man. Yeah. So, um, so, [00:04:40] uh, besides being a buddy of mine, James and being really well [00:04:45] versed in modern Go-To-Market, he has his own, um, show with his new, uh, [00:04:50] group called GTM Shift, um, where if we [00:04:55] judge people by their guests, he had the right guess, and that includes, uh, assert [00:05:00] somebody you may know.

Craig Rosenberg: But, but one of the things Matt, that would, [00:05:05] um, when I was prepping Matt on having you on James, is that we like [00:05:10] when. We could talk about these carve outs in the Go-To-Market that nobody talks [00:05:15] about. In the case of u it's pre-sales se sc [00:05:20] stuff. And like Matt can agree 'cause Matt advises small companies too.

Craig Rosenberg: [00:05:25] That is actually a question we get, you know, and I don't know the answer. And [00:05:30] there's a lot happening in the world of tech sales where the, the, the role of the [00:05:35] sc at least the stuff that they do is moving forward in the sales cycle. [00:05:40] And there's a bunch of really interesting stuff. So that's, I, you know, with James we [00:05:45] get to not only have Agra who fits our personality, but um, he has a carve out in [00:05:50] Go-To-Market that we don't talk about.

Craig Rosenberg: So I'm really excited everyone now [00:05:55] the, uh, leader of GTM shift, but had originally all the, I'll just go through some of the [00:06:00] things he mentioned. He started Pre-Sales Collective, which was the biggest community of [00:06:05] scs.

James Kaikis: Mm-hmm.

Craig Rosenberg: Um, so like if you had a question, which happened to me a lot, I [00:06:10] would go to James. Now, he didn't always answer it, James, by the way, I gotta tell you that.

Craig Rosenberg: But like, he ca came pretty [00:06:15] close and then went to TestBox to run, basically Go-To-Market and is now, [00:06:20] uh, you know, doing his own thing with GTM Schiff. So transaction audience, welcome. James [00:06:25] Cake is my guy.

James Kaikis: Yeah. Thanks for having me. It's awesome. It's awesome to be here. You know, I was, I was [00:06:30] actually thinking about that, right? Because it, it's, it's funny you guys bring this up because for as [00:06:35] long as this solutions engineering profession has been around, it is still just like this [00:06:40] unknown. And like, even as someone who co-founded the pre-sales collective, there's still [00:06:45] not like best practices out there and guidance out there.

James Kaikis: And even like when I was [00:06:50] at Pavilion last week and they were like talking about all the roles, no one said sales engineering yet. Like [00:06:55] data will, yeah. Data will tell you how important the role is. And it's just like, you know, I'll tell you, it's [00:07:00] like I had a couple, I've had a couple moments in my career.

James Kaikis: It was like I could be one of the people who know this profession [00:07:05] inside and out. I've also been like, I want to own, I want to own all of Go-To-Market and be a CRO and get that [00:07:10] different perspective on this profession. And still to this day, man, I, I was given a presentation to a company [00:07:15] last week. I still think that so many companies are not deploying this role [00:07:20] effectively.

James Kaikis: And like, as the world is changing, this role can be a superpower. [00:07:25] And, um, you know, I, I just like, you know, have always been trying to sing, sing the good word [00:07:30] of, uh, the pre-sales profession, uh, and solution. So I'm just happy to be talking about it, [00:07:35] right? Like it needs an opportunity to speak to it because it's such a black box for so many [00:07:40] folks.

Craig Rosenberg: Matt, I think by his, so when he makes the, [00:07:45] uh, noises, um, that means he's down. So I heard multiple [00:07:50] noises during that, so,

Craig Rosenberg: yeah. Uhhuh,

Matt Amundson: Mm mm

Craig Rosenberg: uh.

Craig Rosenberg: No, [00:07:55] you didn't do the lazy podcaster. You did make some noises. We're just really, 'cause [00:08:00] sometimes Matt, you're just looking straight ahead and so we don't know what's going on with you and then you'll make a [00:08:05] noise and we'll be like, oh, okay, good.

Craig Rosenberg: He's, he's in good shape.

Craig Rosenberg: So, quite figured out how not to [00:08:10] look at myself. Or am I supposed to look at you guys or am I supposed to look straight ahead and [00:08:15] like, you know what, um, Sam is about to tell me what I'm supposed to do, and I, I just don't want to know, so don't [00:08:20] tell

Craig Rosenberg: Yeah, Sam don't tell. Um, but that, that is a good point. 'cause like right [00:08:25] now I'm looking to the left 'cause that's where you guys are, but I'm supposed to be looking up and going, hello, my name is [00:08:30] Craig Roosevelt. Okay, so we got two parts of the show. So, uh, first part [00:08:35] we're gonna ask you to tell a go to, Go-To-Market story.

Craig Rosenberg: It could be anything, you know, um, [00:08:40] and, uh, you've listened to the show so you know, um, but just to, not to put [00:08:45] pressure on, but our best guests tell the best stories. That's just how

Craig Rosenberg: it's

Craig Rosenberg: number. Then the [00:08:50] second part with the framing, we just laid like what are the things that we're not thinking about in [00:08:55] today's modern Go-To-Market playbook and, uh, you know, one to three things and we'll just take it from there.

Craig Rosenberg: [00:09:00] Okay? So first one story. What do you got for us

Matt Amundson: Yeah. [00:09:05] Tell us a story

James Kaikis: I'm gonna,

The Life-changing Impact AI Innovation Had on James
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James Kaikis: I'm gonna tell you guys a story and I was actually thinking about what story to tell you, and there's a [00:09:10] couple of like selfish stories about like how Pre-sales collective started or how I got my [00:09:15] career start. But I'll actually tell you a meaningful story that has rocked [00:09:20] my world and actually caused me to quit my job and go back on my own.

James Kaikis: And I gotta GI [00:09:25] got

Craig Rosenberg: she says, alright, well yeah,

Craig Rosenberg: uh, I'll tell you one.

James Kaikis: I don't even know that Craig [00:09:30] knows that I'm gonna talk about the Scale Summit this year because I, it, [00:09:35] that conference rocked my world. So I'm doing a keynote presentation [00:09:40] to, uh, about five or 600 people in London next week. And my whole premise is the [00:09:45] future of Go-To-Market is customer power, customer focused, and AI powered.

James Kaikis: And if you take a [00:09:50] step back, you know, Craig, I've always got to know Craig, when, when scale's hosting an event, I wanna show up to that [00:09:55] event.

James Kaikis: But Craig was like, Hey, why don't you come to these, uh, [00:10:00] small councils that we have? And I had to like beg Craig like four times to let me into [00:10:05] one of those councils.

James Kaikis: Uh, but I was like, let me go. He is like, which one you wanna go to? I was like, let me go to the rev [00:10:10] ops council. So I was like, Hey, this is just probably some random like walk and talk, like get to know a couple [00:10:15] people before I get there. Um, I was late 'cause my flight was delayed. I flew in San Francisco, [00:10:20] got to my hotel, dropped my bags, went up to the hotel.

James Kaikis: I walk into this Rev council [00:10:25] and a guy by the name of Antonio Garcia at Motion is on the screen presenting.

Craig Rosenberg: Yeah. Yeah, that

Craig Rosenberg: [00:10:30] dude.

James Kaikis: And I sit down and I like, you know, kind of feel like the, you know, there's already [00:10:35] introductions and everything else in the room, but I'm like, all right, I'll just sit down and see what's happening.

James Kaikis: And this [00:10:40] guy starts fucking, this guy starts presenting some things on his screen. [00:10:45] And I swear to God, like I have always felt like I'm like super innovative and head on ai. [00:10:50] I started to see ghosts man. Like I, I was like, what the heck is [00:10:55] this guy doing? And what is he talking about? And he started talking about AI first [00:11:00] Go-To-Market and how he was scaling himself and how he was building, you know, [00:11:05] taking call transcripts, running them through GPT, scoring them based off his [00:11:10] methodology, cross-referencing it with, uh, Gemini [00:11:15] 2.5 to look at non-verbal cues and come up with a score.

James Kaikis: My whole [00:11:20] foundation was rocked, man. Like, it literally rocked. I grabbed a notebook from some person that [00:11:25] wasn't there, started writing some notes, and I was like, okay, what are these technologies? What is the [00:11:30] point of this? And I remember grabbing my phone and texting my rev ops person. I was like, do you know this [00:11:35] Antonio Garcia guy?

James Kaikis: Because like he's saying some things that I have never heard in my entire [00:11:40] life. And, you know, for that, like next 45 minutes, I will tell you the, the [00:11:45] core foundation of my entire Go-To-Market motion. Just changed because the things that [00:11:50] he was presenting on screen and how tactical it was and the takeaway it was happening in their [00:11:55] business.

James Kaikis: I actually had a moment like, holy shit, we're, we're all in trouble. You know what I mean? Like if [00:12:00] you, if you really don't lean in and figure this out, we're in trouble. And I actually went and like [00:12:05] introduced myself to him. I sat next to him at lunch. I started picking his brain. I've met with him probably [00:12:10] half a dozen times.

James Kaikis: But it was that moment where I actually realized like, man, [00:12:15] this AI thing is real. And there is something here. [00:12:20] And as like a former entrepreneur solutions engineer, if I can lean into this and [00:12:25] figure this out. Like I can be this next wave of Go-To-Market operators, man. And I will still tell [00:12:30] you, like there was like three presentations after Antonio and I left that meeting with like a, [00:12:35] what am I doing?

James Kaikis: Am I at the right company? Am I selling the right thing? Where are moats [00:12:40] going? And uh, that was the impetus. Ultimately, six months later, I left my job and went back out on my [00:12:45] own man. So I just wanted to throw that out there because I tell people that that was a fundamental [00:12:50] moment in my career where I'll look back and be like, my entire perspective [00:12:55] changed.

Craig Rosenberg: Jesus. All right, let's go through a couple things. Well, one [00:13:00] is Matt, um, noises kind of late in the story. Were you, were you good? [00:13:05] Was that a good one or?

Matt Amundson: Well, the thing was is like, I think. Uh, I mean, and I don't wanna blow [00:13:10] a ton of smoke here, but like, I had a very similar reaction to this year's GTM [00:13:15] summit. It felt like a time where like [00:13:20] AI hyperbolic LinkedIn musings transitioned into [00:13:25] this is how, this is actually how you do it. This is [00:13:30] a step by step guide of like what I do, what systems I [00:13:35] use, how they interplay with one another, how I feed it back into my systems of record, [00:13:40] whether it was like a marketing automation or a CRM, like.

Matt Amundson: To, to me it went from like, oh, [00:13:45] there's a lot of people like sort of proselytizing about like the future of ai. And then suddenly it was like, [00:13:50] here's 10 people that are doing it, and here's a step-by-step guide on how to, so I thought that that was [00:13:55] like, one of the biggest takeaways I had from that conference was like, it wasn't very fluffy.

Matt Amundson: [00:14:00] It was highly tactical and tactical, um, in spaces where [00:14:05] people didn't have a good understanding of what to do. So in a lot of ways it reminded [00:14:10] me back in like, I don't know, the mid 2000 tens or early 2000 tens when people [00:14:15] were suddenly like telling you how to do SalesLoft or how to run Marketo [00:14:20] effectively.

Matt Amundson: And it was like nobody knew what to do. They knew these systems were the future, [00:14:25] and people were like, oh, here's how you build the workflow. And here is like at that show it was, here's how you build the [00:14:30] workflow for ai.

Craig Rosenberg: Yeah. Can I, let me, let me comment. That was well, well, well said. [00:14:35] Obviously I'm involved in the creation of that Mark Gustafer on my team. Really? And, uh, the team put [00:14:40] that together. But the, um, so here's the, here is the [00:14:45] thing that's so nuts. 'cause you brought up Marketo where one of the keys to Marketo was [00:14:50] they built an army of people that were the only people that knew how to do it.

Craig Rosenberg: And then, [00:14:55] and the value got so, was so legit that these people [00:15:00] became like that army of people they like. I remember like, uh, bill Bench [00:15:05] was like, I know we've arrived. 'cause VCs are asking, do you know how to use Marketo when [00:15:10] they're meeting a CMO?

Craig Rosenberg: But, but here's the thing. That took three or four years, this [00:15:15] took.

Craig Rosenberg: Days like so, so James, Matt presented at [00:15:20] Summit. He's okay with the fact they didn't go to his session because I didn't let you in that, that, that's why [00:15:25] otherwise he'd be, but Matt, dude, we were, so, I, I had Matt come on because he [00:15:30] had packaged apps, uh, come talk at one of my virtual councils. And [00:15:35] we also, what do we have?

Craig Rosenberg: Boskovich and so Cure on there. Uh, [00:15:40] Boskovich the Beast. If you haven't seen a show, it's just, it's unbelievable on the [00:15:45] transaction. Uh, follow us or what, what's our ad?

Matt Amundson: Like follow us like and subscribe. [00:15:50] So the, um, but Matt afterwards goes literally, [00:15:55] just to make you feel comfortable, he said, fuck this, that weekend Matt [00:16:00] fucking with college and pro football in the background goes and [00:16:05] builds his persona, his personas, and starts running that [00:16:10] persona, uh, through everything he's creating in marketing by Monday.

Craig Rosenberg: [00:16:15] He's like, holy shit dude, I did this. Then he's refining it. Then we had him speak at [00:16:20] the show two months later with all this stuff he had built [00:16:25] and that's the same Antonio built everything over a weekend. And so like that's [00:16:30] what's so nuts about it. So dude, that was a great story. The other thing on the great story was just [00:16:35] um, um, you know, this is that [00:16:40] time now what it will be for you, I don't know, but it is that time and it is [00:16:45] so cool.

Craig Rosenberg: And I see on LinkedIn comment this guy's like, well there's no good use [00:16:50] cases. And lemme tell you, in my opinion right now, the Go-To-Market [00:16:55] AI is in this, um, incredible phase of productivity driving [00:17:00] and, um, the real test of any good app is if you went to the [00:17:05] employee. So if I went to Matt and said, you're not allowed to use AI anymore, he'd be [00:17:10] like, over my dead body.

Craig Rosenberg: Right. And that, that's, that's the ROI [00:17:15] people don't calculate when they're from MIT, but that's the one I know is true, [00:17:20] which is like, once it becomes like the R you know, what's the Gary Vaynerchuk? What's the [00:17:25] ROI of your mom? If it becomes how you work and you can't see work any other way, [00:17:30] that's like where, where we're getting out.

Craig Rosenberg: And then Matt and Antonio and these guys are doing the [00:17:35] advanced use cases, which do drive real ROI now, Matt, I mean it's probably nuanced for [00:17:40] Matt, but like he builds a webpage, he runs it through his personas, he sends an [00:17:45] email and like, so that, I mean, that's pretty extraordinary. We've [00:17:50] never seen anything like that.

Craig Rosenberg: So,

James Kaikis: Yeah,

James Kaikis: the speed component is just so [00:17:55] remarkable. Right? And I think that's the big thing that also has me shook in this whole thing is like companies that I [00:18:00] considered working at two years ago have been commoditized overnight. Like they're literally non-existent. And [00:18:05] Craig, you actually brought this up on my interview series.

James Kaikis: He is like, those companies are [00:18:10] dead. Like they're literally dead. They've been funded, but there's nowhere to go. And I think [00:18:15] this is just like such a crazy inflection point, uh, for Go-To-Market and for the [00:18:20] playbook and what this next wave is. And AI is real. And I think you guys both [00:18:25] nailed it, is like, this isn't like hyper hyperbole and like [00:18:30] pontification, like there is real ROI being driven.

James Kaikis: That's why I have a massive issue with that [00:18:35] MIT study, like bullshit, you know, like I've literally created things, my, myself in my [00:18:40] own business. I've created ai, Go-To-Market business. I've seen the success. So to [00:18:45] tell me that like, there's not success there. That's not true. I've seen plenty of companies that have [00:18:50] massive success and massive ROI, but you know, I think we're still in this like [00:18:55] hype cycle because there's billboards in San Francisco that says, replace your AI with, uh, or [00:19:00] replace your humans with ai.

James Kaikis: So like, there's like the existential like risk at, at [00:19:05] threat.

Craig Rosenberg: Yeah, for sure. You know what you should do, dude, when you go up and do that keynote, [00:19:10] go, uh, think of something you want them to do and just be like, okay, one [00:19:15] of you today who has not started with ai will hang out with me, [00:19:20] will go get dinner, will go get drinks, and by the end of the night, you'll be [00:19:25] using AI in your Go-To-Market.

Craig Rosenberg: It's like, that's the, that's your lead, because it is [00:19:30] true. Again, Matt did it over the weekend. I remember calling him, he's like, dude, I'm on a rush. I did six [00:19:35] hours in this AI stuff, and it's like, um, yeah, you could do it. All right. I love [00:19:40] it. Okay, so good story. Great story. What do you think, Matt, out of five, five being [00:19:45] extraordinary, one being terrible.

Craig Rosenberg: Go.

Matt Amundson: Uh, I give a 4.96.

James Kaikis: [00:19:50] Wow, it was really good. It was compelling. No, we don't do that well. Yeah, you're right. I don't know if we'd [00:19:55] give it to

Matt Amundson: here's the thing. good. Here's the thing. Your competition, uh, for the [00:20:00] story is either a great story like what you told, or I'm not quite sure that I [00:20:05] ever learned what the word story means.

Craig Rosenberg: We often have to train people on

Matt Amundson: [00:20:10] we have to.

James Kaikis: Well, I'm a sales engineer, right? My whole job is to tell [00:20:15] stories, you know, Uh, you'd be surprised some

Matt Amundson: other sellers, some other people, like not [00:20:20] sales engineers, but some other people with sales backgrounds are just like,

Craig Rosenberg: [00:20:25] Um, what about you, Sam? Sam? Rank, rank the story?

Sam Guertin: oh. I'd, I'd [00:20:30] go a six out of five.

James Kaikis: Let's go. Sam,

James Kaikis: are you guys. up. [00:20:35] No,

Matt Amundson: it was six. Six butters out

Craig Rosenberg: Why, why would we need a butter up [00:20:40] cakes?

Craig Rosenberg: I don't know.

Craig Rosenberg: Yeah. See, take those, take those grays. By the way, I was [00:20:45] distracted 'cause I was texting this guy who canceled a meeting with me this afternoon. I wrote great. Gimme a [00:20:50] fantasy backup running back right now. 'cause I, I, have some injuries I gotta handle. [00:20:55] Um, all right.

Craig Rosenberg: So, uh. Uh, by the way, there's been some [00:21:00] gruesome

Craig Rosenberg: injuries on the fantasy

James Kaikis: gosh.

Craig Rosenberg: Tyreek is my [00:21:05]

James Kaikis: injury? That

James Kaikis: was,

Craig Rosenberg: man.

James Kaikis: That was awful.

Craig Rosenberg: Oh [00:21:10] man.

Matt Amundson: Put a graphic of it right here. Thanks.

Matt Amundson: Yeah. There we go. oh,

Craig Rosenberg: oh,

Sam Guertin: just [00:21:15] slow-mo zoom in to

James Kaikis: His, his foot was facing the wrong way.

Craig Rosenberg: I [00:21:20] know, I know. Uh, by the way, I have this theory 'cause Matt's a football coach that [00:21:25] he wants to hear, you know, he wants the gossip 'cause he follows the sport. But like when I told him [00:21:30] the other day, he is like, oh, okay, bye.

Craig Rosenberg: He doesn't do not want to embrace that shit. He's [00:21:35] got 35 players he needs to take care of. He don't wanna see Tyreek Hill's foot the other way. [00:21:40] You know what I mean?

Matt Amundson: no, I also, yeah, I don't like gruesome injuries. no.

James Kaikis: Matt, for what [00:21:45] it's worth, a fun fact about me that most people don't know is my, uh, college minors in [00:21:50] athletic coaching and my master's degrees in sports sciences, and I did a master thesis on athletic [00:21:55] coaching, so that's a fun fact. Most people don't know about I used to coach youth football.

Matt Amundson: Wow. [00:22:00] That,

Matt Amundson: that's awesome. Look at the two of us. Yeah. Let's cut.

Craig Rosenberg: Dude, would you guys be at Sam to [00:22:05] click off? Yeah. Yeah. Let's, um, so I got two [00:22:10] youth football coaches. That's good to know. Yeah. and a my, [00:22:15] my claim to fame, my claim to fame is that I was a receiver's coach for Randall [00:22:20] Cunningham and Randall Cunningham moved to Vegas and his son was on my team when he was in sixth grade. And [00:22:25] so I was on a coaching staff with Randall Cunningham and a couple of NFL guys. That was pretty

Craig Rosenberg: Oh [00:22:30] wow. That's really cool.

Matt Amundson: That's awesome.

James Kaikis: That was

Craig Rosenberg: Yeah. That, that, you know what? [00:22:35] That's, that was a, that is the by, that's definitionally [00:22:40] a fun fact.

Matt Amundson: Yeah, that is. Yeah.

Craig Rosenberg: Yeah. Um, okay, so let's get, [00:22:45] uh, let's get the one to three things you're seeing that are working out there in [00:22:50] Go-To-Market. The, you know, the show, we started it because we were trying to figure this [00:22:55] all out and now we bring on folks to come tell us some, give us really traditional [00:23:00] stuff that we actually agree with.

Craig Rosenberg: Others give us really like modern, crazy [00:23:05] ideas, like, you know, and we love that too. We just wanna help sort of put this all together at some [00:23:10] point. And I know you do too, because your show, uh, the videos you created were under that [00:23:15] same theme. So talk to us, what do you got?

B2B SaaS has Forgotten about the Customer and their Experience
---

James Kaikis: Yeah. I, I think, you know, there's a lot of things [00:23:20] that I'm like very passionate about here, but like I, I've been running under a core concept [00:23:25] that I, I believe that we have lost sight in B2B SaaS of who matters. [00:23:30] Because it's the customer, right? Like I actually have this like hot take is like, we actually give a shit about our [00:23:35] customers.

James Kaikis: And I don't think that that has been the standard over the last 10 years. And because of that, [00:23:40] we've like sold snake oil. We stopped caring about implementation and [00:23:45] value realization. You know, like the celebration is at the signature. But if you think about the [00:23:50] buyer and the customer, like their journey's just getting started and you know, if you mix [00:23:55] in like the antisocial buyer, people don't wanna talk to salespeople.

James Kaikis: I've just been like leading [00:24:00] on this core competency or this core tenet that trust and [00:24:05] value are the ultimate currency and this next wave of B2B SaaS. And like, [00:24:10] what does that actually mean? Like, like, I don't know if, if you guys have ever bought software recently for [00:24:15] yourselves, like the process sucks.

James Kaikis: Like it, it literally sucks. And half these products suck as well, [00:24:20] right? And you wonder why AI is commoditizing people overnight. And so I think like the [00:24:25] pendulum has shifted so much to buyers and that's why we're seeing such. [00:24:30] Change and like consolidation happening is that you've got, you know, a lot of convergence of [00:24:35] trends.

James Kaikis: But you know, at the end of the day, like we're running these Go-To-Market motions from the predictable [00:24:40] revenue model 20 years ago that just fundamentally don't work with all this tech [00:24:45] float today. And like the buyer shifted. And so that's like a core competency, like I'm happy to expand on, [00:24:50] but like, I just don't think companies actually give a shit about their customers, which is why now you have everyone [00:24:55] who's just churning things out and they've got all these point solutions that won't survive over these next couple of [00:25:00] years.

Matt Amundson: could you give us Yeah, that's, I like that. Can you, [00:25:05] can you tell us who's doing this well, because I think that like, there's universally, our [00:25:10] listeners will hear that and they'll be like, yes, but like, what is the North Star and [00:25:15] how do I, how do I look at a company that does this well Yeah. what they're doing?

James Kaikis: So [00:25:20] I'm gonna shout my own interview series. 'cause as Craig mentioned, this is literally why I created it, right? [00:25:25] So I was, I, I was, I was, um, I interviewed Jeff Margolis. Jeff [00:25:30] Margolis is the global solutions leader at ServiceNow. Jeff has been there from 300 [00:25:35] million to 12 billion or whatever they're gonna end this year at.

James Kaikis: Okay. [00:25:40] Um, Jeff has seen it all. And what we were talking about, and I actually just shared a [00:25:45] clip on social media, um, the other day is he says that the enterprise [00:25:50] has shifted from, oh, you know, ServiceNow wants to come in and give an AI strategy. [00:25:55] He's like, yawn, yawn. They don't give a shit about that anymore.

James Kaikis: What they actually wanna [00:26:00] see is their data in your product right then [00:26:05] and there delivering value before I even sign. And I think that's [00:26:10] why like this whole Palantir, FDE thing is getting more traction. But I think like [00:26:15] ServiceNow is a company that's doing this at scale, where they are coming in and they are [00:26:20] literally in a sales process and they are building before the signature even happens.

James Kaikis: Like they're [00:26:25] not just doing POCs, they're doing as close to custom deployment [00:26:30] and value realization before they sign so that they can see the value, they can [00:26:35] understand what they're gonna get, and then it justifies the contract. And so like at a big macro company [00:26:40] like that doing that, there's no reason that like small startups can't emulate [00:26:45] that.

Craig Rosenberg: Dude, that was, I thought Matt, Matt was going to get [00:26:50] you on that, by the way. That's not a get get you question, but he does get people all the

Craig Rosenberg: time with it. You [00:26:55] gotta admit, Matt, that's, I mean, it's important what you're asking. Um,

Matt Amundson: mean, [00:27:00] it's, uh, the reality is, is like there's so many people who do everything wrong and people know that, but like, where, [00:27:05] where are people doing things? Right. I think is, is what people really want to hear.

Craig Rosenberg: [00:27:10] yeah, let me follow, let me, let me follow up for a sec. So, um, I, [00:27:15] I'm going to say a bunch of stuff that may not make any sense and then I'm gonna pose it back to you [00:27:20] guys.

Matt Amundson: on brand.

Craig Rosenberg: Yeah. Very on brand. So like, and by the way, [00:27:25] you asked if Matt spots, so Matt is a. Actually a technical buyer, right? Like he [00:27:30] needs, like what you just described.

Craig Rosenberg: He would be like, no, guys, just show me that. Right. He [00:27:35] would, I could fi, he's like, I could figure everything else out. You know, and this, and he's like [00:27:40] dealing with sales reps doing their discovery and he's like, think, oh

James Kaikis: They're getting banted to death. Oh, could [00:27:45] figure this. I know Matt's like, I know what I want.

Craig Rosenberg: Just show it to me. [00:27:50] Right? So, um, but that is true. And I wonder one thing, [00:27:55] you know, the using ServiceNow as an example was actually really good because my [00:28:00] fear is the Scott Albo thing, which is like, the toys are [00:28:05] winning right now. The things you, and he doesn't mean that to insult them, he means you could just [00:28:10] download it and get your data in there.

Craig Rosenberg: And those are the guys who are growing the fastest. [00:28:15] Like the ones Matt Marvels at, what was the one we were, we did a show on Cursor or, yeah, [00:28:20] yeah. So it's like, and, and so my fear is that you know, these folks [00:28:25] that are building enterprise software and they have major implementation teams can't do that.

Craig Rosenberg: And it's a win. [00:28:30] I'll give you guys another fun fact on that, which is. Um, so [00:28:35] NetSuite in the old days, they, um, so I don't know what's happening now, [00:28:40] but preor, they, for their demos, uh, they [00:28:45] would put, they would completely build the application with your data. They would [00:28:50] not do blind demos. The, you like put your data in, your logo in, [00:28:55] they had a 50% conversion rate off

Craig Rosenberg: demo.

Craig Rosenberg: If they got you into the [00:29:00] demo, you had a one to two chance you were winning that deal because of what you just described, [00:29:05] James. And they did that. Now they had rigorous qualification, like they couldn't do it for [00:29:10] everyone, but, uh, but when they did, and, and, and, and [00:29:15] it's that, that is another example. And by the way, that was from 10, 12

Craig Rosenberg: years ago. [00:29:20] So, um, I, but the new buyer, yeah, it, this, this is even more of a priority. So [00:29:25] anyway, ServiceNow is a great example 'cause they're old school. Um, and the fact that they're [00:29:30] doing that is an extraordinary piece to their buyer experience that we

James Kaikis: it, it is. [00:29:35] And, and, and I'll tell you right, to your, your point about Matt, right? It's like Matt is a technical [00:29:40] buyer and you have an AE who doesn't even know the product, trying to tell you how [00:29:45] to use the product, how to show you're going to use it, tell you some bull like, tell you what your problems are.[00:29:50]

James Kaikis: But you know what your problems are then more than they do at the end of the day, right? Like we've got this whole [00:29:55] like structured bullshit qualification, discovery framework that people have been running over the [00:30:00] last decade. And when you mix in, this is my, this is my thing about the solutions engineering [00:30:05] profession.

James Kaikis: We are like, oh, you know, they love demos, like sales engineers love demos, but like [00:30:10] personalized demos are not a logo and a fricking color in your app. Like, that's not a personalized demo. [00:30:15] And I think that, like my whole thesis on this too is like the bar has been low in B2B [00:30:20] SaaS over the last decade because we've been like growth at all costs.

James Kaikis: Like the bar is low, man. [00:30:25] Like, like we just show up and throw up. We don't do prep. We're you spraying and [00:30:30] praying? No wonder these customers are like taking the power back. And they're like, no, we're not doing [00:30:35] this. And um, I think that is the shift that like, is actually the impetus [00:30:40] of like, um, uh, seat-based pricing [00:30:45] to consumption based pricing and whatever you want to call it, is that.

James Kaikis: Okay, great. Like, I'm not [00:30:50] gonna pay you, you know, for six to nine months to implement my software [00:30:55] before I see any value. Oh yeah. I just riff, I just like laid off half my team, so I need a [00:31:00] reduction of those seats. And I think like that trend is like, it, it's, it's, it's [00:31:05] systemically changes how you Go-To-Market, yet many executives have [00:31:10] zero point of view on it.

Craig Rosenberg: Okay, so [00:31:15] let's, uh, I'm sure you have a number two, but you kinda led me down the path.

Why Your Next Account Exec Should be a Solutions Engineer
---

Craig Rosenberg: So a couple things I'm [00:31:20] seeing you guys, and I'll get both your, you know, Matt from, uh, he runs a business and, [00:31:25] and gets bought, sold to, but one is, I hear, uh, we need new [00:31:30] types of sales reps 'cause they should be able to do the demo themselves.

Craig Rosenberg: Is that true se [00:31:35] man?

James Kaikis: You want me to answer that or you want Matt to answer that? It

Craig Rosenberg: Well, Matt, [00:31:40] I'm sure wants to hear what you have to say because he's probably trying to figure it out too, but Yeah. Yeah, I mean, it's up to you [00:31:45] guys.

James Kaikis: Okay. So I believe that the predicted, um, [00:31:50] the, the world of BDRs, AEs ES essays, [00:31:55] PS, CS support AM is fundamentally broken for a strong majority of [00:32:00] businesses. You don't need that many people to be random specialists when you're selling [00:32:05] lower ACVs and transactional models. Okay? Um, I [00:32:10] think if you look at what the profile of the seller has been, [00:32:15] it, we ask our sellers to do too much, right?

James Kaikis: Like, no wonder they fail. We ask them to [00:32:20] pipe to prospect. We ask them to, you know, continue to build pipe to progress [00:32:25] deals, to do demos, to forecast, to know the pitch, to know the product. [00:32:30] You know, depending on the business, like no wonder they're not successful. But with all the advancements in [00:32:35] ai, right, they're the role of the rep should shrink.

James Kaikis: The role of the rep [00:32:40] should be a customer centric problem solver, which I believe is the point, like [00:32:45] is the role of the solutions engineer half the time. And if you can't get on a call and have [00:32:50] a point of view, you can't build trust and you can't deliver value. And so [00:32:55] depending on your motion, what is building trust and building value?

James Kaikis: Is [00:33:00] it providing an industry point of view and acting as like consultant professional sales? [00:33:05] Or is it being able to do a demo because you've got a, you know, a pretty easy [00:33:10] to manage product and I'm a sales rep and I'm trying to get you to buy product for your sales [00:33:15] rep, but I'm not gonna give you a demo.

James Kaikis: What the, what, what is that? You know what I mean? So my whole thing is [00:33:20] like the role of the rep has to change because you can use technology to build pipeline. [00:33:25] To do points of view to help forecast and you can use the frontline [00:33:30] manager to step into that role of the commercial gap. [00:33:35] And so all that to say is like, I think I've been telling people that your best [00:33:40] AEs will come from a solutions engineering background because if we think about the models and [00:33:45] FTEs and the motions, I think we're gonna see a massive amount of solutions engineers that are like me, that are [00:33:50] more business savvy than tech savvy, making that leap to the account executive role and [00:33:55] being supported by a frontline manager, max.

James Kaikis: I don't, I'm curious. Or Matt, well, I'm curious like if you've [00:34:00] got a, a agreement or disagreement on that

Craig Rosenberg: By the way, thank you for calling him Max. [00:34:05] Duly noted as you were.

Matt Amundson: Uh, an accident.

Matt Amundson: that's okay. Don't worry about it. Uh, John, [00:34:10] um, I, I like, I, I mean, [00:34:15] I hate the answer to be like, oh, it depends, right? Like that, that became such like a weak [00:34:20] answer to everything on LinkedIn there for a while in the end. It depends. Um, [00:34:25] but I do like my, what I like is. We're not doing this at [00:34:30] the, the company I work at currently, but like what I like is like more of like this, I don't know what you call it, like [00:34:35] upside down CAE ratio, which is like, you [00:34:40] know, if I was the CEO of my own company and I was selling a highly technical product, I'd [00:34:45] probably have a two to one at minimum ratio between SCS to [00:34:50] AEs.

Matt Amundson: And I'd rather have my AEs being like, deal jockeys and [00:34:55] like worrying about things like negotiation maybe, maybe, um, [00:35:00] discovery at the beginning, maybe.

James Kaikis: Mm-hmm.

Matt Amundson: Uh, and I'd have the ess doing [00:35:05] more of the actual sales process, and I'd have the, the, or the, the, [00:35:10] not the sales process so much. 'cause when I think about sales process, I think of like, you know, um, [00:35:15] uh, all the like, sort of mechanics of selling.

Matt Amundson: But like, you know, like if it's a [00:35:20] technical buyer, they want to talk to technical people. Like, you can be the best AE on the [00:35:25] planet. And they're like, yeah, you don't know my fucking world, dude. Like, I know you don't know my world. There's no amount [00:35:30] of trust that you can build on this call because like you and I just, we, we operate in different ends of the [00:35:35] spectrum, but like this, this sc here that that person knows my world.

Matt Amundson: And so, like, I don't know, [00:35:40] the last couple companies I've worked for, the products have been highly technical and we've had more AEs than sc and the [00:35:45] biggest challenge that we always have is getting SC availability. Um, the AEs screw up more of the [00:35:50] deals than the SC ever will, and it's not because they're, you know, they're, they're bad.

Matt Amundson: It's just [00:35:55] you could never get them enabled enough. It's like, I could, I could spend the next 20 years of my [00:36:00] life trying to become a baseball manager and it wouldn't happen, right? Like, it just wouldn't happen. [00:36:05] So I think like,

Craig Rosenberg: Hmm.

Matt Amundson: I think that's a, a shift we will eventually [00:36:10] see. Is that they'll just be more sc than, than than AEs.

Matt Amundson: And those AEs rolls to [00:36:15] your point. Well, like they'll get a little bit more refined or the, the, the, the, the, it'll narrow at [00:36:20] the very least, and they'll be more focused on like, you know, making sure the mechanics of the [00:36:25] deal happen while the SC will spend more time, you know, talking from a technical perspective.

Matt Amundson: And I [00:36:30] think sales cycles will shorten as a result of that

Matt Amundson: because I, I think so [00:36:35] many people just get lost in the bullshit.

James Kaikis: they do. Well, I think what's so interesting about your [00:36:40] response, right, is if you kind of like go and trace back to the world of like where sales [00:36:45] engineering really kind of came from in the hardware world. From my understanding, that is a [00:36:50] lot of the model, the solutions engineer is leading that sales cycle and then like the [00:36:55] sales manager ae is kind of handling the commercials at the end of the day.

James Kaikis: And so [00:37:00] to that point, like if you're selling a technical product. Yes. Like that should [00:37:05] absolutely work. And if you actually look at what HubSpot did a couple of years ago, about six years ago, [00:37:10] they created like an inside sales coach and they essentially took like a sales engineering customer [00:37:15] success profile and threw it on all the track transactional business.

James Kaikis: And the only time you talk to a sales [00:37:20] person is if you actually wanted to buy a bigger contract than just like clicking a button. And [00:37:25] I think that's a really interesting concept. But you know, the old, the, it's depends. Yeah, it does. But if [00:37:30] I'm a, if I'm selling sales tech or MarTech, you don't really need a sales, a sales engineer [00:37:35] in my opinion.

James Kaikis: You need the profile. You need the profile to be like, if I'm a CRO, I want [00:37:40] to talk to another sales person who gets it. And I think that is like the delineation in my opinion. [00:37:45] But like, yeah, you're still in technical product. The A e's role is to be a quarterback and a [00:37:50] program manager, especially in these big enterprises.

James Kaikis: 'cause the other person across the table doesn't give a [00:37:55] shit what they have to say.

Matt Amundson: Yeah, I

Craig Rosenberg: So let me give you guys [00:38:00] a couple reactions. So one is I don't think we know. I think the first acknowledgement [00:38:05] is that the buyer is, has a predisposition to get into the weeds faster [00:38:10] than they did before. Right. But, and we have to figure out how to solve it. [00:38:15] Because here's the thing with the scs is they are the they, they are trusted.

Craig Rosenberg: I [00:38:20] grew with Matt, I remember when I used to be put Salesforce in, it was like I would just bypass the AE [00:38:25] and go right to the se. Now you don't have to with sales, but like, you know, at the time I did [00:38:30] because I was coming off, off premise. That's how old I am. And uh, and so I [00:38:35] just go to the se, I mean, I get it right, but there is this [00:38:40] characteristic of the AE and I was just talking about with Mark, my associate, he's [00:38:45] like, the reason I couldn't do sales is I have too much shame. [00:38:50] Like I would, I would feel bad calling that guy again to get the deal done. And like, [00:38:55] that's the end of the process. And like the clo like closing and [00:39:00] the amount of sort of, uh, rejection you have to take in does require a [00:39:05] certain kind of characteristic, um, that, uh, the AEs bring to the table. [00:39:10] So that's why I think the models are, what we have to do is reconsider [00:39:15] the model.

Craig Rosenberg: So we had Boskovich on, and Matt, tell me if I'm wrong though, I just wanna make sure what [00:39:20] he was saying is one, he brought on a pitch [00:39:25] specialist, right? Or was it a demo specialist or

Matt Amundson: Yeah. Demo specialist, I think.

Craig Rosenberg: Okay.

Craig Rosenberg: [00:39:30] And no, no. Pitch, right? It was

Craig Rosenberg: pitch. It was like the whole prezzo and it was a, [00:39:35] the, it was like a theatrical guy. Like, he's like, no, not an se, I don't want to get into that first.

Craig Rosenberg: I want [00:39:40] this person who just nails it. Okay. Number two, they had. They [00:39:45] micro segment so well that they can actually create custom demos and send [00:39:50] in, in advance to the prospects. So they get what you were just talking about, [00:39:55] James, do they want to, I think he said that right Matt. And then he said, I'm gonna hire sales reps and go, guess [00:40:00] what?

Craig Rosenberg: You know, you get to work for me and do the things that you [00:40:05] want to do, which is close business and make money. And so like that's [00:40:10] an interesting version of the model you are both, uh, dispositioning for. [00:40:15] I will say what you guys were saying, MarTech will have to be sold in the [00:40:20] future by people that can talk MarTech, uh, from a legit [00:40:25] level.

Craig Rosenberg: 'cause as Matt said, look, he gets on, it's a 27-year-old inside salesperson. He's [00:40:30] like, he already knows everything about your product. Probably. 'cause he does his research and it's just [00:40:35] like, okay kid, let's keep, you know, keep going here. Like they're, and that's why his, he's gonna [00:40:40] move towards the sc But like in business apps.

Craig Rosenberg: The [00:40:45] AE has to be able to handle this on themselves, themselves. The highly [00:40:50] technical ones, though, those are harder. Um, uh, those are definitely [00:40:55] harder. However, I'm gonna make one other thing. So when I had [00:41:00] Chris Degnan on my Gartner show, right? Snowflake, CRO, and I [00:41:05] asked him, what do you think of product led right?

Craig Rosenberg: And he did not [00:41:10] take the standard definition of product led and went on this rant that I'll never forget. He said, product [00:41:15] led means everyone in the Go-To-Market organization is obsessed with the product. [00:41:20] I'm like, whoa, okay, that's product led. And he's like, yeah. Every sales [00:41:25] person that works for me has to show me that they cannot wait to dig [00:41:30] into the product.

Craig Rosenberg: They have to show me that, like they did that research and they love it and I'm [00:41:35] gonna make 'em do demos before they even start. We are like, I want product led [00:41:40] salespeople. It was so interesting. It was like a total misunderstanding on the question, but [00:41:45] he built the team based on people that could talk product.

Craig Rosenberg: And [00:41:50] so to, you know that, that that's, that's another sort of flavor of the way people are [00:41:55] responding to the changing buyer behavior. But, I, I think something has to change, [00:42:00] right? Like something has to change is the reality, right? And I think to [00:42:05] those points is, you know, it sales today still feels like me sitting [00:42:10] across the table from you. It doesn't have to, right? It can feel like, you know, you're on the [00:42:15] same side. Because think about, you know, if you look at the stats from Gardner.

James Kaikis: How much time is someone [00:42:20] actually spending with the vendor versus how much time are they spending internally navigating the [00:42:25] politics? Right? And so once they've identified a vendor, you are almost a [00:42:30] consultant to help them buy the software because especially for like folks who've never been bought [00:42:35] software before or never bought at that current company, that is a massive, massive risk [00:42:40] to your process.

James Kaikis: Like again, in my presentation, 86% of deals stall, and [00:42:45] what I understand it according to Forrester and what it, what it actually stalls for is deal [00:42:50] complexity and ultimately information override.

Matt Amundson: [00:42:55] Mm.

Craig Rosenberg: Them good.

Matt Amundson: Boom.

Craig Rosenberg: Yeah. [00:43:00] Alright. Yeah, it was kind of, yeah, it was, uh, the crowd. We, [00:43:05] we, there's no crowd. Um, okay, cool. Uh, uh, that is a [00:43:10] huge topic that I'm not, I, this is where I, I'll just go back to, I, I don't know the answer and I'm trying to help [00:43:15] people through this stuff and I just, and by the way, transitions like this to a new [00:43:20] flavor of salesperson takes time.

Craig Rosenberg: cause most of the sales leaders are used to [00:43:25] their,

James Kaikis: Yep.

Craig Rosenberg: they roll. Um.

James Kaikis: point, this is a concept I've been talking [00:43:30] about more and more. It's like, the more I think about it, the more I actually feel like the, the playing field has [00:43:35] kind of leveled across software and Go-To-Market, right? Like, this is the first time that I [00:43:40] could really remember that we are at a level playing field where we're all kind of learning [00:43:45] on the fly right now.

James Kaikis: And like people who've actually found success, they've found success [00:43:50] in the last six to 12 months, not the last five to 10 years. And I, I don't know, I [00:43:55] cannot remember a time, maybe 20 years ago when Salesforce was first getting started, where [00:44:00] that was actually what was happening in the world.

Matt Amundson: yeah. James, I want to go [00:44:05] off mic stand here for a minute.

Matt Amundson: I'm gonna go handheld. oh, Uhoh.

Matt Amundson: [00:44:10] I, so I've got a question. I'm, I'm very curious about your opinion on this. Like, where are the next great [00:44:15] salespeople gonna come from?

James Kaikis: And when you ask that question, are you [00:44:20] asking from like backgrounds or companies or what? What does that question come [00:44:25] from?

Matt Amundson: um,

Sam Guertin: Geographical basis.

Matt Amundson: [00:44:30] Arizona? No. Um, [00:44:35] uh, for years in the Valley, you could be like, Hey, I'm gonna hire these people that came [00:44:40] out of Oracle, right? Because like, Oracle had this incredible training and like [00:44:45] their approach to selling, you know, sort of worked in most environments. And [00:44:50] then, you know, you could, you could say like, oh, these x sales force people, [00:44:55] you know, whatever.

Matt Amundson: But like we all, I mean, I think we're, we're sitting [00:45:00] here saying selling is changing, or selling has already changed. Like,

James Kaikis: [00:45:05] Mm-hmm.

Matt Amundson: what, what are the companies, or maybe not even the companies, what are like maybe the skill [00:45:10] sets and who's developing those? Who's a thought leader in this space at this [00:45:15] point, right?

Matt Amundson: Like, who's, who's sort of pied piping? Like this is what the next great [00:45:20] salespeople are gonna look

James Kaikis: Yeah. Wow.

James Kaikis: It is hard to know. I love that. You like, that was [00:45:25] worth taking the mic off the stand for.

Matt Amundson: I'm gonna put it back in.

Craig Rosenberg: Wait, did, did [00:45:30] you take the mic off the stand for that

Matt Amundson: I went handheld.

Craig Rosenberg: Handheld? Totally appropriate. All

Craig Rosenberg: [00:45:35] right. Kakis, what do you got

Craig Rosenberg: for.

James Kaikis: so, you know, I, I could [00:45:40] easily sit here and say like, the service nows of the world, the AWSs [00:45:45] of the world, the snowflakes of the world, I think are building these next waves because [00:45:50] they're running like AI first and consumption based, and they're big enough that like they'll have the brand [00:45:55] to go into these smaller stage companies.

James Kaikis: But that would be an a bit of an easy answer. [00:46:00] So let me take a little bit different of a response. Um, I have been [00:46:05] talking to a lot of AI native companies that have all started in the last six months or [00:46:10] 12 months. And the sales motion, kind of what I mentioned was entirely [00:46:15] different. Where like there was a, there's a company that's selling into, um, pharmaceutical.[00:46:20]

James Kaikis: Okay. That, that world I don't really know a lot about. I was trying to do some research on [00:46:25] it. They get the meeting, there's a highly skeptical technical buyer on the other side. [00:46:30] Their sales process is just give me your data. Let me [00:46:35] put the data into the product and show you the product and literally the [00:46:40] product and the results do the selling in that moment.

James Kaikis: And [00:46:45] so as the seller, the seller's profile, 'cause I talked to the, the founder about this [00:46:50] 'cause we are strategizing, right? Is like, what is the role of [00:46:55] that profile? Well what is the, the, the, the jobs to be done of that seller and what is the [00:47:00] profile that matches? And I think that there's something for industry, right?

James Kaikis: Like I'm very bullish on [00:47:05] vertical SaaS right now as a, as a moat. 'cause there's not too many left. But [00:47:10] two, you have to have someone who can tell a narrative. They [00:47:15] can tell a story with the data and they can be consultative. And so I think those that come [00:47:20] from the enterprise space, that come from, you know, the complex workflow [00:47:25] world, those are the folks that are gonna be able to come in and do well.

James Kaikis: And like, [00:47:30] let me just take maybe like a take a, a shot at something, but like. All, all [00:47:35] these power users with Clay, right? Like I've talked to Everett, I actually met Everett. Um, when I was chatting with [00:47:40] Craig at that scale event, um, and, and got to know him a bit, he was telling me like, clay has [00:47:45] been built for the highest fidelity user, right?

James Kaikis: It has been built for the super user. And if you [00:47:50] go and think about that type of profile and make that person into a seller or a sales like [00:47:55] role, they can build trust. They can, they can, they can deliver value, [00:48:00] they can get hands on the keyboard and they can navigate the buyer, uh, buying [00:48:05] journey because they've been on that side.

James Kaikis: And I just don't think we have a lot of those types of [00:48:10] profile folks. And so like, that's where I tend to think things are rolling. So I, that's a [00:48:15] multi-part answer for you. Um, how I would approach it.

Matt Amundson: that was a good [00:48:20] answer. 'cause that was a difficult question and one, I, I don't think you were prepared to answer. Uh, so I [00:48:25] just kind of threw it at

James Kaikis: No, it was great. It is good. It was a really good question. I mean, it's a really thought, thought provoking [00:48:30] question, right? Because like, this is actually a data point in my keynote presentation, is like, according to Garner, [00:48:35] like 79% of CROs and CSOs believe that the [00:48:40] AE workforce needs re-skilled. Uh, but the question is like, what is, what are they being re-skilled to?[00:48:45]

James Kaikis: You know, and I don't, I don't know that we've answered that, but I think this fundamental shift, if like, if [00:48:50] I'm, I was at Showpad, I was gonna use Showpad back in the day, right? I would, um, have [00:48:55] to, you know, give a demo and I built these industry specific demos and then I had to get their [00:49:00] content and this giant cumbersome process to speak to their marketing team and they go to their sales [00:49:05] team.

James Kaikis: If I'm now competing against a product that's just gonna get the customer [00:49:10] data, plug it in, and be able to show instant value. [00:49:15] That's unlike anything we've really seen before. And that's gonna fundamentally [00:49:20] change everything about velocity and value delivery. And I would actually argue that like most [00:49:25] of the rules in the predictable revenue model ultimately break down in, in that [00:49:30] type of, uh, Go-To-Market motion.

Matt Amundson: yeah.

Craig Rosenberg: Matt, [00:49:35] what'd you think of that answer?

Matt Amundson: It was another good answer, [00:49:40] James, is quickly becoming one of my favorite guests.

Matt Amundson: Because he could think on his [00:49:45] feet like crazy

Craig Rosenberg: but Matt, I don't know to, to go specific like you were saying, [00:49:50] you like, yes, we used to, we go in waves. We used to hire everyone out of Oracle [00:49:55] and, um, then we hired everyone out. We've been hiring everyone outta Salesforce [00:50:00] for a while.

Matt Amundson: and we still do it. Yeah.

Craig Rosenberg: Still do it. And then, um, [00:50:05] uh. And so like, there's that sorta, these are the guys that do go get them.

Craig Rosenberg: [00:50:10] I don't know that we're, I think we're in this crazy transformation now. [00:50:15] Um, and per what James said, it's like everyone knows they need to [00:50:20] change, but like, how do you do it? You're addicted to the classic [00:50:25] sales processes. How do you do it? I think it's gonna have to come once [00:50:30] again from founder led change to the Go-To-Market.

Craig Rosenberg: Like, it's gonna be [00:50:35] the young companies coming up that sort of, you know, uh, redo the [00:50:40] type of sales person and then we will sort of learn more. Is that a good assumption or [00:50:45] no?

James Kaikis: I, Yeah, I, the right answer. So,

Matt Amundson: I think

Matt Amundson: there's this [00:50:50] opportunity for a lot of experimental selling right now. You know, like I've been advocating [00:50:55] for a long time, especially for things that are lightweight, like really easy to install, [00:51:00] the onboarding processes, you know, maybe a couple of clicks. It's just integrating, right? Like in [00:51:05] these scenarios, the sales motion I've been advocating for is like, Hey, on [00:51:10] your first call, like te, tell them exactly the value that you're going to [00:51:15] provide for them.

Matt Amundson: Say like, Hey, you're gonna sign a contract today that's gonna come with a three [00:51:20] week optout at the end of this three weeks. If I've provided you not in [00:51:25] inadequate value or no value whatsoever, like you'll just opt out. But between now and then. [00:51:30] The way I'm gonna run the sales process is I'm gonna onboard you, I'm gonna enable you, we're [00:51:35] gonna run your first couple jobs, whatever that is, programs, whatever.

Matt Amundson: And you're gonna [00:51:40] see so much value that at the end of the three weeks, the contract is already signed and we're done. And you're just a [00:51:45] customer that's fully onboarded. So this'll be a sales cycle unlike anything that you've ever done before. [00:51:50] And like that's like, if someone sold me that way, I'd be like, [00:51:55] fuck yeah.

Matt Amundson: That was badass. Right. Like, you, you're, you're, you're basically [00:52:00] saying you're giving me the sort of the illusion of choice, but also giving me an optout anytime I [00:52:05] want.

James Kaikis: I, I, I've talked to some early stage [00:52:10] investors who are suggesting, especially in this AI led world, to run with that motion. [00:52:15] Now it does come with like some a RR and revenue rec, you know, [00:52:20] issues, but at the

James Kaikis: same time, like, hates you at that

James Kaikis: of course, but but it de [00:52:25] it the business, right? If you think about it, it de, it de-risks it on both sides at the end of the [00:52:30] day, and then you can try to get a little more predictability.

James Kaikis: Uh, but that's actually why, to your point, I do [00:52:35] think the consumption, uh, world could really make an impact because somebody buys a con [00:52:40] a contract for so many credits, and then all of a sudden, like they found value in the first, you know, [00:52:45] three weeks to your example, and then boom, they're upselling and upselling and upselling and that, [00:52:50] uh, LTV looks really nice over time.

Matt Amundson: Yeah,

Craig Rosenberg: Can I give you guys a, [00:52:55] I I'm sure you had other ones, James, was he your first one was too good. And now we're six minutes [00:53:00] left. Okay. That's the show. So you could come back on and get the rest of it. But [00:53:05] did Matt, did I tell you the email I got from Dave Brock? So [00:53:10] James, I don't know if you know Dave. Yeah, he's old school dude.

Craig Rosenberg: He's one of the best guys you [00:53:15] could ever hang out. I mean, he is incredible. Wears a suit to everything. He didn't wear a suit for the [00:53:20] transaction, but. Matt gave him some choice words. Yeah. But like he is, uh, Matt and him [00:53:25] did a, a webinar together, I think. Um, right? He did, uh, he's, [00:53:30] so he, his thing, so he works primarily, well, not primarily like, you [00:53:35] know, 50 50 with non-tech, non-software, non-tech companies in tech.[00:53:40]

Craig Rosenberg: And so he had sort of misread a thing that I was speaking at, and he [00:53:45] went on this rant. He sends these long email rants. And what he said though was like, I [00:53:50] just want you to know that No, no. He said, I want you to think about this [00:53:55] statement. And it was one of the speakers said, uh, the number one thing you [00:54:00] should do right now is sell to your customers.

Craig Rosenberg: And he's like, just look at that quote and [00:54:05] realize how fucking ridiculous you guys are in tech. He's like, I have [00:54:10] taken that quote from a thought leader and shown it to my non-tech [00:54:15] CROs. And they're like, what? What's happening over there? They're like, [00:54:20] what? What? They don't know that like, you could sell to [00:54:25] customers and make a lot of money.

Craig Rosenberg: It, it was, it was, dude, he got me now. [00:54:30] Thankfully, he misunderstood. He thought that was my quote. It was not. But like, I have [00:54:35] just been sitting there. I honestly have been just going, what a great email. [00:54:40] Like he's just like, you guys are ridiculous. Like how, how that statement is so basic [00:54:45] and now you're figuring that out after, you know, 35 years [00:54:50] of enterprise software, whatever, like, uh, whatever the number is.

Craig Rosenberg: I don't know. What do you guys think? Is [00:54:55] that, is that great? Or what

Matt Amundson: I mean, I spent a big part of [00:55:00] my career not in tech and coming into tech, there's there, there's a whole host of [00:55:05] silliness here, whole host of silliness,

James Kaikis: That's totally fair.

Craig Rosenberg: [00:55:10] the cake is? You gotta look, yeah.

James Kaikis: well I think it was your conference at that conference or maybe it was the year [00:55:15] before where you guys presented like of your portfolio companies, there was more net [00:55:20] new revenue from customers than new logo for the first time. I don't know if it was ever [00:55:25] right. And it's, I think that there's been such an emphasis on like growth at all costs and add new [00:55:30] logos.

James Kaikis: And it's okay if you're churning logos 'cause you're adding enough on the top end and like [00:55:35] why would you not sell to customers? Like literally, I'll be honest, that was my entire motion at TestBox [00:55:40] and every single one of my customers expanded. Multiple [00:55:45] times in the first 12 months. I mean, I had one customer that had over 10 expansions in, in, in less than [00:55:50] 12 months.

James Kaikis: Like, it was amazing. Why would, why would I try to go, uh, you know, wall to wall [00:55:55] to land a big enterprise company when I could just continue to get upsells across? Because once we've [00:56:00] delivered value, it's a lot easier to show the other divisions, like, oh, we already got a value. But again, [00:56:05] we've got these segmented Go-To-Market teams, we've got hunter farmers, we've got CS orgs.

James Kaikis: Like, [00:56:10] it just doesn't make sense to the point. It, it doesn't make sense. But I think to Matt's point, like there's a lot [00:56:15] of that in software. There's a lot of that in

Craig Rosenberg: Yeah, yeah. [00:56:20] But, but what, what you're saying is that instinctively, like Dave's, right? 'cause [00:56:25] instinctively you're like, of course, like, I got these guys. We have a good relationship. Why wouldn't I sell 'em more stuff? I think the [00:56:30] models didn't, uh, uh, they were not, um, conducive to that. And [00:56:35] so, but it is that, that one.

Craig Rosenberg: I just thought that was a great quote. All right, [00:56:40] so you got two minutes left. Any famous last words? What do you got? I know you can't do [00:56:45] a big one.

James Kaikis: Famous last words. Um, look, I, I think at the [00:56:50] end of the day, anybody who's, who's watching this and thinking about this, like, you've gotta [00:56:55] lean in, right? Like, I'm not gonna, like, I've been like working on this concept of a framework, right? Of like a [00:57:00] innovators framework for Go-To-Market. And I've defined it as insight, [00:57:05] experimentation, implementation, and impact.

James Kaikis: And like, this is part of my keynote presentations, because [00:57:10] if you aren't going from zero to one right now, you won't have a job in the [00:57:15] next couple of years. Like, I think, like I don't think people realize the severity of that. If they're not taking [00:57:20] the leap and jumping in, there's not gonna be a job for you.

James Kaikis: And I think [00:57:25] that's fairly dire. And it may be not the AIs and the robots replacing the humans, but like that [00:57:30] is real. Like if you don't have AI proficiency and this new lens on how to win in this [00:57:35] market. be extinct. That's a harsh reality

Craig Rosenberg: [00:57:40] Wow. Extinct going by way of the dinosaurs.

James Kaikis: that word was used by a big time [00:57:45] executive who actually told me that a year ago. He's like, there's a whole wave of us that are going extinct, so.

Craig Rosenberg: [00:57:50] yeah. All right. Well there that, that is a famous last word. I like

Craig Rosenberg: where you [00:57:55] went there. All right, so let's just call this a wrap, man. This was a great show, [00:58:00] James. Good job, buddy.

James Kaikis: Thanks for having me, guys. I really appreciate it. I'm a big fan. I watched the show, watched the clips, so [00:58:05] I really Yes.

Craig Rosenberg: Yeah, man, you gotta watch the cl You know, the folks that [00:58:10] watch the clips are just, they get it when they

Craig Rosenberg: come on. It's the ones that don't know, you know?

Matt Amundson: Yeah. [00:58:15] We know ones that have watched. We know it.

Craig Rosenberg: yeah, we could tell the, [00:58:20] uh, and I'm starting to like, do this thing 'cause you know, you were good. And then we had this woman Rachel, [00:58:25] um, on the show, the, we just launched it.

Craig Rosenberg: Released it, and it was like, [00:58:30] just the personality thing is really important. Like, she was so game to go to [00:58:35] war with us in like a fun way. Like it was, it was just amazing. [00:58:40] Um, and so were you, so good work, dude. Uh, good luck on your stuff, uh, on [00:58:45] your keynotes, et cetera, but, uh, but that sounds really good, what you're doing.

Craig Rosenberg: [00:58:50] Um, I think by the way, that that, uh, 24 hour guarantee [00:58:55] getting you up on Go-To-Market ai, what do you think of that? That's pretty interesting.

Matt Amundson: that's pretty interesting. [00:59:00] Yeah. Uh,

Craig Rosenberg: That was, yeah. Your, your enthusiasm was infectious.

Matt Amundson: I had a final [00:59:05] question before he goes,

Craig Rosenberg: Oh, go ahead.

Matt Amundson: James, are you, you're in Chicago, [00:59:10] right?

James Kaikis: I am.

Matt Amundson: What's your favorite restaurant in Chicago?

James Kaikis: [00:59:15] favorite restaurant. I thought you were gonna ask me. Like the pizza restaurant. [00:59:20] Um, I, I, this is maybe, uh, we have [00:59:25] amazing restaurants in Chicago. I mean, Yes, I moved from San Francisco to Chicago [00:59:30] I, love Chicago

Matt Amundson: just for the food.

James Kaikis: Okay. When I, before I moved here, I was bougie in San Francisco. I was like, [00:59:35] Chicago can't have a good food scene.

James Kaikis: No way. It's better hot take. It's better, It's better.

Matt Amundson: [00:59:40] it's not that hot of a take. It's, it's

Matt Amundson: better. That's a fact. my my my answer though [00:59:45] is I'm gonna go with a classic steakhouse because it, it really sets itself [00:59:50] above every other steakhouse. And that's vets. If you can get into BTS from a steakhouse [00:59:55] perspective, it's old school. The food is very good.

James Kaikis: The vibe is great. [01:00:00] And it's like one of those hard to get into, even though it's been around for a couple decades, which I gotta respect. We got a [01:00:05] lot of good places. That's one of my favorites.

Craig Rosenberg: I love it.

Matt Amundson: A big [01:00:10] I'm I like on a, on a, on a more mid-level scale, like I'm a huge tra tavern guy.

James Kaikis: [01:00:15] Oh, nice. nice. I'm a Like every, Seattle Boqueria. I like Boqueria a lot down in the [01:00:20] West Loop. that's yeah, yeah. go-to for me.

Craig Rosenberg: this. That was a [01:00:25] great question at the end. Oh, I love Chicago food. I don't remember the places that I've [01:00:30] been, uh, but, uh, but I, I love it. And my f uh, step [01:00:35] father-in-law was from Chicago and he didn't eat anything but steak and [01:00:40] hamburgers. Uh, but

Matt Amundson: place to do that.

Craig Rosenberg: Was it called the Lake Superior [01:00:45] Whitefish or something like that, or Lake something, Whitefish.

Craig Rosenberg: He had this obsession with this [01:00:50] whitefish that was served only in old school Chicago places. So we'd go back to Chicago and he'd be like, [01:00:55] there was nothing I could do. And by the way, it was delicious. But yeah, [01:01:00] it was a little fun fact for me there. Um, but yeah, no, I, I think [01:01:05] Chicago, this is gonna sound crazy 'cause it's a massive, metropolitan is the most [01:01:10] underrated city for fun and to visit

Matt Amundson: agree with [01:01:15] you. Totally agree. It's uh.

James Kaikis: especially.

Matt Amundson: I just love every time I'm in [01:01:20] Chicago, I would say I've had like three, maybe not three of the best meals in my life, but three of my most [01:01:25] memorable meals were in Chicago. Uh, grace before it closed. I mean, you know, at one point the [01:01:30] number one rated restaurant on the planet, Gibson's Italia.

Matt Amundson: Fantastic. And then I [01:01:35] just, I mean, the first time I ate a Trivoli tavern, it was just like, this place is, it's like walking into like a, a [01:01:40] bar in an Indiana Jones film. It's just like the vibe just is set off right off the bat. Like [01:01:45] we're gonna put a little graphic of the entryway right here. Okay.

Craig Rosenberg: Oh shit.

James Kaikis: That's awesome. [01:01:50] You gotta love that about Chicago. I thought it. having me. This has been awesome. This has been [01:01:55] fun.

Craig Rosenberg: Take care, guys.

Matt Amundson: off.

Thanks for joining us for another episode of the [01:02:00] Transaction, Craig, and I really appreciate the fact that you've listened all the way to the end. What are you [01:02:05] actually doing here? For show notes and other episodes, please visit [01:02:10] us@thetransactionpod.com, like and subscribe on Spotify, apple Podcast or any other place you get your [01:02:15] podcast from.

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