The Transaction

TT - 084 - Jim Wilson
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Jim Wilson: [00:00:00] With the whole AI and agentic era right now, if you're not on the learning train, you are in [00:00:05] trouble. Absolutely in trouble. And then I always tell the younger up and comer salespeople like, man, [00:00:10] this is a great opportunity for you to differentiate yourself. You don't have to be a gray hair, gray [00:00:15] beard, or whatever that analogy is.

Jim Wilson: Just go in and learn the crap out of AI and what you can do to improve [00:00:20] your personal productivity. And you can leapfrog people faster than ever. It's a great time to be in

Jim Wilson: sales [00:00:25] actually. I love the idea that the narrative is the key thing with salespeople. Strong point of view doesn't [00:00:30] always need to be the market. I love sales teams that have a strong point of view on how you should [00:00:35] evaluate our product.

Jim Wilson: I think a lot of salespeople run away from

Jim Wilson: being labeled cheap.

Jim Wilson: And the [00:00:40] reality is no, they're just at a nice price point for what the product does.

Jim Wilson: with Craig [00:00:45] Craig tying his shoes.

Craig Rosenberg: What we're going, I

Craig Rosenberg: like it.

Matt Amundson: Are you a [00:00:50] loop, swoop, pull guy?

Craig Rosenberg: A what?

Matt Amundson: Are you a bunny ears guy? Which one [00:00:55] are you

Craig Rosenberg: I don't know. I, I'm not sure I know where you're [00:01:00] going.

Matt Amundson: with? Your tying your shoes, you're a loop, swoop pull guy, or.

Craig Rosenberg: know [00:01:05] what I

Jim Wilson: I was wondering about that

Craig Rosenberg: You know what I do now is I copy the kids and I don't tie 'em. [00:01:10] I tighten them and put 'em, I tie 'em under. I put 'em under. So you can't see the [00:01:15] tie,

Matt Amundson: Look at that.

Jim Wilson: That's very progressive, Craig. I'm a, I like that. I'm a, I'm a loop [00:01:20] guy, Matt.

Craig Rosenberg: are you,

Jim Wilson: Yes.

Craig Rosenberg: what are you, Matt?

Matt Amundson: I'm a [00:01:25] loop swoop and pull. Been been that since day one, baby. Since I came out the [00:01:30] Velcro.

Craig Rosenberg: Look you ever do the doubles, the dubble, so you loop it twice? That's, I have one [00:01:35] of my daughters that does the double loop.

Matt Amundson: Yeah, with, I mean, both my kids have [00:01:40] gigantic feet and their shoes are always untying, so yeah. We're, we, we double [00:01:45] knot all their shoes

Craig Rosenberg: This is a kind of interesting

Craig Rosenberg: conversation.

Craig Rosenberg: [00:01:50] that our, our, uh, audience loves you guys

Matt Amundson: Yeah,

Matt Amundson: it's.

Matt Amundson: it's. kick [00:01:55] in with talking about not, not is just they, they, they, everyone had listens to the show. That's what they always [00:02:00] mentioned, so I love that.

​

Craig Rosenberg: [00:02:05] [00:02:10] [00:02:15] [00:02:20] all right, so, but let's get to business. [00:02:25]

Introducing Jim Wilson,
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Craig Rosenberg: Today's guest, you ready for this?

Matt Amundson: I am.

Craig Rosenberg: [00:02:30] Because he's a peer of mine.

Craig Rosenberg: Um, he's the [00:02:35] Sales Advisor at Costanoa Ventures like and I, we share [00:02:40] some portfolio. I mean, people love Jim. Now, I loved Jim before he went to Costanoa, [00:02:45] so, uh, I've known him as like a killer. Uh, sales [00:02:50] operator for years before, um, before he joined Costanoa, but [00:02:55] we've done a bunch of stuff together.

Craig Rosenberg: We meet all the time and trade notes, and I always like the [00:03:00] conversations we have about him, sort of helping companies sort [00:03:05] through their sales and his stories are range. Just helping people [00:03:10] get, get their sales feet under them to optimizing teams going [00:03:15] forward. And so, you know, guys like him have seen a lot [00:03:20] over the years

Craig Rosenberg: and so we just love having guys like this on the show.

Craig Rosenberg: And [00:03:25] so, ladies and gentlemen of The Transaction community, today's guest [00:03:30] is Jim Wilson from Costanoa Ventures, my buddy, [00:03:35] and a potential, depending on how you do Jim.

Craig Rosenberg: A potential,

Craig Rosenberg: uh, [00:03:40] multi-time guest

Matt Amundson: Oh wow. You're calling your

Jim Wilson: that's

Jim Wilson: my goal. That's [00:03:45] what to shoot for. All right.

Jim Wilson: Exactly, exactly. And first time though. But [00:03:50] Craig, back at you,

Jim Wilson: you know, I, uh, admired you from the days of Topo. I was always [00:03:55] at those events. They were great learning events and, uh, I consider it honor to be [00:04:00] working with you at our two different venture firms.

Craig Rosenberg: Actually, you know what? That is a good [00:04:05] point. I wanna say this, Matt, about yeah. Uh, you know, a lot of

Matt Amundson: [00:04:10] of

Craig Rosenberg: CROs, presidents, et cetera, like his level, don't like to [00:04:15] learn anymore.

Craig Rosenberg: He

Craig Rosenberg: did. He was always a learner, [00:04:20] always listening, taking that stuff in, and obviously offering back. It's a good lesson

Jim Wilson: [00:04:25] Very you don't know everything.

Jim Wilson: And man, with the whole AI and [00:04:30] agentic era right now, it's

Jim Wilson: if if you're not on the learning train, you are in trouble, [00:04:35] absolutely in trouble. And then I always tell the younger up and comer salespeople like, [00:04:40] man, this is a great opportunity for you to differentiate yourself. You don't have to be a gray [00:04:45] hair, gray beard, or whatever that analogy is.

Jim Wilson: Just go in and learn the crap out of [00:04:50] aI and what you can do to improve your personal productivity. And you can leapfrog people [00:04:55] faster than ever. It's a great time to be in sales actually. It really Is it, it it actually is. [00:05:00] It's funny 'cause it reminds me a lot of like the era of, um. I mean it's [00:05:05] bigger, but it reminds me a lot of the era when like market automation was just like coming

Matt Amundson: [00:05:10] into fold and people were like, oh, I'm so behind. Like I don't [00:05:15] understand the concept of a nurture, how to build it.

Matt Amundson: And everybody was looking to their peers to help them [00:05:20] sort of design the work. And it feels a lot like that. Although clearly the stakes are a lot [00:05:25] higher.

Jim Wilson: Yeah, very much. Totally agree, man. Totally agree.

Craig Rosenberg: All right, [00:05:30] so let's, uh, we got two essentially sections of the show. [00:05:35] One is we just ask you for your, uh, best and greatest [00:05:40] Go-To-Market stories and then two, we'll ask you about the, you know, two or three things you're seeing [00:05:45] working today with your travels. Um, so the first one is, [00:05:50] Jim, tell us a story. What do you got for

Jim Wilson: All right. Well, I got one funny story [00:05:55] for me personally, which I'm gonna get to. Before I do that, I just wanted to point [00:06:00] something out that

Jim Wilson: Craig and I talked about. And Matt, you'll appreciate also with your [00:06:05] marketing background, which.

Jim Wilson: What's up with company's swag game these days? [00:06:10] So, you know,

Jim Wilson: uh, not to date myself, but I remember back to where [00:06:15] swag was just a t-shirt and it was maybe some pencils and a notebook.

Jim Wilson: Someone reminded me the other [00:06:20] day that like

Jim Wilson: you know, you used to get these branded notebooks, but now swag is [00:06:25] hat right swag. If it's cold weather. Right. You got your [00:06:30] beanie, you got your beanie with the top on it,

Jim Wilson: [00:06:35] you got socks. Right? So these are all our portfolio companies. By the way, this is great [00:06:40] branding for me with our portfolio company.

Jim Wilson: It's this little subtle branding, right?

Matt Amundson: Yeah. I've never [00:06:45] wanted to build,

Matt Amundson: buy workflow tools more.

Jim Wilson: Yeah.

Jim Wilson: And then, and then I was looking in, [00:06:50] in my garage last night, so there's my

Jim Wilson: old look at that. Oh [00:06:55] Logic Damn.

Jim Wilson: Club,

Jim Wilson: right? This. This. was a beach [00:07:00] bag that is still my wife's favorite beach bag. And then we have a company in [00:07:05] the defense tech space ion, they did it.

Jim Wilson: They one upped it. This is one of these ones where you [00:07:10] can stick, uh, a, a beer and, and drinks in it. It's a cooler. It's got [00:07:15] this whole thing in the top. And I use that all the time. And then the last thing I'll just show [00:07:20] you is again, like the, the level of the swag. 'cause I know Craig, you've [00:07:25] posted about it before.

Jim Wilson: Lululemon, right? One of my nicest jackets [00:07:30] Arctix, by the way, this is Costano. This is the one I like about Costano. The [00:07:35] rule of swag is not a big, huge logo, nice and small, right in the back of the neck [00:07:40] area. So it's a nice one. We just sold a company signal [00:07:45] to CrowdStrike, got this nice coat of SY jacket, right?

Jim Wilson: [00:07:50] So I'm wearing that.

Jim Wilson: Um, and

Matt Amundson: wonky sizing from Cotopaxi.

Jim Wilson: Yeah, [00:07:55] actually, great point.

Jim Wilson: The, the arms were way too long. I had to return it, you know, [00:08:00] I'm never a medium and this is the one time I had to return it for a medium. Very good point. [00:08:05] Matt spoken like a marketing person. And then this is the new,

Jim Wilson: uh, this is one of our company's [00:08:10] run Reveal and they gave me a Lululemon.

Jim Wilson: This is one of these old school [00:08:15] sweatshirts, uh, you know, the, the old sweat hoodies.

Jim Wilson: And man, it is fantastic. It's my current [00:08:20] go-to one, but. Yeah.

Jim Wilson: the, the swag game is just awesome. And I think if you're a [00:08:25] startup and you're, it's actually a message to salespeople, like, go talk to your [00:08:30] founders or your counterparts in marketing, but up your swag game.

Jim Wilson: It's good stuff. Makes it [00:08:35] fun, you know, makes it Yeah. industry.

Craig Rosenberg: You can't send me any more, [00:08:40] by the way. I don't get them anymore, thank God. But the stress balls with

Jim Wilson: yeah, on it, [00:08:45] please. I, I don't need those. yeah. you gotta go big or go home on [00:08:50] these things. They gotta be memorable. You know the uh, Kacie Jenkins, who we had on the show, it's [00:08:55] a favorite of me and Matt's, you know, she was at CMO at Sanso and, [00:09:00] um, she has all these incredible swag stories, but [00:09:05] also just like, uh, direct mail stories. One of my favorites, as she said, was like, they're [00:09:10] working on a deal. Uh oh no. It was a prospect in their ICP that they've been working [00:09:15] on for a while. They noticed on social, he's hosting a barbecue that weekend.

Craig Rosenberg: [00:09:20] They sent him meat, barbecue sauces, everything [00:09:25] for the barbecue.

Craig Rosenberg: He takes a picture of course with that before he [00:09:30] does the barbecue and you know, and they're engaged with him right after, you know, [00:09:35] there, there's a lot you have to do. So much to pattern disrupt. You have to not [00:09:40] have to do so much.

Matt Amundson: You have to be creative.

Jim Wilson: You have be creative.

Matt Amundson: right,

Craig Rosenberg: [00:09:45] meaningful in your pattern disrupt. And like the, if you just send swag for the [00:09:50] sake of sending swag, that actually doesn't work.

Craig Rosenberg: 'cause I don't care. I've got, I was [00:09:55] getting, when I saw that you wanted to talk about it, I was like, I gotta get ready. And we have obviously a lot of good stuff here too, [00:10:00] but like, you know, you, you gotta, you gotta make it. You know, make it meaningful. [00:10:05] And, uh, just a little bit of either like a coat ax jacket. That's something that I [00:10:10] don't want to have to go buy myself, but I would wear as long as it fits. As Matt said,

Craig Rosenberg: oh my God, man, the thing [00:10:15] was so tight around my belly, I don't even understand. But then, you know, like, [00:10:20] it, it was wild.

Craig Rosenberg: It was like everything else

Craig Rosenberg: fit, yours. Oh, you've got a different fit [00:10:25] problem. Because my coat of

Jim Wilson: ies Matt was the first one I got. Like, the arms were like gorilla arms. [00:10:30] Like, I didn't know, I don't know what was going on there, but I ha I looked at it, I was like, you

Jim Wilson: know, I have short [00:10:35] arms, but they're not that short.

Matt Amundson: short. there's thing.

Matt Amundson: They brought that up in your draft grade,

Jim Wilson: But I th [00:10:40] Craig, I agree with you by the way. the the thing that is fascinating to me is, um, [00:10:45] there's more opportunities than ever to brand things, foods, you know, wine bottles, things [00:10:50] like that. And just to be creative and, you know, we'll talk about it a little bit later, but buyers care about [00:10:55] that stuff.

Jim Wilson: Buyers care that you actually are. Looking at them and thinking about [00:11:00] them. And you did some research on 'em and they know what they like.

Matt Amundson: The double-edged, the double-edged sword [00:11:05] of sending swag and direct mail is like, um, it is definitely not, [00:11:10] uh, it's the thought that counts type activity as like crappy as [00:11:15] that sounds. You're like, oh yeah, I'm just trying to give somebody something great.

Matt Amundson: You know, like you can [00:11:20] miss in a big way.

Matt Amundson: Like it's part of the reason why like you either gotta focus on something that's [00:11:25] really. High quality or high. Cool. Um, it's typically why I tend to stay away from [00:11:30] alcohol. There's nothing like sending somebody something and they're like, Hey, cool. I've been in the, [00:11:35] I've been in the program for seven years. Thanks a bunch. And

Jim Wilson: Yeah. Have you tried coffee? [00:11:40] We had one of our companies do coffee.

Jim Wilson: They, and they actually in the, in the era of Covid,they [00:11:45] did a webinar, which was a breakfast time, or you know, they did it during, during the morning [00:11:50] and they send

Jim Wilson: people out

Jim Wilson: coffee,

Matt Amundson: coffee. Yeah. and that

Craig Rosenberg: Oh, I love that.

Craig Rosenberg: Yeah.

Craig Rosenberg: I, I, [00:11:55] I have two things to mention. One is for everyone listening to the show, if you wanna send me anything, you send me [00:12:00] bottles of whiskey or bourbon, because I, it just, it, it's a pain in the butt to go to the store and [00:12:05] get something good. And then, um, but You know, I have another, you know, Carilu is saying, um. [00:12:10] She, uh, has a, it's called, I think, business Bricks. They do Lego, they do [00:12:15] custom Lego

Craig Rosenberg: and developers have a predisposition for Legos, a large [00:12:20] percentage of them. And I was like, that is brilliant.

Craig Rosenberg: You know, like if, and [00:12:25] it's just out of the

Matt Amundson: out the box.

Craig Rosenberg: different,

Jim Wilson: Yeah, also consider it, and we're gonna talk about [00:12:30] events, but consider that as a little gift for an event.

Jim Wilson: Uh, one of our company's [00:12:35] BugCrowd sells to securities and hackers, and they're, one of the things they had is [00:12:40] a little lock pick set, so literally something that you can go and practice and [00:12:45] learn how to pick locks.

Jim Wilson: Now

Jim Wilson: I don't know how, you know

Jim Wilson: if there's liability associated with that, [00:12:50] but it was just a great creative idea for their community of hackers. That you could [00:12:55] get this little tiny thing and learn how to pick a lock.

Craig Rosenberg: I, I want in on that [00:13:00] next time,

Craig Rosenberg: Jim,

Craig Rosenberg: let me know. Um, I could, the mail.

Craig Rosenberg: be one of the worst thieves of all time. [00:13:05] My fingerprints would be everywhere. I mean, like, I don't know.

Craig Rosenberg: What

Jim Wilson: You'd be the guy picking the lock. And there's

Jim Wilson: a ca, [00:13:10] there's a

Jim Wilson: ring camera right above the door.

Craig Rosenberg: Hey, the, the [00:13:15] guy who stole from us, he left

Craig Rosenberg: his wallet. Wait, are those his car keys?

Craig Rosenberg: Um, [00:13:20] so,

Craig Rosenberg: uh, anyway. Okay, All right. So anyway, that's the swag stuff. Look the story. [00:13:25] Um.

Jim Wilson: I think these things are always great for these stories. So I'll tell a story from, unfortunately a [00:13:30] long time ago for me as Craig, I think, you

Jim Wilson: know, I started my career, um, [00:13:35] at a company called Parametric Technology, and one of the stints I did was over in Asia.

Jim Wilson: So [00:13:40] I lived in Asia for eight years and built up that region and I was a [00:13:45] young whipper snapper, but this was back, you

Jim Wilson: know. Before electricity, let's just say[00:13:50]

Jim Wilson: where

Jim Wilson: you'd, you'd go to meetings and you didn't have Google Maps, you didn't have Uber, [00:13:55] right? You were just doing it old school where you had to figure out how to get there,

Jim Wilson: And I was in [00:14:00] Japan and I distinctly remember it was a bank. I don't remember what bank, but you know, [00:14:05] being a good young sales person with good sales hygiene, I got there about[00:14:10]

Jim Wilson: 30 minutes early. Uh, unfortunately I had to take the subway the whole way and I had [00:14:15] to go to the bathroom, right? So

Jim Wilson: I'm down in the lobby and this is in [00:14:20] Tokyo, and this is, again,

Jim Wilson: a long time ago.

Jim Wilson: There wasn't a lot of English translation [00:14:25] going on, right? So I, so I find a bathroom and,

Matt Amundson: and,

Matt Amundson: uh, [00:14:30] are you

Jim Wilson: with Toto Bide?

Matt Amundson: of Yeah,

Jim Wilson: Okay, so no [00:14:35] surprise. But in Japan it's

Jim Wilson: kind of the standard there, right?

Jim Wilson: So, lucky [00:14:40] me, I find the public bathroom. And the other thing about [00:14:45] Japan that I don't know if this is standard, but for the bathroom I happen to be in, it was one of those configurations [00:14:50] where it was a whole bunch of stalls, and the stalls were super skinny, right?

Jim Wilson: So you get your privacy, but there [00:14:55] wasn't a lot of room in there. And by the way, this is also in the era where you guys like me, wore [00:15:00] suits. So I've got a nice suit and tie on. I remember it was a light gray suit, which you'll understand why that's a [00:15:05] problem a little bit later. So I find, find the, find my nice, you know, pit stop [00:15:10] here,

Jim Wilson: pleasantly surprised. I've got a nice warm toilet seat. Do my [00:15:15] business. Then I get, I I finish and I turn around. Well, it turns out with [00:15:20] Toto bidet, if, if you know them, they've got this big panel, and that's [00:15:25] great, except that it was all in kanji, all of it, right? And I had this very [00:15:30] simple problem, which is how to flush the toilet.

Jim Wilson: So I'm standing up, I'm all, [00:15:35] I'm all done. I'm in my suit. I'm in this little tiny, you know, thing, and [00:15:40] I'm like, all right. I came up with the bright idea that I'm just gonna press every single button. And see what [00:15:45] happens. So I just lean over, press all the buttons, and the toilet magically starts [00:15:50] flushing.

Jim Wilson: Well, the mistake I made was I wanted to know what that [00:15:55] symbol was so that in the future if, if I ever had ran into this problem, I'd know which to press. [00:16:00] So I lean over. I'm in the process of looking, trying to figure out the kanji. [00:16:05] All of a sudden, the bidet arm pops out, shoots water. Right in my [00:16:10] crotch, like literally a

Jim Wilson: direct shot. Uh uh. Not [00:16:15] only that, but I'm stuck. I'm stuck in this, you know, four by four box [00:16:20] trying to wiggle. I couldn't get out of it.

Jim Wilson: And so obviously I, I [00:16:25] escape. The bidets attacked me. I'm now 20 minutes out from my meeting [00:16:30] and it looks like I have a nice huge pee stain right in my suit. And, uh, [00:16:35] I made a, a game day decision to decide that I would show up to the meeting 10 minutes [00:16:40] late, which in Japan is a little bit of a faux pa, but it did work. [00:16:45] And let's just say that I was in front of the bank walking back and forth, air drying [00:16:50] a little bit, my suit, uh, before the meeting.

Jim Wilson: So

Craig Rosenberg: you get [00:16:55] the deal?

Jim Wilson: I, I don't know if we got the deal. I know the meeting went well. And more [00:17:00] importantly, Craig, I didn't walk into the meeting and they all asked me and Jeff and Kaji [00:17:05] like,

Jim Wilson: uh, did you pee your pants right before the meeting?

Craig Rosenberg: Yeah. Wow. You know what, [00:17:10] Jim? That. It. We love stories like we have this thing, it's the [00:17:15] craziest thing on the show, like we want people to tell a story.

Craig Rosenberg: It's actually been really hard for some people. [00:17:20] That's exactly what we've been asking for the whole time.

Craig Rosenberg: So message to people that are [00:17:25] listening that were on the show. Can you have some fun and tell a story like Jim about getting sprayed by the [00:17:30] bidet on his crotch.

Craig Rosenberg: You know.

Craig Rosenberg: like I, I, by the way, I was, I [00:17:35] knew there was a bidet part of this, but I wasn't sure where you're going there.

Craig Rosenberg: And so that was even better. And I can [00:17:40] imagine the small stall, the that. See now that's the kind of story I like.

Craig Rosenberg: Matt, your thoughts story [00:17:45] ranking

Matt Amundson: We love

Matt Amundson: bathroom. Yeah, that's a, that's a solid five. Uh,

Matt Amundson: [00:17:50] we, we love bathroom humor around here. Here's what I think happens, Craig. I think [00:17:55] you tell people, Hey, can you tell, or you ask people, Hey, can you tell us a story? [00:18:00] Could be funny. Interesting. And then you hit them with heroic at the [00:18:05] end. And that like, I think that they're like, okay, I know a funny story, a heroic story.

Matt Amundson: [00:18:10] I,

Jim Wilson: Yeah.

Matt Amundson: I think that throws 'em off. I think we should ask for funny.

Craig Rosenberg: You're [00:18:15] blaming me. I like

Matt Amundson: I'm not blaming you at all. I'm not. I think you're a great pod podcast [00:18:20] host. I think. I think you really get it right,

Jim Wilson: Craig, I'm with Matt on this one. I was thinking [00:18:25] like, I don't know, man, salespeople is heroes in those stories. Those are, it's somewhat of a dime [00:18:30] a dozen. It's more, uh,

Jim Wilson: embarrassing. Focus on, embarrassing is the key word, [00:18:35] probably

Jim Wilson: more than anything point. Because Maria Bolden,

Matt Amundson: Yeah.

Craig Rosenberg: [00:18:40] Maria Bolden had the, the probably the best on the embarrassing story one, right? The one where [00:18:45] she got off the train and had her dress was wide open. That was a good one.

Matt Amundson: Yeah, he should, the [00:18:50] back bottom of her dress tucked into her, into her undergarments. I, I don't know. Um,

Jim Wilson: you [00:18:55] had good,

Jim Wilson: uh, zoom ones? Because I gotta figure in the post COVID and pre COVID era, like [00:19:00] some of the zoom felt, pause, have gotta be off the charts.

Craig Rosenberg: haven't

Craig Rosenberg: seen as many. [00:19:05] There was at least one. That

Matt Amundson: yeah, Yeah. There's

Craig Rosenberg: the

Sam Guertin: Sam McKenna.

Craig Rosenberg: Oh Yeah.

Craig Rosenberg: [00:19:10] Mine. I,

Sam Guertin: yeah.

Craig Rosenberg: by the way, just

Craig Rosenberg: to be clear, that was a Citrix [00:19:15] Go-To Webinar problem.

Craig Rosenberg: Is that thing even around? Yeah. I don't even know if that's around, [00:19:20] um.

Craig Rosenberg: Alright, awesome. that

Craig Rosenberg: was, that was perfect. Jim. You

Craig Rosenberg: got a five from Matt. [00:19:25] Sam, you're ranking on the story one to five, five being

Craig Rosenberg: dead on

Sam Guertin: five, [00:19:30] absolutely

Craig Rosenberg: yeah.

Jim Wilson: Oh, there shy

Craig Rosenberg: You can't break the system. [00:19:35] Yeah, status. yeah, yeah. You, we

Craig Rosenberg: might just do.

Matt Amundson: do.

Craig Rosenberg: if you have stories like [00:19:40] that, we gotta, you know, that, that

Craig Rosenberg: was great. And

Craig Rosenberg: I did forget, by the way.

Craig Rosenberg: I did forget, 'cause [00:19:45] I think Jim and, and Brian Halligan ran around Asia

Craig Rosenberg: selling deals for [00:19:50] PTC.

Jim Wilson: correct.

Craig Rosenberg: two notes on that for any you young folks out there.

Craig Rosenberg: [00:19:55] PTC was the, probably the best sales team [00:20:00] maybe in the history of all time. Right? Because

Craig Rosenberg: you're one, yeah. They were [00:20:05] the CorrectMEDDICic MEDDIC. MEDDIC.

Craig Rosenberg: MEDDIC [00:20:10] They were the best enablement back then of all time, [00:20:15] uh, the best alumni of all time. I mean,

Craig Rosenberg: you don't [00:20:20] see any PTC guys not go on to big things 'cause they were just so [00:20:25] good at making great reps and managers.

Craig Rosenberg: It's, it's pretty, it's pretty amazing,

Craig Rosenberg: you

Jim Wilson: [00:20:30] Yep. It was a good, good culture. My funny Brian Halligan story is we were also up in [00:20:35] Malaysia once and we were, and again, this is before Ubers and stuff, right? And. We [00:20:40] both had a meeting at a car company, I think it was called Proton. And we were flying in separately 'cause [00:20:45] he, I was in Singapore. He was in Hong Kong.

Jim Wilson: And I'm in a taxi again. No, Ubers like, this [00:20:50] is literally a taxi where I'm paying him in cash and I, it doesn't speak any English. And we're [00:20:55] heading out there and we're, and we're on the side road and all of a sudden I drive by and there's another [00:21:00] taxi on the side of the road and there's a guy, an American guy, you know, not [00:21:05] Malaysian in the backseat, completely sprawled in the back sleeping.

Jim Wilson: And it turns out it, was [00:21:10] Brian Eddie. He'd gotten there early and, and he wanted to take a little nap.

Jim Wilson: [00:21:15] And for those of you that know Brian, he's famous for his naps.

Jim Wilson: And so, uh, yeah, [00:21:20] that's, it was fun times over there. Fun times,

Craig Rosenberg: That's amazing. See, look at that. You even threw another one [00:21:25] in. I like it.

Craig Rosenberg: Brian. Halligan

Craig Rosenberg: humor.

Matt Amundson: a big car napper.

Craig Rosenberg: A huge car. [00:21:30] Napper huge. I used to travel all the time, right? Like, you know, all of us. And

Craig Rosenberg: [00:21:35] like, um, uh, I met a guy who was, uh, you know, had [00:21:40] served in Iraq and Afghanistan in one of the airport, you know, when I'm waiting at the [00:21:45] gate and he was, I said, well, gimme one thing you've learned. And, uh, he said, [00:21:50] here's, here's the one thing I've learned is if you have the chance to [00:21:55] sleep. Take it. Even if it's 10 minutes, even if it's 20 minutes, just take it.

Craig Rosenberg: [00:22:00] Right. Because You know, when we were out there, if you, we had 10 minutes to to sleep, we would take it. [00:22:05] And so I've been like, okay, well I'm in a car, let's just go to sleep.

Craig Rosenberg: [00:22:10] I sleep in the. air. I can't sleep on planes, which is a different story, but like when I'm in the airport waiting [00:22:15] for my flight, I sleep if I'm like, I just, even for 10 minutes, it's, that [00:22:20] was the best tip I've ever had.

Jim Wilson: That's a good tip. I have the same problem. Can't sleep in [00:22:25] planes. All right, so what do you, let's look, one of the things, maybe Craig, to tee [00:22:30] up the, what's working well? Is, um, as you

Jim Wilson: know, we both do this but [00:22:35] for our portfolio at Costanoa, we are early stage. So a lot of the times I'm working with the first [00:22:40] sales hire and the founder.

How a Strong Founder POV Helps Sales Teams
---

Jim Wilson: And my, my kind of soapbox [00:22:45] thing that I'm onto right now is just having a strong founder point of view when you [00:22:50] Go-To-Market. Because, and Matt, you'll appreciate this, but man. The [00:22:55] biggest challenge in, in sales and early stage sales and marketing is getting heard,

Jim Wilson: [00:23:00] right, and, and rising above the noise because you've got 10 other people that[00:23:05]

Jim Wilson: have a product that sounds like yours.

Jim Wilson: You have massive channels that are going everywhere. The [00:23:10] buyers are getting bombarded with emails, with event requests, with, with [00:23:15] everything. But what I do find works well. Is having a strong founder [00:23:20] point of view, and then having the founder kind of sing [00:23:25] to the rooftops about that blog posts and everything, but then have it percolate down to the sales [00:23:30] team.

Jim Wilson: And in particular, the example I'll use is a company run Reveal, right? That [00:23:35] is, uh, uh, has some great swag, by the way, but also their founder, Evan. [00:23:40] He, he, uh, built a, basically a modern [00:23:45] security product. That is a modern sim, right? And so his whole [00:23:50] message and is, is in his point of view is like the sim market sucks.

Jim Wilson: The existing [00:23:55] products are old. They're built on poor architecture. They're too expensive. [00:24:00] You don't, you don't get any value for what you pay for. And he's got,

Jim Wilson: you know, he's [00:24:05] got t-shirts made that talk about this. He writes about it. But here's what I think is really [00:24:10] cool is Aaron Trott, his VP of sales and Kira head of marketing, [00:24:15] lean into that messaging in their sales and their Go-To-Market.

Jim Wilson: So for example, [00:24:20] Aaron will talk about when he gets on the phone with the company, he's doing discovery, he'll say, look, [00:24:25] here's what we think. It's built on a modern architecture. We're focused on user interface. He'll [00:24:30] lean into the fact that it's not expensive to get started. I think a lot of salespeople run [00:24:35] away from.

Jim Wilson: Being, being labeled cheap.

Jim Wilson: And the reality is no, they're just at a nice price [00:24:40] point for what the product does, right? But then at some point they'll say [00:24:45] in a discovery call, look, we think that the SIM products suck. By the way, what product do you have? [00:24:50] Right? And I love this because that allows the buyer to react.

Jim Wilson: And you [00:24:55] know, if the person says, Hey, I've invested $10 million in Splunk and I [00:25:00] don't think it sucks, and we're pretty happy. Great. Much rather know that now the beginning [00:25:05] of the discovery call than after five or six, uh, calls afterwards, [00:25:10] right? So they use it as a really good tool in a respectful and a professional way to [00:25:15] qualify their accounts and to qualify their opportunities.

Jim Wilson: So I just think having a [00:25:20] strong counter founder point of view is key right now. And for salespeople, I think [00:25:25] salespeople can use it as much as founders.

Craig Rosenberg: Yeah. So I, you know, [00:25:30] we just had Chris Orlob, uh, speak to our portfolio and he had like the [00:25:35] four rules of successful revenue teams at this time, like number one was [00:25:40] like, know where you win and take out those that don't. So ICP. the second [00:25:45] one though was, uh, have a narrative and, and [00:25:50] like, uh, if you don't, he's like, I've, you know, worked with 5,000 companies, the [00:25:55] companies without a narrative. Uh, are the ones where their salespeople, you [00:26:00] know, struggle.

Craig Rosenberg: So that, and what you're saying is even bigger, which is [00:26:05] like, so like, I'll just, like Scott Albro, you know, we're having

Craig Rosenberg: him speak at our event. He has the [00:26:10] Yeah, of course you do. And one of the things that he says is, uh, you know, [00:26:15] our objective with the founder is for the [00:26:20] founder to become personally synonymous. With the market or category [00:26:25] that their company exists in. In order to do that, you can't just hang around.[00:26:30]

Craig Rosenberg: You can't just tell the same story as everyone else. You, your narrative [00:26:35] is what makes you interesting and allows you into this club.

Craig Rosenberg: And that is [00:26:40] like really important. Now, uh, you don't, and everyone thinks you don't always have to say. [00:26:45] The current thing sucks, although it does work well, it's like the basis of [00:26:50] challenger,

Craig Rosenberg: Right.

Craig Rosenberg: But like you can also just speak to the future.

Craig Rosenberg: You can tell your [00:26:55] personal story. There's a lot of ways for the

Craig Rosenberg: narrative to come out. And then as you said, [00:27:00] if we can package that narrative because you know, a founder is going to have [00:27:05] 20 conversations a week where that narrative is being stress tested and [00:27:10] becomes personal. In the, in the part of them that we [00:27:15] want the company to be part of the company and the way that they talk to the market. And I think [00:27:20] that's a big one. I'm not sure everyone thinks about, I think

Jim Wilson: I know, I don't think they think enough about. It [00:27:25] and, and Craig, you know, to your point, I love the idea that the narrative is the key thing with [00:27:30] salespeople. Strong point of view doesn't always need to be the market. I love sales [00:27:35] teams that have a strong point of view on how you should evaluate our product, right?

Jim Wilson: And I [00:27:40] always tell sales leaders and the best ones do this so well, and the best salespeople, they'll say, [00:27:45] Hey, listen Mr. Customer, let me just tell you how we think it would be [00:27:50] best for you to evaluate our product, can can be any product in the space, can be whatever you want. [00:27:55] And they go. And again, it's very, it's not super controversial, but it's very specific and very [00:28:00] prescriptive.

Jim Wilson: And it's, it gives buyers, I think, so much confidence. A buyer [00:28:05] doesn't wanna get on a phone call and feel like everything he says the rep agrees with, [00:28:10] and he is just super compliant. You ever been on these calls where it's just, you can just tell like you're just, oh, you [00:28:15] wanted, you wanna do a free proof of concept?

Jim Wilson: Great. Sure, we'll do that. Oh, you want to have the product for a little while? You wanna do. [00:28:20] Third or fourth demo. What works so much better is sales have a strong point of view [00:28:25] on how to evaluate the product they go through and they give the logic to it. You got it. It's gotta be [00:28:30] logical. It's gotta really make sense, and then let the buyer react to that.

Jim Wilson: That's how the point of view point of [00:28:35] translates down to the sales process and the sales playbook in my mind.

Matt Amundson: Jim, [00:28:40] I cannot agree with you more, uh, now and like this is my [00:28:45] biggest pet peeve in early stage businesses, is not [00:28:50] having, uh, a prescriptive approach to the sales process in [00:28:55] co-creation. And what I mean by that is like. You're getting off this great discovery call [00:29:00] and may, maybe you've got a novel product or you're in a novel category and [00:29:05] the and, and the sales rep goes, well, what do you wanna do next?

Jim Wilson: Yeah. I. [00:29:10] And the prospect's, like,

Matt Amundson: I have no

Matt Amundson: idea. I'll tell you what I want to do. I wanna, I want to go watch [00:29:15] the, you know, the se season finale of industry. Like,

Matt Amundson: I, I, I don't want to think about the [00:29:20] research that I'm gonna have to do or building a buying committee for this or, you know, one, [00:29:25] like how challenging this might be to, to to, to onboard, right?

Matt Amundson: Like, I think [00:29:30] having a strong point of view. Not just on your product and on the category and on the space, [00:29:35] but also on how to manage your way through a cycle, especially when someone's not bought. [00:29:40] Someone's buying something for the first time. Look, if we all started companies and got to a point where we [00:29:45] needed to adopt Salesforce as our CRM, we know how to buy that product.

Matt Amundson: We've bought it two [00:29:50] dozen times already, and now you know someone's introducing AI [00:29:55] technology and there's maybe three or four players in the space, and you're kind of like, well, I don't know.

Jim Wilson: Yeah. [00:30:00] No.

Jim Wilson: So, and look, what's the, what's the worst thing that can happen? They disagree with you. Great. [00:30:05] Now let's hear from them.

Jim Wilson: Why, why they want to follow a [00:30:10] different process, why their company, for example, may not be able to do it this way. Fine, let's [00:30:15] have a conversation. Now you're engaged on something that's actually gonna deliver value for your [00:30:20] sales process.

Jim Wilson: By the way, the, the best person that does this, I think is gonna be on your call. Soon, [00:30:25] Craig, uh, David Morris, DMo, there's another guy named Mike Leonard. And both of them, [00:30:30] when I worked with them at a company, Merced Systems, they, they said their whole goal was always to be [00:30:35] trusted advisors, but have the buyer believe that you are the trusted advisor.

Jim Wilson: Uh, and [00:30:40] you know, and the ultimate compliment of that is like you're helping them craft the RFP, you're helping [00:30:45] them craft like how to frame all the competitors. But the way you get there is by being [00:30:50] prescriptive and having a point of view of how the product should be evaluated.

Craig Rosenberg: Yeah. By [00:30:55] the way, Jim, I, I want to remind you of a story from our [00:31:00] past.

Craig Rosenberg: Uh, and it's both a story that's relevant to this and, [00:31:05] uh. And we did it together. So remember when we did that workshop together up in the [00:31:10] city and you said, let's do like a challenger esque sort of workshop for my [00:31:15] sales team, so you guys will enjoy this.

Craig Rosenberg: So people were weighing, it was really [00:31:20] cool. They were in, you know, packs. There was like three, you know, folks from the sales team at their different [00:31:25] tables and um, and we had everyone come up with, you know, a [00:31:30] challenger like. You know, point of view on, on their company and product and [00:31:35] whatnot. So we get this one young guy, and here's, here's the thing.

Craig Rosenberg: He [00:31:40] is, uh, one of the reasons why Jim's point [00:31:45] that it, it, it's a founder down point of view, is because it's not [00:31:50] instinctive necessarily for the sales rep, like, you know, one who's not very experienced. They gotta be really [00:31:55] good and experienced in point of view and narrative. Um, and so. [00:32:00] So it's not necessarily, that's not their instinct.

Craig Rosenberg: Their instinct is actually, well, I have this product, I'm [00:32:05] selling against these people and this is what I'm gonna, you know, this is how we're different feature wise. [00:32:10] So he is like, well, I have this problem, there's like a hundred companies in my market. And it [00:32:15] was, it was a crowded market. I don't remember what it was.

Craig Rosenberg: And I said, well, how about this? Why [00:32:20] don't you go to the market and say, you know, whatever the category name was, doesn't work. [00:32:25] Right.

Jim Wilson: Right.

Craig Rosenberg: And um, and he goes, well, why would I do that? [00:32:30] We're in that category. And I just said, ah, you're fucked. Because your example Jim [00:32:35] was right. You have to shake them. You have to say, if there's a hundred people in the market, [00:32:40] then you, the only way you differentiate is like, is to be really bold and [00:32:45] really aggressive.

Craig Rosenberg: And I'm like, dude, if there's a hundred people in the market. And you think you're better [00:32:50] than them, well then tell 'em that market's broken, it doesn't work,

Matt Amundson: It's why

Jim Wilson: [00:32:55] be, yeah, exactly. The, The, here's why is just as important. Be able to back it up and then, you know, look [00:33:00] for salespeople out there, if you're at a company like this and you don't believe.

Matt Amundson: don't believe

Jim Wilson: Don't work [00:33:05] there 'cause it ain't gonna, you're not gonna be successful in sales. People believe, you know, they can tell when you [00:33:10] believe something or not. So have yeah, for sure.

Craig Rosenberg: Okay. I love that one. [00:33:15] By the way you tra just so everyone knows, Jim transitioned Matt and I,

Craig Rosenberg: [00:33:20] into the top two or three things that he's seen working today. That was number one.

Jim Wilson: [00:33:25] yep.

Craig Rosenberg: Matt's gonna say he transitioned you, Craig. Yeah, it was a really good transition. [00:33:30] Uh, but I had to say something because I was like, oh my God, he's doing my job, but

Jim Wilson: I dunno. [00:33:35] Uh, like, look, the other,

Events are Back as a Major GTM Channel
---

Jim Wilson: the other one that I'm kind of passionate about right now is, no, no surprise, right? But [00:33:40] events are back, like, the way I think of it is like you just have all these different [00:33:45] channels and routes to market and, and ways to engage buyers. And [00:33:50] one falls out of favor, one falls in favor.

Jim Wilson: Like, you know, um, before [00:33:55] COVID, right? It was, it was, uh. You know, emails weren't working right. Like [00:34:00] you just too, too many emails. There's phone calls go in and out, right? Obviously during COVID that just [00:34:05] fell off of the, off of the ladder. But, um, I think in this [00:34:10] post COVID world where buyers have gotten comfortable with Zoom.

Jim Wilson: Being [00:34:15] probably more standard than it absolutely was before they really relish [00:34:20] events and being able to connect with potential buyers or anybody in the [00:34:25] company. That's the one mistake people make, I think is trying to get too fancy with the events [00:34:30] like that, it has to be the, your specific buyer persona at the event.

Jim Wilson: Um, I think that [00:34:35] events are, are back. It's a great opportunity for sales and marketing to work together. [00:34:40] Uh, Matt, to me, it's one of these other things where, uh, creativity really matters. You know, [00:34:45] everybody's doing dinners, who's doing breakfasts, who's doing, you know, uh, uh, [00:34:50] coffee meetings? Who's doing different things out there? So, um, I don't know [00:34:55] what you guys are seeing, but I'm absolutely seeing events. And then the specific story I'll tell [00:35:00] is Bugcrowd, right? In our portfolio, I feel like Bugcrowd, they, they sell [00:35:05] a, uh, a a a a hacker platform, if you [00:35:10] will. Right. And they have a community. It's a two-sided community where they have a group of hackers [00:35:15] and they figure out how to do events. And they have an art, uh, a publication called [00:35:20] Inside the Mind of a Hacker where they leverage these hackers to show up at their events and give [00:35:25] perspective on it. We did an event with them two years ago at RSA where we pulled [00:35:30] together CISOs, which for those of you that know the security space, that's the top buyer, like the CIO in an IT [00:35:35] organization and hackers, and we put 'em together on a panel and they really are kind of [00:35:40] opposite ends of the spectrum, right? You had two people with like one had purple hair and nose rings and the other [00:35:45] one still had a suit on and we put 'em together on a panel and it was one of the best [00:35:50] events we did. It was entertaining, it was useful, the information was useful. [00:35:55] We did it at the Giants ballpark, so it was a cool place that people wouldn't normally go to up in that cloud club.[00:36:00]

Jim Wilson: But I would just really encourage companies to think about events and [00:36:05] doing things definitely at conferences, but um, doing events outside of that as [00:36:10] well.

Craig Rosenberg: Okay. I love that.

Matt Amundson: may I, give an example of a [00:36:15] non-traditional event

Jim Wilson: yeah.

Matt Amundson: yeah. Uh, I'm I'm actually, this is where I wanna learn [00:36:20] other ideas for non-traditional Okay. So, uh, this, this will [00:36:25] maybe not serve our audience well. Uh, uh, Craig knows I've, I've [00:36:30] recently joined a, a very large, uh, well, very large, uh. Like large, mid-size [00:36:35] company. Uh, so I'm in my, I'm in my third week.

Matt Amundson: Uh, one of the things that I had to [00:36:40] sprint to when I joined the organization is that we did a, uh, closing bell [00:36:45] at nasdaq, which is generally, you know, like great celebration of the business. We [00:36:50] had a big announcement that we were making, which was a hundred consecutive quarters of growth. [00:36:55] Big deal for the company. And, um, one of the decisions that we [00:37:00] made is we wanted to bring customers to it. So we wanted, you know, a hundred quarters of growth, let's get a

Matt Amundson: hundred customers [00:37:05] out to it. Um, and it's not necessarily something that you would bring [00:37:10] customers to, right? Like, 'cause you more think about it as like an executive team or, [00:37:15] um, uh, maybe members of your board would come for, for something like that.

Matt Amundson: And we turned it into this [00:37:20] absolutely rocking customer event for us. We got, you know, the, you got the big [00:37:25] video sign outside and you know, traditionally you just put your own employees on there. We made sure [00:37:30] all of our customers got on that.

Matt Amundson: Uh, and then in addition to that, we're. Giving [00:37:35] them all like a framed photo of themself,

Matt Amundson: uh, up on the, up on that wall.

Matt Amundson: [00:37:40] And it's just like, you know, I wouldn't say there was, uh, any [00:37:45] pushback against doing it, but people are like, oh, would customers really want to come to that? And then, [00:37:50] I mean, they had a fantastic time and the, the feedback was great, which is awesome. But [00:37:55] we really had that moment that you want to have with a customer where we had like two or three dozen of those [00:38:00] customers go out, take their photo that we had given them.

Matt Amundson: Posted onto [00:38:05] social and, you know, we didn't block out the sun or anything like that, but like, these are just these [00:38:10] moments where sometimes you feel like it's just for you or for your business, but like, bring [00:38:15] customers along. Customers, especially for early stage businesses, those early customers, they, they [00:38:20] feel very aligned to your success as an organization.

Matt Amundson: And the more you bring them into [00:38:25] your business celebrations, the more they're gonna, you know, really turn into great advocates for your [00:38:30] business going forward.

Jim Wilson: Totally like the customer thing is so overlooked, like. People want to talk to [00:38:35] other customers. But the other thing too, Matt, and you touched on it, the one faux pa [00:38:40] that I see sometimes not often is don't sell. Like if you do all this event [00:38:45] stuff, just get to know people where they went to college, their kids, their interest.

Jim Wilson: It's [00:38:50] so much easier to do the follow-up the day after and say, Hey, I'd love to [00:38:55] schedule something with you. By the way, I, really loved talking to you. We had a great laugh about where we went to [00:39:00] school and our fraternities or sororities. Leave the selling for later. Get to know [00:39:05] people.

Craig Rosenberg: Yeah, I, I totally agree. I I have a fun one for you guys on [00:39:10] this one. So I wrote this post on Topline about, uh, driving [00:39:15] demand, and I talked, I mean, we've seen it too. Events are. Uh, [00:39:20] working and actually I think Omar Akhtar had, um, data on that where the event, [00:39:25] didn't he say like, event budgets, Matt, were like significantly higher than in the [00:39:30] past, I think. Yeah.

Craig Rosenberg: So he, David Politis, who's been on the show, if you don't [00:39:35] know him, Jimmy should meet him. He's based in New York. He, he's like a. He has like a [00:39:40] c uh, CEO founder group there, um, where he, you know, brings them all together, [00:39:45] works with 'em, those events. So he wrote in-person events. It feels like we're on our way to peak [00:39:50] in person events. Uh, um. People. But right [00:39:55] now people like to be in person. They like to have experiences, they want to build relationships. [00:40:00] And, um, here's the, what I've seen work, I'm sort of reading

Craig Rosenberg: paraphrasing a bit. So [00:40:05] one that he's seen coffee and co-working. He's like, find a physical space that [00:40:10] could host 20 to 40 people of your target customers and invite them to come work.

Craig Rosenberg: He's like, [00:40:15] a lot of people are still in remote hybrid environments and it give them a low stress, non-salesy environment [00:40:20] to work. Uh, it helps build trust in community. I think that's a great idea. All right. [00:40:25] Second one, workshop, he said, I've seen a couple companies do this recently, [00:40:30] especially for AI and AI and Enterprise Sales Roundtable Workshop, for example, [00:40:35] target a set of like prospects and customers, invite them to the workshop with a third party expert.

Craig Rosenberg: That's pretty [00:40:40] classic. I used to do that all the time with Topo three to four hours, et cetera. I, I, [00:40:45] that used to work well for people. It sounds like it's working well again, especially with AI being such [00:40:50] a, a topic. Everyone's trying to wrap their hands around um dinner.

Craig Rosenberg: So this [00:40:55] kind of goes with what Jim just said. My, he said my strong opinion is dinner should be 10 to [00:41:00] 12 people max. Um, they, uh, you should [00:41:05] never do a structured pitch never sell. Let the conversation

Craig Rosenberg: flow. If customers [00:41:10] want to talk about you, do it. Same thing

Craig Rosenberg: as you said, Jim. to 12, that's what we've [00:41:15] found

Craig Rosenberg: It's a beautiful number. Yeah, I

Craig Rosenberg: agree. Um, and then [00:41:20] Highend experiences. So this could be anything from amazing tickets to a sporting event or [00:41:25] hard to get tickets to a Broadway show.

Craig Rosenberg: You could tell he is New York. Dinner at the very best restaurants in the [00:41:30] world. Small group sessions with famous speakers personalities, um, [00:41:35] you

Craig Rosenberg: know, the things you you want to do is something that they, they, they could. [00:41:40] Not necessarily do themselves. And so that was high end experiences. [00:41:45] This one was interesting.

Craig Rosenberg: He is like, he's seen this work, which is choose your own [00:41:50] adventure. So you message a group of prospects and customers tell 'em you wanna put together an [00:41:55] event with them for them and give them the choice. And he was like, [00:42:00] you know, some of them done whiskey tasting, ax throwing, which I've never done. Um, [00:42:05] you know, even a, one of 'em just said, let's just walk around Central Park. You know, and [00:42:10] so like, pretty interesting. Um, and then, uh, yeah, I would just leave it at [00:42:15] that. So you can see people are back to sort of figuring out. [00:42:20] Since events, everyone's craving 'em. I mean our, event, by the way that Matt and I are putting on Jim, that you're [00:42:25] coming to and your portfolio might be coming to is, uh, I mean we, we, we got to like [00:42:30] 75 signups with just some social posts and we can only fit 200,

Craig Rosenberg: you know, so [00:42:35] people, want to do this stuff again.

Craig Rosenberg: So anyway, I, I throw those things out

Jim Wilson: [00:42:40] But that's for, for all the people that end up listening to this. I'd love it if they put this for this part, put in the [00:42:45] comments, some ideas and things that you've done because you know, there's no playbook on it. [00:42:50] There are a couple things. What's interesting, uh, Craig is golf. [00:42:55] Uh, you don't hear golf anymore.

Jim Wilson: Like I feel like the one thing about events is time's been [00:43:00] compressed, right? And you just, the days where you can do the full on, [00:43:05] full day, you gotta commit. You gotta go out to Half Moon Bay and we're gonna golf with you. I don't see [00:43:10] as many of those. I feel like they're four hours max. It's a dinner, it's a half day.[00:43:15]

Jim Wilson: Um, those are the kind of things. And then one last bit of advice that, again, the thing that I, [00:43:20] I see in our portfolio, this is a great place to try to leverage. Your investors [00:43:25] and your board. Um, we are doing something to Costanoa roadshow where [00:43:30] we're, uh, bringing a guy that's, that's with us, Joe Sullivan. He's a kind of a luminary in the [00:43:35] security space, and he goes and talks to folks, but we're doing a road show and we'll bring one or two portfolio [00:43:40] companies along and we're kind of bringing it out to them versus making everybody come back to the Bay Area, [00:43:45] into Silicon Valley. I'd love as a follow up to hear from other people about event [00:43:50] strategies.

Craig Rosenberg: yeah, we should do that. Um, and just, you know, best events that you [00:43:55] guys have held and, um, get some new ideas. I love that. Okay, so that's two. [00:44:00] You got another one for us. Uh.

Jim Wilson: Uh, well look, we could talk about AI all day long. I do think [00:44:05] AI is gonna be huge in in sales. I do think AI in particular, Craig and I, are both [00:44:10] passionate about top of funnel and things that work for top of funnel, and I feel like there was [00:44:15] this initial backlash of the, I'll call it the AI SDR [00:44:20] right that people said, oh, let's try it.

Jim Wilson: Oh, it absolutely doesn't work well. Eh, it's somewhere in the [00:44:25] middle. Like there's a lot of functions that I think agents now can do [00:44:30] around systems of record and automating tasks, automating research, [00:44:35] putting things together. And I think for all the salespeople out there, experiment, push [00:44:40] it. Especially with Claude.

Jim Wilson: Um, I'll go back to your existing and vendors, right? [00:44:45] HubSpot's got some amazing stuff they're doing that it's a lot easier to. [00:44:50] Incorporate from your existing tool, then try to build something from scratch. I'm not a believer in the, [00:44:55] the builds build that from scratch, but I feel like,

Jim Wilson: uh, top of the funnel is where we're gonna see the [00:45:00] next boost of productivity.

Craig Rosenberg: Okay.

Jim Wilson: But, all

Jim Wilson: right. So, but but [00:45:05] I,

Jim Wilson: I, I digress Craig. 'cause that could be its whole other section. Right? I think the [00:45:10] last thing that I see working right now is paid POCs. [00:45:15] Right.

Craig Rosenberg: Ooh.

Jim Wilson: And yeah, a little bit. A little bit of a counter. Right? And [00:45:20] by the way, and I say that in POCs, Proof of Concept, proofs of value. [00:45:25] I also think that POCs in two or three years may go away entirely if people [00:45:30] really start to build out consumption model products and you can just let them try it, [00:45:35] that's probably the best.

Jim Wilson: And that, the reason I always like that from a sales perspective is it forces the [00:45:40] engineering team to build a product that actually can be. Used without [00:45:45] massive human intervention to stand it up. That said, there are still products out there that [00:45:50] are complex that do take a while to, to set up and deliver huge amounts of [00:45:55] value.

Jim Wilson: And I've just seen a, a big trend in this, in the company I'll talk about in our [00:46:00] portfolios, Feldera, uh, sells a product to that really [00:46:05] allows for improvements in batch processing to do it using deltas. So they can make [00:46:10] a, a company that has a huge amount of data and moving huge amounts of data, do it in a [00:46:15] much, be much faster, much cheaper and better quality.

Jim Wilson: But they've had a lot more [00:46:20] success with early companies. Again, back to the strong point of view saying, listen, our product works [00:46:25] great. It's, it's complicated to set up. There's a whole bunch of integrations, there's a whole bunch of [00:46:30] workflows you need to build, but once you do it, we will show you how much value we'll add to [00:46:35] this, and they charge for it.

Jim Wilson: And they don't run, they don't shy away from it. And I feel like that [00:46:40] that's somehow as we got to where products are always easy to use and [00:46:45] no one charges professional services anymore and customer success is out there. People forgot that [00:46:50] sometimes there's products that, uh, do, do require that and you should just

Craig Rosenberg: Yeah,

Jim Wilson: it.

Matt Amundson: [00:46:55] Yep.

Craig Rosenberg: embrace it.

Craig Rosenberg: I love that. I had, yeah, we had, [00:47:00] uh. This was a couple years ago, and the portfolio company came in. I mean, they were early [00:47:05] too, which is where you get, you know, you get scared to charge for the POC, [00:47:10] um, and they were charging on the POC because they wanted some skin in the [00:47:15] game. On the other side, they kind of have to, you're right, I mean, ultimately at the end of the day, you want to build a [00:47:20] product that people could just start using. Um, but in absence of that, or if there's [00:47:25] complexity that. You know, requires that they do something a little [00:47:30] heavier. Uh, the paid POC is like a level of commitment that, you know, [00:47:35] ensures that they're going to, you know, have resources on their side to go make sure this [00:47:40] thing, you know, works or doesn't work. Um, but yeah, I mean, I, I do think that's [00:47:45] a, that's actually a kind of a big one you brought up. 'cause

Jim Wilson: Yeah,

Craig Rosenberg: kind of shied away from that for [00:47:50] a

Jim Wilson: it's one of those things where I get it. I get that we look, we all wanna sell a product that magically sells itself. [00:47:55] Right. That's who doesn't want that. But the reality is that's not [00:48:00] where most of products are. And I think that it's really gets back to [00:48:05] companies knowing their product and, and really understanding what's that unit of value, what's the magic moment [00:48:10] I'm really into right now?

Jim Wilson: Salespeople understanding the magic moment they can have with a [00:48:15] buyer, interaction with their product and how to do that. And a lot of times it's not a quick [00:48:20] hit, it's something that's gonna be, require a little bit of commitment. And you need to know [00:48:25] that ahead of time. And the consultant we brought in, we had a, a Go-To-Market consultant, Amy [00:48:30] Eros, who, uh, helped Felder kind of figure that out and then credit to [00:48:35] Lilith, the CEO.

Jim Wilson: He, he was initially nervous about it, it, but man, he leaned into [00:48:40] it and he really understood it. Who was super credible. Again, Matt, [00:48:45] back to the strong point of view, he would lean into it and they would ask why, and then he would go through [00:48:50] all the things they're gonna do. In the proof of concept, what they were gonna get out [00:48:55] of it, they had documentation to support it. They had a, you know, POC test [00:49:00] plan and customers left not only convinced, but more importantly, kind of armed with the [00:49:05] information they needed to go get approvals for it. Yeah. And I think they've been like [00:49:10] in all their POCs.

Matt Amundson: it sounds trivial, but even things like timelines, right? Like [00:49:15] people want to understand like how much time investment they're gonna have to make in evaluating a solution.

Jim Wilson: [00:49:20] Yeah.

Matt Amundson: It may be long, but at least they know that going into it. Otherwise [00:49:25] what happens?

Jim Wilson: Right,

Matt Amundson: ghost you in the middle of the cycle 'cause they're just like this taking forever.

Jim Wilson: and for [00:49:30] God's sakes, don't do the POC that I call the kick the tires, and it's got no end date [00:49:35] POCs. Like, it's just, it's, it's a slow death if you're selling [00:49:40] software, you know, and, and every technical, and this is mostly for technical buyers, [00:49:45] right? But most technical buyers, especially developers in that space, they'll do that all day long.[00:49:50]

Jim Wilson: You know,

Craig Rosenberg: Yeah, for sure. Uh, yeah. You know, we at, at [00:49:55] topo, this was a while ago. Now, by the way, guys, uh, you know, we, everyone [00:50:00] was doing, you know, whether it was paid or not, proof of concepts and [00:50:05] like if we. We would look at the guys who had, I mean there are a lot [00:50:10] of companies at the time that would have like an 80% conversion rate outta the [00:50:15] POC and above.

Craig Rosenberg: And then we had somewhere like we'd go in. It's like, how? How is it [00:50:20] possible to have a 30% conversion rate off of POC? Like they shouldn't even be in [00:50:25] the thing.

Craig Rosenberg: But what Ro yeah, Robert Koehler on my team, what he did was he created this [00:50:30] sort of template for managed what he called the managed trial, managed POC.

Craig Rosenberg: [00:50:35] And so we looked at like what these successful guys do. One of the things we learned was [00:50:40] that if you gave someone 60 days, at the end of the day, once it was [00:50:45] installed, the, the highest usage rate and was within two [00:50:50] days, 48 hours, and, and you wanted them to do that because once it got punted. [00:50:55] Then, uh, you was, you were dead.

Craig Rosenberg: So what, like, it was a small trick, but [00:51:00] what he'd say is like, first you gotta do a kickoff. And as Matt said, there has to be a timeline that you share with [00:51:05] them, that you work them through. And he's like, and then you say, great, we will [00:51:10] check in you, this is your install, et cetera. We will, we will do a call that we're gonna set [00:51:15] right now for 48 hours after you launch, because they're gonna say, well, let [00:51:20] us do it and we'll check back with you. And like that. For a lot of these guys, like [00:51:25] that is where you can actually go in for the close on the sec on that first call [00:51:30] because they've, the majority, they're, you have to a, one of the things you would train 'em is like, [00:51:35] what are they fo remind them what they're focused on and point them to look at [00:51:40] that like you're not saying, oh, go, you know, if they don't care about the ui. They don't [00:51:45] tell 'em, oh, and check out the beautiful ui. No. Like, this is what you're trying to solve. Here's how [00:51:50] you're gonna go look at whether you solve it, put it in and go watch it. And within two days, they [00:51:55] will know whether it solved their stuff. Now, if they need more time after that, that's fine, but you've [00:52:00] reestablished what they're doing, the POC four,

Craig Rosenberg: and then what he, you [00:52:05] know, he had, he would tell people, create a report at the end that you use [00:52:10] for everyone. And put in the timeline that you want to present this report to [00:52:15] the decision making team. And he's like, that way it doesn't end. Also with the [00:52:20] user who's most likely to be doing the POC or the lower level folks, [00:52:25] them saying, well, this worked great, and them not knowing what to do next. A, you've gotta, [00:52:30] you know, do your discovery upfront so you know what they're trying to solve, and create a report that shows how you solved it [00:52:35] and then set it up so that you as a salesperson or an executive can go and bring [00:52:40] that to the broader team. So it's these like, these like little tactical plays that fit within [00:52:45] the POC trial process that, uh, you know, helped [00:52:50] manage, it, helped bring it to, to close. And like, it was like [00:52:55] when we looked at the folks with the terrible conversion rates there, it was like, yeah, go try it.

Craig Rosenberg: You know, see what

Jim Wilson: no [00:53:00] no control. But you, you brought up something that reminded me. You know, I always tell people in [00:53:05] the topic of POCs, everyone focuses on the technical validation of the POC, but [00:53:10] the reality is a good proof of concept proof. Proof of value does technical validation and business [00:53:15] validation. And the business validation is what you have to focus on.

Jim Wilson: I work with a company, [00:53:20] Rafay Systems, and they sell a very complicated product that does [00:53:25] orchestration for ai, neo clouds, right, for all these big data centers that are setting up.

Jim Wilson: [00:53:30] The technical part is super hard, and it all is, and this is the other surprising thing is, you know, or, [00:53:35] or not surprising, is most good products, the technical stuff will work. It'll work as advertised, [00:53:40] will work in their environment. But you as a salesperson, what you gotta do is figure out how to get the business [00:53:45] validation and the business justification done. And that's what the best salespeople do, is [00:53:50] they do technical validation and business validation and accomplish both of those in A [00:53:55] POC.

Craig Rosenberg: Bam. Bam. At the buzzer.

Matt Amundson: easy.

Matt Amundson: right?[00:54:00]

Craig Rosenberg: Yeah.

Craig Rosenberg: Now go do it everyone.

Craig Rosenberg: Yeah.

Craig Rosenberg: Um, awesome. All [00:54:05] right, so with two minutes left on the clock, we did it. Um, you [00:54:10] got some multiple good stories in there. You got three very, uh, [00:54:15] specific actions that people could take from this, uh, [00:54:20] episode. So I would call this a raging success, Jim.

Craig Rosenberg: Good work.

Jim Wilson: right. All right. [00:54:25] Well thank you. I'm happy to be out here. I apologies for everybody that is in a cold weather place [00:54:30] and is looking at Craig's background and those Oh man. lake and the beautiful [00:54:35] sparkling and sun. I know. and sunny out in California. I apologize to everyone,

Jim Wilson: [00:54:40] but I will say this, it's beautiful in the day right now, but the nights are [00:54:45] colder

Craig Rosenberg: than when there's rain. Yeah.

Craig Rosenberg: man, it's

Craig Rosenberg: pretty nuts, but, we've got our [00:54:50] swag, oh geez. Here he goes. Swag man. We're gonna start.

Craig Rosenberg: Yeah, [00:54:55] man, Jesus. Anyway, Jim, thanks for coming on the, the transaction [00:55:00] folks. That's the transaction and we are going to call this one a [00:55:05] night and move

Jim Wilson: Thanks. Thanks. Matt.

Jim Wilson: Thanks Craig.

Matt Amundson: Thanks

Jim Wilson: Bye. Bye.

Matt Amundson: Thanks, Jim.

[00:55:10] Thanks for joining us for another episode of the Transaction, Craig, and I really appreciate the fact that you've [00:55:15] listened all the way to the end. What are you actually doing here? For show notes and other [00:55:20] episodes, please visit us@thetransactionpod.com, like and subscribe on Spotify, apple [00:55:25] Podcast or any other place you get your podcast from.[00:55:30]

Either you have walked away from your podcast device. [00:55:35] Or this is playing somewhere in the background. Someone in your house would really like for you to shut [00:55:40] this off [00:55:45] [00:55:50] now.