The Transaction · 2026-07-21 · 56 min
Key moments - from our scoring
Substance score
65 / 100
Five dimensions, 20 points each
Jim Wilson brings a wealth of sales leadership experience to this conversation about what's resonating with buyers today. As a Partner at Costanoa Ventures with a track record building sales teams across regions, Wilson emphasizes the critical importance of founder point of view - not just market positioning - as a differentiator in sales conversations. He argues that salespeople should develop strong opinions on how buyers should evaluate products, moving beyond simply being labeled 'cheap' to owning a compelling price-to-value narrative.
The episode digs into AI and agentic systems as a major inflection point for sales teams, with Wilson advocating that younger salespeople who invest in learning AI and automation can leapfrog experience. Beyond the technology piece, Wilson and the hosts explore the psychology of buyer engagement through swag, direct mail, and pattern disruption - drawing examples from portfolio companies like BugCrowd (lock-pick sets for hacker audiences) and strategies from CMO Kacie Jenkins (contextual barbecue supplies). The conversation lands on a core insight: buyers respond when they feel genuinely seen and researched, not when recipients perceive generic outreach.
Jim Wilson advises younger salespeople to aggressively learn about AI and what it can do to improve personal productivity, arguing this is a major differentiator in an agentic era and allows them to leapfrog experienced peers faster than ever.
Swag and direct mail work when they're high-quality, memorable, and contextual to the buyer's interests - like sending barbecue supplies when a prospect is hosting a barbecue, or lock-pick sets to a hacker community. Generic branded items actively backfire.
Wilson argues that being at a 'nice price point for what the product does' is a legitimate and confident positioning; salespeople who run from this label miss the opportunity to own a strong narrative about value and affordability.
Founder point of view - having a strong opinion on how a buyer should evaluate a product - builds buyer confidence more effectively than general market positioning and gives sales teams a compelling narrative beyond features.
Wilson spent eight years building the Asia region for Parametric Technology in an era before Google Maps and Uber, learning to navigate complex international sales dynamics and cultural nuances, including a memorable bidet incident in Tokyo that taught him about handling unexpected obstacles with composure.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode delivers solid, actionable insights around founder POV in sales, event strategy, and POC management with specific examples (Reveal, Bugcrowd, Feldera). However, substantial runtime is consumed by extended tangents (swag discussion, bidet anecdote, shoe-tying jokes, weather commentary) that dilute the substantive density. The core frameworks are proven rather than novel.
having a strong founder point of view when you Go-To-Market...having a strong founder point of view is key right now
paid POCs...there's products that are complex that do take a while to set up and deliver huge amounts of value
The core thesis - founder POV drives sales effectiveness - echoes established Challenger Sale and narrative-driven sales frameworks already well-circulated in the industry. Event strategy and POC management advice, while practical, largely repackages conventional wisdom about buyer engagement and trial structures. No counterintuitive or first-principles thinking that meaningfully departs from mainstream GTM discourse.
I love the idea that the narrative is the key thing with salespeople. Strong point of view doesn't always need to be the market
events are back like the way I think of it is like you just have all these different channels and routes to market
Jim Wilson is a credible, experienced operator - a former CRO/VP Sales at PTC (elite sales organization), now Sales Advisor at a tier-1 VC (Costanoa). He has genuine domain expertise and portfolio access. However, his role as a VC advisor (not founder or current practitioner running a revenue org) slightly diminishes his ground-level credibility compared to someone actively selling or leading GTM at scale today.
I started my career at a company called Parametric Technology and one of the stints I did was over in Asia
I'm the Sales Advisor at Costanoa Ventures
The episode grounds claims with named companies and detailed examples: Reveal (modern SIEM, founder Evan, VP Sales Aaron Trott), Bugcrowd (hacker platform, RSA event with CISOs), Feldera (batch processing), Rafay Systems. However, evidence is largely anecdotal and qualitative; few hard metrics, conversion data, or quantified outcomes are provided. The POC discussion references Topo's 80% vs. 30% conversion rates, but minimal supporting detail.
the example I'll use is a company run Reveal...his whole message is like the sim market sucks
Bugcrowd, they sell a hacker platform and they have a community...we did an event with them two years ago at RSA
Craig Rosenberg demonstrates solid interview skills - he asks follow-ups, challenges Jim on POV vs. narrative, shares relevant counterexamples, and transitions smoothly between topics. However, substantial airtime is surrendered to comedic banter (shoe-tying, swag reviews, bidet anecdotes) that, while entertaining, does not serve the substantive agenda. Missed opportunities to pressure-test claims or dig deeper into nuance when Jim glosses over complexity.
So he is like, well, I have this problem, there's like a hundred companies in my market...I said, well, how about this? Why don't you go to the market and say, you know, whatever the category name was, doesn't work. Right.
Craig: You're fucking, you have to shake them. You have to say, if there's a hundred people in the market, then you, the only way you differentiate is like, is to be really bold
Computed from the transcript - who did the talking, and the words that came up most.
Jim Wilson is an Operating Partner at Costanoa Ventures and cut his teeth leading global sales teams for decades at major companies including SumoLogic, Microsoft, Merced Systems, PTC, and NICE Systems. Jim joined Co-Hosts Craig Rosenberg and Matt Amundson to discuss the impact that strong Founder vision has on the sales team’s narrative, why paid POCs (Proof of Concepts) are making a comeback in B2B sales, and what truly sets B2B events apart for buyers. Plus, Jim examines why corporate gifting swag has gotten so bland while also providing some great examples from B2B brands that are doing it well. Also, Craig reads verbatim from the article of a past guest, Matt extolls the virtues of the loop-swoop-pull technique, and Producer Sam shouts out a fellow Sam. Critical Takeaways Develop and weaponize a strong founder point of view, and then cascade it to sales. The single biggest differentiator in a crowded market is a bold, opinionated narrative that challenges the status quo. Train sales reps to lead with a prescriptive point of view on how to evaluate your product.
Transcribed and scored by The B2B Podcast Index.
TT - 084 - Jim Wilson === Jim Wilson: With the whole AI and agentic era right now, if you're not on the learning train, you are in trouble. Absolutely in trouble. And then I always tell the younger up and comer salespeople like, man, this is a great opportunity for you to differentiate yourself. You don't have to be a gray hair, gray 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 your personal productivity. And you can leapfrog people faster than ever. It's a great time to be in Jim Wilson: sales actually. I love the idea that the narrative is the key thing with salespeople.
Strong point of view doesn't always need to be the market. I love sales teams that have a strong point of view on how you should evaluate our product. Jim Wilson: I think a lot of salespeople run away from Jim Wilson: being labeled cheap. Jim Wilson: And the reality is no, they're just at a nice price point for what the product does.
Jim Wilson: with Craig Craig tying his shoes. Craig Rosenberg: What we're going, I Craig Rosenberg: like it. Matt Amundson: Are you a loop, swoop, pull guy? Craig Rosenberg: A what?
Matt Amundson: Are you a bunny ears guy? Which one are you Craig Rosenberg: I don't know. I, I'm not sure I know where you're going. Matt Amundson: with?
Your tying your shoes, you're a loop, swoop pull guy, or. Craig Rosenberg: know 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. I tighten them and put 'em, I tie 'em under. I put 'em under.
So you can't see the 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 guy, Matt.
Craig Rosenberg: are you, Jim Wilson: Yes. Craig Rosenberg: what are you, Matt? Matt Amundson: I'm a loop swoop and pull. Been been that since day one, baby.
Since I came out the Velcro. Craig Rosenberg: Look you ever do the doubles, the dubble, so you loop it twice? That's, I have one of my daughters that does the double loop. Matt Amundson: Yeah, with, I mean, both my kids have gigantic feet and their shoes are always untying, so yeah.
We're, we, we double knot all their shoes Craig Rosenberg: This is a kind of interesting Craig Rosenberg: conversation. Craig Rosenberg: that our, our, uh, audience loves you guys Matt Amundson: Yeah, Matt Amundson: it's. Matt Amundson: it's. kick in with talking about not, not is just they, they, they, everyone had listens to the show.
That's what they always mentioned, so I love that. Craig Rosenberg: all right, so, but let's get to business. Introducing Jim Wilson, - Craig Rosenberg: Today's guest, you ready for this? Matt Amundson: I am.
Craig Rosenberg: Because he's a peer of mine. Craig Rosenberg: Um, he's the Sales Advisor at Costanoa Ventures like and I, we share some portfolio. I mean, people love Jim. Now, I loved Jim before he went to Costanoa, so, uh, I've known him as like a killer.
Uh, sales operator for years before, um, before he joined Costanoa, but we've done a bunch of stuff together. Craig Rosenberg: We meet all the time and trade notes, and I always like the conversations we have about him, sort of helping companies sort through their sales and his stories are range. Just helping people get, get their sales feet under them to optimizing teams going forward. And so, you know, guys like him have seen a lot over the years Craig Rosenberg: and so we just love having guys like this on the show.
Craig Rosenberg: And so, ladies and gentlemen of The Transaction community, today's guest is Jim Wilson from Costanoa Ventures, my buddy, and a potential, depending on how you do Jim. Craig Rosenberg: A potential, Craig Rosenberg: uh, multi-time guest Matt Amundson: Oh wow. You're calling your Jim Wilson: that's Jim Wilson: my goal. That's what to shoot for.
All right. Jim Wilson: Exactly, exactly. And first time though. But Craig, back at you, Jim Wilson: you know, I, uh, admired you from the days of Topo.
I was always at those events. They were great learning events and, uh, I consider it honor to be working with you at our two different venture firms. Craig Rosenberg: Actually, you know what? That is a good point.
I wanna say this, Matt, about yeah. Uh, you know, a lot of Matt Amundson: of Craig Rosenberg: CROs, presidents, et cetera, like his level, don't like to learn anymore. Craig Rosenberg: He Craig Rosenberg: did. He was always a learner, always listening, taking that stuff in, and obviously offering back.
It's a good lesson Jim Wilson: Very you don't know everything. Jim Wilson: And man, with the whole AI and agentic era right now, it's Jim Wilson: if if you're not on the learning train, you are in trouble, absolutely in trouble. And then I always tell the younger up and comer salespeople like, man, this is a great opportunity for you to differentiate yourself. You don't have to be a gray hair, gray 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 your personal productivity. And you can leapfrog people faster than ever. It's a great time to be in sales actually. It really Is it, it it actually is.
It's funny 'cause it reminds me a lot of like the era of, um. I mean it's bigger, but it reminds me a lot of the era when like market automation was just like coming Matt Amundson: into fold and people were like, oh, I'm so behind. Like I don't understand the concept of a nurture, how to build it. Matt Amundson: And everybody was looking to their peers to help them sort of design the work.
And it feels a lot like that. Although clearly the stakes are a lot higher. Jim Wilson: Yeah, very much. Totally agree, man.
Totally agree. Craig Rosenberg: All right, so let's, uh, we got two essentially sections of the show. One is we just ask you for your, uh, best and greatest Go-To-Market stories and then two, we'll ask you about the, you know, two or three things you're seeing working today with your travels. Um, so the first one is, Jim, tell us a story.
What do you got for Jim Wilson: All right. Well, I got one funny story for me personally, which I'm gonna get to. Before I do that, I just wanted to point something out that Jim Wilson: Craig and I talked about. And Matt, you'll appreciate also with your marketing background, which.
Jim Wilson: What's up with company's swag game these days? So, you know, Jim Wilson: uh, not to date myself, but I remember back to where swag was just a t-shirt and it was maybe some pencils and a notebook. Jim Wilson: Someone reminded me the other day that like Jim Wilson: you know, you used to get these branded notebooks, but now swag is hat right swag. If it's cold weather.
Right. You got your beanie, you got your beanie with the top on it, Jim Wilson: you got socks. Right? So these are all our portfolio companies.
By the way, this is great branding for me with our portfolio company. Jim Wilson: It's this little subtle branding, right? Matt Amundson: Yeah. I've never wanted to build, Matt Amundson: buy workflow tools more.
Jim Wilson: Yeah. Jim Wilson: And then, and then I was looking in, in my garage last night, so there's my Jim Wilson: old look at that. Oh Logic Damn. Jim Wilson: Club, Jim Wilson: right?
This. This. was a beach bag that is still my wife's favorite beach bag. And then we have a company in the defense tech space ion, they did it.
Jim Wilson: They one upped it. This is one of these ones where you can stick, uh, a, a beer and, and drinks in it. It's a cooler. It's got this whole thing in the top.
And I use that all the time. And then the last thing I'll just show you is again, like the, the level of the swag. 'cause I know Craig, you've posted about it before. Jim Wilson: Lululemon, right?
One of my nicest jackets Arctix, by the way, this is Costano. This is the one I like about Costano. The rule of swag is not a big, huge logo, nice and small, right in the back of the neck area. So it's a nice one.
We just sold a company signal to CrowdStrike, got this nice coat of SY jacket, right? Jim Wilson: So I'm wearing that. Jim Wilson: Um, and Matt Amundson: wonky sizing from Cotopaxi. Jim Wilson: Yeah, actually, great point.
Jim Wilson: The, the arms were way too long. I had to return it, you know, I'm never a medium and this is the one time I had to return it for a medium. Very good point. Matt spoken like a marketing person.
And then this is the new, Jim Wilson: uh, this is one of our company's run Reveal and they gave me a Lululemon. Jim Wilson: This is one of these old school sweatshirts, uh, you know, the, the old sweat hoodies. Jim Wilson: And man, it is fantastic. It's my current go-to one, but.
Yeah. Jim Wilson: the, the swag game is just awesome. And I think if you're a startup and you're, it's actually a message to salespeople, like, go talk to your founders or your counterparts in marketing, but up your swag game. Jim Wilson: It's good stuff.
Makes it fun, you know, makes it Yeah. industry. Craig Rosenberg: You can't send me any more, by the way. I don't get them anymore, thank God.
But the stress balls with Jim Wilson: yeah, on it, please. I, I don't need those. yeah. you gotta go big or go home on these things.
They gotta be memorable. You know the uh, Kacie Jenkins, who we had on the show, it's a favorite of me and Matt's, you know, she was at CMO at Sanso and, um, she has all these incredible swag stories, but also just like, uh, direct mail stories. One of my favorites, as she said, was like, they're working on a deal. Uh oh no.
It was a prospect in their ICP that they've been working on for a while. They noticed on social, he's hosting a barbecue that weekend. Craig Rosenberg: They sent him meat, barbecue sauces, everything for the barbecue. Craig Rosenberg: He takes a picture of course with that before he does the barbecue and you know, and they're engaged with him right after, you know, there, there's a lot you have to do.
So much to pattern disrupt. You have to not have to do so much. Matt Amundson: You have to be creative. Jim Wilson: You have be creative.
Matt Amundson: right, Craig Rosenberg: meaningful in your pattern disrupt. And like the, if you just send swag for the sake of sending swag, that actually doesn't work. Craig Rosenberg: 'cause I don't care. I've got, I was 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, but like, you know, you, you gotta, you gotta make it. You know, make it meaningful. And, uh, just a little bit of either like a coat ax jacket. That's something that I 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 was so tight around my belly, I don't even understand. But then, you know, like, it, it was wild. Craig Rosenberg: It was like everything else Craig Rosenberg: fit, yours. Oh, you've got a different fit problem.
Because my coat of Jim Wilson: ies Matt was the first one I got. Like, the arms were like gorilla arms. 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 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 Craig, I agree with you by the way. the the thing that is fascinating to me is, um, there's more opportunities than ever to brand things, foods, you know, wine bottles, things like that. And just to be creative and, you know, we'll talk about it a little bit later, but buyers care about that stuff.
Jim Wilson: Buyers care that you actually are. Looking at them and thinking about them. And you did some research on 'em and they know what they like. Matt Amundson: The double-edged, the double-edged sword of sending swag and direct mail is like, um, it is definitely not, uh, it's the thought that counts type activity as like crappy as that sounds.
You're like, oh yeah, I'm just trying to give somebody something great. Matt Amundson: You know, like you can miss in a big way. Matt Amundson: Like it's part of the reason why like you either gotta focus on something that's really. High quality or high.
Cool. Um, it's typically why I tend to stay away from alcohol. There's nothing like sending somebody something and they're like, Hey, cool. I've been in the, I've been in the program for seven years.
Thanks a bunch. And Jim Wilson: Yeah. Have you tried coffee? We had one of our companies do coffee.
Jim Wilson: They, and they actually in the, in the era of Covid,they did a webinar, which was a breakfast time, or you know, they did it during, during the morning 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, I have two things to mention. One is for everyone listening to the show, if you wanna send me anything, you send me bottles of whiskey or bourbon, because I, it just, it, it's a pain in the butt to go to the store and get something good. And then, um, but You know, I have another, you know, Carilu is saying, um. She, uh, has a, it's called, I think, business Bricks.
They do Lego, they do custom Lego Craig Rosenberg: and developers have a predisposition for Legos, a large percentage of them. And I was like, that is brilliant. Craig Rosenberg: You know, like if, and 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 events, but consider that as a little gift for an event.
Jim Wilson: Uh, one of our company's BugCrowd sells to securities and hackers, and they're, one of the things they had is a little lock pick set, so literally something that you can go and practice and 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, but it was just a great creative idea for their community of hackers. That you could get this little tiny thing and learn how to pick a lock. Craig Rosenberg: I, I want in on that 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. 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, there's a Jim Wilson: ring camera right above the door. Craig Rosenberg: Hey, the, the guy who stole from us, he left Craig Rosenberg: his wallet. Wait, are those his car keys?
Craig Rosenberg: Um, so, Craig Rosenberg: uh, anyway. Okay, All right. So anyway, that's the swag stuff. Look the story.
Um. Jim Wilson: I think these things are always great for these stories. So I'll tell a story from, unfortunately a long time ago for me as Craig, I think, you Jim Wilson: know, I started my career, um, at a company called Parametric Technology, and one of the stints I did was over in Asia. Jim Wilson: So I lived in Asia for eight years and built up that region and I was a young whipper snapper, but this was back, you Jim Wilson: know.
Before electricity, let's just say Jim Wilson: where Jim Wilson: you'd, you'd go to meetings and you didn't have Google Maps, you didn't have Uber, right? You were just doing it old school where you had to figure out how to get there, Jim Wilson: And I was in Japan and I distinctly remember it was a bank. I don't remember what bank, but you know, being a good young sales person with good sales hygiene, I got there about Jim Wilson: 30 minutes early. Uh, unfortunately I had to take the subway the whole way and I had to go to the bathroom, right?
So Jim Wilson: I'm down in the lobby and this is in Tokyo, and this is, again, Jim Wilson: a long time ago. Jim Wilson: There wasn't a lot of English translation going on, right? So I, so I find a bathroom and, Matt Amundson: and, Matt Amundson: uh, are you Jim Wilson: with Toto Bide? Matt Amundson: of Yeah, Jim Wilson: Okay, so no surprise.
But in Japan it's Jim Wilson: kind of the standard there, right? Jim Wilson: So, lucky me, I find the public bathroom. And the other thing about 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 where it was a whole bunch of stalls, and the stalls were super skinny, right? Jim Wilson: So you get your privacy, but there wasn't a lot of room in there.
And by the way, this is also in the era where you guys like me, wore 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 problem a little bit later. So I find, find the, find my nice, you know, pit stop here, Jim Wilson: pleasantly surprised.
I've got a nice warm toilet seat. Do my business. Then I get, I I finish and I turn around. Well, it turns out with Toto bidet, if, if you know them, they've got this big panel, and that's great, except that it was all in kanji, all of it, right?
And I had this very simple problem, which is how to flush the toilet. Jim Wilson: So I'm standing up, I'm all, I'm all done. I'm in my suit. I'm in this little tiny, you know, thing, and I'm like, all right.
I came up with the bright idea that I'm just gonna press every single button. And see what happens. So I just lean over, press all the buttons, and the toilet magically starts flushing. Jim Wilson: Well, the mistake I made was I wanted to know what that symbol was so that in the future if, if I ever had ran into this problem, I'd know which to press.
So I lean over. I'm in the process of looking, trying to figure out the kanji. All of a sudden, the bidet arm pops out, shoots water. Right in my crotch, like literally a Jim Wilson: direct shot.
Uh uh. Not only that, but I'm stuck. I'm stuck in this, you know, four by four box trying to wiggle. I couldn't get out of it.
Jim Wilson: And so obviously I, I escape. The bidets attacked me. I'm now 20 minutes out from my meeting and it looks like I have a nice huge pee stain right in my suit. And, uh, I made a, a game day decision to decide that I would show up to the meeting 10 minutes late, which in Japan is a little bit of a faux pa, but it did work.
And let's just say that I was in front of the bank walking back and forth, air drying a little bit, my suit, uh, before the meeting. Jim Wilson: So Craig Rosenberg: you get the deal? Jim Wilson: I, I don't know if we got the deal. I know the meeting went well.
And more importantly, Craig, I didn't walk into the meeting and they all asked me and Jeff and Kaji like, Jim Wilson: uh, did you pee your pants right before the meeting? Craig Rosenberg: Yeah. Wow. You know what, Jim?
That. It. We love stories like we have this thing, it's the craziest thing on the show, like we want people to tell a story. Craig Rosenberg: It's actually been really hard for some people.
That's exactly what we've been asking for the whole time. Craig Rosenberg: So message to people that are listening that were on the show. Can you have some fun and tell a story like Jim about getting sprayed by the bidet on his crotch. Craig Rosenberg: You know.
Craig Rosenberg: like I, I, by the way, I was, I 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 imagine the small stall, the that. See now that's the kind of story I like.
Craig Rosenberg: Matt, your thoughts story ranking Matt Amundson: We love Matt Amundson: bathroom. Yeah, that's a, that's a solid five. Uh, Matt Amundson: we, we love bathroom humor around here. Here's what I think happens, Craig.
I think you tell people, Hey, can you tell, or you ask people, Hey, can you tell us a story? Could be funny. Interesting. And then you hit them with heroic at the end.
And that like, I think that they're like, okay, I know a funny story, a heroic story. Matt Amundson: I, Jim Wilson: Yeah. Matt Amundson: I think that throws 'em off. I think we should ask for funny.
Craig Rosenberg: You're blaming me. I like Matt Amundson: I'm not blaming you at all. I'm not. I think you're a great pod podcast host.
I think. I think you really get it right, Jim Wilson: Craig, I'm with Matt on this one. I was thinking like, I don't know, man, salespeople is heroes in those stories. Those are, it's somewhat of a dime a dozen.
It's more, uh, Jim Wilson: embarrassing. Focus on, embarrassing is the key word, probably Jim Wilson: more than anything point. Because Maria Bolden, Matt Amundson: Yeah. Craig Rosenberg: Maria Bolden had the, the probably the best on the embarrassing story one, right?
The one where she got off the train and had her dress was wide open. That was a good one. Matt Amundson: Yeah, he should, the back bottom of her dress tucked into her, into her undergarments. I, I don't know.
Um, Jim Wilson: you had good, Jim Wilson: uh, zoom ones? Because I gotta figure in the post COVID and pre COVID era, like some of the zoom felt, pause, have gotta be off the charts. Craig Rosenberg: haven't Craig Rosenberg: seen as many. 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: Mine.
I, Sam Guertin: yeah. Craig Rosenberg: by the way, just Craig Rosenberg: to be clear, that was a Citrix Go-To Webinar problem. Craig Rosenberg: Is that thing even around? Yeah.
I don't even know if that's around, um. Craig Rosenberg: Alright, awesome. that Craig Rosenberg: was, that was perfect. Jim.
You Craig Rosenberg: got a five from Matt. Sam, you're ranking on the story one to five, five being Craig Rosenberg: dead on Sam Guertin: five, absolutely Craig Rosenberg: yeah. Jim Wilson: Oh, there shy Craig Rosenberg: You can't break the system. Yeah, status.
yeah, yeah. You, we Craig Rosenberg: might just do. Matt Amundson: do. Craig Rosenberg: if you have stories like 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 I think Jim and, and Brian Halligan ran around Asia Craig Rosenberg: selling deals for PTC. Jim Wilson: correct. Craig Rosenberg: two notes on that for any you young folks out there.
Craig Rosenberg: PTC was the, probably the best sales team maybe in the history of all time. Right? Because Craig Rosenberg: you're one, yeah. They were the CorrectMEDDICic MEDDIC.
MEDDIC. Craig Rosenberg: MEDDIC They were the best enablement back then of all time, uh, the best alumni of all time. I mean, Craig Rosenberg: you don't see any PTC guys not go on to big things 'cause they were just so good at making great reps and managers. Craig Rosenberg: It's, it's pretty, it's pretty amazing, Craig Rosenberg: you Jim Wilson: Yep.
It was a good, good culture. My funny Brian Halligan story is we were also up in Malaysia once and we were, and again, this is before Ubers and stuff, right? And. We both had a meeting at a car company, I think it was called Proton.
And we were flying in separately 'cause he, I was in Singapore. He was in Hong Kong. Jim Wilson: And I'm in a taxi again. No, Ubers like, this is literally a taxi where I'm paying him in cash and I, it doesn't speak any English.
And we're 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 taxi on the side of the road and there's a guy, an American guy, you know, not Malaysian in the backseat, completely sprawled in the back sleeping. Jim Wilson: And it turns out it, was Brian Eddie. He'd gotten there early and, and he wanted to take a little nap. Jim Wilson: And for those of you that know Brian, he's famous for his naps.
Jim Wilson: And so, uh, yeah, that's, it was fun times over there. Fun times, Craig Rosenberg: That's amazing. See, look at that. You even threw another one in.
I like it. Craig Rosenberg: Brian. Halligan Craig Rosenberg: humor. Matt Amundson: a big car napper.
Craig Rosenberg: A huge car. Napper huge. I used to travel all the time, right? Like, you know, all of us.
And Craig Rosenberg: like, um, uh, I met a guy who was, uh, you know, had served in Iraq and Afghanistan in one of the airport, you know, when I'm waiting at the gate and he was, I said, well, gimme one thing you've learned. And, uh, he said, here's, here's the one thing I've learned is if you have the chance to sleep. Take it. Even if it's 10 minutes, even if it's 20 minutes, just take it.
Craig Rosenberg: Right. Because You know, when we were out there, if you, we had 10 minutes to to sleep, we would take it. And so I've been like, okay, well I'm in a car, let's just go to sleep. Craig Rosenberg: 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 for my flight, I sleep if I'm like, I just, even for 10 minutes, it's, that was the best tip I've ever had. Jim Wilson: That's a good tip. I have the same problem.
Can't sleep in planes. All right, so what do you, let's look, one of the things, maybe Craig, to tee up the, what's working well? Is, um, as you Jim Wilson: know, we both do this but for our portfolio at Costanoa, we are early stage. So a lot of the times I'm working with the first sales hire and the founder.
How a Strong Founder POV Helps Sales Teams - Jim Wilson: And my, my kind of soapbox thing that I'm onto right now is just having a strong founder point of view when you Go-To-Market. Because, and Matt, you'll appreciate this, but man. The biggest challenge in, in sales and early stage sales and marketing is getting heard, Jim Wilson: right, and, and rising above the noise because you've got 10 other people that Jim Wilson: have a product that sounds like yours. Jim Wilson: You have massive channels that are going everywhere.
The buyers are getting bombarded with emails, with event requests, with, with everything. But what I do find works well. Is having a strong founder point of view, and then having the founder kind of sing to the rooftops about that blog posts and everything, but then have it percolate down to the sales team. Jim Wilson: And in particular, the example I'll use is a company run Reveal, right?
That is, uh, uh, has some great swag, by the way, but also their founder, Evan. He, he, uh, built a, basically a modern security product. That is a modern sim, right? And so his whole message and is, is in his point of view is like the sim market sucks.
Jim Wilson: The existing products are old. They're built on poor architecture. They're too expensive. You don't, you don't get any value for what you pay for.
And he's got, Jim Wilson: you know, he's got t-shirts made that talk about this. He writes about it. But here's what I think is really cool is Aaron Trott, his VP of sales and Kira head of marketing, lean into that messaging in their sales and their Go-To-Market. Jim Wilson: So for example, Aaron will talk about when he gets on the phone with the company, he's doing discovery, he'll say, look, here's what we think.
It's built on a modern architecture. We're focused on user interface. He'll lean into the fact that it's not expensive to get started. I think a lot of salespeople run away from.
Jim Wilson: Being, being labeled cheap. Jim Wilson: And the reality is no, they're just at a nice price point for what the product does, right? But then at some point they'll say in a discovery call, look, we think that the SIM products suck. By the way, what product do you have?
Right? And I love this because that allows the buyer to react. Jim Wilson: And you know, if the person says, Hey, I've invested $10 million in Splunk and I don't think it sucks, and we're pretty happy. Great.
Much rather know that now the beginning of the discovery call than after five or six, uh, calls afterwards, right? So they use it as a really good tool in a respectful and a professional way to qualify their accounts and to qualify their opportunities. Jim Wilson: So I just think having a strong counter founder point of view is key right now. And for salespeople, I think salespeople can use it as much as founders.
Craig Rosenberg: Yeah. So I, you know, we just had Chris Orlob, uh, speak to our portfolio and he had like the four rules of successful revenue teams at this time, like number one was like, know where you win and take out those that don't. So ICP. the second one though was, uh, have a narrative and, and like, uh, if you don't, he's like, I've, you know, worked with 5,000 companies, the companies without a narrative.
Uh, are the ones where their salespeople, you know, struggle. Craig Rosenberg: So that, and what you're saying is even bigger, which is like, so like, I'll just, like Scott Albro, you know, we're having Craig Rosenberg: him speak at our event. He has the Yeah, of course you do. And one of the things that he says is, uh, you know, our objective with the founder is for the founder to become personally synonymous.
With the market or category that their company exists in. In order to do that, you can't just hang around. Craig Rosenberg: You can't just tell the same story as everyone else. You, your narrative is what makes you interesting and allows you into this club.
Craig Rosenberg: And that is like really important. Now, uh, you don't, and everyone thinks you don't always have to say. The current thing sucks, although it does work well, it's like the basis of challenger, Craig Rosenberg: Right. Craig Rosenberg: But like you can also just speak to the future.
Craig Rosenberg: You can tell your personal story. There's a lot of ways for the Craig Rosenberg: narrative to come out. And then as you said, if we can package that narrative because you know, a founder is going to have 20 conversations a week where that narrative is being stress tested and becomes personal. In the, in the part of them that we want the company to be part of the company and the way that they talk to the market.
And I think 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 and, and Craig, you know, to your point, I love the idea that the narrative is the key thing with salespeople. Strong point of view doesn't always need to be the market.
I love sales teams that have a strong point of view on how you should evaluate our product, right? Jim Wilson: And I always tell sales leaders and the best ones do this so well, and the best salespeople, they'll say, Hey, listen Mr. Customer, let me just tell you how we think it would be best for you to evaluate our product, can can be any product in the space, can be whatever you want. And they go.
And again, it's very, it's not super controversial, but it's very specific and very prescriptive. Jim Wilson: And it's, it gives buyers, I think, so much confidence. A buyer doesn't wanna get on a phone call and feel like everything he says the rep agrees with, 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 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.
Third or fourth demo. What works so much better is sales have a strong point of view on how to evaluate the product they go through and they give the logic to it. You got it. It's gotta be 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 translates down to the sales process and the sales playbook in my mind. Matt Amundson: Jim, I cannot agree with you more, uh, now and like this is my biggest pet peeve in early stage businesses, is not having, uh, a prescriptive approach to the sales process in co-creation. And what I mean by that is like.
You're getting off this great discovery call and may, maybe you've got a novel product or you're in a novel category and the and, and the sales rep goes, well, what do you wanna do next? Jim Wilson: Yeah. I. 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 the, you know, the se season finale of industry. Like, Matt Amundson: I, I, I don't want to think about the research that I'm gonna have to do or building a buying committee for this or, you know, one, like how challenging this might be to, to to, to onboard, right? Matt Amundson: Like, I think having a strong point of view.
Not just on your product and on the category and on the space, but also on how to manage your way through a cycle, especially when someone's not bought. Someone's buying something for the first time. Look, if we all started companies and got to a point where we needed to adopt Salesforce as our CRM, we know how to buy that product. Matt Amundson: We've bought it two dozen times already, and now you know someone's introducing AI 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. No. Jim Wilson: So, and look, what's the, what's the worst thing that can happen? They disagree with you.
Great. Now let's hear from them. Jim Wilson: Why, why they want to follow a different process, why their company, for example, may not be able to do it this way. Fine, let's have a conversation.
Now you're engaged on something that's actually gonna deliver value for your sales process. Jim Wilson: By the way, the, the best person that does this, I think is gonna be on your call. Soon, Craig, uh, David Morris, DMo, there's another guy named Mike Leonard. And both of them, when I worked with them at a company, Merced Systems, they, they said their whole goal was always to be trusted advisors, but have the buyer believe that you are the trusted advisor.
Jim Wilson: Uh, and you know, and the ultimate compliment of that is like you're helping them craft the RFP, you're helping them craft like how to frame all the competitors. But the way you get there is by being prescriptive and having a point of view of how the product should be evaluated. Craig Rosenberg: Yeah. By the way, Jim, I, I want to remind you of a story from our past.
Craig Rosenberg: Uh, and it's both a story that's relevant to this and, uh. And we did it together. So remember when we did that workshop together up in the city and you said, let's do like a challenger esque sort of workshop for my sales team, so you guys will enjoy this. Craig Rosenberg: So people were weighing, it was really cool.
They were in, you know, packs. There was like three, you know, folks from the sales team at their different tables and um, and we had everyone come up with, you know, a challenger like. You know, point of view on, on their company and product and whatnot. So we get this one young guy, and here's, here's the thing.
Craig Rosenberg: He is, uh, one of the reasons why Jim's point that it, it, it's a founder down point of view, is because it's not instinctive necessarily for the sales rep, like, you know, one who's not very experienced. They gotta be really good and experienced in point of view and narrative. Um, and so. So it's not necessarily, that's not their instinct.
Craig Rosenberg: Their instinct is actually, well, I have this product, I'm selling against these people and this is what I'm gonna, you know, this is how we're different feature wise. So he is like, well, I have this problem, there's like a hundred companies in my market. And it was, it was a crowded market. I don't remember what it was.
Craig Rosenberg: And I said, well, how about this? Why don't you go to the market and say, you know, whatever the category name was, doesn't work. Right. Jim Wilson: Right.
Craig Rosenberg: And um, and he goes, well, why would I do that? We're in that category. And I just said, ah, you're fucked. Because your example Jim was right.
You have to shake them. You have to say, if there's a hundred people in the market, then you, the only way you differentiate is like, is to be really bold and really aggressive. Craig Rosenberg: And I'm like, dude, if there's a hundred people in the market. And you think you're better than them, well then tell 'em that market's broken, it doesn't work, Matt Amundson: It's why Jim Wilson: be, yeah, exactly.
The, The, here's why is just as important. Be able to back it up and then, you know, look 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 there 'cause it ain't gonna, you're not gonna be successful in sales. People believe, you know, they can tell when you believe something or not.
So have yeah, for sure. Craig Rosenberg: Okay. I love that one. By the way you tra just so everyone knows, Jim transitioned Matt and I, Craig Rosenberg: into the top two or three things that he's seen working today.
That was number one. Jim Wilson: yep. Craig Rosenberg: Matt's gonna say he transitioned you, Craig. Yeah, it was a really good transition.
Uh, but I had to say something because I was like, oh my God, he's doing my job, but Jim Wilson: I dunno. 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 events are back, like, the way I think of it is like you just have all these different channels and routes to market and, and ways to engage buyers. And one falls out of favor, one falls in favor.
Jim Wilson: Like, you know, um, before COVID, right? It was, it was, uh. You know, emails weren't working right. Like you just too, too many emails.
There's phone calls go in and out, right? Obviously during COVID that just fell off of the, off of the ladder. But, um, I think in this post COVID world where buyers have gotten comfortable with Zoom. Jim Wilson: Being probably more standard than it absolutely was before they really relish events and being able to connect with potential buyers or anybody in the company.
That's the one mistake people make, I think is trying to get too fancy with the events like that, it has to be the, your specific buyer persona at the event. Jim Wilson: Um, I think that events are, are back. It's a great opportunity for sales and marketing to work together. Uh, Matt, to me, it's one of these other things where, uh, creativity really matters.
You know, everybody's doing dinners, who's doing breakfasts, who's doing, you know, uh, uh, coffee meetings? Who's doing different things out there? So, um, I don't know what you guys are seeing, but I'm absolutely seeing events. And then the specific story I'll tell is Bugcrowd, right?
In our portfolio, I feel like Bugcrowd, they, they sell a, uh, a a a a hacker platform, if you will. Right. And they have a community. It's a two-sided community where they have a group of hackers and they figure out how to do events.
And they have an art, uh, a publication called Inside the Mind of a Hacker where they leverage these hackers to show up at their events and give perspective on it. We did an event with them two years ago at RSA where we pulled together CISOs, which for those of you that know the security space, that's the top buyer, like the CIO in an IT organization and hackers, and we put 'em together on a panel and they really are kind of opposite ends of the spectrum, right? You had two people with like one had purple hair and nose rings and the other one still had a suit on and we put 'em together on a panel and it was one of the best events we did.
It was entertaining, it was useful, the information was useful. 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. Jim Wilson: But I would just really encourage companies to think about events and doing things definitely at conferences, but um, doing events outside of that as well. Craig Rosenberg: Okay.
I love that. Matt Amundson: may I, give an example of a non-traditional event Jim Wilson: yeah. Matt Amundson: yeah. Uh, I'm I'm actually, this is where I wanna learn other ideas for non-traditional Okay.
So, uh, this, this will maybe not serve our audience well. Uh, uh, Craig knows I've, I've recently joined a, a very large, uh, well, very large, uh. Like large, mid-size company. Uh, so I'm in my, I'm in my third week.
Matt Amundson: Uh, one of the things that I had to sprint to when I joined the organization is that we did a, uh, closing bell at nasdaq, which is generally, you know, like great celebration of the business. We had a big announcement that we were making, which was a hundred consecutive quarters of growth. Big deal for the company. And, um, one of the decisions that we 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 out to it. Um, and it's not necessarily something that you would bring customers to, right? Like, 'cause you more think about it as like an executive team or, um, uh, maybe members of your board would come for, for something like that. Matt Amundson: And we turned it into this absolutely rocking customer event for us.
We got, you know, the, you got the big video sign outside and you know, traditionally you just put your own employees on there. We made sure all of our customers got on that. Matt Amundson: Uh, and then in addition to that, we're. Giving them all like a framed photo of themself, Matt Amundson: uh, up on the, up on that wall.
Matt Amundson: And it's just like, you know, I wouldn't say there was, uh, any pushback against doing it, but people are like, oh, would customers really want to come to that? And then, I mean, they had a fantastic time and the, the feedback was great, which is awesome. But we really had that moment that you want to have with a customer where we had like two or three dozen of those customers go out, take their photo that we had given them. Matt Amundson: Posted onto social and, you know, we didn't block out the sun or anything like that, but like, these are just these moments where sometimes you feel like it's just for you or for your business, but like, bring customers along.
Customers, especially for early stage businesses, those early customers, they, they feel very aligned to your success as an organization. Matt Amundson: And the more you bring them into your business celebrations, the more they're gonna, you know, really turn into great advocates for your business going forward. Jim Wilson: Totally like the customer thing is so overlooked, like. People want to talk to other customers.
But the other thing too, Matt, and you touched on it, the one faux pa that I see sometimes not often is don't sell. Like if you do all this event stuff, just get to know people where they went to college, their kids, their interest. Jim Wilson: It's so much easier to do the follow-up the day after and say, Hey, I'd love to schedule something with you. By the way, I, really loved talking to you.
We had a great laugh about where we went to school and our fraternities or sororities. Leave the selling for later. Get to know people. Craig Rosenberg: Yeah, I, I totally agree.
I I have a fun one for you guys on this one. So I wrote this post on Topline about, uh, driving demand, and I talked, I mean, we've seen it too. Events are. Uh, working and actually I think Omar Akhtar had, um, data on that where the event, didn't he say like, event budgets, Matt, were like significantly higher than in the past, I think.
Yeah. Craig Rosenberg: So he, David Politis, who's been on the show, if you don't know him, Jimmy should meet him. He's based in New York. He, he's like a.
He has like a c uh, CEO founder group there, um, where he, you know, brings them all together, works with 'em, those events. So he wrote in-person events. It feels like we're on our way to peak in person events. Uh, um.
People. But right now people like to be in person. They like to have experiences, they want to build relationships. And, um, here's the, what I've seen work, I'm sort of reading Craig Rosenberg: paraphrasing a bit.
So one that he's seen coffee and co-working. He's like, find a physical space that could host 20 to 40 people of your target customers and invite them to come work. Craig Rosenberg: He's like, a lot of people are still in remote hybrid environments and it give them a low stress, non-salesy environment to work. Uh, it helps build trust in community.
I think that's a great idea. All right. Second one, workshop, he said, I've seen a couple companies do this recently, especially for AI and AI and Enterprise Sales Roundtable Workshop, for example, target a set of like prospects and customers, invite them to the workshop with a third party expert. Craig Rosenberg: That's pretty classic.
I used to do that all the time with Topo three to four hours, et cetera. I, I, that used to work well for people. It sounds like it's working well again, especially with AI being such a, a topic. Everyone's trying to wrap their hands around um dinner.
Craig Rosenberg: So this kind of goes with what Jim just said. My, he said my strong opinion is dinner should be 10 to 12 people max. Um, they, uh, you should never do a structured pitch never sell. Let the conversation Craig Rosenberg: flow.
If customers want to talk about you, do it. Same thing Craig Rosenberg: as you said, Jim. to 12, that's what we've found Craig Rosenberg: It's a beautiful number. Yeah, I Craig Rosenberg: agree.
Um, and then Highend experiences. So this could be anything from amazing tickets to a sporting event or 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 world.
Small group sessions with famous speakers personalities, um, you Craig Rosenberg: know, the things you you want to do is something that they, they, they could. Not necessarily do themselves. And so that was high end experiences. This one was interesting.
Craig Rosenberg: He is like, he's seen this work, which is choose your own adventure. So you message a group of prospects and customers tell 'em you wanna put together an event with them for them and give them the choice. And he was like, you know, some of them done whiskey tasting, ax throwing, which I've never done. Um, you know, even a, one of 'em just said, let's just walk around Central Park.
You know, and so like, pretty interesting. Um, and then, uh, yeah, I would just leave it at that. So you can see people are back to sort of figuring out. Since events, everyone's craving 'em.
I mean our, event, by the way that Matt and I are putting on Jim, that you're coming to and your portfolio might be coming to is, uh, I mean we, we, we got to like 75 signups with just some social posts and we can only fit 200, Craig Rosenberg: you know, so people, want to do this stuff again. Craig Rosenberg: So anyway, I, I throw those things out Jim Wilson: 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 comments, some ideas and things that you've done because you know, there's no playbook on it.
There are a couple things. What's interesting, uh, Craig is golf. Uh, you don't hear golf anymore. Jim Wilson: Like I feel like the one thing about events is time's been compressed, right?
And you just, the days where you can do the full on, full day, you gotta commit. You gotta go out to Half Moon Bay and we're gonna golf with you. I don't see as many of those. I feel like they're four hours max.
It's a dinner, it's a half day. Jim Wilson: Um, those are the kind of things. And then one last bit of advice that, again, the thing that I, I see in our portfolio, this is a great place to try to leverage. Your investors and your board.
Um, we are doing something to Costanoa roadshow where we're, uh, bringing a guy that's, that's with us, Joe Sullivan. He's a kind of a luminary in the security space, and he goes and talks to folks, but we're doing a road show and we'll bring one or two portfolio companies along and we're kind of bringing it out to them versus making everybody come back to the Bay Area, into Silicon Valley. I'd love as a follow up to hear from other people about event strategies. Craig Rosenberg: yeah, we should do that.
Um, and just, you know, best events that you guys have held and, um, get some new ideas. I love that. Okay, so that's two. You got another one for us.
Uh. Jim Wilson: Uh, well look, we could talk about AI all day long. I do think AI is gonna be huge in in sales. I do think AI in particular, Craig and I, are both passionate about top of funnel and things that work for top of funnel, and I feel like there was this initial backlash of the, I'll call it the AI SDR right that people said, oh, let's try it.
Jim Wilson: Oh, it absolutely doesn't work well. Eh, it's somewhere in the middle. Like there's a lot of functions that I think agents now can do around systems of record and automating tasks, automating research, putting things together. And I think for all the salespeople out there, experiment, push it.
Especially with Claude. Jim Wilson: Um, I'll go back to your existing and vendors, right? HubSpot's got some amazing stuff they're doing that it's a lot easier to. Incorporate from your existing tool, then try to build something from scratch.
I'm not a believer in the, the builds build that from scratch, but I feel like, Jim Wilson: uh, top of the funnel is where we're gonna see the next boost of productivity. Craig Rosenberg: Okay. Jim Wilson: But, all Jim Wilson: right. So, but but I, Jim Wilson: I, I digress Craig.
'cause that could be its whole other section. Right? I think the last thing that I see working right now is paid POCs. Right.
Craig Rosenberg: Ooh. Jim Wilson: And yeah, a little bit. A little bit of a counter. Right?
And by the way, and I say that in POCs, Proof of Concept, proofs of value. I also think that POCs in two or three years may go away entirely if people really start to build out consumption model products and you can just let them try it, that's probably the best. Jim Wilson: And that, the reason I always like that from a sales perspective is it forces the engineering team to build a product that actually can be. Used without massive human intervention to stand it up.
That said, there are still products out there that are complex that do take a while to, to set up and deliver huge amounts of value. Jim Wilson: And I've just seen a, a big trend in this, in the company I'll talk about in our portfolios, Feldera, uh, sells a product to that really allows for improvements in batch processing to do it using deltas. So they can make a, a company that has a huge amount of data and moving huge amounts of data, do it in a much, be much faster, much cheaper and better quality.
Jim Wilson: But they've had a lot more success with early companies. Again, back to the strong point of view saying, listen, our product works great. It's, it's complicated to set up. There's a whole bunch of integrations, there's a whole bunch of workflows you need to build, but once you do it, we will show you how much value we'll add to 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 that's somehow as we got to where products are always easy to use and no one charges professional services anymore and customer success is out there. People forgot that sometimes there's products that, uh, do, do require that and you should just Craig Rosenberg: Yeah, Jim Wilson: it. Matt Amundson: Yep.
Craig Rosenberg: embrace it. Craig Rosenberg: I love that. I had, yeah, we had, uh. This was a couple years ago, and the portfolio company came in.
I mean, they were early too, which is where you get, you know, you get scared to charge for the POC, um, and they were charging on the POC because they wanted some skin in the 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 product that people could just start using. Um, but in absence of that, or if there's complexity that. You know, requires that they do something a little heavier.
Uh, the paid POC is like a level of commitment that, you know, ensures that they're going to, you know, have resources on their side to go make sure this thing, you know, works or doesn't work. Um, but yeah, I mean, I, I do think that's 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 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.
Right. That's who doesn't want that. But the reality is that's not where most of products are. And I think that it's really gets back to companies knowing their product and, and really understanding what's that unit of value, what's the magic moment I'm really into right now?
Jim Wilson: Salespeople understanding the magic moment they can have with a buyer, interaction with their product and how to do that. And a lot of times it's not a quick hit, it's something that's gonna be, require a little bit of commitment. And you need to know that ahead of time. And the consultant we brought in, we had a, a Go-To-Market consultant, Amy Eros, who, uh, helped Felder kind of figure that out and then credit to Lilith, the CEO.
Jim Wilson: He, he was initially nervous about it, it, but man, he leaned into it and he really understood it. Who was super credible. Again, Matt, back to the strong point of view, he would lean into it and they would ask why, and then he would go through all the things they're gonna do. In the proof of concept, what they were gonna get out of it, they had documentation to support it.
They had a, you know, POC test plan and customers left not only convinced, but more importantly, kind of armed with the information they needed to go get approvals for it. Yeah. And I think they've been like in all their POCs. Matt Amundson: it sounds trivial, but even things like timelines, right?
Like people want to understand like how much time investment they're gonna have to make in evaluating a solution. Jim Wilson: Yeah. Matt Amundson: It may be long, but at least they know that going into it. Otherwise 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 God's sakes, don't do the POC that I call the kick the tires, and it's got no end date POCs. Like, it's just, it's, it's a slow death if you're selling software, you know, and, and every technical, and this is mostly for technical buyers, right? But most technical buyers, especially developers in that space, they'll do that all day long.
Jim Wilson: You know, Craig Rosenberg: Yeah, for sure. Uh, yeah. You know, we at, at topo, this was a while ago. Now, by the way, guys, uh, you know, we, everyone was doing, you know, whether it was paid or not, proof of concepts and like if we.
We would look at the guys who had, I mean there are a lot of companies at the time that would have like an 80% conversion rate outta the POC and above. Craig Rosenberg: And then we had somewhere like we'd go in. It's like, how? How is it possible to have a 30% conversion rate off of POC?
Like they shouldn't even be in the thing. Craig Rosenberg: But what Ro yeah, Robert Koehler on my team, what he did was he created this sort of template for managed what he called the managed trial, managed POC. Craig Rosenberg: And so we looked at like what these successful guys do. One of the things we learned was that if you gave someone 60 days, at the end of the day, once it was installed, the, the highest usage rate and was within two days, 48 hours, and, and you wanted them to do that because once it got punted.
Then, uh, you was, you were dead. Craig Rosenberg: So what, like, it was a small trick, but 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 them, that you work them through. And he's like, and then you say, great, we will check in you, this is your install, et cetera.
We will, we will do a call that we're gonna set right now for 48 hours after you launch, because they're gonna say, well, let us do it and we'll check back with you. And like that. For a lot of these guys, like that is where you can actually go in for the close on the sec on that first call because they've, the majority, they're, you have to a, one of the things you would train 'em is like, what are they fo remind them what they're focused on and point them to look at that like you're not saying, oh, go, you know, if they don't care about the ui.
They don't tell 'em, oh, and check out the beautiful ui. No. Like, this is what you're trying to solve. Here's how you're gonna go look at whether you solve it, put it in and go watch it.
And within two days, they will know whether it solved their stuff. Now, if they need more time after that, that's fine, but you've reestablished what they're doing, the POC four, Craig Rosenberg: and then what he, you know, he had, he would tell people, create a report at the end that you use for everyone. And put in the timeline that you want to present this report to the decision making team. And he's like, that way it doesn't end.
Also with the user who's most likely to be doing the POC or the lower level folks, them saying, well, this worked great, and them not knowing what to do next. A, you've gotta, 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 and then set it up so that you as a salesperson or an executive can go and bring that to the broader team. So it's these like, these like little tactical plays that fit within the POC trial process that, uh, you know, helped manage, it, helped bring it to, to close.
And like, it was like 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 no control. But you, you brought up something that reminded me. You know, I always tell people in the topic of POCs, everyone focuses on the technical validation of the POC, but the reality is a good proof of concept proof.
Proof of value does technical validation and business validation. And the business validation is what you have to focus on. Jim Wilson: I work with a company, Rafay Systems, and they sell a very complicated product that does orchestration for ai, neo clouds, right, for all these big data centers that are setting up. Jim Wilson: The technical part is super hard, and it all is, and this is the other surprising thing is, you know, or, or not surprising, is most good products, the technical stuff will work.
It'll work as advertised, will work in their environment. But you as a salesperson, what you gotta do is figure out how to get the business validation and the business justification done. And that's what the best salespeople do, is they do technical validation and business validation and accomplish both of those in A POC. Craig Rosenberg: Bam.
Bam. At the buzzer. Matt Amundson: easy. Matt Amundson: right?
Craig Rosenberg: Yeah. Craig Rosenberg: Now go do it everyone. Craig Rosenberg: Yeah. Craig Rosenberg: Um, awesome.
All right, so with two minutes left on the clock, we did it. Um, you got some multiple good stories in there. You got three very, uh, specific actions that people could take from this, uh, episode. So I would call this a raging success, Jim.
Craig Rosenberg: Good work. Jim Wilson: right. All right. Well thank you.
I'm happy to be out here. I apologies for everybody that is in a cold weather place and is looking at Craig's background and those Oh man. lake and the beautiful sparkling and sun. I know.
and sunny out in California. I apologize to everyone, Jim Wilson: but I will say this, it's beautiful in the day right now, but the nights are colder Craig Rosenberg: than when there's rain. Yeah. Craig Rosenberg: man, it's Craig Rosenberg: pretty nuts, but, we've got our swag, oh geez.
Here he goes. Swag man. We're gonna start. Craig Rosenberg: Yeah, man, Jesus.
Anyway, Jim, thanks for coming on the, the transaction folks. That's the transaction and we are going to call this one a night and move Jim Wilson: Thanks. Thanks. Matt.
Jim Wilson: Thanks Craig. Matt Amundson: Thanks Jim Wilson: Bye. Bye. Matt Amundson: Thanks, Jim.
Thanks for joining us for another episode of the Transaction, Craig, and I really appreciate the fact that you've listened all the way to the end. What are you actually doing here? For show notes and other episodes, please visit us@thetransactionpod.com, like and subscribe on Spotify, apple Podcast or any other place you get your podcast from.
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