Side piece to main squeeze | Kaleb Jessee | TDSU Ep. 64

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It strikes me as so bizarre that anybody still thinks I am going to make a buying decision based on when your people decide to knock on my door, that I will be in the right headspace, that I might happen to be in the buying cycle, that I need new siding when your salespeople are in my neighborhood, and that I don't know what the buying cycles are and that I couldn't just go online and figure this out for myself. Do a lot of the pre-sales work myself. Cool.

All right. You guys want to get started? Let's go. What's up, lifers, and welcome to The Daily Standup with Lifetime Value, where we're giving you fresh new customer success ideas every single day.

I got my man JP here. JP, do you want to say hi? What's up, y'all? I should be wearing the chain. I've got my man Rob here.

Rob, do you want to say hi? What's up, CS Pyromaniacs? And we've got Kaleb with us. Kaleb, do you want to say hi? Hey, everyone. And I am your host, the designated fire marshal on this floor.

My name is Dillon Young. Kaleb, thank you so much for being here. Kaleb, can you please introduce yourself? Yeah.

Kaleb Jessee. I am the founder and CEO of Krafted Revenue, a boutique revenue consulting agency that just got its LLC documents in the mail this week. So we are brand new, but I spent my entire career building and scaling SaaS organizations.

So past 15 years, seed stage, series A, series B. Yeah. That is a fresh new baby. LLC documents, you said earlier this week? Yep.

Wow. And for everybody listening, it is Krafted with a K, like Robert Kraft. Like Kraft macaroni and cheese.

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Kraft macaroni and cheese. Yes. I'm just trying to get a rise out of Rob here.

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Anyway, Kaleb, you know what we do here? You know what we do here? We ask every single guest one single question, and that is what is on your mind? Usually we say as it relates to customer success, but I think you're going to deviate a little bit. Why don't you tell us what it is, Kaleb? Yeah. What's on my mind is that for far too long, customer success has played Robin to sales as Batman.

When I would argue that 98% of the sellers out there aren't great in the market today. And the CS team behind them, especially in enterprise organizations, are just as, if not more important to the sales process and keeping things going, but more important to net retention revenue that the organization needs, especially when capital is as expensive as it is today. Kaleb's got his stump speech hand gestures down.

You guys know this one? This is a classic. And I'm going to make more jobs in this county. Kaleb coming out here breathing fire.

I love it. I attribute all of that to my debate background. So I spent a decade- Are you also a former debater, Kaleb? Me too.

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National champion, baby. Which type of debate? I did policy in high school and then LD in college. Me too, man.

Both. The NFA National Championship trophy is hidden back there behind Patrick Mahomes. So I won it as an individual and then I coached.

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Let's keep it moving. Some real bastard debaters here. I'm so excited to know this about you, Kaleb.

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Yeah. So yeah. What's up, guys? It's Dillon here and you know why I'm here.

Hat in hand. I got a favor to ask of you. If you like what we're doing, give us a like on whatever platform that you find us on.

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We want to make sure we're giving the best content we can to you and others within the community. Thanks so much, guys. I'll let you get back to the show.

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So real quick, I'm going to say this because this conversation is so spicy. I'm going to say I work pretty closely with my sales team currently. And so I've had some different relationships with sales in my career.

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In general, I respect what they do, but it really does come down to sometimes the individuals that I'm working with and the compensation structure. I'd be remiss if I don't talk about I feel like sales more than any other role since they have more variable comp and their compensation structure is so important that they're driven to do things very much by and large by what's going to get them paid. Sometimes people are ethical about that.

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Sometimes they're not as ethical about that. Sometimes there's a culture allowed for people to maybe not be as ethical, especially if someone is a quote unquote great seller, right? I've seen this phenomenon before where there's one person who sticks out like a sore bleeping thumb, but they sell, they really do sell. They're bringing in people into the pipeline.

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So even if there's a culture where even other sales people are not like this particular individual, because they're bringing this in, they are tolerated. So when it comes to CS, working with sales, I think that sometimes the culprit is the lack of, for lack of a better word, standardization that keeps them in sync with one another, whether that is complementary compensation structures, that is tough to say, complementary compensation structures, or the other C word I guess would be the culture, making sure that there's a we versus a me mentality, which is what causes some of these splinters to go off, where someone's like, oh, no, this person's great. They always get back to me.

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And I'm like, well, they didn't get back to me, but are they racist? No, I'm just kidding. All right, y'all have a good day. All right, JP.

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Disappeared. Race party drop. Yeah, exactly.

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Great. Love it. Perfect.

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I don't know how to follow that one up. No, you have to. You have to.

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I'm going to start out just by saying, first of all, don't hate on Robin. I have a Robin figurine five feet away from me. I was going to go grab it.

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I loved Robin growing up. He was undersized. He came from the circus.

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He's weird. When I was a kid, I just loved him because his name was Rob. My favorite episode of, well, Robin, Rob Robin.

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My favorite episode was where he rebelled against Batman. Because he's 12. He's going to have those moments.

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Well, yeah, you know what? I was four. So I feel like I can't wait to grow up to be like Robin. Yeah, that's where.

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Anyway, no, I think, you know, it's really crazy. Like I've probably worked with, I don't know, like over a dozen companies in the last year. And Kaleb, I'm sure you're going to see this too.

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The number of companies that have this relationship documented between CS and sales is remarkably low. I've never seen such a disproportionate ratio of like internal issues and complaints and documentation. The ratio is way off.

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And it's so crazy because so many times this, the challenges that, you know, exist between CS and sales can be resolved way much more simply than you realize. If you just document protocols for sales handoffs, protocols for upselling accounts post-sale, protocols for clawback, that one's a really hot topic, of course. But it's really just, it's crazy how little it happens.

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And I can't figure out why. I think it's mostly just because people just don't want to take the wind out of sales. Yeah.

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I don't know. But you don't, for sure. I mean, Kaleb, I'm going to say something that I have a feeling you're going to agree with, but there is a chance that you'll think I'm being an asshole.

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Sales, they're such prima donnas. They seem to be other than possibly the C-suite, who are pretty high up there in terms of the drama scale. Spoken like a prima donna himself.

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Takes one to know one, bro. Sales is so sensitive to the temperature being just right. And to everything being situated exactly the way they want it.

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And then nothing can ever change for as long as they are there. Or they will flip tables. They will make a stink.

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They will immediately leave. And so I don't know where I'm going with this, but I do find that is interesting that we continue to kowtow to that group of folks that is as volatile as sales is. I imagine that's going to change going forward as the realization of how much of revenue, a customer success or team or strategy affects compared to sales.

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But Kaleb, why don't you tell me what you think about that? You know, I would agree. I wouldn't say it's the sales person's or persona's fault. I think it's a reflection of leadership and specifically going to your VP of sales or CRO all the way through the rest of the C-suite.

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Because the message to the sales team is always different than the message to the rest of the company. It's you're special. You're the lifeblood of the organization.

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All the way down to the recruiter overselling what a sales job is, making it sound like it's going to be this glorious thing where everyone's at your beck and call when that's really not how the market's going to work anymore. I think the most accurate reflection of where sales is going in today's market, regardless of if you're an SMB or selling into the enterprise, is this product-led growth phenomenon. And do you know why that's taking the market by storm? Because nobody wants to talk to a damn sales rep because they're all bad at what they do.

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I want to call this out only because I had this conversation irritatedly with my wife last night because I live in a decent neighborhood and it's sort of like a bedroom community, right? Like you can walk around on the sidewalk, walk your kids around, leave the door wide open like in the middle of the day, nothing's going to happen. But every once in a while, we get these solicitors that will knock on your door. I know for me, it's a huge pain in the butt because I have three dogs.

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They go absolutely bananas if a fly is heard in the house, let alone somebody knocking on the door. For me, I get irritated. I'm like, this is inconvenient.

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I don't get why they're like here. From a more logical standpoint, it strikes me as so bizarre that anybody still thinks I am going to make a buying decision based on when your people decide to knock on my door, that I will be in the right headspace, that I might happen to be in the buying cycle, that I need new siding when your salespeople are in my neighborhood, and that I don't know what the buying cycles are and that I couldn't just go online and figure this out for myself, do a lot of the pre-sales work myself. It blows my mind even when we have SDRs, cold calling out to people, that's a much more economical approach, but I would guess not much more efficient than the analogy that I just posed.

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There's math, right? There's math behind it. So any executive team, any board, any VCPE, whoever it may be, it has the math that says if we make X number of knocks or X number of calls, we'll get X number of people to answer and convert. And so it's a numbers game at that point, but it's a hope.

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It's a wish and a prayer. Aren't those numbers based off of certain assumptions? Whereas the folks who want to truly try to innovate might find new channels, might find new methods where the conversion ratio is far and away better, it ends up being cheaper, but there's way less data to show it. I mean, the SDR, it's been around for a while, and so every new CRO comes in, they came from the SDR world, and they're going to be like, oh, this is definitely how you do it.

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I know this math like the back of my hand. It's way less likely that a CRO comes in and has decades of experience in inbound marketing. Yeah, 100%.

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And I think there will always be new channels. I think generative AI will take us to new levels, but only if we do it right. It just makes the problem so much worse, and that's what we're seeing today.

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I think the sales process should be like from the very beginning of this prospecting idea needs to be less about the organization and what you're trying to sell and more about adding value and building a brand. Predicting when you're going to be in the right buying cycle using the intent data that 99% of the time is going to be inaccurate, but you're paying a pretty penny for is helpful. It's better than nothing, but the outreach should be to think about it like a 401k or your investment account where you're continuously adding value.

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Those are the emails I'll open. Those are the people I may not respond to, but when I'm in a buying cycle, I'm going to let you know. Know when to make the withdrawal versus the, hey, we work with X, Y, and Z competitor.

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Here's my Calendly link. Do you have 15 minutes? In the first email, that's not going to work. And I'll tell you, putting co-founder or founder and CEO on my LinkedIn and then updating it, I got inundated with a bunch of people trying to sell me stuff.

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And it's just like, oh, this is awful. It's like a reminder of just why I want to do what I'm doing right now. Rob, you got any last words before we close it out? Nothing to add.

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That was great. That's a good concluding point. Yeah.

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Kaleb, that's our time. Thank you so much for bringing this to our attention. I have been craving a conversation that's not specific to CS, but it's still kind of within our tech world.

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So thank you so much for leading the charge on that. Would love to talk more about this and just to hear more about the journey you go through as you start Krafted Revenue. But for now, we've got to say goodbye.

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Thanks, everyone.