GTM Crossroads Podcast Ep5: Growth Hacking to Sustainable Strategies

In this episode of GTM Crossroads, hosts Rob Jones, Zach Vibidor, and Harris Kenny talk about how growth strategies are evolving. A few hot topics include the role of transparency in leadership, personalization vs. humanization in marketing, storytelling in sales, and the how the buyer’s journey is changing for buyers and sellers. The conversation also touches on predictions for the future of sales.

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Disclaimer

Please note that the GTM Crossroads Podcast is co-hosted by Harris Kenny (Founder, OutboundSync), Brendan Tolleson (Co-Founder & CEO, RevPartners), and Zach Vidibor (Co-Founder & CEO, Octave). This guest host episode features Rob Jones (Creative Lead, RevPartners). Each episode features discussions on go-to-market (GTM) strategy, revenue operations, and sales execution from industry leaders.

The views and opinions expressed in this podcast are those of the individual speakers at the time of recording and do not necessarily reflect the official stance of their respective organizations. Statements made during the conversation may be speculative, evolving, or based on personal experience rather than company policy.

This transcript below is provided for reference and accessibility but should not be interpreted as official guidance, policy, or endorsement by any company mentioned. 

Transcript

Rob Jones (00:02.099)
What’s up? This is, I’m Brendan Tolleson today and we’re GTM Crossroads with Zach and Harris. How are y’all, man?

Zach (00:08.942)
Good man, good to see you in the flesh. It’s been a slack relationship up until now, so I’m

Rob Jones (00:16.467)
Yeah, we were slacking too much. So I decided to bring the noise with the orange suit. I just got this neon thing, which I think is pretty cool. yeah, I’m not sure how Brendan has has done a great job. He’s hosted two or three or four podcasts now. getting into this, I know we were talking before the recording about kind of the meta conversation on what is GTM Crossroads? Why is there a need for it? What does that mean? It immediately for me growing up in the South evokes images of

Robert Johnson and the Devil and Blues. So there’s some stuff there, but if either one of you wants to kind of, you know, lean into that and start talking about why we even thought this podcast, there was a need for it in the first place, it’d be a good place to start.

Harris Kenny (00:59.714)
Yeah, I’m happy to jump in here. We’ve done a few episodes and I think that, you know,

there’s this like everybody knows that the way, especially on the growth side, things weren’t working. And I think that even applied on the inbound side. Two years ago at inbound, you still had some partners being like, well, we’re gonna do an ebook a month. And you’re like, yeah, but nobody’s reading them, right? And you know that. And I know that, and everybody knows that.

things have really changed a little bit and it felt like there was room to have a conversation about, it’s tactical of like, okay, but like what specifically is different? It felt like there was like, from my perspective, there’s this like gap between these like deep clay loom, you know, recorded videos of someone showing this crazy engineering wizardry stuff. And then like these actual conversations with leadership at these growth teams where they’re like, look, I know we’re landing in spam. I know we’re paying a lot of money for all this. I’m not sure exactly what we’re supposed to do next.

And so it felt like there was room to talk about bridging that gap between the of the growth hacking movement and as it’s now that it’s kind of growing up and we’re seeing these mid-market companies adopting these tactics and then now there’s like more tooling and things like that kind of filling in these gaps. that to me was, and I think that’s like, I think that’s going to be true for a while. I think for a couple of years, I mean, we, still talk to companies that are really, really, really early in this process where they’re just like, I think our reps are landing in spam. And so they’re kind of, you know, two years.

behind the market sort of thing. So that to me was the why, why it’s needed. What do think, Zach?

Zach (02:41.978)
I agree with that. think there’s like another interesting kind of undercurrent to all of this is like the, you know, the old playbook, if you will, like the old playbook was written like when things were progressing and evolving in like a pretty linear fashion and you have these product development cycles and these 12 and 24 month roadmaps. And like, I think another big thing that’s changed is like,

All that is out the window. If you have a three month roadmap that you can stick to, you are now Nostradamus. Things with the products are changing so fast.

new competitors and like the markets are evolving so quickly that it just like this old like, hey, let’s, you know, let’s get together and kick off and like put together the story and then go build like a content marketing calendar around that. Like it’s, just feels almost impossible. It’s like you have to kind of almost live everything.

close to real time and like that is now just going like, all right, like now in that world, like what does my stack look like when I have to be so much more responsive and quicker and nimble and like it just, I think that’s like another thing that’s just like the shifting sand underneath all this is just like the product, I guess the like, how dynamic like product development and like the markets are is like causing a lot of this just like, all right, we need to reinvent the wheel of it.

Harris Kenny (04:09.08)
Mm-hmm.

Rob Jones (04:10.023)
Yeah, I mean that kind of leads into a prompt that I had to discuss. So really good segue. You mentioned Harris said growth hacking seems that it has been hacked or it was hacked so much that it’s now somewhat broken. I know that everything is apparently dead now, but there’s there’s also growth sustaining. I don’t know if that can be hacked as well. So the concept is is or the question I have is how do you adapt strategies?

as quickly as possible while retaining kind of a narrative or vision or overall value for customers. When you just said everything changes seemingly on the week, you know, weekly, there’s a lot of, it seems like there’s a lot of tools, a lot of best practices that are kind of like kale, right? Kale is a really fun example because apparently, and I’m not a doctor or anything, but it’s like, it’s not as good for you at all as they used to say. How do you, how do you adapt and change and remain agile?

to keep up with all of the change that’s happening.

Harris Kenny (05:14.29)
I think there’s and I can take some notes from you in terms of like the transparency even just like down to your personal story. But to me, there’s like two stories happening right now. You have the LinkedIn highlight reel. It’s all wins. It’s like watching ESPN top 10 plays of the week. But then you have actual WhatsApp conversations and Slack DMs where people are really talking about. There’s a lot of things aren’t working. And to me, that’s where all the learning is happening and where all this like hyper iteration is happening is when people can find a space sort of semi

private where they feel comfortable saying, like, you know, in a previous episode, we talked about intent data and I was like, I tried it for nine months and I ripped out both of the tools, you know, and I posted about intent data, I put about LinkedIn and somebody was like, Hey, this is, know, you got to use it the right way. And I was like, how, how, how, how are you using it? And I didn’t get any response back. And I’m like, I want to know, you know, I want to, I want to use the tool. I want to make, I want to make money.

Show me show me and and so I think that I think that that’s like a piece of this of the conversation that That I hopefully we can do I think we have I think a good openness in the dialogue here in general Where we could talk about stuff that’s not working because it’s just it’s just too much like one or the other either It’s like you said everything is dead, right? Either it’s dead or like I’m crushing it and we just printed like ten meetings in the last hour And there’s just like new want new to me. The only thing that’s dead is nuance

I feel like nuances get dead and now it’s like everyone’s just trying to hack LinkedIn.

Zach (06:39.674)
Yeah.

Rob Jones (06:42.569)
Yeah, if I wouldn’t be off frame, I would have stood up and given you a standing ovation for that. That’s really on point. I guess kind of the follow-up question for Zach is specifically to LinkedIn and being able to ask, are there any other places for that where it’s okay as a leader, a CEO, a founder, a thought leader, a guru, whatever you want to call them, to show need?

Zach (06:47.578)
Ha ha.

Rob Jones (07:09.895)
I feel like that’s a barrier at times to those honest conversations, specifically publicly, because if you come out and say, we’re really struggling with this right now, that reflects poorly on not only yourself, but the brand that you represent.

Zach (07:13.198)
Yeah.

Zach (07:22.552)
Yeah, I mean, I think, I guess a couple thoughts. think one is like, I think there has been this rise of like community, know, like lots of companies are building community and there’s, you know, independent communities developing around different functions and it could be sales or it could be, you know, Lenny’s podcast around like product management that’s like blowing up and like he’s built this incredible audience and like, I think it’s really built around like these like super

honest, authentic conversations. It feels like, think, again, nuance. I think people are starting to appreciate some of the nuance more of people saying, yeah, here’s what’s working, here’s what’s great, here’s what’s not. This is effing hard and we’re all dealing with it. And when you own that, I think you get to be a voice that them people go to and trust a bit more. And so I think there’s…

less need than maybe in the past to be like, hey, everything’s roses and sunshine. I think people respond to the more authentic, yeah, we’re growing, but startups are hard. Half this stuff is broken, it’s gonna break again. I’m gonna make a ton of mistakes. I’m gonna make a thousand mistakes, I need to be right about five. I think people respond to that. They feel that, because we all know that’s the truth.

I might have lost the thread on your question a little bit.

Rob Jones (08:53.297)
No, you were hitting it pretty well because the nuance is dead. I’m going to steal that immediately, so hopefully you haven’t trademarked it yet. that seems like the only thing that’s either lost or incomplete or dead or whatnot is you mentioned intent data earlier. I had two things, I scrapped them both, and somebody said you weren’t using it the right way in this specific situation. with that, there’s an element of

Harris Kenny (09:00.448)
You

Rob Jones (09:22.087)
being open, being vulnerable, and I’m trying to get to a word, the P word, personalization. With AI and with everything else that kind of does stuff for you, I wanted to ask both of you who are pretty close to this, is there a difference in personalization and humanization? And how would you incorporate context into that? Even further as my tagline, which now I’m jealous because you gave me one, but if it’s a token, it’s broken.

is like if there’s an infographic or demographic or whatever component to it and you can use a token to insert it, that’s per to me, that’s personalization. what I could ask both of you, is there a difference? What does it look like? Like how do you break through now the personalization buzzword to create those connections that, you know, facilitate the growth of communities to facilitate actual change in conversation.

We’ll go Zach first and can keep the, can re, I can re ask in a much shorter way.

Zach (10:14.106)
Alright.

Zach (10:18.01)
yeah, there is a different, I think for a long time, personalization became equated with, yeah, to your point, I got a variable token, let me go find a bit of data and plug it in. And there wasn’t this like, all right, does that really make sense here? It was like being used as this like proof of work of like, I can go acquire data, I can stuff it into a template and it’s.

ostensibly about you, but like, I don’t think that cuts it anymore. And I think there’s like, and even in like, I guess we’ll call it like gen one of AI, it started to become really easy to be like, all right, let me scrape LinkedIn for the last post.

that you’ve posted about anything. And then I’m going to like glue my value prop onto that. So I’m going to, I’m going to graft onto that and like call that personalization. And it’s like, we’ve all seen this stuff and you’re like, you’re repulsed by it. You know, it’s like, it’s like, it’s worse than just like a here’s the offer. I can save you 40%. You want to meet, you know, it’s like that becomes better in that world. So I think it’s like, and I think people have like cooled on that pretty quick. They realize it doesn’t work because it feels to your point, like it feels in service of trying to

it becomes inhuman. You know, you’re like, no one talks like that. Like no one thinks like that. And so I think, you know, personalization is like, it’s this blend of like, how do I be relevant and resonant at the same time? And like, that doesn’t always take me knowing.

Rob, what you do, where you went to school. But you know, like that doesn’t necessarily take that. can take, I can have this tapestry of like your job, your responsibilities, the type of company you’re at. And like I can graft on like a pretty strong, like a hypothesis is kind of like the spinal column of like, where do relevance and resonance like combine? How can I tell a story that like has a hypothesis, has a perspective, like has some, some.

Zach (12:24.952)
tooth to it. Like I think that’s like where people are going and people respond to, know, and it’s not about

Did a person write this? And I think we talked about this in another episode. Like for us, like we talk a lot about like, I don’t think people care if a human or AI wrote something to be honest. I think they just go like, you have my attention for eight seconds. Is this written for, what was this meant for me or not? And like, that’s the goal is like, you just want people to feel like, no, this wasn’t a mistake. You know, like I know who you are. I know what we do. Here’s my take on like where we intersect.

you up for it? You know, like that’s kind of the gold standard. And then it’s not a mystery. It’s not a riddle. And then people figure out, yeah, I want to chat or hey, now I guess what? Like that brand is now logged in my brain and they’ll ping me eight more times and I’ll respond to one of them, you know?

Rob Jones (13:18.609)
Yeah, that’s great.

Harris Kenny (13:19.763)
Yeah, yeah, it’s like why now, right? Why now? Why me? Why now? I mean, I feel like those are kind of the two things. I do think that what I’m starting to see, in my opinion, that like, think a little bit of, there’s sort of this like, became this normal way of communicating ways of writing sentences, ways of acting on LinkedIn, and I feel like because AI is trained on that, that to stand out is to

to not do that. And so I’m finding myself getting more unhinged in the comments on LinkedIn. And not being profane or inappropriate, but if you’ve ever replaced a door, unhinged is one of my favorite terms, because I feel like it’s like an automata. I don’t know the right way to describe it, but when something is unhinged, when a door is unhinged, it’s really unwieldy, right? And so I’m having fun using exclamation points, using all caps, using weird inside jokes.

and just like really being a person. And I find the same thing is happening sort of on calls and stuff like that. I’m trying to just be myself more and not be this like what I felt like pressure before to be, you you kind of want to fit in, but now it’s like, oh, everybody’s fitting in. Everybody’s like kind of talking the same way and writing emails the same way. And your brain is just like, tunes it out, I feel like. And so I think by being, you know, I started posting more memes, but to me, you’re the OG of this, I mean, with the mayor of inbound thing.

Zach (14:40.58)
Really?

Harris Kenny (14:47.842)
You know, I to me you did this before it was cool in the CRM space. I mean maybe somebody else was doing it for waffle irons or in some other category in some other space, but nobody was doing it for CRM. So to me Rob, like you get the credit for that, because I feel like it was pretty, I don’t know, you’ve just been funny and yourself and personal and talking about stories, and to me that like is incredibly resonant. So I don’t know, that’s kind of where my head’s at on this topic.

Rob Jones (15:14.409)
The mayor of inbound thing was a joke that backfired and is now three years and running. I walked into the inbound conference, long, long story short, to detract or I guess distract from the very, to me, obvious fact that I did not know very much about HubSpot. I’d only been at Red Partners for six or seven months. I was like, yeah, I’m going to need to wear something or have a icebreaker conversation piece. So yeah, the unhinged part, feel…

Harris Kenny (15:19.192)
Hahaha

Rob Jones (15:41.885)
It’s almost the beauty of being ignorant and also very curious. A lot of that is just kind of who I am. You said earlier nuance is dead if anything is. I also think that formality as soon as you are exposed to something is kind of maybe it’s not dead but it’s dying. I don’t think it’s as requisite as it used to be. There’s this concept of you mentioned becoming numb to something. Habituation is that but it’s more than just I think the most

The best example is spraying on cologne or perfume. It’s awesome for a minute and then you forget you even have it, but somebody else gets near you and they immediately can kind of pick that up. That’s how a bit tuition and it’s happening with copy with, you know, different tactics to where a week ago, a year ago, five years ago, they really kind of helped you to stand out and get noticed and they don’t anymore because everybody is trying to get on this train of like, what’s the next thing? How should I act? How should I write? How should I type interact? Um,

Zach (16:17.911)
Yeah.

Harris Kenny (16:19.372)
Hmm

Rob Jones (16:39.581)
I’m going to transition very ungracefully to what we talked about before we started recording in that we talked about the need for GTM Crossroads as a way to talk about this and unearth some of the things in a closed setting and be more, I’m not going to say unhinged necessarily, unless we need it today, but just more open about not only the successes and challenges, but the state of the market.

Zach (16:42.532)
Here we go.

Rob Jones (17:06.267)
And one of the things that we’ve talked about here already today is like kind of this evolution of the buyer and trust. Like we know that people are spending less time in a, in a sales cycle because they’re doing their own education. The buyer’s journey is, you know, stats kind of vary, but it’s like 70 to 85 % done by the time somebody reaches out to sales. How has that changed and why? Like some of the answers I feel like are more obvious with AI and tech and the internet candidly, but

What is the buyer changing and kind of the trust factor? What does that look like in reality? What does that feel like to you guys?

Zach (17:45.274)
Looks like you’re cooking something good Harris, I’ll let you go.

Harris Kenny (17:47.694)
I’m just thinking I mean I’ve been like focusing more on storytelling to me it’s like it’s it’s like it felt like it used to be more of You know people talk about like sales process and making them go through things and sign NDAs and sit through demos and it’s people are just kind like okay like What what are you doing? Like what’s the point? Why are we here? Do you do can you do you can do these couple of things? I have I mean so to me I’m trying to like again like split of like it’s either a story or it’s

Rob Jones (17:48.124)
Yeah, he’s…

Harris Kenny (18:18.008)
just really unvarnished, like this is how the product works and let’s get a little technical. And I’m trying to like not be in this middle of, know, of like, okay, like how are you communicating with me? I’m trying to move in that direction a little bit with how we think about these things. Cause like people remember stories and then in my opinion, and then they have technical questions. Can you do this? Do you have this feature? Can you support that? You know, in the HubSpot data model, like how are you doing associations? Like that’s a question with an answer. I should give you that. But then tied to that, I want to…

tell you a story about why we’re here and why we started this. I mean, because to me, yeah, it’s like, those are the things that people carry on. And then there’s like digital tools, like sales rooms and stuff like that, where they can carry the data forward. But to me, that’s like the selling process and has been my focus when I think about our own go-to-market and how we sell, how I sell. It’s just me, so what do mean? I’m talking about me, because I do all our sales and all of our marketing. So if anything’s bad, it’s my fault. So that’s where I’ve been.

Zach (19:14.426)
Yes.

Harris Kenny (19:16.768)
I attended a thing this morning on storytelling and I’ve been thinking about what is the story, why? Why are we here? What problem are we solving? Why should you talk to us? Why us versus make versus Zappier versus rolling it yourself versus building a chat GPT? What’s the difference? So you have less time and so that time you have, you have to either be answering questions or telling a story is how I’ve been thinking about it lately. I’m curious what you guys think about that.

Zach (19:43.694)
I think the story point really resonates with me. It’s funny for all what we were talking about before, of all the community and all these conversations are online and blah blah blah. I think another one of these, cold email is dead and it’s like salespeople are dead too. There’s this conventional wisdom almost that it’s like everyone hates a sales process, everybody hates talking to sales. And it’s like.

Yeah, everyone hates being railroaded through a process that doesn’t provide them any value, but…

your point about storytelling and like there’s all this community blah blah whatever out there. A lot of people are still detached from that and like people want to know like what are other people doing like what are other people like me doing? You know it’s like I find that’s like you know my my sales processes that go the best like it’s like hey I’m curious about your business and they’re curious about like what are you doing with other people? You know like why are people buying from you? What are they doing? How are they finding success? And like people do want that.

Harris Kenny (20:30.99)
Hmm.

Harris Kenny (20:40.419)
Mm.

Zach (20:45.852)
and like they’re, the human being the storyteller for like the translation layer of like turning like all, like AI ain’t gonna replace that anytime in our lifetime as far as I’m concerned, you know? And it’s like that’s what people seem to be really hungry for. And so I think the, you know, the modern sales process is more just like, yeah, how can you provide value? How can you provide,

Yeah, trust I guess is implicit, but it’s more just like, everybody knows there’s like risk and…

software’s tough, shit’s gonna break, it’s not all gonna work, but tell me where it’s gonna kinda fail and I will trust you a thousand times more. People just like, they want to have conversations like that in a honest sales process and then those people, the folks you get, where that works on both sides, that ends up being the best partnerships and your best customers and the people you grow with and you set the table for like, hey, we’re changing too, we need feedback.

like

Yeah, I’m like in some ways it’s like we’re moving into this world of AI, but it’s also like encouraging this like return to like, all right, when people are involved, like let’s make the most of our time together and be real and useful and valuable. And like, it’s a good forcing function for that as well, it becomes more, conversations have felt more meaningful in like the last year, I’d say, like then in the last 15 I’ve been selling for sure. When it was more just like, I’m a transactor of information.

Harris Kenny (22:04.504)
Mm-hmm.

Zach (22:21.98)
you

Rob Jones (22:23.027)
Yeah, I mean, two really good prompts came from listening to that. So shout out. One of them is, you know, I would like to hear some thoughts on yourself as a buyer, right? Like at this point, I feel like most people in a role where they could be a seller had either been a buyer themselves or have needed to. So there’s this kind of concept of how, not only how are you a good sales person or how do you facilitate sales effectively, but how do you help sales being a good buyer that sets expectations upfront?

And part of that, think, has been ruined by Amazon. Legitimately, the Amazon effect in B2B is like, if I want to change the neon, like order a custom RP brand neon sign, I can go to Amazon, type it in, it’s at my doorstep later that day. That is not the same for B2B sales at all. But the expectation is there. Harris is about to start cooking again.

Harris Kenny (23:12.92)
No.

Harris Kenny (23:16.597)
my gosh my gosh dude i’m chomping at the bit we i mean we have i mean we have i was just

Zach (23:19.236)
you

Harris Kenny (23:27.02)
We work with growth agencies and growth hackers and there is like sometimes where they’re like, look, like, you know, can you just have an API or whatever? Like we don’t do, do we even need to talk during onboarding? can we just onboard our clients really quickly? And I’m like, no, you have to ask your customers how they want this data in their system. I’m sorry. Like there’s no other way. We have to talk to the user about how they’re using their system.

Are they using a lead object or not? Do they want these kinds of associations or not? Do they want custom contact properties created or not? Do they want the workflows to be managed inside of HubSpot? Who manages the workflows? How are they gonna get notified of this? There’s nuance, there’s just nuance. We have to talk about it and the user has to tell us.

There’s just no way around it. You know, they have a business, they have a business process. This is an important system of record for them. And we just have to talk about how it’s being done. There’s no like quick prompt. There’s no like VA we can hand this to. There’s no API call I can create to substitute the fact that we have to have a conversation about how their business runs so that we can get them this data in the right way. And then we will potentially reveal problems. And that’s kind of where like the RPs of the world come in. They’re like, hey, like, by the way, like you don’t have a sales process. We should do that. We should build that.

But it’s like, yeah, there’s not a quick and easy answer. I can’t just hallucinate an answer for them of like, we should do it like this. Like a GBT would be like, well, we should just write it to this record. It’s like, no, they need to decide that. Well, can’t you do it for us? like, no, I can’t. There’s no control. We’re a software company. You can’t just give me admin, super admin seat in one of your client’s HuffBot accounts.

And so, know, and it’s not like coming from a bad place or malicious or anything, but I find myself genuinely like, I don’t know how to talk about this. I’m not sure how to explain, but it’s like the old medieval maps, like there’s dragons over there. I don’t know how else to say it, but like we have to talk about it. You know what I mean?

Rob Jones (25:32.809)
Yeah, that’s I mean that’s part of the context that’s missing right is the nuance because there’s so many I don’t know if it’s infinite But it it’s it’s one of those numbers with the e and the other you know exponent so many different variations for all the different possibilities of how they could be using it what the You know what the use case is what they do or don’t have involved and so Zach I’ll throw you this one that came out of this because I think it’s

Harris Kenny (25:43.852)
Yeah.

Rob Jones (25:59.611)
Intended to give a reaction and I don’t mean this any bad way if it gets clipped weird But I am starting to think more and more. Yeah, I’m setting myself up for failure here starting to think more and more that like this concept of the future of sales is marketing and the future of marketing is customer success and I mean that from the perspective of if people are educating themselves on their own time asynchronously and don’t need you then you better make sure they’re educated in the right way you have lots of You know content or whatever it is available to them

Zach (26:04.506)
side.

you

Harris Kenny (26:08.589)
You

Zach (26:29.38)
Yeah.

Rob Jones (26:29.649)
In the same way, whenever you do go to Amazon or you do, you know, enter a buying process for whatever, don’t you check reviews and social proof and all that first, or at least at some point to make sure of their context and like how it went, how they felt about it. So just throwing that out there, Zach, what do you think about that as a concept?

Zach (26:49.658)
I dig that. think that as a trend line, I’m totally behind. I will say, and kind of like, to tie in what Harris was saying a second ago, it’s like, you’ll get these questions and it’s like, do you integrate with HubSpot? Do you integrate with Salesforce? And it’s like.

What does that even mean? It’s so vast and it’s like, do think there are, again, how do I say it in nice way? There are people who think they’re informing themselves, but like.

they’re just scratching the surface. like, I guess you were asking a sec before this Rob, like as buyers, you know, it’s like, I love a good sales process. Like when Harris was rattling off those questions, like, hey, who’s gonna own this? What about the workflow? And like, when you go through a sales and like somebody’s asking you good discovery questions and you’re just like, man, like I have not, I haven’t thought this through. Like they’re helping me, you know? And it’s like, that is the, I’m with you. Like we’re definitely going towards like people that they’ve gotten themselves

further down the track, but like I still think it’s very diff, you know, if we’re talking about anything of like magnitude has got some gravity. If you’re buying a widget, make it easy as pie, you know, but like, if something has some like, we’re gonna make an investment here. It’s like, I think it’s still pretty hard to get to those like next level things. And I think.

you know, us as organizations selling, we got to make it easy and be accessible and transparent and provide lots of resources and lots of like, yeah, we hopefully can be your, you know, Sherpa in a really light, light touch manner to get somewhere. But then like the smart people that are going to make a bet, they know like, all right, I, don’t know all the right questions to ask. And then how do you bring them into a process that feels not like a interrogation and a I’m doing Bant and MedPic on you, but like, Hey, let’s

Zach (28:44.404)
Let’s figure out if there’s a fit here and here’s some things you should go get the answers to yourself. I want to know them too so I can help, but you should figure this stuff out too.

Harris Kenny (28:55.855)
Yeah, yeah, yeah, for sure. Hey, regardless of whether we work together or not, whether it’s a fit or not, you should be thinking about this kind of thing. Yeah.

Zach (29:01.882)
Yeah.

Rob Jones (29:02.995)
Yeah. it’s, mean, I started in sales, before RP. was in sales at RP and I’m not in any way saying sales is not needed. know some people are kind of moving there with like, AI can do your job for you. It’s more to me specifically in software and in things that require more scoping is like the human in the loop is a, is a, it is there. I watched Chernobyl recently. So this is coming from that angle a little bit, but it’s like, it’s meant for, it’s meant for like critical risk mitigation.

Zach (29:22.127)
Yeah.

Zach (29:29.305)
Ha ha ha.

Rob Jones (29:32.925)
So all of the lower touch things that can be like, eh, if there’s a typo, there’s something off here, it’s not really necessary. The more critical risk, which would be, you know, Harris, you were talking about the integration question and like, there’s a lot of stuff that goes into that. If they don’t know or care, there’s a ton more risk in doing it incorrectly. So the human or humans or pod, whatever the sales person and delivery for what we do has moved into the sales process. know Salesforce is kind of doing this.

Harris Kenny (29:52.333)
Yes.

Rob Jones (30:02.089)
same thing, which the one thing they’ve ever gotten right, is bringing SEs into AE roles because they know it’s going to require that scoping and the word of the day, the nuance, the context that goes along with it. To me, it’s an interesting observation that the more, almost the less time that you spend in sales process, so if the buyer’s journey is 85, 90 % of the way done by the time they reach out.

That last 10 % needs to be transformative or uncover something like really super specific that shows value. That to me, I don’t know how that works with efficiency or like building the playbooks for that, but it requires a human to still be in that seat.

Zach (30:36.953)
Mm-hmm.

Harris Kenny (30:49.966)
Yeah. Can I ask you guys a question? Tell me what you think. I’ve been thinking about like forcing two calls during our sales process. I’ve been like, listen, during this first one, I’m going to ask you some questions and then I’ll give you like a preview of the product. But in the second one, I’ll give you a demo that shows you exactly what, and whatever. We can talk about pricing whenever you want. I can show you the product whenever I want. I’m not, I’m not trying to hide pricing or hide the demo, but like I need to ask you some questions. And then we need to have a second conversation where we talk about like specifically, I can show you how to do those things. Do you guys think that’s a good idea or a bad idea or?

Cause I find like in the one calls, like we don’t have enough to like hook onto. Like it’s just 30 minutes is not enough time. And then in my follow ups, feel like I’m like trying to like keep the ball rolling, but it feels like I don’t have like stuff to hold onto, stuff to follow up on and be like, listen, like, are you willing to commit to two 30 minute calls with me? You know, and we can get on the calendar and you can cancel the second one or you can even leave this first one early if you really don’t like me. But you know, what do you guys think about like asking for a little more upfront?

Zach (31:24.036)
Yeah.

Zach (31:36.633)
Yeah.

Zach (31:45.39)
Love it.

Harris Kenny (31:45.646)
Because I feel like the intuitive thing is like, like ask for less, shrink more, try to make it tighter, try to make it smaller. But it’s like, what if it’s the other way? What if you try to be more demanding? What do you think?

Zach (31:54.49)
I love it. think like thoughtful friction in a process, like thoughtful friction that doesn’t feel like I’m deliberately trying to like torture us and like.

fill out my manager’s checklist for our sales process, but like, yeah, I’m asking for some commitment and some time, and it’s gonna, if you’re serious, this is what it takes, and like, great way to disqualify people too. If they can’t sign up for a second 30 minutes, then guess what, this thing’s got a pretty low probability of getting done anyways, so I think it’s a good filter for that. we honestly, this isn’t exactly what you’re saying, like,

Harris Kenny (32:26.509)
Yeah.

Zach (32:34.294)
in our product as an example, like we have a self-serve kind of onboarding that’ll get you some percent of the way. And like we have some questions in those that like we make you answer and like we honestly got like we see a ton of people drop off. Like it is friction and they got like, I’m done. I’ve spent my two minutes already. I’m not going to spend the last 30 seconds, but it’s like, we know for the people that like they spend that last 30 seconds and like answer these two questions, we give them a way better output.

and their first aha moment is gonna be that much better. So not exactly what you’re saying, but I think there is that, the thoughtful friction, I’d say yes, and one.

Rob Jones (33:14.473)
I love the term thoughtful friction and I would plus one this just by equating it to the almost a triage mindset. It’s like if you go to the doctor, whether it’s for an emergency or preventative care, there is a nurse or a generalist that evaluates you first to see, your stomach hurt. They don’t just write your prescription for Finnegan or whatever. You could have something far more serious or you could like that concept is requisite. I think it would help to DQ people that weren’t serious buyers.

And then the 30 minute second concept, obviously they can cancel or leave the first call early, but it really, it kind of validates their, how serious they are. It also serves to show the nuance that you’re talking about. It’s like explaining that briefly and well. 30 minutes is just to kind of get to know each other, figure out the use case. I am not going to interrogate you. Like this is won’t be rapid fire, you know, you know, 50 questions in 30 minutes. Therefore.

Harris Kenny (34:06.936)
Mm-hmm.

Rob Jones (34:12.627)
so that I can present some of the stuff or show you how we would solve it. I’m asking for a second 30 minute call. Do that more concisely, but yeah, I love the concept.

Harris Kenny (34:21.134)
Yeah. Okay. Yeah, because it’s hard because like founder led, it’s messy. And I’m so used to like doing whatever like what’s the price? Well, what do you need the price to be? I can change the price. I can I can change the features. I can make engineering finish this. And it’s like, we’re growing now. We’ve got some mojo. It’s like, got to get out of that. So feel like I need to I’m the one who actually needs to be restrained. And I need to sell like I were a salesperson. Because if I tried to hire somebody to do whatever the hell it is that I’m doing, when it comes to selling, they would fail spectacularly.

Zach (34:45.882)
Thank

Harris Kenny (34:49.068)
because like how, you know, it’s not a job, it’s just like a improv. You know, I’m just like making it up. And so I feel like I’ve got to get myself out of that and then ask more of them and then force them to like, be like, listen, like we’re gonna have to get into the details here. There’s no other way for us to, for me to make, to me to promise you that we can help you succeed than if we get talk about it. Yeah.

Rob Jones (35:09.597)
Yeah, I mean, do you want this to be successful? Yes or no? If yes, then I cannot provide the level of care that I expect from myself and our business without doing another 30 minute call. Yeah, somebody was about to jump in, I think.

Harris Kenny (35:15.693)
Yeah.

Harris Kenny (35:20.054)
Yeah. Yeah.

Zach (35:23.68)
no, I think that

Rob Jones (35:25.257)
Could have been the FedEx

Harris Kenny (35:27.565)
I mean, I feel like a SaaS company maybe wouldn’t normally do that, right? Cause we’re a software company. I feel like maybe a services company would be more obvious to do that. But it’s like, if we want to keep churn down, I don’t know. I mean, that 30 minute, that second 30 minute call, if it saves our CSM like four hours, kind of worth it, right?

Zach (35:42.266)
Totally.

Rob Jones (35:42.665)
I was leaning in this direction. I know we have only a couple of minutes left, but there’s two. I’ll address this quickly and then give Brendan the handoff for an excellent episode next week if he comes back. But it’s like, how do you position stuff in marketing and sales to almost prepare the customers for retention and expansion? I think you guys both know the math of it’s more valuable, it’s cheaper to keep a customer, it’s more valuable to upgrade and expand into accounts. So there’s that.

We’ve talked about past today, we’ve talked about present current state. We haven’t talked about the future much. So as kind of a fun sign off, I’d like to introduce a new segment called Nostradamus or Nostra dumbass. Give me a prediction on trends that we’ll see in the next six months or this year.

Zach (36:31.715)
Anything we talk in sales.

Rob Jones (36:33.905)
Yeah, it could be buyers, could be sales, could be demand or demand generation or brand, anything that we haven’t talked about yet. I feel like both of you have been sitting on some stuff and cooking, so this is your chance to make a bold prediction.

Zach (36:46.68)
I’ll go short and sweet and I don’t think this is too unique of a thought, but I think brand is coming back. I think there’s been a over-reliance on tech and process and everything is a science experiment and I think, again, counter-intuitively, think as we’re veering hard into AI automation world.

people want brand, things they can trust, they want to talk to people, I think we’ll be seeing more investments in that area would be my prediction.

Rob Jones (37:22.825)
think you’re right. Harris, can you top that?

Harris Kenny (37:25.902)
I don’t know if I can top it, I, cause I agree. Um, and yeah, I mean, like these in-person things like events, I feel like are picking up more people, inviting people out and doing these interesting dinners and stuff like that. So yeah, I think that’s really interesting. And it’s again, like counterintuitive cause it’s not measurable at all. It’s not AI at all, but like chili Piper has that chili Palooza event. And I’ve seen some interesting posts about that and I’ve wondered like, Oh, it seemed like it was fun, you know, to go to that. Um, but I think for me,

I think I’ve referenced this maybe once in the past briefly, but I think that over the next, let’s just say a couple of years, but moving forward, I think there will be fewer people in go-to-market org with more spend per person. I think the GTM engineer and like, we’re hiring for a new GTM engineer, but I think like in general, there’s going to be a compression of head count. And I think you’ll see fewer people. And then the people that are left are going to be doing much more human things. I mean, we’re seeing this now with

people rolling out our product and then the reps are on the phone like way more. so the like sort of semi technical data stuff they were doing before trying to play around with filters and zoom in phone stuff, that’s just being taken out of their hands. And it’s being done by someone else within the org. And then the person that’s in the role is doing much more human stuff. So I think it’ll, I think there will be a reduction in head count over time in go-to-market orgs. I, I, and I, guess is my, my, my theory would be that

If I want to double down on it, think that instead you’ll see growth in customer success and more people being put on the customer success side. I don’t think like maybe mass layoffs or whatever. I just think like the average organization 12 months from now will have fewer people in under a sales like function and more under a success type function.

Rob Jones (39:14.947)
I love both of those. agree with the second one. More so just because of the tagline thing I just introduced where sales is becoming more marketing and awareness education. then, yeah, so that fits in pretty nicely. Gentlemen, it was a pleasure. Hopefully I filled in Nobly and Brendan Stead. He should be back on the 12th. Yeah, I mean…

Harris Kenny (39:24.386)
Yes.

Zach (39:33.454)
Who needs him now?

Harris Kenny (39:34.774)
Yeah, coup d’etat. I’m already anticipating the comments section. The mayor seized power.

Rob Jones (39:40.989)
Bring him back. It’ll be like this for whenever they see it. It’s like I’ve got an idea. We should hire the mayor full time So we can do that. Well, someone will see both of you next week. I’m gonna end this real quick

Harris Kenny (39:45.27)
You know.

Zach (39:45.749)
Hahaha!