GTM Crossroads Podcast Ep8: The Human Side of GTM AI Can't Replace

AI is rewriting the rules of go-to-market—but it can’t replace the people who run it. That’s the big through-line in this week’s Go-To-Market Crossroads conversation with founders Harris Kenny (OutboundSync), Zach Vidibor (Octave), and Brendan Tolleson (RevPilot).

• MicroConf takeaways. Fresh back from Rob Walling’s MicroConf, Harris shares why bootstrapped founders still obsess over copy, positioning, and face-to-face events—because shipping features ≠ winning customers.

• The “everything’s fake” era. The crew calls out inflated ARR screenshots and AI snake-oil: revenue may be easy to model, but trust is hard-earned—and impossible to synthesize.

• Pricing in a post-seat world. Zach breaks down Octave’s credit-based approach (“batteries included” PLG) while Harris wrestles with OutboundSync’s high-touch, partner-led tiers. Both agree: the tech risk is lower than ever; packaging and GTM risk are what kill you.

• Why events still matter. Inboxes and feeds are automated; relationships aren’t. That’s why the team is doubling down on Southbound (May 21) as a human-first antidote to AI hype.

If you’re navigating the tension between automation and authenticity—or debating seat vs. consumption pricing—this episode will hit home. Dive in for candid founder math, battle-tested event tactics, and a reminder that the heart of GTM is still human.

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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). 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

Brendan Tolleson (00:00.775)
Gentlemen welcome back to go to market crossroads. I’ve missed you. It’s been about two weeks since our last recording Harris I know you were at a show may we’ll start there. How was the event that you were at last week?

Harris Kenny (00:12.482)
Yeah, I went to Microconf. So we raised a pre-seed round from Tiny Seed. I’ve been a long time fan of Rob Walling and his Startups for the Rest of Us podcast. And first time I got a chance to go to Microconf and it was awesome. It was like totally what it says on the tin. It was exactly like what I had hoped. And there’s like a of bootstrap founders talking about positioning, pricing, kind of scaling the team. And there’s like kind of the ongoing joke of like,

product focus founders always wanna ship more features. And I was like, maybe you should focus on marketing. So I’m kind of an external processor. I talk a lot sometimes. It’s my wife can test, but I left after two days. I was like, I need to just sleep on this. It was just a lot to think about, but the positioning conversation was excellent. Fletch, PMM, think Fletch, yeah, the talk they gave was.

Zach Vidibor (01:04.877)
Yeah, I know that’s good.

Harris Kenny (01:08.914)
Awesome, Liana patch gave a very good talk on copywriting. So yeah, I left thinking about marketing And kind of how we position and how we talk it was it was great and then we got southbound coming up Ethan from our team is gonna be going to southbound So I’m bullish on events all this like AI kind of stuff I kind of I think it’s like being face to face is pretty pretty important

Zach Vidibor (01:18.62)
Thank you.

Zach Vidibor (01:28.019)
It becomes almost more valuable and more potent. In a world that’s gone virtual and AI-led, it’s like the, yeah, can’t rip this and anything go to market. It’s gonna be a long time before you can rip the soul out of it. There’s human psychology at the foundation of all this.

Harris Kenny (01:32.439)
Yeah.

Harris Kenny (01:45.795)
Yeah.

Harris Kenny (01:50.35)
I mean, at some of the companies, even the revenue numbers are fake, That’s kind of what we’re talking about. Everything’s fake, even the books. It’s kind of what we’re talking about. LinkedIn lately, feels like.

Brendan Tolleson (01:53.421)
Yeah

Zach Vidibor (01:53.785)
Yeah

Zach Vidibor (01:59.699)
Yeah, mean, yeah, the 11X drama, think, yeah, everybody in the space, I think there was a 0 % surprise. I feel like that was like the world’s worst kept secret. Everyone knew those customers weren’t real and there’s a bloodbath of churn everywhere. But yeah, think it’s like, again, whether it’s them or anyone else, not to like throw shade, think there is like, there’s a class of people that believe

like go to market is some riddle that you can like solve in a laboratory, you know, and it’s just like, it’s different. It’s different at each company. There’s people involved. is trust involved. There are relationships, you know, it’s just like, there’s so much art left. And I think, know, the fundamental, whatever happened on the business side, who cares? But it’s just like, I think a lot of companies, like they end up setting themselves down the wrong path when it’s like, we’re just

building a thing that has to pass this like sales touring test, you know, and it’s just like, it’s just not gonna work. You know, like I just, I think any of us who have like done this, you just kind of like laugh at it. You’re just like, all right, I guess that’s like competition on some level we have to address, but it’s just like, I know it’s not gonna work. So I’m like not really scared about it. I don’t know.

Harris Kenny (03:21.336)
Mm-hmm.

Brendan Tolleson (03:21.367)
That’s a good segue for that segue, but a promotion point for southbound. know Harris, you brought it up and then Zach, you went deep into it, but it really speaks. That’s the whole theme and it gets into.

Like some things change, but some things stay, like some things always stay the same. And what it’s getting into is this idea of connection, the human relationship, the idea of trust. yes, AI is really powerful and we should all embrace how it can be used, but it’s, it’s not the solution to how you go to market. and so really making sure we have that, front and center of our humans, selling humans and make sure we have that connection being, kind of going back to like Elon Musk first principles, like what are the first principles that go to market? And it’s like getting back into that element that I think we’ve, we have.

Over indexed. To your point about art and science, we over indexed to science and it’s like, well now how do we get back into this happy medium of leveraging the data, leveraging tools, but using that when we’re actually interfacing with the human, which is the art.

Zach Vidibor (04:18.971)
Right, right, can’t rip out the heart and soul of your go-to-market and replace it with AI. know, it’s like AI is just yet another tool in the toolbox, you know? And yeah, there’s gonna be like increasing leverage because of like the nature of AI, but it’s like, yeah, it’s not a panacea in and of itself. It’s still a, it’s an engine, you gotta put a car around it, you know?

Brendan Tolleson (04:46.939)
Well, Harris, I guess going back to even just your event and thinking about, I mean, you’re bootstrapped and what, like, what are, know you mentioned some of the things that you were thinking about from a marketing perspective, but what are some of the key takeaways as relates to go to market or kind of the advice that, that was being shared at that event? mean,

Harris Kenny (05:06.371)
Yeah.

Brendan Tolleson (05:07.043)
I’d love to start there and I can circle back to something. talked to Liz Christo from Stage 2 recently and just getting her perspective of what’s going on in the market that I can kind of wrap that around. be interesting to hear your perspective.

Harris Kenny (05:17.9)
Yeah, for sure. mean, I think, you know, I mean, one thing I’d love not to like, pat my own back or whatever. But I, I do focus a lot on growth, and our partnerships and our partner relationships. And I did leave after talking to a bunch of other people.

feeling like, okay, we’re actually further along than I thought in terms of our like actual MRR and our turn is actually pretty low and we have a really nice expansion, revenue expansion that’s coming from partners as we like help them deploy App OnSync to more customers. So I left feeling better. think that, you know, it’s always like, one more feature, one more feature. I release this feature and then we’ll be, know, but I left kind of feeling like, maybe I’m doing a better job of this than I was giving myself credit for.

And so I’m thinking about like marketing and partner marketing and more like we’ve been doing some webinars that have been really like super engaging and really well attended, which everyone kind of laughs at. At least I always thought it was like funny the idea of the webinar. But what my experience is actually been it’s it’s been really great. I think I’m also thinking about like our pricing. You know, I priced our product a certain way because we like just had to have a certain level of ARPU, but because it was really high touch.

But I’ve had this experience with a couple of users where they come in at a lower price point, they’re still discovering this new go-to-market motion. like, they’re using some combination of like Octave and Clay and, you know, a smart lead or something like that. And it’s just like, it’s a lot to get going in the beginning. And so we have basically, our philosophy has been like, we’ll get you when you’re like really ready to commit. Unless you’re working with an agency in which case we have like a different price. But I’ve been wondering like, as this is moving more into the middle of the bell curve, like,

Do we need to have a lower price? It doesn’t have to be cheaper, like the unit economics can scale down, but do we need to have an option to let people like dip their toe in? That’s like a much, much, much broader thing that I don’t know the answer to, but I’ve been thinking about that. Cause it’s like, how do people adopt these new tools? What does that look like? What does the actual evolution look like? And are we leaving some chunk of the market by having such a high bar in terms of the price point for the product, you know, and requiring they have this big team or they’d be working with an RP.

Brendan Tolleson (07:29.633)
Yeah.

Harris Kenny (07:33.048)
kind of things. don’t know. Anyway, sorry, those are like my random thoughts.

Brendan Tolleson (07:36.035)
Well, Zach, how has Octave approached that to your point about, you know, for our audience may not be familiar with ARPU, average revenue per customer or per user depending on you look at it, but like getting into what Zach was just saying, Zach, what Harris was just saying, Zach, when you think about Octave’s go to market, have you thought through like, do we lower the barrier entry on this side versus having this higher barrier? Because you also have partners that you’re working with. I’m curious to how you’ve thought through that problem.

Zach Vidibor (07:58.93)
Yeah.

We are, I guess, at our soul, not like, we wanna build this hyper.

PLG company, but we are definitely like i’d say our core belief is like Product lead is like the way we have to be like in you know in an ai world of like a lot of snake oil and garbage out there like even if it costs us money to have like a and it it does like you know, you can sign up for free and come in and We do a bunch of stuff to like prove like this mousetrap does something it works like check it out and like I think that’s a pretty

the concept we talk about internally is like, especially in a lot of go-to-market tools, they’re like, batteries not included. You buy these systems and they’re just empty and you’re just like, okay, now what? This didn’t do anything.

I conceptually understand I need these tools and systems and like what we’re doing, we have the opportunity we’re trying to take advantage of. Like we can create a batteries included experience. Like, hey, what’s your website? Let me start figuring out. Like here’s how you might talk to different personas and like we can do a quick proof of value and it costs us money. And we obviously, you know, we’re not.

Zach Vidibor (09:19.175)
We’re not gating you on like, need to do a discovery call, like figure some stuff out. We’re to let you in and maybe you have a wow aha moment. Maybe you don’t and you walk away and like, that’s okay. But like, I think on the bias, are more for the like lower the barrier to entry, make it easy to start seeing value, make it easy to start consuming. And then, and then yeah, like we’re, we’re trying to drive a business and we’re going to feature gate you and meter you and all that. But I think we’re gravitating more towards the.

how do we demonstrate value quickly? How do we show you this thing’s real? And then, you know, we’re really anchoring around consumption and features versus seats, you know, like in this new world, I think it’s much more like that’s a much closer proxy for value than like the traditional seat model.

Harris Kenny (10:07.565)
Mm-hmm.

Brendan Tolleson (10:09.815)
Yeah. Which is, go into that a bit further. Like when you have like consumption, seat, credits, I this is always a fun topic, but, it sounds like what you’re saying is I, you’re really approaching it more for solve for the customer versus like solve for, not to use a derogatory, like the bean counter looking at the, the value of the company. We’d love to get y’all’s thoughts on how to be mindful of even that kind of that, the, the pricing level you just described that could be fun. think not fun, but interesting to unpack that a little bit further.

Zach Vidibor (10:40.147)
I mean, I think, you know, especially like for us, and I don’t think there’s like too specific to us, but like, we’re like, we kind of have to own it in a way of like, we’re saying there’s this new paradigm and there’s this new way to do outbound and like.

Hey, if you just keep hiring SDRs and trying to give them yet another Bazooka launcher, like that isn’t gonna work. like, we were going like, hey, you need to buy a Seats of Octave, like for who? Like, you know, like, I think we like kind of have to own it and we have to go like, all right, yeah, like you get value somewhat derived from like how much you use the product and like we need to create the experience and kind of the…

pricing and packaging that reflects that. I will say, it’s not without its challenges as well. We do have customers that are just like, give me a number. I don’t wanna think about credits. I don’t know. All we do is buy seats of stuff for our sales and marketing team. Consumption is still a new, for the bean counters, they’re like, I don’t know how this fits in our model. So we do have customers and we’re flexible to it. just like.

I need, I got this much to spend, what can I get? You know, like, we can reverse engineer it, but it’s, it’s, know, like, it’s not without its challenges for sure.

Brendan Tolleson (12:00.535)
Yeah. How about you, how about you Harris? guess, is it more just flat rate or how do you think from a pricing perspective?

Harris Kenny (12:05.248)
Yeah, I mean, right now we just have these like, basically, you know, it’s like, you know, a few hundred bucks a month and up depending on your volume. And it’s like, if you have this problem enough where it’s important to you to get this data and HubSpot or Salesforce, then you sign up for our product because we’ve built the best way to do that. But it just doesn’t feel like there’s like a great logic to the pricing. It’s just like, yeah, if I have it, that price works. And then, you know, there’s

But like I’ve had people who like they signed up at a lower tier, they set it up and then they’re like, okay, it’s working. I like the motion, we’re going to hire an SDR and I’m so glad I have all this stuff in place already. So that was like some testing I’ve been doing at a lower price point. And so like looking at octaves pricing, like you do have depending on if it’s monthly or annual, you do have a couple options. You do have that option under 200 a month. And I think where we get is like we’re in between these tools like HubSpot and Salesforce charge per user, you know, something like a clay.

Zach Vidibor (13:00.371)
Yeah.

Harris Kenny (13:00.542)
Charging on per credit and so people are like, yeah, but like okay, we’re like the CRM But we’re connecting to both and you know, I think like there’s a world where we just do like a consum more of a consumption model and it more floats I think like ultimately is like what is the most valuable thing for our users? How do we price in a way that our pricing helps them like make? Like make a decision that makes sense to them I think like right now our pricing does work like we’re growing every month, you know, very healthy growth

And so I don’t feel I need to like necessarily immediately change everything. But I think the version of this company where revenue, you know, where we’re a million dollar ARR, we’re not there yet. I don’t think that this pricing gets us there. And so it’s like, what does a mature version of this company look like? That’s kind of like what I’m thinking about. It’s like we’re growing and it’s working, but I just feel like it could be better. And if we could have

more revenue from customers who value it more than we can spend more on engineering, which is like build a better product. You know, like we don’t, I think there’s like a tons, tons of problem areas. And so sometimes I feel like resource constrained and I’m like, well, is it because my pricing is dumb? Like if I had better pricing, could I solve these problems for people who want me to solve them? And like by not figuring this out, I’m like not doing my job really, which is like solving problems for customers because I don’t want to spend 10, 20, 30 hours just sitting down and coming up with a better pricing model, you know?

Brendan Tolleson (14:12.691)
All right.

Harris Kenny (14:27.854)
because it’s uncomfortable and annoying and risky kind of thing.

Zach Vidibor (14:31.613)
Mm-hmm.

Brendan Tolleson (14:33.315)
Well, I think we will.

This could be a whole nother long conversation because I pricing is not a small topic. And thinking about evolution of the company and based off your go-to-market motion, we talk about the PLG model, we’re talking about the partner. When I say PLG, product-led growth, and there’s also the partner-led motion. know both of you guys work with agencies or kind of the end user, but there’s like that element that impacts it. There’s also company stage, the value that can ultimately dictate pricing. And maybe we’ll have to bring that up in another conversation. But Zach, I know you need to go for another

Zach Vidibor (14:41.288)
Yeah.

Brendan Tolleson (15:08.054)
Any final thoughts on kind of more ad hoc, just around the horn type of conversation as we have three founders building companies?

Zach Vidibor (15:17.103)
we should, sorry for, I know I’m cutting this one short. I think this is like worthy of like, can go deeper here. I think one of the big things is like an interesting, like macro trend line. like, know a lot of like investors are talking about it as well as like. Technical risk is like really lowering, you know, like when they’re like diligence in companies, there’s like a lot more belief in the like.

the science experiment of like, yeah, like I believe you can build the tech. Where like it used to be 30 years ago, was like, all right, well like if the science experiment works, like we know there’s a market for it. And now it’s really kind of shifted. It’s like there’s a lot more belief in like, you’ll figure out the tech, but like.

Brendan Tolleson (15:48.363)
Okay.

Zach Vidibor (15:55.121)
Can you market it? Can you price it effectively? Can you package it effectively? Do you know your ICP? so like, yeah, like I dig on this. Like I think there’s a lot we can like unpack here and yeah, share what we’re all like struggling through. And this is a fun one.

Brendan Tolleson (16:09.997)
Yeah, I mean, the barrier to your point is somewhere I mean, the barrier entry that relates to product development has never been lower. Like you’re seeing just the proliferation of smaller shops with fewer people because of what you can do with AI allows for what you’re just describing where sales market becomes even more and more relevant. Harris, any final thoughts on your side?

Zach Vidibor (16:14.909)
bread.

Harris Kenny (16:15.075)
Mm-hmm.

Harris Kenny (16:25.198)
Hmm.

No, this is a big one. To be continued. I love these conversations.

Brendan Tolleson (16:33.251)
Alright gents, well, it’s good to see you again. I miss y’all. yeah, southbound, May 21st, hopefully see y’all there. See y’all.

Zach Vidibor (16:37.009)
Likewise. See you, man.