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From Hiring Scrappy Teams to Rethinking AI Pricing | GTM Crossroads #11

GTM Crossroads Podcast · 2025-07-04 · 37 min

0:00--:--

Key moments - from our scoring

Substance score

34 / 100

Five dimensions, 20 points each

Insight Density7 / 20
Originality5 / 20
Guest Caliber8 / 20
Specificity & Evidence9 / 20
Conversational Craft5 / 20

Harris walks through concrete use cases he's built with Breeze workflow actions inside HubSpot - automatically categorizing outbound replies, drafting response emails, and capturing activity summaries - demonstrating that the long-hyped AI product is finally delivering measurable value for RevOps practitioners. The hosts unpack HubSpot's broader AI-first platform strategy, including the Dashworks acquisition for knowledge base integration, and debate whether these capabilities justify moving beyond seat-based pricing toward consumption models. Zach shares his perspective on pricing complexity from his time at Docusign and offers a counterpoint about how simpler, more intuitive consumption models (like Outbound Sync's email-based billing) can actually drive better buyer experience. The conversation shifts to startup scaling realities: Octave is hiring go-to-market engineers rather than traditional enterprise sellers, prioritizing grit and product-led motion over expensive pedigree, while navigating the chaos of distributing company knowledge beyond founders' heads.

Key takeaways

  • →Breeze's workflow actions enable practical RevOps use cases like categorizing inbound replies and auto-drafting responses within HubSpot, reducing the need to manage outbound campaigns across disconnected tools.
  • →Consumption-based pricing likely represents the market's future as automation reduces headcount needs and platform consolidation creates fewer, more generalist roles across organizations.
  • →Mixing seat-based and consumption pricing simultaneously creates deal chaos for sellers; companies must choose one model to avoid customer confusion and internal conflict.
  • →Hiring for early-stage startup sales requires seeking grit, product-led motion aptitude, and technical curiosity rather than expensive, experienced enterprise sellers seeking inflated salaries.
  • →Simpler, more transparent pricing models - even consumption-based - can paradoxically improve buyer experience compared to complex multi-tier structures.

In this episode

  1. 1Introduction and Breeze AI Platform Overview
  2. 2Breeze Workflow Actions and Real-World Use Cases in HubSpot
  3. 3Building Outbound Email Campaigns with AI Categorization and Reply Drafting
  4. 4HubSpot's AI-First Strategy and Dashworks Acquisition
  5. 5Seat-Based vs. Consumption-Based Pricing Models
  6. 6Outbound Sync Pricing Model Changes and Success
  7. 7Octave Growth and Hiring Strategy for Go-to-Market Engineers

Mentioned

HubSpotBreezeDashworksClayOctaveOutbound SyncClearbitSalesforceChatGPTLoomYaminiZach

Guests

ZachHarris

Topics in this episode

HubSpotConsumption-based pricingSeat-based pricingBreeze AIWorkflow actionsDashworks acquisitionOutbound reply categorizationClearbit enrichmentClay (platform)Octave

Questions this episode answers

What is Breeze and what does it do inside HubSpot?

Breeze is HubSpot's AI product that summarizes conversations, creates and remixes content, provides enrichment through Clearbit, and now includes workflow actions that let users categorize replies, draft responses, and surface activity summaries - all marked with a distinctive pink highlight in the UI.

How are Harris building value with Breeze workflow actions for outbound campaigns?

Harris built three use cases: automatically categorizing off-platform replies as worth following up on, generating draft response emails based on sent and received messages, and providing unified activity summaries that blend inbound signals like site visits with outbound campaign context.

What did HubSpot acquire with Dashworks?

Dashworks is a knowledge base tool that captures structured and unstructured data across an organization's tools, functioning as a universal search and AI assistant for employees to quickly find information across disparate sources.

Why is consumption-based pricing likely to replace seat-based pricing?

As automation reduces headcount and platforms consolidate data sources, organizations have fewer people using more volume; seat-based pricing becomes misaligned with actual usage, making consumption models more logical for both vendors' revenue sustainability and buyer fairness.

What profile of sales hire is Octave looking for?

Octave is hiring go-to-market engineers who prioritize grit, technical curiosity, and product-led motion aptitude over expensive pedigree; they want people excited to grind in-office and learn sales rather than experienced enterprise reps expecting six-figure compensation.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

7 / 20

There are a handful of moderately useful operational nuggets - Breeze workflow use cases, the dual-pricing chaos at Docusign, and scrappy hiring philosophy - but the episode is heavily padded with banter, Chick-fil-A analogies, and meta-commentary that crowds out substantive content. The insight-to-noise ratio is poor.

I hope they don't find out about the other pricing model. You're always in this, like, oh my God, if they find out about the API volume pricing, like, this deal is going to fall apart.
the source code that runs the business, like it only runs in our heads and like, we need to start downloading that into more people

Originality

5 / 20

The episode rehashes widely circulated takes - consumption pricing is the future, hire for grit not pedigree, founders are their own bottleneck - without adding a contrarian angle or first-principles argument to any of them. The Docusign dual-pricing anecdote is the lone moment of genuine colour.

It just, just feels like the water's going to find the crack and that's kind of like seats are just going to like feel more and more kind of like obtuse
I'll optimize for green and somebody that's like, just been trying to grind it out at a bunch of places you haven't heard of

Guest Caliber

8 / 20

All three speakers are working founders with direct hands-on experience in the HubSpot ecosystem and early-stage GTM, which gives the conversation practitioner credibility; however none of them have demonstrably done this at meaningful scale, and the episode reads more like a peer check-in than an expert interview.

I don't consider us app on sync and AI company. I consider us just like a data connector. Um, I think there's AI use cases around our stuff, but, like, fundamentally we're kind of plumbers.
we just get to say all right, it's consumption, like let's just make the business model work

Specificity & Evidence

9 / 20

The Breeze workflow section is the strongest portion, naming specific tools (Clay, Octave, Clearbit, SuperD) and describing three concrete automation steps with enough detail to be reproducible; elsewhere the conversation stays vague, with no revenue figures, customer counts, conversion rates, or timelines offered.

I built a categorization prompt within the context of you get a reply, it needs to be categorized
I included like a HubSpot meeting link in the prompt so that it generated a pretty decent little two sentence reply back

Conversational Craft

5 / 20

This is a co-host roundtable rather than a structured interview, and the format shows - questions are gentle prompts ('What's new in your world?'), claims go unchallenged, and the conversation drifts freely into Chappelle's Show and Chick-fil-A without a steering hand to recover substance.

Zach, what's uh, what's new in in your world, Octave? I feel like a week in startup world is like a year.
I'll get off my soapbox. I feel like I talked way too much in this one.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker A42%
  • Speaker C33%
  • Speaker B25%

Most-used words

hubspot24breeze21feel12trying12sales12data11build11reply11starting10product10team10pricing10zach9love9back8market8

Episode notes

In this episode of GTM Crossroads, the hosts explore how AI is reshaping business strategy, with a focus on HubSpot’s new Breeze AI. They break down its practical applications, pricing structure, and implications for growth-stage teams. The conversation also highlights the challenges of hiring in a startup environment and the critical role of company culture and values during scaling.

Full transcript

37 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Foreign. Welcome back to another episode of Go to Market Crossroads. Uh, how we doing?

Speaker B: Hanging in there. I'm m fighting something, I'm not gonna lie. So if you hear some. Some raspiness and if my voice is gone by the end of this, that's why.

Speaker A: But good M points if you throw up on camera, so.

Speaker B: Gotta find a way to go viral somehow.

Speaker A: I probably shouldn't say that, as you don't feel well. That's kind of a cruel, um. Harris, how are you doing, man?

Speaker C: Well, I'm relieved that Zach clarified that he was fighting an illness, because when he said I'm fighting something like, what's going on over there? I was worried we should move the recording or something. I was worried you were engaged in some kind of physical combat.

Speaker B: No, no, not. Not these days. Those days.

Speaker C: Those days are over. No, things are good. Things are good. I, um. I've been a little bit of a skeptic, but I been building some stuff with Breeze workflow actions, and, uh, it's got my attention, so I'm pretty. Pretty excited about that. So there's, like, parts of Breeze AI inside of HubSpot that are starting to work, I think, really in interesting ways. Others that are still a little shaky. But, um, some really interesting stuff that was like, oh, man. If I'm a Rev Ops person, this is nice. I, uh, could stand this up really quickly. So. So I'm. Yeah, I just finished recording that, so I'm a little. I'm still coming off of that, like, loom, uh, loom sesh. Loom session. But, uh, yeah, so otherwise, things are. Things are. Things are cooking. But I. I've been watching Breeze forever, and I feel like it's finally like, oh, I mean, and I know it takes a long time, and I. And I appreciate that HubSpot just ships quickly, but I love when use cases start to come together where, you know, you feel like, okay, yeah, this is actually going to save people time, and it's not speculative anymore. So.

Speaker A: Yeah, well, ah, let's dive into that for a second. I mean, for our audience who may not be familiar with what Breeze is, maybe give them a little background on the Breeze story and then ultimately, where you're starting to see value, because I know that's to your point, I think people have been patiently waiting for impact, uh, from that product.

Speaker C: Yeah, I could talk a little bit, but also, I mean, you were just at the Spotlight event in New York City, so, I mean, you can probably share a little more inside baseball than I can about it, but, um, I mean, just in short, it's HubSpot's AI product. I mean it does a lot of different things. Um, Yamini I think has spoken about it pretty um, effectively at like an executive level about how HubSpot thinks about AI. But you know, for me, as a very product focused founder, I always like to, you know, see how we can use it right now, what can we ship right now. And there's like maybe a little bit of impatience, um, because I think HubSpot has shown that they are patient in pursuit of the vision over time. So they so breezes AI inside of HubSpot and it does a lot of things, it summarizes things, it can create content, remix, mix content. Uh, it includes some enrichment as well through their Clearbit acquisition. Um, but I think that it's this little sparkle icon basically sprinkled throughout the uh, or sparkled, I don't know, throughout the app. Um, uh, and they've done actually an interesting job in the UI highlighting when something is AI related, like a little pink uh, box around it, which is helpful to see. Like, okay, AI is doing this. Um, but yeah, I mean that would be my, that'd be my like elevator, elevator pitch. What would you add there? What did I miss?

Speaker A: Uh, I mean there's a, there's probably a lot to unpack. I mean it's, it, it really is. I mean I think that there's a distinct way in which HubSpot's trying to go to market, which is to be an AI first platform. I think the way it frame is the AI first platform as uh, opposed to point solution. And so Breeze is kind of that connective tissue that allows for them to go across all, um, meaning marketing, sales, service. We'll see about commerce, but let's just use marketing, sales and service, um, and then having the agents on top of that. But I think that, um, candidly, I think Breeze has been underwhelming, um, for a long period. I think patient is a nice way of framing it here. So I think that it has been um, very slow, uh, in terms of getting anything. Anything's too strong a word. But for like mass adoption where you're seeing true value and impact, it's been more of like a, um, a hype train for a long time. And so it's interesting to hear that you're starting to see value from it. So yeah, would love to kind of see what you're seeing or would love to hear what you're seeing in terms of value or impact since you've been playing with It.

Speaker C: Yeah, for sure. And I, I'll answer that and then I really want to know. Just. Zach building an AI company, I. I don't consider us app on sync and AI company. I consider us just like a data connector. Um, I think there's AI use cases around our stuff, but, like, fundamentally we're kind of plumbers. Um, so I would love to know what Zach thinks, just from like a product and engineering perspective, what it's like to build and scale this stuff out. Because, you know, I'm. I don't. I'm in the cheap seats and don't want to be a hater about it. I know it's hard. Um, and you know that better than me, Zach. But, um, in terms of use cases. So, like, what I've been building, this is like just my experience and I'm sure there's other things, but Outbound Sync, basically, you're running these outbound campaigns off platform and then you're getting them into HubSpot. And so the two things that I just. Well, the three things that were in this video, um, first thing is you get a reply that's off platform. Um, and a lot of things happen before getting that email sent out the door. So maybe, you know, you used Clay to build a table, you used Octave to get killer messaging, and then it worked. But there's a lot of stuff that's missing that's not captured in that ultimate product of, you know, a 50 to 100 character email and then a, uh, 25 character response. Right. So that drops in there. It's sort of devoid of context. So we push all the data in. And so the first thing I built out was using Breeze to categorize the reply of. Is this worth following up with or not? Some sequencers do this natively, but it's a little bit of a black box. And so being able to say, hey, if I'm a Revops admin or sales leader or marketing leader, and I want to define what's worth following up on or not, and I want to be able to do it in HubSpot and I want traceability. When I see that categorization, I want to see which workflow it came from. You got to do that in a workflow like you just do, and so Breeze gives you the ability to do that. Um, so I built a categorization prompt within the context of you get a reply, it needs to be categorized. And now that we have a category on the reply, what do we do with it? The second one was developing a draft of a Response back to the reply based on the sent email based on the response back. Now we have our third email in the thread, which is what the sales rep would say. And I included like a HubSpot meeting link in the prompt so that it generated a pretty decent little two sentence reply back. So if I'm a rep now, I log into the record for my new contact that's just been generated, I can see the sent email, the reply, a suggested response, and then in the top right of Breeze with Bree's record summary, I also have a summary of all the activity on the record capturing those sent emails, including, hey, by the way, there's a response for you. And this is where the HubSpot piece comes in is like if there's inbound activity that's also potentially captured. Like if they were to have site visits, if they were to download a piece of content, um, if they were to interact in some other way with the company, it wouldn't just be an outbound record, it would be an all bound, blended record that would show maybe multiple things in there. Um, and so yeah, I mean to me that's really, really compelling. Uh, versus I'm going, and I'm handling that reply inside of my inbox somewhere else, missing all of that stuff, 95% of that stuff. And then when you talk about Once you're in HubSpot, last thing, I'm sorry I'm monologing here, but there's also like process enforcement, right? So if you're using a tool like SuperD and you say like, okay, well when we get an outbound reply, we want to make sure that we do this, fill this out or whatever, whatever the rules are, um, around getting that new opportunity that came into HubSpot from, you know, externally. And now we need to like absorb it into our organization and our process and our data hygiene rules and whatever else. Um, again, being in HubSpot, it does a lot. So it's about more than just handling reply. So to me those were like three really objectively useful things that I shipped in a, in a Breeze test account with not a lot of time spent. And um, like I'm going to share with our users and say, hey, you should think about this. Now you could do some of those things if you had a ChatGPT workflow, workflow action, you could do those. It doesn't have to be Breeze, literally. Um, I think the key is just like making that accessible within a workflow. Um, I think there's. But, but Breeze does the summary part well and then the other two parts of categorizing and drafting the reply, those technically could be API calls to another. Another tool. But Breeze. Breeze did it well and you've got the credits and you're already paying for it anyway and so there's benefits to what you. Why you might want to do that anyway. Monologue off. But that's what I'm working on the last day or two and yeah it's been a real change of mind for me uh, in terms of how I'm thinking about it. It's a lot closer than I would have thought. Um, a week ago.

Speaker A: Yeah, I think it's. I know you had posed a question Zach. I think we're starting to see that and I think it's only going to accelerate. I was going to show you guys a. Um, I was trying to find this. We actually this is uh, I had the team put together was this a three by four um, but really kind of around Breeze Intelligence the copilot the data source of the agents on the good, the bad the considerations I think what you're describing is the workflows. There's a lot you can start to do there which they haven't had ah access to that there's of course things to be worked on. So it's just kind of a snapshot for us to be mindful of um, how we should be thinking from a product perspective. Um and it's also been interesting too because even since that you referenced Spotlight which is all about kind of how they're thinking about AI within their platform. Um but since then they announced the acquisition of dashworks um, which I don't know if we can talk about that too if you guys want but um, it's not slowing down. Um and Yami is very adamant on how do they enable organizations to be AI first companies by leveraging HubSpot. So I think we're only going to see this accelerate in terms of use cases and benefits. Um, I don't know how much more acquisition but it's nice to see that what you just described is possible because they do want that to be on platform um, and taking unstructured and structured data and giving that um, insights inside of HubSpot for go to market leaders.

Speaker B: What was the acquisition they made? I missed that one.

Speaker A: Dashworks. Um, and so they. A lot of what they're talking about like one of the big kind of concepts is structured and unstructured data. Ah and the way I just think about that is like on and off platform and so dashwork serves almost like A knowledge base, um, that can capture information, um, across all the apps within your, or your, um, within your organization. Um, and so it becomes almost like an AI assistant for anybody in your organization. So bdr sales rep that's trying to find things. It just becomes a quick, um, assist tool for them. Got it.

Speaker B: Like a universal search kind of like chat. Okay.

Speaker A: Almost like your own, like your own intranet of like all these different but disparate, um, sources. So it's again outside of HubSpot, allows all that data start coming in, uh, into one place, which is a pretty compelling vision. Um, that's probably going to take a little time to integrate it. But that's, that's ultimately where they're going.

Speaker C: I think that was just like yesterday or something. I think it like just.

Speaker A: Yeah.

Speaker C: Or maybe it was Monday.

Speaker A: Yeah, it was, it was middle or late last week. It started to come out. Actually it was, it was the day we recorded this because I just met with, I just met with the HubSpot team and they announced the same day.

Speaker B: So is the, the Breeze, they. You have to purchase credits on top of your licenses to use Breeze? Is that how it works?

Speaker C: That part is not totally clear to me. Brendan. You can probably speak to that with more authority. I think that if you're on a certain tier of plan, you get a certain amount of Breeze credits without a separate subscription that I know because I've just like started using it, but I don't know fully.

Speaker A: Yeah, they've, they've been up. They're up. I mean the short answer is they're updating their pricing. Uh, and so all this is being flushed out. A lot of what their focus was historically is let's make it cross platform as opposed to one product and let's give people access to it to see the value and then we'll figure out how to monetize it. Um, and so that's where it's going to start. I think we're getting, as you heard Harris talk about you starting to see the impact and now I think they feel like they can capitalize on that. So, um, that the credit concept is in place now. What thresholds and things of that nature is. I think it's going to come out more and more in the next few months.

Speaker B: What, what's your uh, what's your feeling about the longevity, uh, or not of seed based pricing? Like in this new world, do you think seats are. There's just so much gravity around that and people. It sticks around or are we really going to see a fundamental Shift.

Speaker A: I'd be curious to know. I mean you guys are, y' all are more in the seat based pricing early. Well, not you carrots necessarily. But Zach, I mean, what do you mean? You're more in the software category. I can give you some buyer sentiment on what I'm seeing but um, man, I think you got, you probably live in that all day every day. So what, what's the, what are the recent trends you're seeing?

Speaker B: It feels, I'm getting, I'm getting more bullish I guess on a, ah, like the future is consumption of some sort. It just, it just feels like the, the water's going to find the crack and that's kind of like seats are just going to like feel more and more kind of like obtuse as more stuff gets automated and stitched together with APIs and humans are becoming more generalists in ways, you know, like it just, it just, that's what it's feeling like to me. I don't know, I think for the big, you know, for the hubspots and the salesforces, it's gonna, it's gonna be a painful transition. I think for if you're a younger company like uh, us, we just get to say all right, it's consumption, like let's just make the business model work, you know.

Speaker A: Well, I think, I mean salesforce, our signal, they're moving that direction over time.

Speaker B: Yeah.

Speaker A: I think if we take a step back, I think it's important to understand why it would go that direction. Um, and so if we take like macro themes, you've got technology providers moving from point solutions to platforms and they want to own that kind of go to market journey. They're trying to get all data sources connected inside of that. Uh, and there's just a reality that like with efficiency gains from data and technology there's going to be fewer people. And so even just from a pure like revenue, how do we continue to grow? Um, the usage based concept makes a lot of sense. Um, and I think all these kind of concepts around talking about data kind of are ways to kind of start to build that momentum and movement towards that. Um, um. So I, although that's a long winded answer to your or long winded response to your question, Zach, which is uh, I do think it will become the norm now how fast that is, I think it's a different question. But that is, I think that is where the market is headed.

Speaker B: Yes, it's, it's interesting. We uh, it reminds me I was when I worked at Docusign back in the day we had, they had seat based pricing and consumption based pricing at the same time. And it was basically the best way to create absolute chaos of like, you ended up as a seller being in all these scenarios of like, okay, low volume use case, but lots of people, I need to sell seats, you know, few people, high volume, I need to sell volume. And then you were just like, in every deal you're just like, I hope they don't find out about the other pricing model. You're always in this, like, oh my God, if they find out about the API volume pricing, like, this deal is going to fall apart. Um, so you definitely can't have both. I know that.

Speaker A: Yeah. And I think it's going to be, I mean, to your point. I mean, I get why companies want to go that direction. I think from a customer perspective, look, things change all the time and people adapt. But like the education around, I mean, Harris, you're. You. Well, it's kind of funny because, I mean, you, you just change your pricing model. Um, so you are very much in this world of like, how do you, how does a buyer experience? And your example actually was super, like it was more intuitive for the buyer to understand. So I was going to argue the opposite, but you had the data suggested. It actually is easier for the buyer. Uh, and maybe it depends on who you're selling to and what the product is. Um, but it feels more confusing just because people don't, aren't accustomed to that type of consumption model.

Speaker C: Yeah, in our case it was more intuitive to go more consumption based. Like, how many emails have you sent? I think we talked about that a bit in previous episodes. So if you're new to GTM Crossroads, go listen if you want to hear me talk through that. We did retain though our per client billing for the agency side and for agencies that made more sense for them, it's like, look, we sign a new client, if they want the service, we add it. We know what the cost is. And I simplified our agency pricing too. So it's same cost per, per client, no matter whether it's Salesforce or HubSpot or it's your first client or your third client. It's always the same price for each new client and they have a ton of volumes. They can do whatever they need to do to help that client be successful, basically. And for us, from like an inputs perspective, we do have to do a fresh install each time. Um, and we have to work with their customer's team to define what they want in HubSpot. How they want it in HubSpot or Salesforce. Um, so, so we're aligned with them and it just seems to work. And as they grow, we grow with them. It's possible that there are people who are getting more value from our product than we are charging. I think that if it's easier to buy from us, it'll net out in the long run. Um, but maybe that's naive, but I just was on too many calls. I was like, this just doesn't make sense. And since then, I mean, this week, just like last week, has been much, much, much noticeably better. M. Noticeably different and better versus under the previous pricing. So I think that for us that, that that change made a lot of sense.

Speaker A: Yeah. Well, Zach, what's, What's new in, in your world, Octave? I feel like a week in startup world is like a year. So what. What's been, uh, happening, man?

Speaker B: We're, uh, we're doing good. Made a few hires. I got some people starting on the, on the sales team next week. So excited about that. I'm gonna get a little, uh. Reprieve isn't the right word, but I need some, I need some help. I'm get. I'm getting some help in the trenches, which is good. Um, so, yeah, we're, um, Things are good. We're. We're growing. We're in that. The, uh, I was describing, I forget if we were talking about it here before or not, but we're in that phase of like, me and my, my co founders, Julian, we're in that, like, right now it feels like the source code that runs the business, like it only runs in our heads and like, we need to start downloading that into more people so we can. Like that. That feels like the biggest limiter on our growth right now is like, right now everything requires Julian and I to like, execute and drive and kind of be the owner of. And so we're starting to bring more people on, having more people take on more. So it's, it's exciting, but it's also pure chaos. You know, we're trying to. There is no process. We haven't been through this before. So, um, we're figuring it out. But, uh, it's good. We got some, some cool, um, customers that are growing fast with us and opening up new use cases and yeah, we just got a. One foot in front of the other.

Speaker C: How is hiring for a sales, uh, role these days? Like, what's the market like? I mean, obviously don't share anything, you know, secret, but just in general, what Was that like. I mean, I'm curious how you found candidates, what, what people's feelings were about.

Speaker B: Yeah.

Speaker C: AI company, being an sf, being in office, just like kind of all that great questions.

Speaker B: Um, yeah, we're starting a. As we've talked about here before, getting

Speaker C: an office and yeah, I don't think that's secret.

Speaker B: Yeah, yeah, we're, we're going to start some irl. Uh, um, you know, make that again to the point of like we need to osmos, like octave into some people. That's just going to be easier in person. But um, so what I'm hiring for right now is, you know, we are. I'm not trying to exactly copy what Clay is doing, but the like the notion of the go to market engineer as the sales and success person, I do think that maps very closely to like what we need, which is we are by and large a product LED motion. We need to drive people to our front door. They walk through the front door, we need to grab them by the collar. What are you doing, what's your stack, what's the motion, blah, blah, blah, and help them. So, um, hired a couple go to market engineers as the position. So you know what I was looking for there. Transparently it was kind of a challenge to find some people. You're looking for people with like, all right, I'm not looking for super experienced med pick enterprise sellers that, yeah, sure, like they have some attributes I want, but they also want to W2 a number that like I ain't got the business. You know, it's funny, it's like those are all my friends. You know that.

Speaker C: Um, sir, this is a startup, right?

Speaker B: I'd love to hire you but like, this ain't the like come make 600k a year sales job. Um, so you know, it was kind of a challenging profile where you're looking for kind of ops and some technical savviness mixed with some sales savviness and mixed with like, what am I truly optimizing for? Like I want grit and hustle, you know, like that is. That was like what I was kind of optimizing for, at least thus far. Like the, the people I'm looking for is, hey, if you are uh, you know, green on some of the sales acumen, like that's not as big of a concern. Like if you want to come into the office and grind with me and are excited about this modern stack and stitching tools together and really curious about sales, like, game on, let's go build. And so that's um, What I've been kind of optimizing for thus far. And, um, had some recruiting agencies help me out. Honestly, like, it was, you know, I couldn't. I couldn't do it all on my own. Um, but, um, yeah, I'm excited. We'll see. We'll see how it works. I think next year will be, like, starting to line up more of, like, what does a Octave Enterprise Motion look like? But really right now I just want to have a team that's optimized for onboarding, activation, success. Just, you know, I want everyone to feel like this is a company that we are honest, high integrity, we will tell you what we're great at, and we will tell you what we're not great at. And like, you can come here, you can get somebody on the phone, and like, that's, you know, I just want to build a team of people that are excited and hungry and savvy and like, want to build cool stuff and want to do that out in public and post about it on LinkedIn. And like, all those things I think is kind of like the, the modern playbook. So, I don't know, I feel like I'm just rambling on now, but, like, that's been, like, what I'm trying to optimize for. And, yeah, I found some people that I'm, I'm, um, excited about and interviewing some more.

Speaker C: Not rambling at all. It's a big topic.

Speaker B: Yeah.

Speaker A: What's, uh, that.

Speaker C: I said not rambling at all. It's a huge topic. I mean, you could talk about.

Speaker A: We talk about it for three hours.

Speaker B: Yeah, yeah, yeah.

Speaker A: Well, it's, It's a fun. I mean, I think the, um. I mean, we're all founders here. And I think one of the things that I've kind of realized, like, we are either, like, it's a really scary statement, but I think it's a true statement. Like, we are the biggest impediment to scale. Um, and if we can't get meaning, if we can't scale beyond ourselves, then, like, we don't have a viable business. And so, like, that's a, that's always a scary path, like scary season you're in, but, like, such a necessary one to say, like, hey, I need to delegate and empower a team so I can work on the business in the business kind of narrative. And, um, I think the way that you were just. Even the reps you just described make a lot of sense. And I was, I was trying to find my notes because I, I interviewed Jeremy Donovan, who Runs, uh, the sale or is a run it. But he's part of the center of Excellence for Insight Partners, and he has this framework for reps, uh, that. That he talks a lot about, which is icce. I'm probably going to butcher it because I'm trying to remember it's like intelligence, coaching, curiosity and like experience. But I think that's. I think I screwed up one of the Cs, because curiosity, coachability, to me are pretty similar. But there's just like this idea, like the type of rep that you're looking for, um, uh, kind of speaks to what you're talking about, like the humility of the grid and just like being able to attack. That's not looking for that high price tag. Those are the fun hires though, if you can find, you can really build.

Speaker B: Uh, we're still a pirate ship. You know, I'm looking for people to board the ship and hey, it's going to be messy and we're going to have fun, but it's going to be chaos and you have people that can thrive in that. And you know, I was like, I was pretty fearful, honestly, of like, okay, you know, like somebody that has like a depth of experience but has only done that at larger companies with the infrastructure and scale and brand and all those things. It's like, uh, ah, I'll. I'll optimize for green and somebody that's like, just been trying to grind it out at a bunch of places you haven't heard of because, like, I, I know what that's like, you know, like, that takes a different type of, uh. Yeah, just.

Speaker A: Just hustle I just found is it's actually not curiosity, which I love curiosity, by the way, but it's. It's, um, it's character. So it's intelligence, character, coachability and experience are kind of the big four that he talks a lot about. Now, what season, like, what season of your business obviously changes by what. How you index to what's most important. Yeah, I think I've realized too, like, where you were going with, um, it. I think it's so easy to be caught in, like, how we think and not realizing, like, there are different seasons of life and things that people want and like, what you're experiencing is like, they're. There's still that, like, profile of people that want to build, like, something special. And, uh, there's a guy named, uh, Horse Schultze who, you know, I, I guess I haven't even had my southbound hat on this whole time, guys, but he's speaking at, uh, there's a little plug for Southbound, but also we're talking about, there's Horse Schultze, who used to, uh, run the Ritz Carlton. Um, and one of these he talks about is like, if you think about the interview process, we think so much about the paycheck being the most important thing. But on a scale of like 1 to 10 of like, priorities for people, uh, pay is actually number seven. Um, so it's like way low on like the. Yes, it's a need. But really what motivates people, the number one thing is purpose. Uh, and so being able to invite people into a purpose that they can get excited about that's bigger than themselves is actually the number one thing that people want. Um, and so like, when you think about Octave or Outbounds, think to be how you're looking to build. It's like, how do we. It's something we talk a lot about. RP is like, how are you inviting them into something bigger than just what we do? Um, that will motivate people to want to come and then build their careers here. So, um, I'll get off my soapbox, but that is. I get very passionate about these topics.

Speaker B: Yeah, no, no, I, I, uh, I'm. I've been meditating. It. Meditating on this a lot lately because it's, you know, I feel like, yeah, we're about to like, cross that threshold and like, okay, like, we're starting to grow a team and culture up to this point has been a, uh, not an afterthought, but it's just like a. It is, you know, like, it is what it is. It's de facto and it's like, oh, we're now gonna like, start bringing in some new people. Like, we need to be thought, like, what. What are the norms? And like, why, you know, like, how do we. You know, like, I've been thinking a lot about. It's just like, okay, like, you know, Julian and I, like, we jump, like, if I see somebody ping us on Sunday morning on intercom, like, like, I'm on. You know, and it's like, oh, like, those are the things of, like, do I need to tell people that? Like, is that the written down expectation? Is that just the. I need to just live that out and show people and they mimic it and if they don't, then, uh, you know, I'm disappointed, but I have to share that, you know, Like, I don't know all these things. I've been like, thinking about it all. Lot of just like, okay, I need to be Very, very clear on, like, what my expectations are and what are not just mine. You know, it's like, what are. What are Octave's expectations? Like, we're, uh, we're all a servant to this. To your point. Like, the, the bigger purpose, the idea, like, let's turn this thing into something great, or we're. We're busting our hump for nothing, you know, so it's like, how do we. How do you really instill that in. In new people? Is something I've been thinking about a lot.

Speaker A: I love. Uh, well, this is probably another topic for another day, but I could even just show. Yeah, you're. I mean, you're codifying your ethos and the things that you guys. What you care about. Um, I could even share. Like, this is something that we. Oh, gosh, click up. So we call, like, our operating principles and like, we have our values and then like, the actions and behaviors associated with that. Um, so that, like, it's very clear what we expect from you and what you should expect from me. Um, there's a ton of stuff in here, but, like, this. These are the type of things that we spend a lot of time on the. And you're kind of that season of like, hey, what do we.

Speaker B: Yeah.

Speaker A: What do we, like, truly value? Not only just value from, but like, what are those actions and the behaviors we want from our people? Highly encourage. You do it.

Speaker B: Yeah.

Speaker A: Is a time suck. Yes. But like, we have an onboarding. I, uh, do like, three sessions with every new RPA we go through. That's like one of our sessions. And every week we go through a principle. And then it's like we. And then we have other ways that we gamify it and reward it, because what's rewarded is repeated. And so there's this whole. And I'd be happy to talk about it.

Speaker B: Uh, yeah, I might need to pick your way. Is this. I have to ask. Um, like on Slack, I see everybody's name has, like a appendage on it. Is that. Does that have to do with those, like, the ethos stuff?

Speaker A: Uh, it does and doesn't. We've. We've tried to figure out how. Because we're fully remote. Um, so, uh, we've tried to figure out, like, how do we, like, what are the personalities of our people? And it's like, how do we effectively communicate with one another and so that we have that context going into conversations. And so we've played around with those different, like, ways of. There's so many different tests that you can do, but that's what that one's about.

Speaker B: Okay, cool. I dig it.

Speaker C: You got one of them over your shoulder there and um, uh, Bluff.

Speaker A: Right.

Speaker C: I've seen Caleb at Super talk about that bottom line up front idea and it's a pretty interesting like I can say just from an outsider perspective I've seen Now with those RP's ideas being in super and seeing super people talking about them on LinkedIn and stuff like that, it does seem like um, what, you know, whatever those ideas are, it does seem like people are picking them up. And like Caleb has been pretty open about. He used to work for HubSpot, now he's at Super. He's been pretty open about like his. How he felt about that coming in and now how it affects how he works. And it seems like it's a pretty good um, I don't know, testimonial or something like that. I mean not, not to be too evangelical about it, but it's. That's kind of like how it feels a little like uh, like it has like a little kind of a. There's a strong cultural. Yeah, yeah, no, yeah, yeah. Your, your words, not mine.

Speaker A: I, I think the way that, the way that we try to frame it is that this is an invitation and it's like you either like buy in or you don't. So like either you opt in in terms of like the culture and the things that we care about or you don't. And it's perfectly fine if you don't. But like just know we want you to have complete visibility coming in that this is. This, these are the expectations. And I know that can be a powerful, uh, like powerful is the wrong word. But what's the right word? Expectations has like, like weight behind it, but it's intentional to have weight behind it because that's what. Yeah, so like that emblem, it has all our principles inside of it. Um, and super carries a lot of the same principles. But yeah, like bluff is a great example of. Well, we try to come up with this. What is the RP way? So there's like 40 principles that we have in total, but we said we don't. There's no way that every RP is going to know all 40 principles. But like what are the. They do these few things right, that if we do that well, it'll, it'll permeate other areas of the organization. And so like the RP Way statement is RP Will Bluff recap. Give um, Excuse me, an RP will Bluff. Use RP format recap. And give feedback to those who don't. And it's like, if we only do four things, those are the four things that we need our team to do. Um, and then that will kind of really set us apart. And so you've experienced the bluff. The bluff is like, how do we create an executive summary before we go into the details? And that was all inspired. I'm going to use a southbound plug here. Again, that's all inspired by, like, the Chick Fil A model. And regardless how you feel about Chick Fil? A, like, if you. If you go into a Chick Fil? A, uh, store, um, and I'm assuming you guys have Chick Fil A's around you. If you say thank you, do you. What do they respond with?

Speaker C: You're welcome.

Speaker A: Oh, gosh, guys. All right, next time you go Chick Fil A, just think about. They'll say, my pleasure. Um, and it's this idea, and that's actually from Horse Schultze, the guy we talked about earlier. But it's this idea, like, how do we go the second mile from a service perspective? And, like, they've ingrained it into every single Chick Fil A person. If, uh, they don't, they actually, like, give. They take them back to the kitchen and reprimand them. But it's like, hey, this is what the expectation is. Uh, and so then it's like, there are flowers on the table. They bring the food out to people. It's just. It's a way that they kind of capture that sentiment of the second mind. Uh, and so that's. That's what we're. We've tried to do on our side.

Speaker C: I love it. Do you guys ever watch? Remember Chappelle's Show?

Speaker B: Yeah.

Speaker C: It's like that. It's like the opposite of the pop copy skit. You remember that? It's like a. It's like a copy center where they don't care about service. Like, talk to the manager. I am the manager.

Speaker A: I'll get off my soapbox. I feel like I talked way too much in this one. But, uh, those are. Those are some things that I do get pretty passionate about. But, um, I know we're at Time, so as we wrap up, um, Harrison, final thoughts on your side?

Speaker C: No, things are. You know, I'm going to be posting on Breeze. We'll see what people come back with. I'm, uh.

Speaker A: I don't.

Speaker C: I don't want to say I'm a convert. That's a strong word, but I don't think I needed to be converted. I mean, I'm already pretty orange pilled, uh, run basically our entire company, and I've spent, I don't know, four or five years of my life focusing on HubSpot, so I think I'm already pretty much on board. But, uh, yeah, I'll be keeping. Keep an eye on that. So if you hear this and you're playing around with it, give me a holler because I think, um, I mean, it's just features we don't have to build. So if we can do this with AI and HubSpot, and we can have our engineers do other stuff, I'm pretty jazzed about that. So. Yeah, this.

Speaker A: Is this what you're trying to do to get a session at inbound conferences?

Speaker C: No, no, no. I don't get invited to those kinds of things. I'm just, uh, you know, I'm just a simple guy.

Speaker A: Well, my whole team got alternate, so, uh, we're a little salty, but that's just. That's how it always is for us. But you never. Yeah, I didn't.

Speaker C: I didn't even get that. I'm just. I'm just.

Speaker A: I'm just here.

Speaker C: I'm just a simple farmer just trying to, you know, help people log their emails. It ain't much, but it's honest work.

Speaker A: Zach, how about you?

Speaker B: Um, well, m. I made it without. Without puking or fainting. So I guess we'll, uh, we'll call this a success and live to fight another day.

Speaker C: Yeah. Some listeners just lost bets.

Speaker A: That's right. Well, feel better. Um, that. Keep us posted on breeze, and if you haven't, um, register for southbound, hopefully. I give you a few reasons to. Wednesday, May 21, Atlanta. We'd love to see you there. All right, guys, have a great rest of the week. I'll talk to you later.

Speaker B: See y'. All.

Speaker C: Thanks.

Speaker B: Bye.

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