About the speaker

With over a decade of experience, Bryan Ossa had the privilege of working alongside SMBs, SaaS startups, and agencies, helping them navigate the complexities of strategy, technology, and operations. Currently the Principle Technologist Partner at White Raven, Bryan also spend several years at HubSpot.

Mark Lerner:

Okay. All right, everybody. Welcome to this episode of the RevAmp podcast. My name is Mark Lerner. I’m the director of growth marketing here at DealHub. Super excited for today’s guest. We have Brian Ossa, who will be joining us. Brian and I chatted recently on a different podcast that I co-hosted, and we got into a pretty interesting conversation about the CRM ecosystem in general and the differences between the different ecosystems. And so before we jump into jumping further into that conversation, Brian, why don’t you introduce yourself to the folks at home, tell a little bit about yourself and what you’ve done and what you’re doing and how we got to have this conversation.

Bryan Ossa:

Heck yeah. Thanks for having me, Mark. I really appreciate it. For those of you who don’t know me, which is probably most of you, my name is Brian Ossa. As the title mentioned, I’m a partner at White Raven, but I also have my own consultancy and dabble in a few other businesses as well. My focus is very much on the intersection of strategy, operations, and technology. So essentially, taking the concept of revenue operations but applying it to a full-stack business cycle so you can really ensure that you’re aligning not just sales and marketing but also your technology, your it, your finance, and all of those other departments that live behind the scenes. And kind of got brought on today, as Mark mentioned, to dive into the whole CRM conversation ecosystem because it’s really been interesting the last couple of years. And I don’t know about you, mark, but the dichotomy is just, it’s so fascinating looking at HubSpot, who’s pushing so many updates a year, versus larger tools like Salesforce, who’s like every quarter and nothing but

Mark Lerner:

Right. Yeah, I think the juxtaposition has never been clear. Before we started recording, I wanted to let you know that I got into a LinkedIn conversation today because someone had pointed out that some of the tools, such as Salesforce, aren’t core CRM but are kind of integral to it. Some of those haven’t had any updates in nine releases, so that’ll be three years. And yeah, that’s pretty wild for a company that big, but I guess there’s this tradeoff, or at least there’s a conception of a trade-off that the larger a company becomes, the less innovative it becomes. The more friction there is, the more the top-down pressure makes it so that they’re not able to move as quickly. But in some ways, if we look at HubSpot over the last year, they’ve kind of been pushing back against that notion because we see just every day there’s a new, it’s wild. I haven’t really seen it. And you actually in a previous life worked at hubs, right?

Bryan Ossa:

Yeah, that’s correct. I was there until about a year and a half ago.

Mark Lerner:

And was the cadence of releases in the way they’re doing it now kind of the same, or is this a relatively new phenomenon?

Bryan Ossa:

It’s honestly accelerated quite dramatically even in the last 18 months. The last providing background context: I’ve been in the HubSpot ecosystem for five years after people started after they went live, and Dharmesh and Brian pushed this thing out to the world. So that was back in at this point, I think 2013. And so I’ve been using it for over a decade in different capacities. And today versus 10 years ago, let me tell you, it’s a big difference. But just that experience in the product release, it’s really flashing back to what things were like between seven and ten years ago where there was just so much happening all the time by the scrappy startup that’s just trying to make its own share in the world and carve out users who might be using some of these other tools that are more established. And answering your question. Yeah, I do think there’s been a significantly accelerated release pattern and I’ve been trying to figure out why and there’s speculation on it in different capacities.

I would love to hear your perspective on that matter because I’ve heard everything from you. We’re launching all of these things to make ourselves more marketable for the Google acquisition, which is no longer the case. We’re launching all these things so that we can compete against Salesforce and be on an enterprise tier, which also is a little bit different. We’ve changed leadership and restructured, and this is just the dynamic of HubSpot as it is today because we’re playing catch up or it’s something outside of that equation. And I have my thoughts, but what’s your perspective? I wonder.

Mark Lerner:

Yeah, I mean, to me, it does. These are pure vibes, but it feels like this is the buildup to something that requires a concerted effort. We have this roadmap, it needs to be in place by this time, and that seems to have been a forcing function for what we’re seeing. And then we’re speaking now in August; we’re recording this in the later part of August in 2024. And so we have less than a month till inbound. So it feels to me again, vibes that this is a lead-up to something that would be announced at Inbound. Last year’s inbound was all AI all the time, and there was a huge splash about it. And yes, there are a few pieces of AI that are like that, but it has not been the fundamental shift that it kind of seemed like. And so I suspect that won’t be the same this year, but my take is that it is partially a play to position itself to support enterprise.

Bryan Ossa:

And I think you have a good thought there and that’s one of my approaches in the thought that I had. But I think there’s something to be said about positioning themselves for where they want to be here in a couple of years, as well as trying to reconcile what the last two and a half to three years have been. If there’s one thing we’ve seen, it’s that the technology sector, particularly tools like HubSpot exploded during Covid and the dawn of remote that has since shifted quite dramatically over the last two years or so. And I know a lot of companies have really struggled to make heads or tails of that and recover from what all that looks like. So, I’m wondering if this is an attempt to regain the user base or make it more attractive for users to adopt the platform and just find new subscribers, particularly at the small business and the very small business stage.

Because if you look at the new seat pricing, it’s not necessarily always buy the package. You can get a service hub, you can get a sales hub at the pro level for individual seats. Now you don’t need to get the minimum seat count. That said, the point you mentioned about enterprise is also really interesting because everything that HubSpot releases has a trickle-down effect. It launches enterprise first and then it makes its way into pro and starter and then free over time. So where my head’s at is again, leaning into that play of wanting to adopt more of those early market folks. I think there are a lot of these products and features that are being released at the pro and enterprise level with the intention of being dropped down to these more accessible tiers probably within the next 12 to 18 months so that they continue to push for that early market adoption.

Mark Lerner:

Yeah, I think that’s a position I actually hadn’t considered, but it makes sense, and I think it’s a good counter to the way I was thinking about it. So, just to take a step back, I actually started working on a book, which takes all the conversations I had doing this podcast over the last year and kind of puts it into this is kind of the way we’re in a changing change environment. Here are the ways that some of the most interesting revenue leaders are adapting and changing. One of the things that has become clear is that when the status quo is really solidified, it becomes incredibly hard to move up. You have the head of the pack, and the barriers to crossing or catching up are just really, really solid when the ground largely

Bryan Ossa:

Looks like a pricing model where you’re going based off of what the competition’s doing.

Mark Lerner:

And there’s also, I think, a consumer or buyer mentality where it’s like, well, it’s Salesforce. We got to go with Salesforce, and we couldn’t even conceive. But when everything gets shaken up, the budgets are cut, and interest rates are wild, which makes this opportunity for people to capitalize on some of the chaos and gain ground. And I think HubSpot has done that, and to me, if they’re consciously capitalizing on this right now, would be very smart of them, which is like now is the time to zoom ahead because things, people are still trying to get their bearings. And so that’s what I see is happening.

The pricing model, as a hint, is interesting. I know that they made a change to the pricing model, and it has more support. One of the things it does is it’ll help a much smaller company leverage its more powerful aspects without having to purchase seats they won’t need. And that’s an interesting calculator argument to the one that says, well, this is really going after enterprise, but I think we’re kind of talking about the two big dogs as it were in the race, but it’s a pretty big ecosystem. You work with clients and things like that. How have you seen the ecosystem or the kind of market of CRMs proliferate over the last few years, and have the kind of upstarts become more palatable to people over that time?

Bryan Ossa:

Well, in all honesty, I think a big part of why HubSpot continues to do what they’re doing is also in tandem to the genesis of pseudo CRMs as they’re kind of being come to name, and when I say a pseudo crm, I’m talking like your bread and butter project management tools that are starting to incorporate a lot of CRM functionality.

Mark Lerner:

So, like monday.com and Air thing,

Bryan Ossa:

You look at Monday, you look at click up or Asana, all of them are starting to incorporate CRM features that are intended to streamline how you’re doing your operations. Honestly, it’s not a bad approach because there are so many companies that are going purely off of the operations and have CRMs only to maintain their client database. And if you can maintain your project management and your clients in one spot, what’s the need for having a third-party tool? It is the same market play that HubSpot decided to really push forward with back in 2017 when they really made the intention to expand and open out the different hubs instead of just being Marketing Hub, and the sales hub started launching out, service Hub had the proof of concept for operations hub, content hub came out, and everything else within it just expanded to fit one of those categories.

And so I think there’s this big rush to try and keep that market share because these other tools are finding ways to eek into the ecosystem, which is why, again, like we were talking about before the call, having conversations with someone who’s using Acton as a CRM, and if you haven’t used Acton, it is a marketing automation system by trade, and many folks probably haven’t heard of it. It is not that prevalent anymore. But if that’s still starting to become a tool that’s been recently adopted, that’s showing an interesting shift in dynamics because a tool you thought was maybe not getting as much traction as you thought is still out there,

Mark Lerner:

The blast from the past, so act on it back in, I don’t know, 2011, something like that. They were a big player. They were right up there with the HubSpot and Marketo. Marketo was the big

Bryan Ossa:

Dog. They were above HubSpot. No one had heard of HubSpot. It was all Marketo or Acton. And if you didn’t have anything, you kind of heard of this thing called Pardot and

Mark Lerner:

You probably pronounced it wrong and said Pardo.

Bryan Ossa:

Yeah, exactly. And honestly, I’m still probably pronouncing it wrong, but who cares?

Mark Lerner:

Yeah, this is the blast. In the past, I’ve used all those tools. So, I have experienced the apps Pardot and Marketo, and I still have nightmares about them. It’s hard to imagine someone using that. It is purely A CRM, but it does. There is a world in which it does make sense, for sure. There’s a world where things like when you think about A CRM, just purely the CRM, and I think we talked about this in our last podcast, it’s at its core, it’s a relational database that’s visual, right? It’s different objects and different fields that relate to different other objects.

Bryan Ossa:

It takes a spreadsheet and makes it pretty and accessible. Exactly.

Mark Lerner:

That’s all it does. And that’s at the core. But when we look at what things like HubSpot are doing and Salesforce in a lot of ways as well as we’re well beyond that, I mean, when we talk about custom objects as using it to the CMS to host dynamic webpages for real estate listings, we’ve gone way beyond what A CRM it

Bryan Ossa:

Jar gone to some people. And that’s fair.

Mark Lerner:

And so there was this movement for a very long time. It still exists, but I think it had a lot more steam, which was the kind of low code, no code thing where basically you build everything. You don’t have to code it, you just have a few tools that connect things together and you can build something. Databases like Airtable, Monday, and Google Sheets often became kind of the backend, and you were able to create whatever you wanted. And there was a time where I thought, you know what? Maybe that’s going to become the thing. And the concept of the headless CRM or whatever is going to take shape. I’m not feeling the momentum I once did, but I’m interested. We think there are a whole bunch of CRMs I haven’t really even come across before. One of them I think that focuses much more on the lower end of the market would be something like Zoho, who seem to have a very similar business strategy to HubSpot; they create lots of hubs, and I but dunno what their nomenclature for it is, and go horizontally and kind of take over an organization. Do you have a lot of experience dealing with that platform?

Bryan Ossa:

Yeah, I played a lot with Zoho and to some degree other ones that are kind of in that space like Pipedrive. Honestly, I disagree with your point about headless CRM. I think that’s why tools like HubSpot and Salesforce are continuing to push out. Well, HubSpot, in particular, is pushing out resources and features left. And because the dawn of gen AI tools has allowed people to really DIY whatever they want, assuming they’re able to articulate that effectively to the machine. And so you can take a tool like Monday and probably turn it into a marketing automation system with some robust campaign tracking just using that and MailChimp, all you really would need to do, and I’m not recommending or advocating for this, but realistically, all you need to do is say, Hey, I want to build this. You tell Zapier to do it. Zapier now has an AI that basically will build you an app based on what you tell it to do. You throw that into play, and then if you’re confused about where to plug things in, you hop onto a cloud or a chat GPT and ask it where to plug stuff in. And there you go. You set up a bi-directional sink in two hours, which would use to take probably a few weeks of complex time and effort to integrate. And yeah, it’s unbelievable.

Mark Lerner:

So I’ve gone down this rabbit hole of building internal tools where at the beginning it was a very clear vision and this would be great for everyone. I was thinking about my own use case. And then you get to the point where other people are starting to use it, and you get input, and they’re like, oh, we need this here and this here. And at a certain point you’re like, HubSpot did all of this pain already. You ever see that meme where it’s like the bell curve, and it’s like, oh,

Bryan Ossa:

I’m flashing back to the nineties meme of how to design a website.

Mark Lerner:

So, I am not familiar with that one. What’s kind of the overall,

Bryan Ossa:

Oh, the premise of it is, oh, what the client described, it’s this beautiful articulate site. And then over a time it just turns into glit, this glittery sparkled nightmare full of animated gif that just is so not what the client was asking for, and yet it’s what you deliver and then it doesn’t work and you should look it up. It’s pretty funny.

Mark Lerner:

Yeah, I think that’s kind of missing the final piece, which is that you realize you know what; you should have just stuck with the original thing. Yeah,

Bryan Ossa:

That’s exactly it.

Mark Lerner:

And so that’s kind of how it ends because once you have organization and other inputs, you realize that a lot of the stuff you hadn’t considered was already baked. They had lots of people thinking through this. And so you end up just going back to the platform thing, and I continuously find myself doing that in all sorts of stuff. But going back to the ecosystem and its CRMs, I think that there was always this conception that Salesforce was the default, especially at a certain size. There was really nothing else out there that you were going to consider. I think Microsoft has had some interesting challenges as well. So Microsoft Dynamics, we rarely talk about it, but they have gobbled up market share in a lot of industries where I think tech companies weren’t competing as hard, which, like manufacturing and some of the more kind of non-techie industries, you see a huge,

Bryan Ossa:

It’s all over banking.

Mark Lerner:

Yeah. Yes, as well. Yeah, because they have this very interesting model where it’s land and expand extreme. You start with the word, you end up with teams, and then you end up with this, and then all of a sudden, you might as well get dynamics, and then you might as well get all these other kinds of pieces to it. It has become an increasingly large ecosystem, which I think actually goes wider than HubSpot does. Focus on back office tools, Word document generation, and other things like that. And then maybe you and I also had this conversation where I think we kind of disagreed about what Google would’ve even done with HubSpot had they purchased it. My initial thing was, oh, well, the innovation cadence they have would just die. There’s no way that they could keep up that pace. But I think you met. It was you who made this point, which is that it allows HubSpot to connect to Google Workspace, which has all of those pieces. And so it really could take over a company entirely in the way that I think Microsoft has done as well.

Bryan Ossa:

And that’s exactly right, and I’m glad you brought that up because I think that you can use that Google versus Microsoft paradigm as a perfect example. When you start up a company, you’re going to adopt as many tools as you can to do everything you can for the least cost. And you’re probably not going to go with a Microsoft Suite because, bluntly, it has office features. You get Office Word and PowerPoint, which is great. And now that OneDrive exists, great, you have a cloud tool, but still, it’s not really as accessible if you don’t have that built into your system already versus I know Google’s a bit more accessible. Granted, Google overcomplicates the simple, but for 20 bucks a month, 15 bucks a month, you have everything you need to run a business plus an email. And that’s pretty powerful. And once you’re able to grow up large enough, you start realizing, okay, well, while this was really powerful and allowed me to go places quickly, you start running into all of that more corporate side of things, which is your IT security, your device moderation, as well as provisioning and everything that comes with the complexity of being a larger business.

And that’s where I think that we can see a similar parallel in that HubSpot had a lot of that, to begin with, where it’s like, okay, great. I can adopt as a small business, and it’ll get me about to, let’s call it 50 a r 50 million a r, sorry. And then once you get past that point, it’s like, all right, well I need to go enterprise now, and this just doesn’t cut it for me anymore. And so when you’re losing market share upstream, a lot of these tools are just trying to adapt for that more upstream so that you can get in sooner and stay there longer. And I think that’s the case with any of these tools that we’ve talked about. They want to get you as soon as they can and keep you as long as they can, which is why there are more and more tools and features that are, yes, they still have their product niche and their market fit, but they’re broader than that. A good example of that is looking at the motion calendar. It’s a fantastic AI-driven calendar that is pretty much trying to do that, plus project management, a meeting booking link, and, to a degree, SCRM. You kind of start thinking, why?

Mark Lerner:

Yeah, I mean, I would imagine that’s a way to raise more money. You have to be able to present a total addressable market to investors. That’s beyond the calendar thing. But there’s something valuable about having the best calendar thing in the world. There is a space for that. But I think that we shifted really, among other shifts that happened, the idea of these point solutions that were just the best in class for a very specific thing. That was a world we lived in for a while. And I think we have now entered the larger ecosystem world where there’s consolidation and fewer tools, less friction to expand those tools. And I think that’s to HubSpot’s benefit and Salesforce’s benefit in a lot of ways and to the detriment of much smaller solutions that are for a very small sliver of the workflow. Man, there are so many different ways I could take this conversation, but we’re actually kind of running up on time here Before we do end, you could tell the folks at home where maybe they can learn more about you or the work you’re doing or maybe just Absolutely. Yeah.

Bryan Ossa:

And this time definitely came up quickly, so I definitely appreciate you having me on. But yeah, more than happy to talk about this with anyone who’s interested. I’m available on LinkedIn. It’s pretty easy. I’m just glad LinkedIn RP Mosa works out really nicely. And the domain is the same thing, rpm o consulting.com. Feel free to reach out to me. And there’s plenty else that we’re doing in the ecosystem on the Let’s build side of things. So definitely look it up, and let’s build media. If you’re specifically interested in the HubSpot side of things, there’s a lot of fun stuff that we’re kind of developing up over there. And don’t forget about SP Rocketeer.

Mark Lerner:

Yes, Sprocketeer is for all the HubSpot folks out there. SP Sprocket here is a community of HubSpot admins helping each other, and it’s a lot of fun and a really great place, especially as we come up to inbound week at this point or Dreamforce week; they’re happening at the same time this year, which is again another interesting data point to consider. Yeah,

Bryan Ossa:

I wonder what that’s all about.

Mark Lerner:

Yeah, they were very, obviously, one week after the other. It seemed like there was kind of a decision that a smoke-filled backroom somewhere last year was about to do that. And I think this year they threw that to the wind, which again, I think is just another point to another kind of interesting data point about this head-to-head going on. Alright. But we’ll have to maybe continue this part two of this at some point in the future. But thank you so much, Brian, and thank everybody who joined today. We’ll check back in with you, maybe a little bit further down the road, to see if some of our predictions here today have come true.

Bryan Ossa:

Yeah, we’ll touch base after inbound. We’ll see what happens.