Shift & Thrive: CEO Insights on Driving Change

S&T_Scott Brown
===

[00:00:00]

Natalie Nathanson: Welcome to a special edition of The Shift and Thrive podcast, our new go to market miniseries. If you're a CEO or business leader wondering how your go-to-market strategy needs to evolve right now to meet today's market realities this episode's for you, we're going to explore hard earned go-to-market truths, what's working, what's not, and how smart companies are adapting their sales and marketing [00:01:00] strategies to drive real growth in today's environment.

And to kick things off, I am thrilled to welcome someone who's seen go to market from every angle. As an operator, a strategist, and now Venture Advisor, Scott Brown is a partner and head of platform and go-to market at Serve in Ventures, an early stage VC firm with around 50 companies in their portfolio, and a reputation for hands-on support and driving excellence.

Scott's career spans over two decades across enterprise tech from working with hypergrowth giants like Cisco and Google to early stage startups and AI companies. And today he works directly with founders to help them build and scale their go-to market engines, developing playbooks, aligning teams, and helping to diagnose what'll help them accelerate their growth.

All of which are topics I know will be top of mind to our listeners. Scott Brown, welcome to the show.

Scott Brown: Thank

you. It's a pleasure to be here, and thank you for such a wonderful, uh, introduction. I, I feel so honored.

Natalie Nathanson: I think your background is just so [00:02:00] interesting for the topics we're gonna be covering, and so I'm very excited to dive in and, you know, you've spent your career really helping companies build or, you know, retool their go to market engines. Uh, especially I presume in moments where something either has to fundamentally change or has to get put in place for the first time.

So to kick things off, I'd love if you could maybe talk about a go-to market strategy or change that you led, uh, that had meaningful impact on the business and maybe first chair, you know, what was happening in the business at the time, what took place, and then, uh, would love to dive into some of what you learned from that.

Scott Brown: Sure that's, that's a lot to cover, but uh, I'll do my best. You know, it was interesting you said that. I've seen it from all angles. Um, and

what's interesting

is there's always something new to

GMT20250522-165949_Recording_1280x720: So I

Scott Brown: think a good example of something I learned, uh, most recently, I was, uh, before joining Servant

Ventures was CMO of an early stage FinTech startup.

And the shift that we saw is I was working with a traditional, uh, chief revenue officer [00:03:00] who had a direct outbound sales motion for our deals. And we were working on securing private capital for, um, startups, essentially from institutional investors. So these are smaller, uh, companies who just don't know how to access private capital.

we were making that

accessible

to them through a more data-driven, uh, Process. And initially all the CRO wanted to do was outbound sales and deals were taking nine to 12 months to complete. They were huge deals, but it was very sporadic.

And

one of the things I noticed given my background, uh, coming from places like Google as I'm very data driven.

And I was looking at the numbers and that we had a lot of inbound leads coming in that the sales team wasn't pursuing qualifying. And those deals were much smaller. So the, the sales team and the CRO weren't as interested in them, and I could see that we had a lot of intense signals, uh, about those companies.

So they were doing things like uploading their financial data so we could actually see how, [00:04:00] uh, qualified they were for

getting institutionalized

capital. And I couldn't convince the, the CRO or the sales team to actually look at those inbound deals. 'cause literally they were a fraction. Of the size of these big whales, uh, that the, the sales team was pursuing ultimately through the data against, uh, the CEO and the CRO to give me a, a struggling ae who I think they were getting ready

to put

on a pip, uh, and exit out of

the organization

to have them focus just on these inbound deals.

And

lo and behold, we saw

a tremendous

kind of, uh. Progress on

those because

these are people who are looking for data or are looking

for financing.

We had data about them. They were highly qualified and so yes, they were a fraction of the size of our typical deal, but they were closing in weeks, not months.

Uh, and ultimately over probably about nine months, this led us

to shift

the entire

go to market

motion from primarily a direct outbound to an inbound product led growth. [00:05:00]

GMT20250522-165949_Recording_1280x720: And kind

Scott Brown: of channel partner strategy. And again, it was all kind of proven out through the data and created more of a high velocity sales motion than kind of the the motion that we had before.

Natalie Nathanson: Yeah, it sounds like a really, uh, kind of major, uh, shift for the business. And I know you talked about kind of data as, uh, kind of the key signal that you.

Scott Brown: mm-hmm.

Natalie Nathanson: Started you down that path. Uh, were there other things that you were thinking about as you were making that, uh, decision? Did you have any concerns about kinda was this the right move?

Uh, what was kind of, what else was going on for you in, in that

Scott Brown: You hopefully always

have concerns, right? Because you're always kind of trying to read the tea leaves and try to figure out with an imperfect view on what's happening, what your best path

GMT20250522-165949_Recording_1280x720: is. so

Scott Brown: for me, and I think

for the

rest of

the team,

it was really around a test and iterate model.

Like, let's come up with a hypothesis. Let's see what's happening. Let's run a, a rational controlled experiment to see [00:06:00] if we get the results we expected. Right. And then if that plays out,

okay, great. Let's

add a little bit more. And at a certain point you can't just keep doing experiments. And then it was, okay, we're gonna go all in on this.

Um, and interestingly enough, in this situation, um, this, that was

a situation

that the CRO, the existing CRO didn't really want to be part of. And so, uh, they ended up exiting and we brought in a new CRO who is a little bit more, uh, focused on all the different. Lead Sources and the ability to kind of manage a portfolio versus a single go to market motion.

And that's when things really started to accelerate for the business.

GMT20250522-165949_Recording_1280x720: Yeah,

Natalie Nathanson: I would imagine that was a much more complex, uh, you know, go to market to, to manage between those different, uh, elements. Can you talk about kinda what went into the kind of product-led growth, uh, component? What were some of those early building blocks to put in place?

Scott Brown: Yeah, so we were lucky enough that our whole, um, product or offering, um, [00:07:00] revolved around startups and small businesses uploading their financial and customer data into our system where we could then, um, go through and kind of analyze and standardize all the information and essentially give them like almost like a credit score.

Um, But it was more for an investability, uh, uh, how investible the company was. So we had all that on the

back end. That

was our core product. What we really did in conjunction with product

was exposing

some of that and making it easier for these companies

to put

bite-sized amounts of information in.

So

actually one of the first PLG kind

of things

we implemented was a simple kind of cost of equity calculator.

where People could go in and put in four or five data points and get a sense of what could I raise?

Right.

So it started the conversation with them where they didn't have

to go and

upload everything and, you know, do all of this work, but we could begin to, uh, answer small questions that led them to the final answer.

And it also, frankly, then [00:08:00] gave us some insight on is this a qualified company or not?

And

that helped us with our lead scoring and prioritization. Then.

Natalie Nathanson: I

think things like that can be so helpful. I even think like more on the demand gen side, like ROI calculators and, and different things like. That which, you know, take longer to create than let's say, you know, a, a downloadable white paper or ebook or something like that. But they can drive such a good engagement.

Um, and to your point, like also some of that early qualification that you're kind of hitting multiple birds with one stone with those kinds of thinking.

Scott Brown: Yeah, I mean, one of my personal philosophies is really the focus of marketing should be around creating

a conversation or a

dialogue with that customer, right?

And so those kinds of tools or calculators are great, give and get models where you're providing some value to them. It's not just like a static ebook or a white paper or something that does have value, but you're creating a conversation a back and forth. Where in our instance, you know, when the

company [00:09:00] provided

some initial information, we could say, oh, looks like you might be qualified for these types of financing vehicles. Do you know anything about venture debt, venture capital? You know, and you kind of list out all the different financing vehicles for them because inevitably these folks are like, no, I had no idea there were all these options. Can you tell me more?

Well,

sure. Like now here's your, your, your ebook, or would you like to talk to a salesperson to learn more?

So I really think it's how do you create those touch points that have the back and

GMT20250522-165949_Recording_1280x720: forth with the customer.

Natalie Nathanson: Yeah. Yeah. Well, and I'm glad you brought up that, uh, kind of the dialogue and the conversation that. Needs to happen. And I think, you know, there's been a lot of conversations, not, not too new, but you know, about ungating content and how much do you ungate, um, and kinda how do you drive those kinds of genuine, uh, interactions and right, like the true of like inbound, uh, philosophy.

Uh, but I know it can feel scary for, uh, for folks to say, okay, well if we're not gonna get our leads from, you know, our white papers, what's gonna [00:10:00] happen? Uh.

GMT20250522-165949_Recording_1280x720: yeah,

Natalie Nathanson: But you know, I'm guilt. I've been guilty of that too. Uh, they'll have come around, um.

Scott Brown: I'm just hoping you don't ask me for an answer to this question because I think this is a really tough one.

Um,

and I think it's unique for every company to try to assess, but I think this is where, I. marketers, CEOs, salespeople really need to sit down and look at the holistic customer journey and really

figure out like what assets or conversations do I need to have

with somebody

on that kind of multi-stage process to getting to a sale. And I think in general, the more that you can ungate things earlier in the process so that you reduce the friction of people learning more, engaging that dialogue, seeing if this really like meets their needs. 'cause at some point you need them to raise their hand and say, yeah, go ahead

and call

me, or I'd like to talk to somebody.

And I think that that's, you know, you still have to gate that at some point, but it's like [00:11:00] figuring out in your journey where that's most appropriate.

Natalie Nathanson: Right, right. Yeah, I would agree. Like it really does have to be a business decision, um, kind of weighing out the different benefits, like the different places to use it. Uh, and then if you are looking at some of those things that drive kinda a greater, more authentic engagement, like be in a position to back it up, right?

So you, you offer a, you know, a consultation following, let's say, kinda some of that data that you were talking about. Uh, you need to have the right people then available, willing to do that, and no, uh, kind of bait and switch type of approaches.

Scott Brown: Yeah. Yeah. Well, and you're always gonna have to have that

conversation with

the sales

lead because

there's kind of a natural tension, you know, again, depending on your sales motion. But my last company, you know, the salespeople didn't wanna deal with or look at any leads

that we didn't

have all the information about a person

or

a

company.

And that just introduces too much friction early on. Right? And so that's actually part of the thinking that led to more of

this PLG motion.

And it's like, okay, well if you need more information

to feel

comfortable [00:12:00] about reaching out to this person. How can we collect a bit more, again, directionally that says, oh, this is actually qualified.

Right? So again, looking at the broader journey, because I think it's, it's far too easy for sales, marketing, and many times customer success on the post transaction side to operate in their side silo

and

know, okay, I've got these checklists and these to do items, and they don't think more broadly. Okay, what does the customer need to hear and do at any certain point?

Natalie Nathanson: Yeah. Yeah,

for sure.

Well, and I'm, I'm glad you brought up, uh, customer success because, uh, in our last conversation you kind of brought that up and in a way that really stood out to me is, you know, how few early stage companies really like build their go to market, uh, with kind of retained revenue as a component.

Um, so wanted to ask you, you know, what have you experienced there and kind of why do you think that, uh, that disconnect exists?

Scott Brown: I really don't, um, have a great answer for you. It's, um, [00:13:00] the discussion that we had really came apparent to me as I was helping

some of our portfolio

companies

with their

annual planning this year.

And what I noticed is there was a lot of

focus and a

lot of, uh, certainty and clarity around the sales and marketing process. Essentially the acquisition side of revenue. But people tended to not include in their annual planning or just kind of quickly, you know, enter a one-liner about what they were gonna do from the expansion and retention side,

which

once I saw that across three or four companies, it was suddenly like, wait a minute.

Why are we not spending more time and effort understanding the retention side? Since we all know it's far more effective and efficient to retain and expand a customer you already know and have a relationship with than to go get a new one. And I have to admit, I've been out talking to smart experts like yourself, like trying to figure out like

why is

it that, especially in early

stage customer

success doesn't get the attention that it deserves.

And there's a. Number of different factors that could be in [00:14:00] there. You know, it's typically that's not where founders, uh, focus or they've had a lot of experience from, they tend to hire a more junior, kind of like customer support person versus customer success who's just really focused on like break fix or onboarding or things like that.

And not necessarily the relationship management side of cs. Um, but ultimately, um, from

a structural

view, I still think we have an issue that, um, sales, marketing

and CS

aren't always on the same technological systems. They don't use the same language and they don't talk about the same kind of customer journey, which is, which is really unfortunate because I think going forward the entire go-to market team, the acquisition and the retention side needs to be fully aligned and on the

same

page.

GMT20250522-165949_Recording_1280x720: Mm-hmm.

Natalie Nathanson: I think you touched on a lot of the areas that, you know, I've experienced, and you said small companies, but I think, you know, I know some big companies that struggle with this just the same, [00:15:00] I think because they have more, uh, kind of manpower. Um, you know, on the marketing side, there must be, might be kind of a customer marketing person or department or, or whatnot.

Um, but that misalignment of incentives, uh, can be just as challenging. And I was talking to, uh, someone that's at a kind of a big enterprise software company with, you know, tens of thousands of employees, um, that is experiencing a lot of churn and it's not as much because of the product. Um, it's kind of lack of connection between the renewals team, sales, engineering, and definitely kinda marketing kinda off to the side in

that. Um, and so it's, it's such a, such a big opportunity, but I think a lot of it is like, what, what you said, if there's junior people, they might be thinking of kind of more of a check the box kind of moment rather than like feeling like they're really in it with the salespeople, with the sales engineering team around kinda customer behaviors and then, uh, kind of on a customer client by client basis.

And then what do you have to do programmatically and [00:16:00] organizationally?

Scott Brown: Mm-hmm.

GMT20250522-165949_Recording_1280x720: Mm-hmm.

Scott Brown: And, you know, you've

talked to a lot of founders,

and

and CEOs and leadership teams.

Like

For you? What's the, what's the signal or the kind

of red

flag that actually makes somebody pay attention to the customer success side and actually say, oh, this is now when we

need to

invest.

Have you noticed any common threads on

that?

Natalie Nathanson: Yeah, I mean I think unfortunately it's usually noticed when it's, when it is too late. So when

you kind of see

the churn numbers going up or you're not hitting your sale, you know, new business numbers or revenue numbers in general. And then, okay, like what are the different levers we have, uh, to push and pull?

Um, I think there's an element that you get, especially at a early stage company, you get such a collective, like adrenaline hit from kind of the, the new logos. And knowing that you, you need those, that that can, you know, sometimes come at the expense, uh, of, uh, the kind of existing, uh, you know, existing.

Business. Um, and then I think [00:17:00] sometimes just a lack of understanding of what are the things that, uh, people outside of sales or outside of customer success can be doing programmatically, and what is the role that, like marketing can play, uh, in that to alleviate some of the kinda heavy lift or look for those early signals.

But I think having a bigger, uh, focus on those leading indicators, uh, versus just the lagging ones is really kinda what needs to happen.

Scott Brown: Yeah, I,

I know, I think you're spot on because it seems like you don't focus on customer success until it's a problem, and at that point it's too late, right? Um, I mean, yes, you can kind of cl something together and make it work, but just think how much more effective

you could

be if you actually laid that foundation early on.

Actually had sales, marketing, and CS at least talking the same language, right? So that to your point, you can identify those leading indicators of potential churn or risk, or even product efficiencies earlier on, [00:18:00] and kind of approach it from a unified go-to market perspective.

Natalie Nathanson: Yeah.

Yeah. I will say we have one client, um, that's done a phenomenal job with this. It's a services based business, so not a, not a SaaS company. Um, but they, uh, really invested. In making sure that, you know, sales, marketing, and customer success, we're all kind of under the same umbrella, all working towards the same goals.

Um, and it's a small team, so it's easier to do, um, but really like, have felt that benefit of everyone rowing in the same direction. Um, which, you know, I think that comes from, from the leadership. So I attribute the, you know, the CEO's, uh, head of mindset, uh,

and how he has, uh, aligned everyone to the success there.

Scott Brown: Yeah. I think it's that evolution. 'cause I've been in large companies like the Cisco, Googles, and Facebooks of the world that had amazing customer success teams.

And I've been, you know, most recently working with very early stage startups who don't even have somebody in that function. It's that gap of somewhere in the middle, the light bulb [00:19:00] goes off for somebody that like, we need to make this work. And I think the really successful ones are the ones who, again, approach it not just from a, we need, uh, this silo of customer success to, to work more efficiently.

And they take that more broader like customer view of how do we make the entire lifecycle more valuable for our customers.

Natalie Nathanson: Yes. Yes, definitely. Um, so Scott, I'd love to shift gears a bit. We're talking about some of those kind of strong foundations for a go to market strategy. We know that the way strategies are executed these days are evolving fast, especially with. AI and how it's, uh, reshaping how we kind of build, test, scale, go to market efforts.

Um, and I think there's people all over the map from leaders still trying to figure out kind of what is this and what do I do with it? Others who have it embedded more deeply, uh, we know it's a moving target. Uh, as you learn kind of the technologies in their current state, they look different a, a week or a [00:20:00] month down the line.

Um, but wanted to hear kinda what's your experience been with kinda AI's impact, um, and I guess kind of mostly generative ai, but we can speak more broadly. Uh, how has it improved, like either your team's efforts or portfolio company, if you have any examples there. Um.

GMT20250522-165949_Recording_1280x720: Yeah,

Scott Brown: so I'm surprised it took us this long to talk about AI since it's like, you know, the,

GMT20250522-165949_Recording_1280x720: du jour. Um.

Scott Brown: Look, I think we're ver, we're still at the very early stages of ai. I think we can all acknowledge this. This will be transformative not only at a like individual workflow level, but at an organizational level.

And I don't think we truly understand how much more efficient and effective these technologies will make us. In the future. Now, I would say a lot of this is still, you know, being ha it's still being baked. Uh, 'cause to your point, the technology's evolving. We're figuring out how to use it. Um, people are adjusting their workflows.

Um, so in marketing [00:21:00] specifically, I've seen a lot of, uh, my team, I. The teams I work with are using AI a lot for kind of the market

research, research,

uh, side of things and just exploring new ideas, making sure that they, um, aren't just filtering out based off

their own

experience opportunities that could be really valuable.

And then I'm seeing a lot of use in generative. AI content development side

of things,

either by helping, you know, co-pilot in terms of writing materials or sequences or things like that, or creating derivative works. So taking a video like this, repackaging it into a blog

post, repackaging

in a three social media posts, things like that.

And that seems to be where, um, I'd say the most value has come from recently. Where I think we're going next and what I haven't seen quite yet is kinda the orchestration, especially on the go-to-market side, how do I get strategy, [00:22:00] content development and distribution to all work together? Um, because I think the strategy and distribution side are still fairly manual processes today because you need a human to have that insight, that intuition, um, to put together the strategy to target the right audience.

Yes, they can really benefit from having the AI Companion help them build all that content, but then deciding how and where to distribute those assets and messages is, I still think, you know, the realm of the human today.

Natalie Nathanson: Yeah. Um, I, I agree with that, like the disparate systems and, uh, you know, there's the, the orchestration piece being an important one to, uh, to look at. I think if you think of how many times people are still like copy pasting things

or even with. Systems that have existed for a while, uh, not very well or fully integrated.

It feels like we still have a long way to go and things [00:23:00] that are very possible and feasible with, uh, kind of technologies that have been around for a while, um, but seem to still get hung up in those places. Um. So I think when it, as it happens and as it continues to evolve, it'll, it'll happen uh, very quickly.

Uh, but also understanding the risks and the more of these, uh, kind of orchestration and workflows that you have, the more room there is to miss that something in there wasn't right. And I think we

talked about

this a little bit, uh, when we spoke before. Is making sure you get the right foundations in place because AI is a force multiplier, but if you're pointing it in the wrong direction, you might be accelerating something that, uh, is broken and you might not even know it as as quickly.

So I think there's some some big risks there as well.

GMT20250522-165949_Recording_1280x720: well.

Scott Brown: You, right?

I mean, I think it comes down to, when I talk to my portfolio

company leaders,

especially the CEOs who are like, I wanna, I wanna have a marketing team of one.

I want an

AI agent to do everything. And it's like. Okay, [00:24:00] what are you really trying to do?

Like what's the job to be done that you're trying to use an AI tool to either automate or make more efficient? Right. And I think it's getting down to those kind of fundamentals of like really like

thinking about your

business and re-engineering the process and workflows you have to leverage the tools of today. So the, the story that you alluded to that we were kinda laughing about earlier was I was working with a portfolio company whose email deliver deliverability for outbound sales, like plummeted. They were going through all sorts of efforts trying to figure out why they rewrote all their sequences. They came up with new assets.

They spent all of these weeks like using fancy tools

to like

optimize the flow and they're doing all this and I just it, something didn't seem right,

so

I just started following back the thread and found that at a basic level, somebody had

screwed up the

email authentication protocols on their DNS settings.

Super basic [00:25:00] stuff.

If

you don't have those in place, all the big email providers will throw your email to, to spam and junk. So what had happened is somebody in it had made a typing mistake on the DNS settings, and suddenly all the marketing programs, you know, got cut in

half.

And here the marketing and sales teams had spent all this time and effort using fancy tools, trying to rework things when it was really more of a

foundational effort

or a foundational issue that nobody.

It Took

the time

to think about

because they

were so focused on using these new tools. And so every, every problem looks like a nail now. 'cause people have the hammer of AI and they're just looking to

use it.

Natalie Nathanson: Yeah, I mean, I think that example just shows the kind of detective work that you have to do. Um. To figure out kind of what's not working. There's also a chance that they wouldn't have been caught if maybe something else in the campaign, maybe personalization or something like that had created a [00:26:00] counterbalance where that had gotten better than average results.

That you don't know that there's something broken that's actually holding back a campaign from being more successful. So I think understanding that like this, it can be something in the systems, like the kind of technical backend, like that example. It can be the messaging, it can be, you know, a personalized campaign like fall that fell flat.

It can be going back to the ICP might not have been right. Um, so, so many different places you need to look. I.

GMT20250522-165949_Recording_1280x720: Yeah.

Scott Brown: I actually worry about the next generation of marketers

GMT20250522-165949_Recording_1280x720: in particular

Scott Brown: won't have had to kind of work through the trenches and beat their head against the wall, like learning a lot of these

manual processes

and.

seeing like,

oh, If I do x, Y happens, or, oh, I should go take a look at these things. I mean, the reason I went to look at the email authentication protocols is I worked for a startup once that was put on the email blacklist for spam. Because they didn't have these things, right? And so I knew like, and I knew how [00:27:00] difficult it was to get off those lists. It's like, oh, let's make sure that those foundational elements are in place. But the next generation of marketers, if they start at the very top with these AI tools and they just input something and they get an answer back, and don't necessarily kind of dig more deeply to figure out why is it saying that, uh, I don't know what's gonna happen in the long term.

Natalie Nathanson: I

think there's such big implications. I've had maybe, you know, three or four discussions this week alone on this kind of a topic is, uh, you know, how do you invest in kinda the younger generation, the people early in their careers so that they can kind of learn the ropes? And I think it's, I. The using an AI and automation and all of that puts a greater onus on each person that is kinda orchestrating to have a more critical eye to look at kind of all the details.

And, you know, you have something that looks or sounds good. It's hard to, you know, for someone to have a discerning eye when they maybe don't know what good looks like [00:28:00] or don't have kind of the, the years of, uh, of experience to kinda couch that into.

Scott Brown: Yeah, I mean a saying along those lines that, uh, CRO in our portfolio company, uh, told me about a year ago when everybody was starting to implement all the AI tools.

He is like, I asked him like, Hey, are you excited to give this to your team? And he's like, I am really excited to give this to my top 1% of sellers and I am deathly afraid to give it to the 99% of the others, um, because I don't know that they will know how to use it well. I actually think that they

could destroy

value and irritate customers because they're not thinking through, how do I use

this tool to enhance

my selling capabilities, not just do it for me? And I think that as

like

business leaders, that's something that we're all gonna have to really watch for is making sure that we're just not outsourcing to ai, but actually using it to enhance all of our existing capabilities.[00:29:00]

Natalie Nathanson: I think that's a really powerful, uh, way that, uh, that person. Articulated that because as soon as you started saying it, I could completely, uh, kinda appreciate and internalize what, uh, what that person was, you know, was, was thinking about and think it's spot on.

Scott Brown: You must have been on the receiving end of some poor sales interactions at some point in your career to, to know like what could happen if you armed somebody with even more tools?

GMT20250522-165949_Recording_1280x720: Yep.

Natalie Nathanson: Yep. Unfortunately, throughout my career, uh, but I think now, right, we see some of these like AI personalization. Campaigns and, uh, they could really fall flat. Uh, I actually had a funny story about one of those, like an AI gone wrong. Uh, it was a colleague of mine, um, they got a personalized email, I think from her supermarket or something, and it was, Hey, like, it's your birthday.

We thought you would love this. And then you could tell that that thing that was generated, um, and it said, baby carrots, like, here's your, here's your treat for your birthday. Some baby carrots. Um, and it must have been something that, you know, in her, in [00:30:00] her shopping history, but not exactly the birthdate treat that she was looking for.

Scott Brown: Right.

Natalie Nathanson: so it was more funny than kind of a, a terrible, like pr, you know, PR fail. Uh, but you know, those are, those are happening too.

Scott Brown: Well, absolutely, and that's why, especially in these early days, it's so important to keep the human in the loop and do kind of like what I talked about doing at my last, um, startup job is like the test and iterate model.

right? Like, don't just turn on an AI chat bot and send it out into the wild, like, do selective tests. Make sure you really, I mean, honestly, you

should spend

as much, if not more time training your AI as you would a new human employee. right? Because first of all, in that training process, you're gonna probably learn a lot about your organization and your existing processes, but also like this is now going to be your brand representative to the world or your internal teams or however,

using that,

that ai, let's make sure it's accurate [00:31:00] and actually again, enhances the interaction, not destroys value.

GMT20250522-165949_Recording_1280x720: Mm-hmm.

Natalie Nathanson: I think it's a good proxy for someone to think about and even when early in the chat GBT days, someone had said, you know, talk to, talk to it. Like you talked to kind of an intern or someone, right? Someone kind of new coming in. Um, and I think that has definitely been like an easy, uh, kind of rule of thumb to give to others who are just getting started in that process.

Scott Brown: Yeah. And then ultimately, you know, once we get through this first phase and you know, I kind of look at, like the chief MarTech, um. I think a Chief MarTech officer report where they have the 20,000 different MarTech systems that are out in the market today. Like if you think about each one of those point solutions, uses a slightly different data definition workflow, like you name it, it's proprietary to them.

So the distribution side is still really tough. right? Because it's taking a human to do that kind of, um, intelligent copy

and pasting

into all those [00:32:00] different systems. Ultimately that's gonna change in the long run, uh, especially as AI agents

become more

fully functional and can like actually figure out what's going on.

But until that point, you really need to have the human in the loop.

GMT20250522-165949_Recording_1280x720: Yeah.

Natalie Nathanson: I'm curious, before I move off of the AI topic, I'm curious of your personal use. Is there something that, uh, you know, whether personal or business that has been, uh, kind of most interesting or fun or, uh, kinda valuable, uh, to your own work?

Scott Brown: Oh, so many different options. I mean, I use, um, I use chat GPTA lot, uh, again as like a writing copilot to help me kind of refine and make sure that I'm thinking about all the different things, um, that all the different points or information I wanna provide. The image generation stuff is

great.

But, um, truly where it probably has the most value in my day to day is just the data enrichment

we do,

[00:33:00] um, both with our existing portfolio companies as well as we source new deals.

So things that, you know, I used to have to put

a human

analyst on and it would take a couple days for them to sort through

all

the PitchBook and Crunchbase and filings and all this stuff. Now you can literally put into one of our AI tools and start to. Not only get information and and insights very quickly, but have a conversation.

Back to our point about treating it like an intern is, having a conversation with that data is like, oh, that's interesting. Tell me more about X, Y, Z, or what about this aspect of the business? Uh, and it just accelerated the process.

Natalie Nathanson: Yeah, I like that. It's just so many examples like that from so many different places that it can have such a big impact. Things that we now take for granted as, oh, this is a simple thing, was going to be my comment, but realized a few years ago that didn't exist. Right? So I.

Scott Brown: Right.

and I mean,

even down to vacation planning, like we couldn't figure out what we were doing as a family. And so I just [00:34:00] put a prompt in the chat.

gave it all the parameters, the budget, uh, the schools, uh, timeline for when the kids were outta school and everything. And just said like, Hey, if you've got seven days to go to these four places, what would

you do?

GMT20250522-165949_Recording_1280x720: do?

Scott Brown: And Give me specifics. Right. And it just accelerated that whole research process rather than like sitting down, you know, for weeks reading magazines and books and talking to people.

It was like we had four options to discuss as a family.

GMT20250522-165949_Recording_1280x720: Yeah,

Natalie Nathanson: I love that I had a similar one, uh, last weekend where, uh, my son is, uh, in fifth grade, so he is finishing elementary school and there's all the kinda year end. Uh, activities including distributing lawn signs to all the families of fifth graders to say, Hey, congrats to our graduates. Uh, so I was one of the parents that was gonna, had a stack of, uh, of names to, uh, to drive around and, and drop off the lawn signs.

And I asked Chachi, BT, I said, here are the addresses. Uh, tell me kinda the best way to go. So it was root optimization, right? [00:35:00] Um, little things like that, but it's that kind of mindset of, you know, how can you use this differently?

Scott Brown: That is fantastic. Um, I definitely

am gonna

steal that and try to, to use that myself. I mean, I will make, I like to cook. I have also been known to pull up chat GPT and say, here's what's in the refrigerator, what can I make with this? Um, and again, it's like,

Is

AI gonna cook it for me? No. But like having it say, oh, did you think about these three different.

Recipes was actually really helpful 'cause it's like, okay, great. Now I don't have to actually put into the thought or cook the same old thing that I always

do.

Natalie Nathanson: Yeah. Uh, Chachi, BT actually is my. My favorite, uh, cooking partner because I too love to cook and I, you know, you've always liked to look at a recipe, but then not kind of come back to it to use it for inspiration and then kind of go and do my own thing. And I find that that works really well with Chachi.

Bt similar to what you're saying, like, here are my ingredients, here's the kind of general direction I'm [00:36:00] thinking. Um, like, what are some ideas or, you know, what do I do with this? One ingredient or, you know, things of that nature. So it's, it's a lot of fun and kinda that blend of bring in some new expertise and information, but then, uh, human creativity on top of that.

Scott Brown: I mean, you've just taken my example to the next level, and again, I'm gonna steal all

GMT20250522-165949_Recording_1280x720: of your expertise and do this, but I think,

Scott Brown: you know, this is a great reminder

for like

all your listeners and the founders and CEOs, you just have to get out there and talk to people about like, how are they using ai?

What has worked, what has not? Because we're still in the very formative stages of all this. And again, we know it will be transformational, but is that gonna be next week or is it really gonna be three to five years from now?

Like

It's still unknown. It's still valuable today, but it can always be better

GMT20250522-165949_Recording_1280x720: and,

Natalie Nathanson: Uh, I couldn't agree more. Um, I, I could talk about AI all day long. Uh,

I would love to, um, get into some other topics [00:37:00] though with you. 'cause I know you have a lot of, uh, expertise to share. So thought we could talk a little bit about, uh, alignment, uh, usually talk about sales and marketing alignment. But I think given, uh, what I know your experience has been, I think looping customer success, uh, into that fold as well as important.

Um, so, you know, tell me about, you know, how do you, how do you think about this and uh, what do you see working well in today's environments?

Scott Brown: So I think, you know, there's been a lot of discussion and a lot of work then that's been put into sales and marketing alignment and

I think,

um, that's a great conversation to have at an industry level.

I think ultimately it comes down to individuals you literally need to have the CRO and CMO or, or whoever the, the leadership level you have, and those functions really be connected at the, at the hip and know that they are mutually responsible for each other's success. 'cause this whole finger pointing on sales and marketing just needs to [00:38:00] go away.

Like you're both revenue generating teams, you're supporting each other in very different ways. Like you just need to, to work together. Um, most recently, as we kind of talked about, like I increasingly realized the customer success folks have been left outta that conversation, and I'm still trying to figure out why.

Or how to get those

customer success

people like a, an equal seat at the table. Um, and so there's been some interesting, um, ideas and whatnot thrown around about like, Hey, do we actually need to have now the go to market function report to somebody like A COO who

can

implement a common operational framework and data model and everything else to force the teams to work together?

Or how do you, you know, make sure that that three-headed monster actually is working, uh, together. Um, and ordinarily, you know, a lot of people will say, oh, that's the CROs responsibility. Um, I would [00:39:00] agree if the CRO was truly a CRO, but most CROs that I engage with are frankly just chief sales officers and they will always come back to that sales.

First mentality

and

not create a big enough sandbox for all three functions to work together.

Natalie Nathanson: Yeah, uh, I've had that similar experience with CROs and I think, you know, I've worked with some fantastic, uh, very talented CROs, but the reality is they usually have the sales background. You're lucky if they have some, like hands-on marketing experience, but in my experience, usually I. Not. And so I think that does a disservice to the organization, um, right.

Have, if it is a CRO, like have them own the revenue, uh, but make sure that the narrative, the positioning, kinda some of those other strategic areas are, uh, being led, uh, led elsewhere. Uh, but I like your thinking around, is it kind of the COO or kind of a more, uh, uh, objective, uh, [00:40:00] unbiased, uh, third, you know, third party, so to speak.

That's, uh, that's looking at that.

GMT20250522-165949_Recording_1280x720: Yeah,

Scott Brown: and I mean, there is a trend, um, or at least you know, a few data points out there where companies

are.

appointing chief market officers, um, not marketing the act of, but actually somebody who has to take that more holistic, um, perspective across sales, marketing, and cs, um, whatever the title is.

Ultimately, I think it comes down to a lot to the organizational design and individual. Who can, to your point, span all these different perspectives and, and do more portfolio management, right? Like, okay, if this is the entirety of the ecosystem, how much effort and investment do we need to put on the acquisition side of the pipeline versus the retention?

And how do I, you know, balance all of this to achieve the most efficient growth, rather than having three different functions, kind of operating a [00:41:00] little bit in their own silos.

Natalie Nathanson: Yeah, I think that chief market officer getting my wheels turning a bit. I'm curious in what kind of environments you've seen that, is it kind of smaller startups being creative and thinking of that from the start? Is it larger companies that, have you been through the, the pains of not having that alignment?

Where are you seeing that?

Scott Brown: Um, I

don't know that there's enough data points that I've seen to really call a through line, but I think it's almost like the mid-sized growth companies, so call it your series C and d later, um, companies on the, the tech startup side where they're scaling rapidly.

Kind of going back to your introduction. It's like they either need know, they need

to retool what

they've been doing

to continue

growing or they need to build something. And in that recognition that like, we've gotta do something differently, they've recognized the alignment across the functions is the critical gating factor for them. And that's why, you know, they're

appointing one

person. Again,

that

title might [00:42:00] be a Chief Revenue officer and really actually be revenue, not just sales.

It

could be chief marketing officer or market officer. Um. I think, you know, in many ways the title is less relevant than the role they play in the

Natalie Nathanson: Yeah. Um, curious, we've talked a little bit about this earlier of how do you know, uh, kind of when something's not working, uh, are there any kind of leading indicators you kind of think about or see, uh, companies reporting on that shows that, uh, kinda that alignment is breaking down? Or is it always kind of revenues not where it needs to be?

Kind of, it's kinda too late, but we're gonna fix it anyways.

Scott Brown: Oh, um.

I think the signals and leading indicators are always, uh, different, but I think especially for CEOs and founders, um, watching the conversations at a, at the board level and when [00:43:00] things start to look like they're a little soft or not working perfectly, like what's the team's response?

Right. If it's immediately the head of sales saying, well, the leads we're getting

from marketing

are crap, or CS is like, well, we can't retain customers because the product is junk. That I think is a huge leading indicator that you've

got an

issue because you should not be having those sorts of conversations at a board level.

Those function leaders should be having those types, types of conversations and coming at some sort of resolution much earlier in the process.

Natalie Nathanson: I

Scott Brown: So

that's what

I,

I kind of watch for. I

GMT20250522-165949_Recording_1280x720: mean,

Natalie Nathanson: Yeah, no, I like that. And it's an easy one to pay attention to, right? So for all the CEOs listening, like if you hear finger pointing right, start

to

dive in and figure out how to make it, uh, a case where everyone needs to be roaring in the same direction and kinda working in the right way and not getting to that point of needing to point fingers.

Scott Brown: Well,

And to your point, even if you don't hear at the board meeting, if you've got your [00:44:00] direct reports coming to you complaining about other functions, that's a clear signal to me. It's like, okay,

well.

either you need to go work it out with

that individual,

or we're gonna have a collective meeting here and we're gonna get to the source of this.

Right. And I'm a firm believer in bringing

data

to support that discussion. And again, you won't always have perfect data, but if it's just an opinion. That's not gonna go very far, right? So if you say, oh, the leads are no good, well, show me why,

What's

happening? Can you, can you point to a specific issue?

Activation. Segmentation, whatever it is that is causing you to miss your revenue numbers. If not, you need to go do more research and diagnose what's going on and propose a solution.

Natalie Nathanson: Yeah. And be ready to accept what. Whatever the answer is, so to speak, of what the data shows because there's been [00:45:00] times when we've gone through some of that analysis and kind of where, where things are breaking down and looking at funnel metrics and all of that. Um, and in one case I'm thinking of the variable was the sales, the new salesperson that had joined, um, and looking at the data.

And it's a tough message to deliver. Um, but if you're trying to fix a revenue problem in the business, it's bigger than any, any one person or one campaign or program or whatnot.

Scott Brown: Right. But what I just heard you say is you had a system that was instrumented well enough for you to be go, to go through the entire process and flow and figure out, oh, we think this is the issue.

Right. Um, and I think another thing that leaders need to keep in mind is then, okay, well if you're not a hundred percent confident that that is the issue, run a controlled experiment. Like figure out like what you wanna test. Um, maybe that, um, salesperson who is causing you, uh, issues. Maybe they've been dealing with all the [00:46:00] inbound leads and the inbound leads aren't good. Right? What happens if we put them into a different sales motion or we give them a different lead set or we get them training? Does that improve things or not?

Natalie Nathanson: Yeah.

GMT20250522-165949_Recording_1280x720: Uh,

Natalie Nathanson: Don't jump to conclusions, right? Look at the data, dig in where the data shows, and then make sure you're kinda solving for the right thing and with all the right assumptions.

Scott Brown: Right. And, and I'm a firm believer, you know, you do need to be decisive in your, uh, actions, but especially when you're dealing with human beings and people and staff, I always think that you need to test a few things just to confirm, like, is this really what's happening before you just make a, you know, a a knee jerk reaction that's gonna impact somebody's life?

Natalie Nathanson: Yeah, yeah. Very important point and one that I, I wish more leaders kept in mind these days.

Well,

that's a whole different topic.

Scott Brown: Yes. Yes.

Natalie Nathanson: so, um, you know, Scott, before we uh, you know, get nearer to wrap up, uh, [00:47:00] I'd love to zoom out a bit and given kind of all your experience in go to market, is there something that you wish more CEOs understood kind of more generally about go to market strategy or kinda a, another common mistake that you see when they're trying to scale up?

Scott Brown: Yeah, I.

Look,

I, never aspired to be a CEO or founder because that's a whole different set of, uh, decisions and anxiety and

priorities you

have to juggle. So it's a little hard to, you know, say, Hey, you need to pay attention more to the go-to-market function. But I think one of the biggest mistakes I see is CEOs

and founders

don't spend enough time truly understanding, uh, the go to market and in particular the marketing.

Uh. Craft, like what does it take? How much effort and investment does it take the team to actually put things in the market? And then how long? Should we anticipate before we start to see those results? [00:48:00] So I see a lot of folks who, um, you know, expect instantaneous results from marketing. That's one reason why I think the, the tenure of A CMO is so short right now is, you know, they expect, first of all, hey,

do a

complete rebrand of the company, have it launched in the next week and show me results the following week.

It just doesn't happen like that, especially if you want a high quality product. Um, so I think it is.

The

mistake is not having empathy for the team. Obviously you still need to hold them accountable and you know, push them hard, but like actually understanding what they're doing and why it's important is I think something that a lot of leaders overlook and they just assume that marketing is running some flashy campaign, not pulling in deep customer insights and helping inform sales and product on what actually needs to be done.

And some of the more. Uh, deep work that

GMT20250522-165949_Recording_1280x720: marketing can do.

Natalie Nathanson: I

think it can be hard to find that right balance of like how. How [00:49:00] close do you stay to it? How much do you pull yourself out? And I think the temptation, especially for A-A-C-E-O or founder that is, does not come from the go-to-market side. Maybe that's more technical of, um, you know, they hire their first senior sales person or senior marketing person and feel like they can now kind of wash their hands of, of that part of the business and go focus in kind of their own core competencies.

Um, but as we know, uh. There's, there's, uh, an element where the CEO always needs to stay at least close to the narrative, even if they can kind of pull further from kind of pipeline and what are the campaigns. And so you don't want someone too involved because that can do a disservice to the business and where the CEO's time needs to go.

But there's kind of a, a careful balancing act there.

Scott Brown: Absolutely. And

I think CEOs and founders always need to stay focused on the vision part of that narrative. And like continue to articulate like where is the company, the industry, the sector going, and what is the company [00:50:00] building to kind of support that vision?

Right. So in some ways it's a,

it's a yin and yang. As the company grows and becomes more successful, I think the, the role of the CEO and founder becomes more visionary and team leadership and less on the tangible, tactical, tangible deliverables.

And

that's what the team needs

to pick up,

right? Because you as a founder can say things and have opinions that the company ever could, right?

Because as soon as the company says that, it's a brand promise to your customer base and to the market.

And

so you kind of need to be in conjunction, but having vision and reality like paired together,

Natalie Nathanson: I think that's a really, uh, smart way to say it. Very clear. Uh, so I think that that'll be a great place, uh, for us to wrap Scott. And, uh, as we do that, can you let our listeners know. How they can reach you if they wanna get in touch.

Scott Brown: Sure, well, you can find me on LinkedIn. Uh, there's 1,000,001 Scott Browns, but, uh, I'm Rs [00:51:00] Brown seven, uh, on LinkedIn. Or you can always reach me by email@scottatventures.com.

Natalie Nathanson: Perfect. Perfect. Thank you. Uh, well this has been a really, uh, insightful and interesting conversation, so thank you.

GMT20250522-165949_Recording_1280x720: Likewise.

Scott Brown: Thank you so much.

Natalie Nathanson: Uh, and thank you too to everyone listening. I know I loved hearing so much of what Scott shared with us and, uh, all the go-to market discussions that we've had. So if today's episode gave you valuable insights, and I am sure that it did, please share this with the CEO founder or go-to market leader in your network.

These are the kinds of conversations that we know help us scale smarter. Build stronger and create more resilient go-to-market strategies. So thank you again Scott, and this has been another fantastic conversation on Shift and Thrive on our go-to-market miniseries. See you all next time.

[00:52:00]