The Clarity Required to Build a Real Revenue Engine with Katy Loria

In this episode of the CRO Spotlight podcast, Warren Zenna sits down with Katy Loria, Chief Revenue Officer at GumGum, to dissect the harsh realities of executive revenue leadership. Too many newly minted leaders operate as glorified sales managers rather than true architects of a commercial system. Katy exposes the fatal error of blindly accepting a leadership title without aggressively defining the mandate upfront.

Warren and Katy tackle one of the most hotly debated conflicts in the C-suite: the turf war between revenue and marketing. While many argue that modern systems demand marketing report directly to the revenue leader, Katy offers a contrarian take. She argues that absolute alignment, not hierarchical dominance, is the true unlock. When leaders share a unified view of the buyer, marketing can sit beside sales and win.

The conversation then shifts to the brutal reality of private equity boards and the relentless pressure of quarterly targets. Katy unpacks the hardest part of the job: balancing short-term demands with long-term transformation. She shares her tactical approach to managing executive expectations and preventing an organization from sacrificing sustainable growth for the illusion of immediate, fleeting quarterly wins.

Finally, Katy breaks down her survival framework for high-stakes roles, emphasizing the critical importance of ruthless prioritization. By forcing her chief executive to define exactly three core objectives, she eliminated systemic noise and protected her team's focus. She also highlights why high emotional intelligence is a non-delegable skill for executives who want their teams to run through brick walls for them.

What is The CRO Spotlight Podcast?

The CRO Spotlight Podcast examines the CRO role from both sides — the companies that hire them and the leaders who take the seat. Host Warren Zenna, founder of CRO Collective and author of “What Chief Revenue Officers Actually Do,” brings diagnostic frameworks and pattern recognition from working both sides of the equation to every conversation.

Katy Loria Podcast Transcript

Warren Zenna: Welcome to this episode of the CRO Spotlight Podcast. This is Warren Zenna. I am the founder of the CRO Collective, and we're really excited. We have a great guest today. We have Katy Loria, who is the CRO of GumGum. GumGum is a contextual advertising platform. Very familiar with them from my background in media.

And Katy's a real superstar. I mean, she's been everywhere. You know, her background is amazing. She was in ad sales at MTV Networks, then she was a national sales leader at Viacom. She was the CRO of Screenvision Media, then she was a US CRO for three years at FreeWheel. They're at Comcast, and now she's the global CRO of GumGum.

It's an amazing career path, and she's got so much to talk about. We had a really, really great conversation and I'm sure you'll like it. So thanks for listening as always. A couple other things to note, our next CRO accelerator course is going to be kicking off on October 1st.

So anybody who's interested in becoming a chief revenue officer or if you are one and you want to make sure you succeed in the role, this course has been completely revamped, and it's incredible. So just reach out to me. It's easy to find me, and I'll give you the information. And then we're doing a road show this fall with Fullcast and a suite of other services.

We're going to be in New York on the 29th. We're going to be in San Francisco there for Dreamforce on the week of the 16th. Then we'll be in Boston, then we're going to be in Austin, then we're going to be in Chicago. If you go to the website, thecrocollective.com to Events, you'll see them. If you're a CRO and you want to come to these events, which I recommend you do, just sign up and hope to see you there.

And enjoy the episode. Thanks.

Yeah, I guess the first thing is a little bit more about that. So how did you get into all this? You know, what was the way in which you found yourself not just...

We'll have this conversation about sales and revenue. That's an interesting topic for me. But moving from that to more of a revenue leader, that would be an interesting arc because my audience is interested in that progression. Most of them are experiencing that, either advancing towards it or they're in the middle of it.

So it'd be great to get your perspective on that.

Katy Loria: Sure. Well, you sort of did a little bit of the resume, and so I have had a fortunate career. I always say it's somewhat accidental. I can't really claim that I mapped it out from the beginning. So...

Warren Zenna: Anybody really map it out? I don't know.

Katy Loria: You know, I'm telling my own kids that now that they're embarking on, you know, adulthood, that sometimes life is a process of elimination and accidental and just embrace it and learn from it and roll with the punches.

But you know, I ended up in sales early in my career and just kind of came up the ranks as a salesperson, and there's sort of a natural progression, right or wrong, into management. And I followed that path and realized, I think, that I really enjoyed leadership. I really enjoyed the mentoring aspects of people management, and so hoped that I was on the right path in a leadership role.

And I think their CRO is just really about embracing the bigger picture of it and wanting to have a seat at the table that really is able to help influence and think about the direction of the business and not just the commercial piece of it. So revenue being, you know, an important part of the bigger picture, but able to sort of influence, you know, what's the North Star for the company.

I think that's what really ultimately attracted me to the CRO position. You know, my career, I've spent most of it at the intersection of media and technology and advertising, and that common thread has always been commercial. It's been a commercial transformation.

So I've ended up in businesses where the market is changing faster and faster around us, and the revenue org needs to change with it. And so that's been, you know, that's been my sweet spot. That's turned out to be what I enjoy doing.

Warren Zenna: That's great. And I agree. You know, we came from the same world. I relate to everything you're saying. I mean, I too accidentally fell into this. I started selling media when I was young. Advertising really. It was mostly advertising because, you know, we're both probably of similar age.

It was in the '90s I was selling, you know, ads. But you know, it became amazing, I think, for both of us, how all of a sudden we unwittingly became part of this maelstrom of technologies. I mean, it's amazing, right? How things change, right? The internet and then Google and then search and then social and all the other programmatic stuff that we sell and how complex it's gotten.

And growing up in that space is just fascinating, you know. And because I was at the agency side, I was selling marketing services, so I got pretty good at both of those two things, right? That's why it was interesting. So on your end of the thing, you're looking really mainly at how you provide ways in which brands can expand their reach and audiences to other people, right?

So when you think about this, I know certainly what it's like to be a salesperson in that realm. When you were looking at that CRO role for the first time, what was the CRO role presented to you as? How was it different from being a sales leader?

Katy Loria: Hmm. Probably, I guess two ways come to mind. One is it's more overtly owning the strategy. So the sales leader is often, you know, contributing to the strategy, executing the strategy, training the team on the strategy, and I think in that CRO role, you really own it. You have accountability in a different way for setting the revenue strategy.

And then the other piece of it is just you're the decision-maker. You're sitting at the top of the sales organization and all of the decisioning that comes with that. So strategy, yes, but, you know, through talent and incentives and really, you know, you're assuming responsibility for the ecosystem, right?

You're really in charge of the machine that drives revenue and not just the number itself.

Warren Zenna: Yeah, so agreed. And it gets into another conversation I'd like to get a perspective on, which is probably our whole thesis for our business is what does a CRO actually do?

Katy Loria: I think that's what the CRO does, is own the commercial system. So I think the CRO is responsible for all of the components that drive the revenue number. And mostly where I tend to focus is, you know, what is the go-to-market muscle that needs to be in place in order for this sales team to succeed?

And so in my current capacity, you know, I own the pieces of the puzzle that build that. So yes, sales and the sales team, but an agency partnership team and a client strategy team that's focused on pre-sales and RFP responding, as well as very bespoke client direct presentations, the rev ops team, the account management team.

So it's each piece of the go-to-market function that enables the sales activity to ultimately drive the revenue goal.

Warren Zenna: Yeah. Well, I squarely agree with you. Unfortunately, not a lot of companies have their CROs operate that way. A lot of them have them run sales organizations, and when you think of a CRO, you mainly think of someone who runs a big sales organization. And so I'd be curious to get your point of view on, because you so, you know, articulated it so confidently, like that's just the way it is, isn't it?

And it's unfortunately not. You know, what we do is we're evaluating this, and in fact, we find that probably, honestly, I'd say between 30% and 40% of CROs operate the way you just described. The rest are all running sales organizations. And I'm curious to know what your thoughts are on, maybe you have a point of view on why that is and what might be done, and why an organization might benefit from expanding the scope of their chief revenue officer and how they should be thinking about that.

Katy Loria: Yeah, that's a great question. I think, you know, maybe I've just been fortunate that, again, I've been able to sort of influence what the remit is, and so, you know, have had good experiences on that front. But there's probably also, you know, there's just a title promotion in there that sometimes happens, right?

You are the sales leader, you're running the sales organization, and then you become the CRO, and there isn't probably the right conversation around what that should entail and what is the expansion in the remit that should come with that title. And so I think, you know, you can sort of end up in that boat if the expectations aren't explicit from the get-go.

So, you know, who is the company hiring for the role, and what is the actual mandate against the title, right? So is it to run a sales organization? Is it to be a sales leader, or is it to execute an existing strategy, or is it to change a strategy? So I think the communication around expectations and mandate at the top of that conversation is important and hopefully where you catch it. If there's a broader definition that should be in place, hopefully you catch it in the beginning.

Warren Zenna: Yeah. Well, you made a point which is astute, and that is you've been fortunate to have control over the way the role is shaped. So to some degree, two things happened there in both those cases: you had a good idea of what it was supposed to be, and you were persuasive in saying so, obviously, because you were able to do that.

And two, the organizations you were at, the environment you were in were flexible enough to listen and make those changes. And those two things are not common, honestly. You either have someone in the role that doesn't know what a CRO does, and they think it's a big sales role, and they're grateful for this great new title, and they just keep doing what they're normally doing with a little bit more of a, you know, target on their back.

The organization's satisfied with that. Or you have the situation where they want somebody to be more transformative, but they hire the wrong person that doesn't really know how to do that, and they're running a sales organization. They're waiting for this person to expand their scope, and they don't know how.

Or the third is the person knows what they want to do, but the company's like, "Yeah, we don't really want to do that. Just run the sales organization. It's just fine," you know? So I think this is sort of an interesting thing where, why do you think it is, if you don't mind, what might be ways to determine some signals about which organizations are more amenable to this sort of larger scope thinking around the way they look at their revenue organizations as opposed to ones that aren't?

Because this is a big problem inbound CROs have, as they're sort of stuck with the environment they're in, and that's going to be a big tell in terms of how the organization's going to run them and how they're going to be successful.

Katy Loria: Yeah, I think there's a lot of homework and conversation and dialogue that has to happen to get a really good sense of what is the role that you're stepping into. So, you know, have that list of questions ready and don't stop until you have answers that sort of satiate your appetite for the right description of the role.

I think, you know, when I look at new opportunities or consider different companies, was somebody in the role? Was there a CRO that vacated the position? Has this company never had a CRO? Have they been working with a fractional CRO? So sort of what part of the trajectory the company is in as far as their own growth and maturity, and I think sometimes that'll help you understand what they might be looking for in the role.

I mean, you know, in simple terms, hopefully it's in the job description. But I think until you really get to sort of sit with the members of the executive team, I think that's where it really surfaces what they're looking for.

Warren Zenna: Yeah, there's no question. We've built an entire tool for this. It's a scoping document that is a collaborative document between the incoming CRO and the company to kind of almost memorialize a very granular detail of things to make sure that you're both on the same page about things. And we find what's happening is CROs are signing the employment agreement too soon, you know, and they sort of think, "Oh, I'll figure this out after I get the job," you know?

"They're about to hire me. I'm not going to screw this up by asking too many questions." And then they get the job and they realize, "I probably should have asked more questions because this isn't going to go the way I thought it was going to go." And it's an important point, you know? And I think you sort of have to have the security to be able...

Katy Loria: Yeah.

Warren Zenna: I mean, if I really need a job, I'm just going to take the job they give me, you know?

Katy Loria: It's really a great question to sort of ponder because you do feel very vulnerable when you're the person interviewing for the job. And I hear myself coach other people on it, and I don't know that I'm very good at it myself, but it's a two-way dialogue.

You're really interviewing them just as much as they're interviewing you. But you're...

Warren Zenna: No doubt.

Katy Loria: It's easy to say, "Okay, I want to do this, and they like me, so I'll get in there, and then I'll figure it out." And again, you're leading the witness on this, but the idea is really to have the best possible understanding of what you're stepping into before you step into it, because once you're in it, it is sometimes hard to unwind it.

Warren Zenna: Yeah, and you know what it's like, because I've been in this situation myself where I've taken a job, I was really eager, I needed a gig, and it was a great gig, and it had the title that I wanted. It had all the stuff that was hanging off of it that was very attractive to me and, you know, all those things that kind of feed the shorter term needs that we have as opposed to thinking longer term, right?

And then it didn't work out really, in some cases really badly. Like these things can be really traumatically bad situations sometimes, you know? And I remember thinking to myself, what was worse, me not getting this job or me getting the job and failing at it so badly? I don't know which one is worse.

At the time, not getting it seemed like the worst thing, but now I would've said no to this a long time ago. But it's hard to advance yourself into the future and know what that's going to look like, but you sort of have to in a way. You know, I think the interesting thing to hear from you would be, so you've got an interesting ecosystem you're dealing with, because you talk about the system, which we're in agreement here.

We think the CRO is really the system builder, the system operator. You inherit a system every time you take a new job, right? So you've jumped into these big companies, and every time you get this new role in these new companies, they're handing you another system that they're putting you in charge of.

How do you start off? What's the way that you onboard yourself to acclimate yourself to this new system, understand the system, and then figure out what level of control you have to either rebuild it or control it in a way that's going to get a better outcome? How do you do that?

Katy Loria: I think the first thing you have to do is ask your boss, in my case the CEO, "What am I accountable for? So as I take on this new system or this new function or this new team, what is the expectation of me?" Like, I think that's what has to be clearly laid out. And then, you know, as far as kicking the tires on the system itself, I rely on my team.

I put a lot of that, you know, delegation and expertise in the hands of the people that are closest to the day-to-day use of the system. And so I, you know, try things out by having subject matter experts that are really a task force on a new resource or a new system to say, "Here's how this thing should work, and here's what's going well, and here's what's not going well."

And at that point of the process, I think I play more of a director or arbitrator than a, you know, than a strategist on the system itself.

Warren Zenna: Yeah, for sure. The key is to obviously have good people around you that know what they're doing.

Katy Loria: People that are better than you.

Warren Zenna: Exactly. That's right. That's a big thing. A lot of CROs I talk to, they really don't want smart people around them. They want to be the smartest person. They realize that's the opposite.

You should be the dumbest person.

Katy Loria: This was a couple jobs ago, but I had somebody say to me that there was a sales leader on my team and this person said to me, "You know she wants your job, right?" And I thought, "Yeah, of course. She damn well better want it." Like, that's the, you know, that's the aspiration. That's the kind of leader that I want to hire, and if it makes you a little uncomfortable, then that's okay too, right?

That there's a little tension that's healthy, I think, in a dynamic like that. But yeah, you want to surround yourself with people who absolutely are capable, when the time is right, of taking over your job.

Warren Zenna: Yeah. You know, it's a great point, and it's so easy to miss that wisdom, right? It's sort of like you're falling into this earlier career self-protection mode where you want to keep everybody around you that you feel like you can control, and you realize later on, like, "What a dumb decision that was. I should have had people around me that were able to run with things," you know?

As long as you have a good sense of where your competencies are and the trust that you've built with the people whom you report to, and that they see you as the leader of these people. And you know, also I figured this out my last big job finally, which was, you know, to kind of surround myself with really smart people and tell them, "Look, you know, look, you're better at this than I am.

That's why I hired you, you know? So it's fine. Like, I'm asking you for answers and it's okay to be smarter than me. I want you to be and do this, and it's great. And then I'll knock down walls for you to make sure you get this done, and I'll make sure you get recognized for it. That's what I'm here for.

And my job is to go to these people and explain it to them and tell them I have the team and the strategy put together to make it done and do it in a way that they trust me, and I'm really good at that. I will do that, okay? And it'll be fine. Like, I'll get that part done. You just gotta do your part, you know?"

And that's where I started realizing, like, that's what the job is. It's really about kind of coalition building and team building and leading and vision. And, you know, you do obviously have to know the business, right? But how much can you know? Like, you're not this super genius, right? You need really smart people that are really good at things, and you put them in the right position and you say, "Go.

Do your job. Make me proud."

Katy Loria: You asked me early what is the role of a CRO, and I probably gave too academic of an answer because the role really as I see it, hits on what you just said. It's to get the obstacles out of the road, right? So my job is really to have the right people in the roles around me, and listen to them and understand what their blockers are and push those boulders off the road, and then be the wind in their sails, right?

Really get behind them and support them and give them the autonomy and the authority to... and the guardrails, but within those guardrails, give them the space to really manage their own businesses and their own teams and again, just clear blockers is a big part of what the role is.

Warren Zenna: Yeah, yeah. I want to switch gears a bit. I'm actually curious about something. What do you feel about... I have a strong opinion about this. I'm curious what yours is. Do you think that the CRO should have oversight over marketing?

Katy Loria: Mm. That's a great question. So we're really in a conversation internally about this right now, and it's an interesting debate. I don't think marketing is one thing, and I think that's how we're sort of trying to think about it internally at GumGum right now. In my opinion, marketing owns what we sell and how we talk about it, and so that sits with the marketing team or the CMO.

But then revenue owns how we sell it, and so there's some intentional gray area or shared territory, let's say, between those two things. But the marketing role here is the one-to-many presentation or narrative or value proposition, I believe sits with marketing. All that is translated through a client lens for a deck that's particular to a client or to a vertical, I think that lives with sales.

So I think there's a sales enablement piece of marketing that does absolutely belong within the revenue organization, but that it is also fine for that broad messaging so that we get it right, so that we really, in a uniform way across an organization, represent our North Star, you know, one way. I think that's a marketing function, and it's okay for it to sit outside of revenue.

Warren Zenna: Yeah, interesting. So, would you like...

Katy Loria: You disagree. What's your perspective?

Warren Zenna: Yeah, I have a bit of a different take on this. So not only do I come from marketing, because I sold it my whole career, but I actually happen to have a marketing agency, and it does very well. So I know this space, and I love marketing, and I have a real love for it.

It's a big part of my life. And I sold it, you know, but I recognize that it has its place in things. And as I developed this business five years ago, six years ago, and started thinking about revenue, like, what is that, right? I asked that question. And then I thought about, so what matters most, right?

When you're thinking about a revenue engine or a revenue cycle or, as you and I already said here, a revenue system, the customer really ultimately is an ultimate important agent in this entire conversation, right? It's... That's it. It's all about that, right? And if you focus on that, any... You and I could probably sit here and rattle off 1,000 businesses that are doing incredibly well, and all of them, probably their customers, are all pretty happy with that brand and that experience consistently enough that they keep...

That's why it's so great. It's just always the case. It's impossible not to be that way. But yet the model seems to be not focused on that often enough, right? It's almost too much focused on the quarter, right? So if in fact we agree, and I know we do, that the customer is most important, then I would submit that marketing sits in a part of the customer journey.

And I would say we define a customer not as someone who's bought something from us, but the person who could buy something from us, right? They're still a customer, because in my world contextually they're a customer of mine. They just don't know it yet, right? They don't know it yet. So that means that if I'm sitting on top of a revenue organization and I run it like you do, I'm thinking that the customer is in this state right now that has a need that we can fulfill, and we can fulfill it in a way that they're going to be satisfied with profitably.

So I want to know how, as a revenue leader, we do that. Because that customer identification needs to be specific enough that I know that not only are they going to buy from us, but they're going to get the value from us in the timeframe that we want, and that the ROI for them is going to be so great that they're going to renew or they're going to buy more from us, and then later on they're going to advocate for us and help us get more customers, right?

That's the relationship I want with this person. So that means that marketing needs to find those kinds of people, not just people that'll pay for our services, but the kind of people who will become advocates down the road. And there's a different set of people like that than just people who buy things.

Which means that the salespeople probably know a lot about those people, because they sell to them. They know the people they sold to. So the salespeople really need to be connected with marketing directly to let them understand that, because marketing doesn't know that all the time. And at the same time too, marketing knows a bit more about buying behaviors and trends and things that the salespeople don't know. ****

So because of that connection, as a CRO, I'd want to own all that because it all ultimately will make for a better, like, data loop for me to be able to control, and I use the word control not in a bad way, but just to have more visibility into the whole system. And if I leave marketing as a separate agent with another C-suite executive, the other layer is that that marketing organization is also going to be collecting their own data, which is going to be more biased against the way that their objectives are as opposed to sales objectives are, which means there are going to be two versions of the truth, which isn't good.

We need to have one. But if they're connected, then they'll have to be one because they're related. And so I think, if I may, the CRO owns all that. It creates much more fluency between where that customer is before we close the deal and how marketing and sales share that data as one set of data points as opposed to two different data points, and it makes for a leaner, more efficient operation.

I understand the challenges there are that most companies have a CMO, and they don't want to report to a CRO, and it's all this stuff that goes on. And I think there's also a lot of traditional muscle memory around the way we structure leadership organizations. But again, our viewpoint is that it's sort of antiquated, and that it needs to be thought of more as a real true loop because the world's changed.

And so that's our point of view. That's how we think about it.

Katy Loria: Yeah, there's nothing that you said that I would disagree with. I think, and man, that feedback loop is so important, and I do think that has to be frontline, right? Like, that has to be a seller to the client. And yeah, it's absolutely critical. But I think, you know, if I differ on the answer, it's really that I think the alignment has to be there.

So you have to be... There has to be alignment, but I don't necessarily, for myself, think that that means reporting always. Like, if the alignment is there, and as an executive team and as a CRO and a CMO, if we're aligned on the North Star of the company, we're aligned on, like, the customer, the client is number one, then, you know, then the right strategy and initiatives and respect, I think should come from that.

So I don't disagree with anything you're saying, but I think if the alignment's there, then maybe marketing can sit next to and not...

Warren Zenna: Yeah, I get it. And I see it working. I see it working a lot.

Katy Loria: Sometimes it does and sometimes it doesn't.

Warren Zenna: Sometimes it doesn't work, right? So I guess it's sort of like your role as a CRO in that scenario is really focused on really making sure that that alignment takes place, right? So we see a lot of times where a CRO gets hired, and their optimal org chart would be that they have sort of systemic oversight over all the functions so that they can, you know, perform it in the way that I described.

And that's what they want. And they're told, "Well, you know, we already have this person who's been the CMO for four or five years, and we're not getting rid of that person, so you'll work together," right? Okay, fine. No problem. I get it. That's the way things are. So then the second part is then, what's the relationship that this person has to the business?

Are we philosophically aligned? Are they... See, marketing organizations, as you know, tend to be victims of the first place that they get cut, right? They're looked at like a cost center for some reason, which it's not, by the way. It's not a cost center. It's a revenue center. And so if they're treated like a cost center, then they're going to be protective of their budgets and protective of their control because they're always concerned about it.

So these are the things that we see happen. I don't want to get in the weeds here too much, but it's a really fascinating thing because this comes up a lot with us. So your perspective is interesting. It seems like you've worked out a good solution to making sure that those organizations are well aligned, and that's good for you because that's the job, and I think it's important.

But thanks for indulging me on that. The second thing is, do you feel like we are going to be seeing more, like, salespeople or sales being done through agents, like AI agents and stuff, or do you think it's going to really maintain human beings? And where do you see that evolution taking place, particularly in your space?

I'm curious to know how you're managing that right now.

Katy Loria: Yeah, I mean, the answer is yes, and somewhere between all and nothing, right? I mean, we're certainly moving. I do believe we will move more and more into a world where agentic buying is a real thing. I think for GumGum as a company, AI is foundational to who we are. It's always been part of what the product is, and so we will continue to build products where, you know, AI is a driving force.

I think the... So yes, but I don't think we will go to a place where humans aren't involved. At least that's a hill I'm willing to die on. Like, I believe to my core this is a relationship business, and that trust and relationship building and dialogue will always be what drives the business, and that AI will enable us to do it better and faster and smarter.

And so I'm a big proponent of figuring out what are those efficiencies and internally, as I sort of think about AI from an operational standpoint, I'm eager to move past, you know, using AI to answer a prompt and really using AI to help drive the efficiency of the business.

I think, you know, there's a long way to go there, and we embrace that very much, but it's, you know, it's figuring out what are those right things. And, you know, I just tease like I don't need AI making my sellers more efficient at doing work they shouldn't have been doing in the first place.

So, you know, where are the areas and the functions that we can lean in, like synthesizing account intelligence and surfacing, you know, where's the moment in a campaign where expansion or upselling is ripe, meeting prep. So I think, you know, I brought that back to sort of the internal side of AI, but that's to me where AI is really exciting right now.

But to answer the question, sure, I think we will see, you know, I think we're kind of pretending that it's experimental right now, but I read an awful lot that says that we'll be really participating in an agentic buying world in 2027, and that's not very far away.

Warren Zenna: Yeah, I know.

Katy Loria: I think...

Warren Zenna: I don't know. It's an interesting thing. I agree with you. I think that as long as you're selling something complicated, you need people involved at the lead, right? But I'm just seeing a lot more encroachment of robots involved in conversations. And as it gets better and better, I could see people just saying, "You know what?

I'm just going to kind of step in a little later," you know? And before you know it, like, we're just not talking to each other anymore. I certainly see people buying things with robots. Like, that's going to happen, you know?

Katy Loria: I tease on that front, and maybe it's not such a tease anymore. I always say that humans will always be an important part of the equation until AI decides that we're not.

Warren Zenna: Yeah, exactly, which looks like it might happen. So to that end, you know, why don't you, if you don't mind, walk the audience a bit through GumGum's business for those who don't know what GumGum does and who you serve and the problems you solve, et cetera?

Katy Loria: Yeah, I'd be happy to do that. We are evolving the business, but the foundation of GumGum is really contextual targeting. We've been at that for 18 years and probably do it as well, if not better than anyone else. But I want to take that contextual targeting and move a conversation beyond who, you know, identifying who is the person and who is the right target, to really landing in the right moment.

And so we're talking more and more. Our positioning is to be the mindset company and really evolve what we know about contextual intelligence and attention, and creative formats, and really bring in more dynamic signaling and more data to understand when is the right moment to serve an ad. So will you be receptive right now based on the device that you're on, based on what you've been doing in your, you know, digital travels for the last couple hours, based on the environment and the content, of course?

Like, is this the right moment to serve you an ad because you'll be receptive and it will make the right impact? And if not, let's not bid on that. Let's move on and find the next right moment. So it's an evolution. It's not a pivot. It's, I think, the direction that GumGum's been headed. And none of it matters unless we deliver a better outcome to a client.

And so what we really want to be able to do is be more consultative, be more, you know, better partner, and really understand the objectives and business solutions that we might be able to help an advertiser solve, and then bring our mindset technology to the table to help solve that. And then the delivery method, you know, for us is across display and online video and CTV, but ultimately we will just want to optimize the media channel to deliver that outcome to a client based on the mindset that we're able to identify.

Warren Zenna: Yeah, it makes sense. And I was very much involved with Contextual for a while. I know your business very well, and I think it's a really smart way to attack the problem. There's a lot of other elements of people's consciousness that are going on in their day, and there are certain times when they're going to be obviously more receptive to a specific type of message based on where they are, the location, or what they're doing right now, or something they're reading, or an ad they're watching, or a video they're looking at.

And, you know, that ad can be really, really appropriate. So it's a really, really smart solution that I would imagine... I would think that AI would be an amazing tool to help enable this to happen, right? It seems like perfectly built for that sort of thing, you know?

Katy Loria: Absolutely. Yeah, absolutely. So as I said, AI is and will always be, I think, integral to how we sort of evolve that machine and that learning, right? You know what? When we talk about developing a mindset, we're hopeful to change the way advertising works, but it won't be done.

It won't be, you know, we're going to deliver a product on September 15th and say, "Okay, that's it. Here it is." It's going to get smarter, and we're going to get better and better at it as we sort of feed that machine and as AI, you know, continues to empower us.

Thank you so much again for listening to the CRO Spotlight podcast. This podcast is an important plank in the CRO Collective communication strategy, and we're really thrilled to have such great guests on here. So listening and sharing the podcast with other people is really vital because we want to get as many people listening to this great stuff as possible.

A couple things to note. If you're an aspiring CRO or a recently hired CRO or even an old, salty CRO, and you're looking to either become a chief revenue officer or improve your chops and gain some more insights and improve your competencies as a chief revenue officer, we offer the CRO Accelerator course.

It's five years now. It's the first CRO-focused course that was out there. It's a 15-week course that is populated by aspiring chief revenue officers and CROs. We're pretty selective in terms of who can be a member of the CRO Accelerator course. It's people who are probably more ready to be a CRO right now.

They have a number of years under their belt as a revenue leader, whether it be a sales leader or a marketing leader or even rev ops leader, and they either want to move into the C-suite or they're CROs that want to just make sure that they win in the role. So if you are interested in being a member of the next cohort, please just write me a note on LinkedIn.

Just DM me, "CRO Accelerator," and we'll set up a time to talk. And then I can send you more information to give you a brochure of the course. So again, CRO Accelerator course, 15-week program for aspiring and newly hired CROs. Take advantage of it. It's been great, and you'll see some more information about it on the website.

Thanks.

Warren Zenna: Yeah. So one other group that we speak to a lot are, you know, PE-backed companies. They have many different sorts of issues associated with managing their businesses, particularly CROs who have to report to a board or a PE board, or maybe they're being managed under a PE model. I don't know, do you have any experience or thoughts on that when you're thinking about someone who is a chief revenue officer at a PE-backed firm, the way in which that they take on those unique nuances of the role when they're dealing with an organization that is managing multiple companies against one specific type of management model, and they're moving all those companies through, like, quarter by quarter growth, and they have much different objectives?

Many times we see non-customer-facing objectives, right? They just want this quarter made, or they want that deal closed, or they want that lift because they're getting a new evaluation. And a CRO is battling against two different clocks. You know, one is the quarterly clock, and the other one is the long-term clock.

So I'm just curious what your thoughts are on how a CRO in your world manages these kinds of different types of objectives at the same time.

Katy Loria: Yeah, I would, you know, I think it might be one of, if not the hardest part of the role of being a CRO, and you just hit the nail on the head, is how do you balance short-term economics with long-term transformation and public or private and I've done both. I've never been anywhere where this wasn't the most important quarter ever.

So...

Warren Zenna: Exactly. Exactly right.

Katy Loria: There's just...

Warren Zenna: It's always the most important election...

Katy Loria: Yeah. It's just...

Warren Zenna: For you, right? It's always, yep.

Katy Loria: That really doesn't change much. And every quarter does matter, of course, right? Like that adds up to the year and the years add up to the long-term plan. But man, if you're optimizing every decision for this quarter, you really run the risk of accidentally training an organization the wrong way and you kind of drift away from what is the longer term goal for the company.

And so I don't think I have a real answer to how exactly you do that other than that it's really important to have that conversation with your board. You know, what are we focused on? Are we focused on three years from now or are we focused on, you know, December 31st? And either answer is, you know, depending again on where the company is and where the PE firm is in their life with the company, the answer can certainly be either.

But if you don't know that answer, you're not going to plan the right way. And so, you know, there are examples where, you know, maybe you're in a building year and so this isn't going to be the year that you knock revenue out of the park, but that's okay because you're building for next year or even the year after.

But if you're not aligned on that as an executive team, you know, with the board, then it's tough, right? Like that's, you know, that's an easy place to fail. So I just think that the understanding of what is the goal? Is the goal, you know, how far out do we want to sort of put the flag in the ground and call that the goal, and then you build a strategy to that.

Warren Zenna: Yeah, I get it and I agree with you. I think there's always going to be a tendency for the organization to always want to pull towards the short term. It's always going to be like an inertia that's there. I would say it goes back to the earlier part of our conversation, which when you first get the job, the question you need to be asking is: "What's our long-term plan, and how do I fit into that," right?

And then remind everybody that, you know, there's two clocks running. One is the short-term clock, and the other is the long-term clock, and they both are ticking, and I have to focus on both of them. And how do I make sure that I'm managing our objectives so that you're not pulling me away from the bigger picture to manage the short term?

And it might be nothing more than getting good people underneath you that can help manage those short-term goals, so that you can focus on the bigger things, but then you need a more sophisticated organization. But this is the key thing we see most happening with our clients is they're like, "I don't know which one to listen to."

And of course, the one that usually wins is the short term, because that's how they keep their jobs, and then they end up becoming like sales leaders all over again, because they're not really pushing towards the bigger changes that have to be made. So it's a really interesting thing.

That being said, it's like when you first get into the job, what is your thought on what's the timeline you think is appropriate for the point at which you can validate that whatever systemic changes you've made are working? Like, how long do you give yourself to say, "All right, you know, Katy was correct.

We have evidence of it, and we can see that it's working." Is it like three months? Is it nine months? And how long into the tenure do you have before you validate your long-term plan makes sense before people say, "All right, look, it's been a while. Let's get going here," you know?

Katy Loria: Am I answering that as the board or as Katy?

Warren Zenna: As you look at your job and talk to other CROs, what do you find is the right way to navigate the tension of, "All right, we're going to give you some latitude here. We definitely want you to do some big things for us, but we need to see that it's working," you...

Katy Loria: Yeah. So I'd love to tell you it's six months or it's nine months, but I think it's just so dependent on what situation you're stepping into, right? Like, did you just flip an entire sales organization and you have a lot of attrition and new sellers coming on? Because I'll tell you, you know, a new seller probably takes, you know, three to six months to ramp, right?

And so, you know, are we flipping a strategy or is there a big company pivot? I think, you know, there's some really critical strategic questions that come into play before you can sort of put yourself on the clock.

But that's what's important to understand is, again, it's the expectations of those around you, your boss and your board on what is the job that I am here to do, and then I can tell you how much time I think I need to do it, and I can tell you that I'm going to spend my first 12 months in the job, you know, really building the system that we're talking about.

If the go-to-market muscle really wasn't there and we need to have the right resources and tools in place to measure the business that we're trying to run, or maybe there's a big product launch that's coming in early, you know, first half of next year and we're really going to put ourselves on the clock to, you know, drive revenue to that goal.

So I think it's, you know, the only way to really answer that, you know, "this is how much time I need to be successful," is to have a clear understanding of what is the task and what is the thing or things that I'm accountable for.

Warren Zenna: Yep, agreed. And you sort of have to put the data together. We help our clients like three months into the job. You probably want to go to the board with a plan, with data that says, "This is what I'm doing based on the objectives. This is how much time it's going to take. These are the results I'm expecting.

Here's the resources I'm going to need from you, and I'm going to get off and do it. And in the meantime, I'm going to have to kill these other, you know, three or four things you guys want me to do in the meantime, and here's how I'm going to do that." And then you have to do it. You have to get it done. Like that's, you have to sort of present a case that's well designed and that's realistic.

And when they ask you to cut it in half, you might have to say, "No, I can't," or, "I'll somehow have to give up this," or some compromise needs to be made. And I think that, again, as a CRO, you sort of have to have the moxie, you know, to be able to do that. You have to be able to say, "Look, fine, I want to fulfill your requests, but here's the realities, here's the implications, here's what I need."

And that's a mature leader who knows how to do that really well.

Katy Loria: I think, yeah, I mean, so much of it comes from experience and, "Hey, I've been here before and here's, you know, what worked or didn't work." I think the data-driven part of that is so important, right? To sort of be able to present your case here based on the data. But then also I think as the CRO or any executive leader, you gotta be able to overlay that with the context and really, you know, articulate the narrative by reading the data.

The thing I think is really interesting there, and I'm curious how you would coach people on it, like so much of what we just agreed on as far as what's important to sort of establish those timelines, like there's... if you're stepping into a new role in a new company, there's so much you don't know until you get there. ****

Warren Zenna: Exactly.

Katy Loria: So I wonder how you sort...

Warren Zenna: Yeah, it's a great question. So the first thing is, we already, you already said it. Like, the first thing is we really emphasize this upfront agreement. Where a lot of the work gets done there. I mean, it's not going to solve everything. But absent those initial agreements and scope agreements, authority, autonomy, like the things that honestly just tend to not be really talked about in a lot of detail, in my opinion, during interviews.

They're just not. Not to the level of granularity. In fact, what I'll do is I'll send you the thing that we use for it. It'd be interesting to get your feedback on. So there's that. So that's going to get you to a place where now, and honestly, what it really is, is just the key to that whole exercise is as much as its data gathering and agreement setting, it's designed to build what we believe, and I'm sure you do, is to establish the most important relationship you're going to have, and that is between you and your CEO.

That's the thing, right? If you have to have that relationship. It has to be solid, right? And if you don't have that, you're always going to be working on trying to fix that, and it's going to be a distraction from you getting things done. It's either we don't agree on what the job is, which means you're talking off not the same book page, or he has misgivings about you, or she has misgivings about you that aren't expressed, and they're hoping that maybe they'll kind of get over them and you'll work through it.

Or vice versa, you have them, and you're hoping that it'll just work itself out. Bad. No good. They're not good. Or you just didn't memorialize things, so there's like, persistence of memory is not the same. Like, "Well, I thought we said this," you know, "I thought I said that," or, "I meant this," or, "I meant that," right?

Stuff like that, right? So it has to be clear. What that does is that gives the foundation for the operating system, so now you can work together. Then the next part is, you're right, it's not just like the magic of waving a wand and saying, "Okay, now I know what's going on here." You have to know what it is you need to know.

Like, what are the actual questions you need to ask? Like, what are you looking for? Because you're looking kind of sometimes for a needle in a haystack, and you have to know what the six really important things are that help you focus more on. What are those... If I know those six things, I probably know a lot of other things.

But if you don't know that stuff, then you'll hunt around a lot, wasting a lot of time getting information that makes people... You look like you're busy, but in fact, you're collecting information that doesn't really matter. So that's it. We have to give that guidance. And then once you get that, you can get to a point where that data can be accumulated in such a way that a board meeting can be scheduled where you do a sort of state of the state sort of meeting with them.

Here's what I discovered. Here's the process I put through. Here's the data points I collected. Here's why. Here's what I came up with. Here are the gaps based on our goals. Here's what I'm going to do. Right? So now you're very, very educated about exactly what you're supposed to get done. And when you present that to a board in a very solid way, you know, the feedback you're going to get back might be a couple of challenges, but if you've done your homework, you have the answers, and now it's a negotiation.

It's like, "Okay, we got it, and we don't like it, but you made your case, and so now let's figure out how we're going to make it done." But what happens is a lot of times that those things don't happen.

Katy Loria: Yeah.

Warren Zenna: You're flat-footed and you're on your heels, and you're sort of trying to negotiate something that you don't have the ability to even defend, and you're screwed right there.

Now six months down the road, and you... So this is the sort of way we try to beat the clock by knowing where to hunt and knowing how to put together the right context for your agreement. That's how we do it.

Katy Loria: It's that again, I violently agree, and it's that open conversation at the beginning, because you're right. If you kind of let it go too long and it festers, then you're six months in and all of a sudden it's kind of too late. And anecdotally, I stepped into a big CRO role at a company where I was, you know, a bunch of lines of business and a big team, and I was running in a lot of different directions, you know, trying to learn the team and the business and the strategy and the opportunity.

And I remember sitting down with my CEO and saying, "I'm, you know, I'm running in a lot of different directions. I'm covering a lot of ground. It all seems really important. What are the three things you want me to do?"

Warren Zenna: Yeah. Yeah.

Katy Loria: And he came back to me the next day with the three things that...

Warren Zenna: The three things, yeah.

Katy Loria: ...to do, and which means he knew what they were, right?

But we hadn't sort of put them on the table, and it was so helpful and so clarifying, and then I would get it in that crazy part of my day where I was trying to do too many things at once and lost track of, you know, what I said five minutes ago. But I went back to those three things and I said to, you know, myself, like, "If what I'm doing right now isn't ticking against one of those three things, it's probably not what my priority for the day needs to be."

And so simple, stupid advice, right? But if you can get that clarity at the top...

Warren Zenna: Yes. It's knowing to have the maturity to ask that question. And by the way, good for you because there are three things. It's always three things, by the way. And you know, you have to know what those are, right? I had a really great boss once who was crazy smart. He ran this business, it was, like, amazing.

And I went into his office, and he said, "Come here, let me show you something." And he had this massive whiteboard in his office, and it was really well organized, and he had these three big, like, blocks, and they were like, you know, operations, da, da, da, da, whatever they were. And he walked me through, like, each one of them and, like, all the things.

And it was like he built this very clear dashboard for himself. It's like when he was sitting at his desk, he always was able to look and see, "Okay, where am I at in these three things, and how do I measure the success of those three things and what I have to do?" And it kept him really focused on all the crap that came at him all the time that would easily pull him away, and now he's doing 10 things.

But he knew that if these three things got done, most of those other things would probably be impacted positively by them. And that takes an incredible amount of understanding of, you know, engineering your thinking and engineering your activity and engineering your focus to know what those are. But you have to come up with an agreement on what they are.

And as a CRO, if you can do that, you create a much more solid, integrous framework with which to run your day. Because I know it's easy for all of a sudden you feel like it's a snowball. Like, it just got huge, and you feel overwhelmed. And it's difficult to know at that point, if you don't have that clarity, what's important and what's not.

Everything seems so important, right? And I think this is the key, is to get that clarity, and I think that's really helped me a lot. So I appreciate the dialogue on that.

Katy Loria: Yeah. It's also just, it's just good, it's healthy for you, right? Because we all want to win, and we all want to feel that we move the ball from, you know, from here to here. So if you know the three things, then you can kind of track your own progress and your own measurement, and then you sleep better. So...

Warren Zenna: Yeah, really it's a good thing to do to share that with the people that you work with and say, "Just so you know, here are the...

Katy Loria: This is what I'm working on. Yes. Yes.

Warren Zenna: Right? "Here's my operating system, and this is... When you look at me, I'm probably thinking about these things." And you know, someone gave me this great document as well.

It was like a user manual for me. Like, here's how I am.

Katy Loria: Yeah.

Warren Zenna: Like a user manual. The Warren Zenna user manual. You know, I can be annoying, you know? Sometimes I say too much. It doesn't mean I'm not listening, it just means I like that. Say things twice, because I sometimes say yes and I don't remember, you know?

Or if I don't say anything, it means it's okay. It doesn't mean that I don't listen. It just, it... I would say something if it wasn't okay, right? Like this type of stuff, if you can create like these understandings of us as people with each other, it's really a great thing. Like, someone had come to me as a leader and told me that stuff, I thought, "Oh, God, I'm so glad I'm working for this person.

That's so great. Like, thank you for giving me..." Because, you know, you're spending a year figuring out what the hell this person means when they don't listen to you, and it turns out that they're just busy, you know? So it's really little cool stuff like that that I learned along the way that I would never have figured out if someone didn't show me.

Katy Loria: No, I love that. There's probably a whole other podcast, right? But understanding work styles and how to work with different kinds of people, which I've always sort of said, like, that is the role of a seller, right? Like, you need to figure out how to get along with lots of different kinds of people and clients, and some clients want to talk to you every day, and some never want to talk to you and prefer to have an email.

Like, you need to know what's the effective communication style. And we do that here. I know more and more companies do it, but we've done it as an executive team, sort of understand, like, what is my profile? What is my work style vis-a-vis my CEO's work style? And then how do we work together based on, you know, how we respond to criticism or deadlines.

And it's really helpful when you sort of have the understanding of what you're, how what you say is being received on...

Warren Zenna: Yeah.

Katy Loria: ...the other end, and then the world goes round better.

Warren Zenna: Totally, and this is real, high EQ stuff that if you possess, and you said it, right? I mean, you're attracted... What was attractive to you about managing was mentoring people. So that's an EQ attraction. Like, you want other people to, like, empower other people and get them where they want to go and, you know, that gives you a lot of juice.

You know, some people like managing people because they like to win, and they have more people, they can win faster, you know? It's a different reason to manage people. And so, you know, I do think, like, when you're a CRO, we see this a lot in our work, it is the high EQ people, it makes up for so many other weaknesses because people can relate to you.

And they go, "Okay, so he might not be that bright about this, but you know what? I really understand him, and I really can listen to him, and I think he listens to me." And that goes a long way. And I think, like, it's an important kind of feature for this job. And you know, another thing about that too is you can't delegate that.

You can't have someone be your EQ person. That's your thing. You gotta do that, you know? So that's on you, and it's a skill that you own and you possess, and it's your brand, and it's your character, and it's your profile, and it's the way you operate. And if you can own it and be really upfront about it and humble about it, people will run through walls for you.

They will run through walls for you.

Katy Loria: Only thing I would tag on that, because I completely agree you need to own it. I think the EQ piece is so important, and you cannot delegate it, as you said, but you can model it.

Warren Zenna: Yeah, that's true.

Katy Loria: You can, you know, hopefully, you know, what you put out there, you know, hopefully is received in a way that it helps others, you know, as they kind of continue on that path.

Warren Zenna: That's a great way to end. And as I expected, this was really great. So great talking with you. Thank you. Was there anything you wanted everybody to know or what you're working on or anything important going on that you can tell everyone?

Katy Loria: Oh gosh, I mean, I think just stay tuned as far as the GumGum mission goes, as we continue the story on mindset and really help advertisers and brands put ads in front of people when they are relevant. So watch this space for more on that story and we'll be back with the proof points to really show that where we're headed is the right direction and that it's working and bring others along for the ride.

So yeah, excited for the future.

Warren Zenna: Great. Well, Katy, thank you so much. I really appreciate you taking the time, and it was great talking with you.

Katy Loria: Thank you. I enjoyed it as well. Thank you, Warren.