CRO Longevity & Navigating Organizational Transformation with Susan Rothwell

Hi, I'm Warren Zenna, founder and CEO of the CRO Collective, and welcome to the CRO Spotlight Podcast. This show is focused exclusively on the success of chief revenue officers.

Each week we have an open, frank, and free-form conversation with top experts in the revenue space about the CRO role and its critical impact on B2B businesses.

This podcast is the place to be for CROs, sales and marketing leaders who aspire to become CROs, and founders who are looking to appoint a CRO or want to support their CRO to succeed.

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Now let's go mix it up. Welcome to this episode of the CRO Spotlight Podcast. I'm Warren Zenna. I'm the founder of the CRO Collective. And today we have a great guest, Susan Rothwell, who is the Chief Revenue Officer of Simplify. She has an amazing career. She was a 3-time Chief Revenue Officer. She was with Veracast and then Epsilon. And she has an incredible story of how she kind of developed her career and built a really great track record of lasting a long time as a Chief Revenue Officer. So I'm really excited to have Susan with us today. So stay tuned. It's really nice to have you here. And, you know, I'm very familiar with Simplify. You know, my background is in media. You know, I worked at Havas, I worked at Publicis. So, you know, kind of crossed paths with your organization quite a bit. So, we have some common background and stuff to talk from. But, it'd be really great, you know, if you could first just introduce yourself a bit. Like, Susan, you have a great, great background. You've been a CRO 3 times. You know, you've also interestingly followed with the same CEO a couple of times, which is really interesting. And you've had a great tenure building some amazing businesses. You were the first business, first CRO at Veracast, which is really interesting, right? So, I'm just curious to know, like, a little bit how your career progressed and how you ended up getting there and a little bit more about your background.

Oh, great. Yeah, sure. So, I've been in sales my whole career and, you know, very early in my career, I ended up into leadership. So, I started out in software sales and then I went to Polaroid, where I spent 14 years at Polaroid and learned a lot about a company that didn't transform and what happens when you don't transform. So that's a little bit of, you know, a little bit of why I like to get involved in companies that want to get to the next level, because I think it's super important to be focused on, you know, getting ahead of the game versus behind the game. Then I spent 14 years at Veracast, Velasys Veracast. I started as a sales director, moved my way up to CRO there, so grew quite a career there as well. Then spent a couple of years at Epsilon focused on bringing them to a unified go-to-market strategy. They had 3 very disparate teams and brought them together. And now I'm here at Simplify working with, uh, Callie Tran again, who's the CEO and was my CEO at Vericast. And, um, we are here taking Simplify to the next level. So I'm really excited about the opportunity and being able to use all of my backgrounds to help a company like Simplify.

That's great.

That's great.

Yeah, I remember the Polaroid Kodak days when those dinosaurs just couldn't seem to make that leap, but it's kind of fascinating to watch that happen. I think a lot of companies are doing the same thing right now with what's going on today, to be honest with you, which I want to talk to you a bit about. But more importantly, I think interesting you had the CRO role the first, you're the first CRO, you know, at your first company, your first CRO role. And I'm curious to like, when you got that job as a CRO at that company, what was the remit there? Like, what was it they were looking for you to do as a chief revenue officer? As I think you and I probably agree, that role is different based on like what stage the company's at and different types and stages of the organization. So how did they view the CRO? Back at that time?

Yeah, I think it was an opportunity to actually kind of create what they were looking for in the CRO role. Right. Again, it was at Veracast and there were two really— that was a bunch of different companies that fell under that umbrella. There was Harlan Clark, there was Clipper, there was a print company, a digital company. And it was the opportunity to take all of those different companies driven under one, one person being the CRO. So that's why it was the first time they had that. And I think the interesting thing about that job was even though the companies didn't seem like they had a lot in common, you were able to drive a commonality amongst the leadership of the, of the different sales organizations to really leverage off of our different, different clients or different products or different services to actually be able to grow our clients across all the different products. So I think it was a unique opportunity because Again, it was one person over many different organizations within the Veracast portfolio.

Yeah, I mean, it's interesting because, you know, back at that time, I mean, granted, it wasn't so long ago, but in terms of CRO perspective, it was a different world even last year for chief revenue officer. Oh yeah, it's changing rapidly. Quite a bit, right? Yeah, exactly. So I'm just interested in that evolution, right? So how the role was initially presented to you and then how it's changed since then and how you've evolved in that respect. Particularly interested in the fact that you stayed with Cali for so long and what that relationship— that shows a lot, but obviously you have good trusted relationship there and how that was formed. These are interesting things because my audience, right, these are chief revenue officers who are many times wondering how they can maintain the kind of longevity that you've had in the role because most CROs last around 17 to 18 months today.

Yeah.

Yeah.

Well, I think, I think one of the biggest parts of being successful in this as a CRO, no matter what size the company is, that you have to have ownership of the revenue streams, right? You have to have a seat at the table. You need to be at the highest level of the executives and you need to be partnering with the CEO. You need to be partnering with the CFO, right? It really needs to be a team that revolves around revenue because I always say Without customers, we don't have a company, right? And sometimes you can have different areas of the business that, that'll push or dominate. Sometimes you have a product-dominated organization, right? But, you know, you really need to be able to, you know, align with the strategy of the overall organization and make sure that revenue really is the focus, meaning our clients are the focus of driving the business forward. And I think that when companies get enamored with just their products or get enamored with their, their systems or things like that, that's when companies don't thrive, right? We really need to be focused on the clients and really need to be making sure that sales has everything in their, in their pocket to be successful. And that's great products, great go-to-market strategy, great execution, all those things that are needed to drive revenue forward.

You know, I agree. I do believe that the CRO needs to have that sort of remit, but many times they don't. You know, many times CROs are essentially sales leaders at organizations. They're functional leaders. So what, what in your view was it about your company at that time? I mean, you had been there for a really long time. So you had built up quite a, you know, reputation there, but what was the process that the organization recognized what you just said, that they need somebody like that as opposed to what happens many times is they promote a sales leader to be a chief revenue officer, which is a different context for the role, as you know.

Yeah, well, I think, I think that's one of the— so two things, right? First of all, I think that the fact that I had longevity when I came into that role and I knew a lot about the business, right? I would say I probably knew more about every aspect of the business than most people in the organization. So that created a value. It was a very balanced understanding too. I understand all the different pieces, not just sales, but how did operations work, how did finance work and things like that. So I was fortunate enough to have a lot of people that believed in me because they knew that I really understood the customers and the business. But second to that was working with Kali. I think what he did for me, which made me have a good career as a CRO person, is he added some rigor around that knowledge. He added my ability to, you know, push me on my financial rigor, make— making sure I really understood how the company made business, how the company made money, how our customer— like making sure we put our customer on it, how our customers made money, as well as that operational aspect of making sure that there was— the foundations were in place to allow a revenue organization to really run. And I think that's where the evolution of the CRO is really going, right? Where I look at my sales leaders, my next line, they are really the people that are the sales leaders, right? I mean, I lead them, but they're, they're the empowered ones. If I don't have them and the next level of leadership engaged, driving strategy aligned with me, I'm never going to get to everyone else in the organization, right? So they're, they're the people that really help with the strategy. And then I sit on top and the operations— not that I don't go into client calls, it's not that I don't talk to sellers and things like that. But I'm making sure that we have all the operational excellence in place so that we can thrive as a sales organization. So we're not, you know, undercut with all the administrative things. We're not, you know, trying to fix things that aren't going well with the organization. So I think that it's really— I really look at that leadership layer as really they're, they're the active sales manager people or sales leaders that are out there. I'm, I'm with them. But I'm really making sure we have operational excellence as well. So I do think there's really two types of CROs in some aspects. There is that one that is the sales leader only, which is great for some organizations, but I think there's also that operational excellence that's needed as well.

Well, I tend to agree. I think that might be the case because companies look at it that way. My belief, and as you probably may have seen from the work that we do, is The full stack, let's call it, or the full cycle chief revenue officer is really ultimately what a company needs. When your company gets to a certain stage of complexity, having functional leaders, as I'm sure you know very well, becomes very difficult to manage. You have a lot of seats at the table, a lot of C-suite executives who have a lot of opinions. You have a lot of silos. It's very difficult also to get to cross-pollinate data and process across organizations like that. You know, we've just changed a lot with the technology and the way that we can do things today that the sort of classic, let's say, you know, cowboy-type chief revenue officer, like from 10, 15 years ago, I don't know if they're as relevant anymore. It's a much more operationally driven, customer-centric kind of a business market right now. And I'm curious what your thoughts are, like if you were to be looking for a CRO, let's say you're a CEO of a company, maybe the size of the one you're working at right now, right? And you're interviewing a chief revenue officer, what are the top qualifications and competencies that you think would make, likely make the best chief revenue officer and Secondarily, what would the kind of remit that you'd give that person to run the organization?

Yeah, so I would be looking for absolutely someone that is a strategic thinker, right? Making sure that they're able to put strategy in place. But I think what goes along with that is also the ability to execute, right? You can have— if you can have a strategy, but if you don't execute the strategy and then constantly look at the strategy, say, is this the right strategy, right? Reworking it. I think that that adaptability, that strategic thinking. I always say that ability sometimes even at the CRO level to sit very strategic and then at times become very tactical and then know when to jump back out and be strategic again. Right. So it's that adaptability and that flexibility. I also think that they really need to understand, you know, what technology can do for a revenue organization, particularly with the onset of AI. And the way AI is really infiltrating and really, I feel like helping, you know, sales organizations and companies in general, but I'm focused on revenue right now. So they'd have to have some type of a technical acumen and business acumen to understand where that makes relevance within the organization and how they can make that happen. And then I think that it's also really important part of it is attracting and developing talent and leadership and teams within your organization, right? You can only do so much as a CRO, but when you bring good people in and good talent in, and I always say people with superpowers, right? Different, some people that have been at companies, some new talent into companies, people that have different things that they're good at, then you really can develop a well-balanced team. So I think it's really a combination of You know, having strategic thinking, being able to be adaptable, think on your feet, make changes when you need to, be really looking at analyzing what you're doing all the time, some technical prowess to understand how that can help the organization, and then the ability to really bring talent in and build the team around you.

Hey everyone, I want to thank you again for listening. Get great comments across LinkedIn and other channels about the show, and it's really gratifying to see that we're having an impact on you. Another thing I wanted to let everybody know is that we also produce events.

About 2 and a half years ago, we started these CRO roundtables predicated on the idea that, well, two premises. One is CROs are looking for other CROs to talk to, which is really true. It's a very lonely job.

How do we get a bunch of CROs in a room where they're not being let's say disintermediated by panel discussions and sponsorship events and demos and stuff, and really give them a chance to talk to each other. So, we created a roundtable event that is essentially that.

It's a 3.5, 4-hour discussion between 20 and 30 chief revenue officers. And these are amazing events.

The format took off, people love them, and I get requests all the time as to when is your next CRO event.

So to that end, I just want to let you all know that we have a number of roundtables coming up over next year, over the next like 2026.

I want to share them with you so you can, if they're in your market, you can come. So the next one we're having is going to be in London actually in February, February 24th in London. So if you happen to be a chief revenue officer in the UK or even in Europe and you want to come by, you'll be hearing about it more on my website and my and LinkedIn, but put it on your calendar. And then following that, we're probably going to be doing an event in San Francisco in March. There's going to be one in New York in March. I'm going to do another one in Chicago probably in April. And then I'm going to do an event in Boston. I'll do an event in Atlanta. I'm going to do an event in Salt Lake City. I'm going to do an event in Austin, and I'm going to do an event in Los Angeles or the Southern California area. So those dates are to be determined, but they'll be going across all next year. And these events are taking on huge momentum. They're the place to be if you're a chief revenue officer and you want to be in a room with no interruptions and have an opportunity to really share with each other in a sort of a private and confidential open discussion about everything that you want to talk about as a chief revenue officer and collaborate with great people.

So Thank you.

And thanks for supporting the show. And I look forward to seeing you at the events.

And would you say you're likely to maybe first look at people who came from a sales background, or are there other areas where people come from today that you think would make them equally or maybe even more suited to be a CRO today?

Well, I always think that one of the pieces of advice I give any person in sales, which I don't think they always think about, is really understanding financials, right? Really understanding how companies make money, understanding, having a financial rigor, you know, what matters to your customer from a financial perspective. So I think someone with a financial background could be interesting, you know, particularly as, you know, everything that you do has to not just be top line, but bottom line as well. So I think that, that, that is definitely something I'd look into. I've hired people from consulting backgrounds, right? So that they've been in many different companies and seen many different things. So sometimes they can bring a view that's, that's very different than you might have from just strictly a sales background. But I do think there's a value to having had a quota, having to have, you know, performed in the past that I would never walk away from, you know, having people that carried a bag at some point in their life on my leadership team as well. So again, I would say a balance of all of that is what would make a really strong leadership team.

Okay.

That all makes sense.

I'm seeing a lot of RevOps people moving into the CRO role right now. They have a really strong understanding of process and operations and connecting the dots and building systems, which ultimately really at the end of the day, a CRO is managing a system that they, uh, either inherited or they have to build it themselves. Right? So let me talk about that a bit. So you, when you were at, when you had this, this long, like, tenure, 13 years, you became a CRO, as you already stated, you already had this really great knowledge of the business. You had to lick your hands on everything and made sense that because you knew so much, it would make it a perfect opportunity for you. But you went to Epsilon, you're like the first CRO, you're like day one outsider. So what did you have to bring? Like, that's a much different situation. So how did you, like, make that change between that? Having such tenure and then all of a sudden starting new day one?

Yeah, that's a great point. I think that one of the, one of the advantages I had is, you know, through my time at Veracast, I was able to create what I called some, like, playbooks and ways that I approach the business. So I have a very data-driven approach to how I like to see sales teams organized and aligned. I focus on who the customers are, where they are, What do they buy from us? What don't they buy from us? Those types of things. And so because I did have a point of view on that type of playbook and I've had instituted some types of those changes, I did come in, you know, with, with a thought of what I was going to do with the business. And those are— it's a very complex company, right? It's not only Epsilon, but it's also owned by Publicis, right? So you have a lot of complexity to the way you drive the go-to-market strategy there. So I think the fact is that they hadn't had a CRO. So that was the first time that that existed within the organization over all three parts of the business. And my main focus was there was creating a unified go-to-market strategy because there were three different companies and we had many people calling on the same customers, right? Not talking, not driving an overall strategy for large enterprise companies. So what we were really trying to do was streamline the way we approached them, made it easier for them to buy from us. And then in part make it easier to function within, you know, the Epsilon ecosystem because there were different systems there that were never married. Right. There was a lot of different things that went on that made it complex to kind of drive one sales organization forward. So I think the fact that I worked with a complex company that bought and sold— at Veracast, we were owned by McCandless and Forbes. We bought and sold companies all the time. So I learned how to integrate and integrate, how to bring teams together, how to take them apart. And because I had that experience, I was able to bring a lot of that into Epsilon and drive some of that change very quickly. If I hadn't had that experience, I think it would have been much more difficult.

Let me get in the weeds there a bit, if you don't mind.

Sure.

So you get into this new job and it's 3 businesses. They're sort of trifurcated.

Right?

You get customers getting called from 3 different business units. I can, I understand all this sort of spaghetti junction stuff that happens.

Yeah.

So what was the way that you figured that out? I'm just curious. Walk me through the process. So imagine you're trying to explain to a CRO who's walking into a similar situation right now, and you're giving them some guidance on like, what do you do first? What do you do second? What's the process by which you guide somebody to untangle and recreate a system that you need to be more streamlined?

Well, I first got alignment, you know, internal alignment with the finance organization. We did not have a revenue operations function there as well. There was not a sales enablement function there as well, like a true sales enablement function. So the first thing I did was I lined up a couple of those functions that would be needed, again, an infrastructure to support a revenue organization. That was kind of the first thing I did. So I assembled my team. And my team wasn't just sales. It was, you know, outside of sales to make sure that I had the support I needed to, to take a look and say, okay, how do we align this very sophisticated organization? The second thing we did was we did hire, hire a consulting company to come in and help us gather all the data because I said the data was in disparate areas. So we gathered all the sales data, all the customer data, and we brought that all together. And then as I literally got— get in a room for a couple of days and we just started to plot, you know, who were all the customers across the entire organization, what were they buying from us, what was their revenue, blah, blah, blah, you know, all that type of information. And then kind of stood back. Literally, I had it on the wall. I could see it right now, big wall, everything diagrammed out. And once I looked, we were able to look at that data. The strategy became very clear that we needed to verticalize. That there were 7 key verticals of the way our customers were buying from us that popped out as you looked at the data. And then once we had that kind of structure, I then had to go and sell that, that, you know, hey, I want to verticalize the sales teams, bring them all together, unified, put them under, under these, these specific verticals. I had to go to the executive team, right? And they get everybody's blessing to go ahead and say, hey, this is how we're going to drive our go-forward strategy. And, you know, it was complex because there's about over 1,000 sellers and CS people in those organizations. And I think the key to the success, though, and this is where in my experience transitions fail, is in the way you communicate and the way you get everyone on board to the changes that you're going to make. So once you get the structure, once you understand the vision, It is now about having people around the table with you making the decisions to take the business in that direction and communicating to anybody that's going to be affected on your organization of the decisions as they're being made. This is the vision. This is what we need to do to drive the vision. These are the steps we're going to take to do that. This is how we're going to support you. This is what your role is going to be. Like all those things. That's where transformation either makes it or doesn't, in my experience. And so, you know, we, we got, we got them there. We got a very large organization. We got it aligned to strategy because I like a vertical strategy, but I don't always want to assume that's a strategy that a company needs to have. And the reason why I liked it for Epsilon was because it really created a value around the products that spoke to a vertical and we could really customize and tailor the way we approach the customers and make sure we were able to tie all those strategies and all those services and products together. So that was— it drove a value, right? Why would a clean room have anything to do with media, right? And making sure we were talking to customers and understanding why it made sense to think about Epsilon as one and not as a— as three different disparate organizations.

Thanks again for listening to the CRO Spotlight podcast. We're excited about all the great guests we have, and more importantly, we're excited mostly about you for being avid listeners and supporting the work that we do here. Feel free, please, to share the CRO Spotlight podcast with any of your colleagues. We just think there's a great wealth of information here and want to get the word out to as many people as possible, and your, your support of the show is really appreciated. I wanted to share information about a program that we offer called the CRO Masters Council. The CRO Masters Council is a bimonthly group of 6 seasoned Chief Revenue Officers who are looking for a Chief Revenue Officer board of directors, so to speak, that they could share what's going on with them, collaborate with ideas, get some feedback on what's going on in their current role. And, um, these are great conversations. I facilitate them. The CRO Masters Councils, again, they're twice a month and, uh, they last for at least 6 months to a year. So if you're interested in having your own CRO suite, your own board of directors of Chief Revenue Officers, it's a private confidential conversation that we have. It's infinitely useful. Imagine having a room full of other Chief Revenue Officers you can talk to and say, hey, I'm working on this, or have you guys figured that out? Or I'm having this issue right now with my business or my results. These are just invaluable conversations with Chief Revenue Officers. Chief Revenue Officers have a very, very unique role. It's a very lonely job and only other CROs understand what you're going through. So that's why we created this program. So if you're interested in being a member of the next CRO Masters Council, which we have a number of them being put together right now, just go to my LinkedIn and DM me Masters or Masters Council, and I'll follow up with you and set up a call or send you some more information about it. Looking forward to seeing you there, and thank you.

That's great. I love this. So you got a couple of interesting things going on there. One is you have to communicate up, right, to a bunch of people who are now gonna entrust you to make some massive changes in a very big business and turn a ship. You know, it's very difficult to do. And then also, like you just said, communicate this downstream to a lot of people whom are gonna have, as you probably well know, a lot of emotional reactions to change. What does this mean for me? Am I gonna keep my job? You know, all the other stuff that goes with this stuff. Am I gonna lose control? Am I not gonna get acknowledged? Am I not gonna get my raise? Is this gonna, how's this gonna affect me? Right. So the hard one though is you have to get that top support first, cuz then when you have that, then now you can strategize the downstream communication. So how did you do that? What were the ways in which this organization said, All right, Susan, you know, come, come with the plan and convince us this makes sense. And what do you think were the successes or the ways in which you were able to effectively get the buy-in from the people who had been running this business a certain way for such a long period of time to get them to give you that level of latitude to redo this? What was it, the external reputation you came in with? Was it the culture that you came into? Or is there Tension? Were there disputes? I'm curious to know how that went down because I speak to a lot of my clients who are entering into a situation like this and they have a great idea and they know that it would work, but they just can't seem to get the coalition built around them to make it happen and they end up having to compromise. So what do you do about that?

Yeah. So, so I think that what you hit on is right. It's not easy. Right. Particularly being a new person coming in and having, you know, executives there with a lot more tenure. Right. That so and people like things a lot of times the way they are.

Sure.

So but, you know, I was hired in specifically to do this work. There was a lot of conversation prior to me coming in with the chairman about what, what he was looking for. We made sure we were aligned. Um, I think that if I would say one of the things that I could do over again, I would do over again, one of my lessons learned for people on this, on this, uh, podcast to be listening is that, um, they were, there was some fear in making the change. So they asked me to kind of double step the change. So just verticalize a couple verticals, see how it works, and then finish the rest of the work. So the work. That would've taken me probably 9 months ended up taking me like 18 months because we ended up two-stepping the process. And that was, that was not easy because part of the organization was running one way and part of the organization was running the other. The positives out of it was we had some key learnings. We understood what things worked and didn't work. But I would say in retrospect, I probably would've pushed harder to say, no, we need to do this all now.. But again, being newer to the organization, I was definitely trying to make sure that I had alignment and bought what got buy-in where I could and probably didn't push back enough to tell you the truth. That was definitely a key learning for me.

That's really great. So you sort of recognized the fact that you, I get it. I mean, you sort of saw the latitude you were given and you took it and you ran with it and you were able to prove out your thesis. And then get buy-in to grab the rest of the organization to kind of follow suit. So you took a two-step motion. Now, okay, so this is interesting. So here you're in a situation which, again, I'm very familiar with what happens here is they say, yeah, you know, this is a great idea, Susan. We think it makes sense, but we're not ready to let you boil the entire chicken right now. So cut the chicken in half and cook the first half, and let's see how it comes out. And if it tastes okay, then we'll give you the second half of the chicken, right? So that, that's fine, but then there's implications of that too, because it impacts your trajectory around your profit margins and your projections for revenue. So how do you manage those things when you know that if you had it the way you wanted it, you probably would've achieved business goals faster, but now this 6 months or 9 months turn into 18 months. What's the way you managed the short-term goals with those long-term goals, which are the big problems that CROs have is they're being asked to solve the quarterly problem while you know they have to solve the, you know, 5-year problem?

Yeah. So I, I think that, you know, it was hard to be focused on the 5-year problem, right? It was more about being focused on the year or 2-year problem. So, so it, it made it much more complex, right? We had to put different KPIs in for the way that the unified business, for lack of a better term, was functioning versus the more siloed way that, that the company was, was out there. And so, um, I would say that we really focused on where the main KPI that proved it out was, were we actually driving more incremental revenue coming to a, a client holistically as one organization trying to drive strategy or all the products across the whole organization? Were we getting a higher lift in those accounts, in those verticals than we were in the verticals that we were not unified in. And by having that comparison and being able to compare the results, that was really the proof in the pudding to move forward as well. So I think that it made it more complex, but that's that adaptability, right, I was talking about earlier. You know, this job would be easy if it was just linear. Right? But it, but it's not. And sometimes, and that takes time. Sometimes you have to take a step back and say, okay, I wasn't planning on that. How do I, how do I now make this work? And I think that's where you have to have teams around you to support you. That's why finance had to be involved, right? I had to have some support people around me saying, you know, yes, we can measure this, we can't measure this. The comp plans had to be different for these people, right? There was a lot of moving parts. That made it, you know, pretty complex. But I do think that as long as you have some type of measurement in place, then you get the permission to say, yeah, let's go through, let's go for the whole thing.

You mentioned in the beginning of this anecdote that you had to get your people together first, right? So how many of those people were ones that were already there that you were able to utilize, and how many did you have to bring in from the outside? And how did you decide on those things? What was the way that you made that people process, the people process work for you?

Yeah, I would say the way I usually make it work for me, and I'm actually doing it here at Simplify as well, is it's, it was a combination of having people that were there in the organization. I always believe that legacy talent that, that has been good talent are important to keep in an organization, right? They've got background and things that other people new don't. But I also do have a vast network of people that I've worked with over the years that are super talented. So I did lean on some of those super talented people to come into the organization who are still there today doing very well to help really round out that leadership team. And some of those people have been through some of the type of change that I was doing there, right? I've done some of that playbook at Veracast as well. So they totally get what we're trying to do, how we're trying to do it. And so that creates a quicker response. And when people go through this type of evolution of an organization with me on part of my, my leadership team, it's really transformational for them. It's that ability to really think about how does an organization align. Like I always say, it's, it's, you know, you put the organization in place and then you think about the people. Right. So, so that ability to think more broadly than just your sales team, really thinking about the overall needs of an organization, right? They're the things that create that next level of leadership and allow people to go on, whether it's with me or within other organizations, to be really successful. And going through a transformational change like I did at Veracast, like we did at Epsilon, really granted a lot of people, you know, good opportunities to really stretch their wings and become better leaders. And as I said, a lot of them are still there doing great work today.

Got it. So let's talk about this CEO-CRO relationship, which I think is the key for any chief revenue officer.

Yes, I do too.

First thing I, right? It's the key thing, right? So I always tell my clients, you go get a job as a chief revenue officer, first thing you gotta be thinking about is the person who you're gonna be working for, which is the CEO of the company. This is your key ally. If that ally's not working, it's probably not gonna be a good situation. In fact, I'd say that's probably the area where most things fail. You've had this great relationship with Callie for, you know, this is the second time they, he brought you back. Talk me through that process. Like, how did you two develop this and what was it that Callie was looking for this second time around? And, and maybe even some insights into that relationship and things about it that you think are important as to how other people can emulate what the qualities that are necessary for a CRO to succeed.

Yeah. So Callie came into my life when we were purchased by McCandless and Forbes. So I was a senior leader. I was not a CRO. I was a VP, a VP at the time. I became an SVP under him and came in as they were taking control of Vericast at the time and the digital business in particular. So, you know, the initial— the initial was a jarring initial, you know, kind of way we came together. And, you know, we, we go back and we laugh quite a bit about it, but when we first got together, it wasn't easy. It was a very difficult relationship. And Callie is a person that gives a lot of feedback. And for me, it was feedback overload at times and, you know, was, was not always the easiest. But I think what I realized through that, that part of the reason why the feedback was difficult was actually me and not him. And like my confidence about, you know, being able to, to go head to head with him because he was a highly, highly intelligent man. And as we started to realize that, hey, we had different strengths that actually really complement each other, that's when I think we really started to see the motion really, really go, go well together. And he, as I talked about earlier, like you know, he's, you know, Harvard MBA guy. I'm not— I did not do my MBA. And so he, he helped me really understand, you know, about certain types of rigors around running businesses and operations and having business plans and, and business objectives, like in a way that I had not been exposed to before. But I was a sponge and open to. And then I think for him, he was very early in his, in his leadership career. And I think having been a more tenured leader, I think that they were the complements that helped him as well. So they were the type of the things that we really came together and, and we, we don't always think alike, right? Which I think is really, actually really good. And so there would be some back and forth, but I think we always got to a place that we, we eventually agree. And there was a lot of confidence. We had a lot of confidence in each other that we developed over the years we worked together. So now we're now in the 2.0. Like, I, I, he was, you know, I became a CRO under him. My career grew tremendously under Kali. So I was personally indebted to him and professionally as well. And I left Epsilon and I was very much thinking about retiring or downshifting quite a bit. And he took this role at Simplify and, you know, I never thought I'd get a chance to work with him again. I just didn't think the cards would align and they did. And I would say we just, the other day we were sitting across the board table from each other and looked at each other and said, wow, it is really even better the second time around. Because we both didn't work with each other for 5 or 6 years and we both went and developed other skills and other perspectives and other experiences, right? That, And in that time kept our relationship as friends going. So we went from a business relationship to more friendly relationship, just through phone calls. And once in a while we meet up in town, have dinner together, and now we're back together to a business relationship, but there is a confidence and comfort level with each other that, um, I would not have had if all that happened didn't happen. So I'm very fortunate that. I know that I have a CEO that 100% believes in me, 100% backs me. I feel the same way about him. And so it's easy because we can have the real talk, the real conversations, and not be worried about the politics of it all and really be focused on what can we do best for this company and best for this organization. Because I feel so blessed that I could come back to work work for Callie at a time when I was thinking about not doing it and be 100% focused on what is best for this organization without Susan worried about what she's going to do next or any of that. It's a, it's a really amazing place to be and to be able to deal with someone that I know has my back and really believes in me is— and not afraid to still give me a lot of feedback. Let me tell you that much. Yeah, I think that I'm really fortunate. And I, I hope other people get that, get that opportunity in their lives.

Thank you so much again for listening to the Sierra Spotlight podcast. This podcast is an important plank in the Sierra 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. Couple things to note, uh, 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 5 years now. It's the first CRO-focused course that was out there. Uh, 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 like more like 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 a RevOps 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. Yeah, no, it sounds great. I mean, I've had a couple of those relationships in my life with people I work with and unfortunately it's not, it's not as common as we'd like, you know, it, Unfortunately, it's a magical thing when it happens.

It's good.

But I think that the important thing is to know like what good looks like, right? At least so, yes. When you get a new job, right? You sort of know what you're shooting for instead of maybe being wrong. I think you make a great point too, cuz I too developed an incredibly thick skin. I mean, I used to be really defensive when people gave me feedback a long time ago. Now I actually love it.

I'm, I do too.

When someone tells me, when someone tells me the truth, I'm like, oh God, I like this person. Great. You know, someone insults me, I'm like, okay, I like this person. They said me the truth. That's, great to me. It's weird, right? My brain completely changed in that respect. In fact, I find if someone's being too complimentary to me, I don't trust them as much.

I don't like that.

Like, what, what, what, what are you not saying? I wanna know what's, what the white space is, not that, you know? But, um, you know, I wanted to switch gears a bit here because it's interesting. When you were at, uh, Veracast, it was essentially like a print and coupon company, and then it, you moved it into more of a digital business.

So, right.

This sort of goes to the whole thing with, we were talking about with like Polaroid and Kodak companies that just didn't know how to transform. And there's a lot of reasons for that. So what are your thoughts on, like, how you were able to move an organization into a new era without kind of making the changes required in the people and the competencies that are still more tied to the older model and the migration to the newer model and moving people across or getting rid of people and simplifying things? I'd be interested in knowing, like, what that transformation process looked like for you.

Yeah, well, we— well, I, I mean, I started on the print side of the business. I was a sales director on the print side of the business. And when they started to spin up this idea called digital media, I kind of raised my hand and said, hey, I want to go do that. Right. And which was probably one of the most best decisions I ever made. And people were saying, well, why would you want to do that? You're so successful on the print side of the business. And I'm thinking, because I think that's the future, right? And it was really difficult. I mean, it was doing maybe $10 million worth of business. We were renting all of our tech and and it was very, very messy, very messy. And people thought I was nuts that I would leave this great print world and go over to that messy, messy part of the world. Um, but, but I think that, you know, having a print person go over and start to, to actually integrate into that media and create those, those bridges between the two organizations— again, even at that time, I'd been there, you know, probably 8 or 9 years. I had quite a quite a few relationships within the company. And, and that's something I think is always important, right, to make sure that you have a lot of bridges, not just in your own world, but throughout the organization. So, you know, essentially what we did was, you know, we got the product to be better and then we built up that business to, to, you know, a $200-some million digital business. Some of it was through acquisition. And then we started to position the two organizations, the print and digital organizations, side by side and saying, How can we make print work better by wrapping digital amplification around it and creating the digital sales team being much smaller than the print sales team? They were the, they were the SMEs, right? They were the leads. And we started to bring them together and started to become like more of a joint selling organization. That was step one. Then step two was again starting to realign the organization, right? And not just— and having people that were digital sellers over print, mainly print business, right? Really driving that integration of the two. So you started to have the company thinking more digital first. Print was the major main engine, but, you know, really getting that business back to growth because print was declining. Right. And the ability to add digital around it and many, many legacy organizations have done this. This is nothing special, right? Right. We ended up, you know, being able to flip the business from a declining business, you know, to a growth business within about a year by really driving that integrated strategy of print and digital and that value to the customer.

This is funny. I love this because, you know, you and I have a lot in common, you and I. So I grew up, my father, my father was a printing, my father had a printing business when I was a kid. So I grew up with a presses. Like, he bet we had, we had two, uh, six-color presses and small presses. And we did commercial printing. And that was his, that was his business for, I don't know, decades. That's how I was— well, my college was paid for through this business. So I grew up in the printing business. And then, um, I watched what happened when the digital business printing came out and how a lot of these old printing companies just kind of just, just didn't make the jump. And I was selling print advertising for many years. I was going door-to-door selling newspaper advertising in the print advertising business. And I too made this similarly, like you're telling this story. It's funny. I remember when the digital business, I was like, this is great. I went into it right away. I jumped right into this and same thing with mobile marketing, et cetera. So I, I am very familiar with what you're saying, not just specifically, but generally about having the ability to see what's coming and know to jump on something that maybe might be good because it's, it's ending. And that something else is exciting and trying to get other people to get on board and make the leap with you and be the first person out there. It's a very exciting place to be, particularly a company that's grounded in a very specific type of industry and that's how their culture is. Yeah. So, and, and the retooling of an organization and the learning and the new education and all the new technologies and different types of ways of thinking. I mean, it's amazing like how different things are. So that leads into the, Next conversation I want to talk to you about is AI. Like, here we are now, you and I, both at the forefront of this whole new world, which I'm in the middle of right now, really dealing with it quite a bit. What are your thoughts on this? So, you know, we look at the way we sell, the way we manage business, the way we manage data, the way we manage people, the way we manage customers. What is your current way in which you're thinking about the usage of artificial intelligence systems in your processes, and what are you doing about it today?

Yeah, well, I mean, I'm leaning in, you know, I, yeah, I believe that it is, you have to lean in. It's gonna, it's the train has come. It's probably left the station already. I agree. And you need to be very much on the forefront of it. I think that it's easier said than done, right? Because there's just are still a lot of legacy processes and systems and things like that in place. But, you know, we here at Simplify, right, like we do, we have a lot of AI baked into everything we do every day, you know, with our advertising and our location data and things like that. But I still do think you need the human touch, right? I think the human overlay is still vitally important at this point anyway with AI. So I think it's really a huge aid versus actually running the business. But that probably will change, you know, in the future. So for me, I'm thinking about it, you know, we're looking at our CRM system right now, right? And, you know, how can we take the customer experience everywhere from that initial introduction of Simplify, who we are and what we do, all the way through the billing process, right? Be AI-aided in every single step of the way. So I'm not just thinking about the revenue portion, I'm thinking about the entire system portion. So as we're looking at a CRM system, what is out there to, you know, update what we're currently doing that can actually take us from, from, you know, through that entire journey. And from a sales perspective, I mean, it can, it can really unleash so much productivity, right? And the way that you can really use AI to tailor your messages, to really understand what's going on with your customers, to make sure you're up to date on everything. So you're really talking to them about their business. From understanding what does the, the forecast becoming much more predictable, right? Understanding, using AI to understand trends of where we lose, where we win, not so much in the background, but what's coming forward, right? What's, what's the leading indicators of the business, which I think is hard in the current state without some of the easy way for AI to analyze some of that stuff. Yep. Again, you still have to have that human overlay, right? And you still have to be looking at it with that human understanding of your business. And same with the people that are in the business. But I think all that expedites how fast you can go. And I think you— we need to go faster. This is a competitive media world, right? We need to be going fast so that we're always on top of what's happening. So I'm thinking about the full system of what we do. But I think from a revenue perspective and operations perspective, it's really it really will simplify the selling process. And I think it will make our messages to our customers much more relevant. And the analysis of how their campaigns and programs did, much more insightful, much faster. So we can pivot if a campaign's working or not working or we're hitting the right audience or we're not. I think all that stuff again will help us go faster.

Yeah, agreed. And I think it's just, it's been amazing to watch how fast this stuff develops. I've never been in a situation, I'm sure I'm not alone here, that something I'm working with all of a sudden becomes sort of antiquated like a month later. Yeah. It, it's difficult to decide or commit to something because it's gonna change. So there is this reluctance in the marketplace for anybody to make a long-term purchase on anything that has AI in it because they're afraid, well, now I'm gonna buy something that is no longer gonna be useful for me and I'm not gonna commit to it. So I see what's happening with businesses there. Working on basically proof of concept contracts for like 3 or 4 months, and that's all they get out of it until they try something else. And I'm even seeing companies who are going to market and saying, well, we're only going to have 6-month agreements with our clients because we want to make sure they're not being locked into something that may change. And it's changing the way people think about things. And I'm not sure when or if we're going to get to a point where it just sort of stops and we've kind of gotten there now. We can sort of make more longer-term commitments. I think this is the kind of thing that seems like it's always going to just keep kind of modifying, you know, because we're working on some things ourselves with this. It's fascinating what it's doing. It's like remarkable, to be honest with you. And so, uh, interesting to see what happens next. And I think for a CRO, what I'm curious to know is, are you finding that it's going to enable you to have less people? Like, are you going to shrink your teams now? Do you see this as being— I don't want to get into this whole doom and gloom thing about my point being about firing people and it's going to take people's jobs. But there is a simplicity, you know, for a lot of administrative and, you know, tasky work where this stuff could replace hours of people. And I think it's a, obviously maybe 3 months ago, 6 months ago might've been seemed like some prognostication, but it does seem like it's probably gonna be the case. I'm curious to know what you think about that.

Yeah, I think, I think in the present time, no, because I think that unfortunately, you know, in, in the past couple of roles I've had, sellers have been very inundated with, you know, a lot of administrative work. Right. And getting and, you know, not— and even within the systems and like making sure, you know, campaigns are, you know, launching and all those types of things. So I look at it initially. So right now I'm looking at initially as better execution, quicker to our customers, quicker revenue generation. Right. I would say longer term, you know, I think there would probably be some areas of the organization you wouldn't need as many people doing things, right? Where there's, like I call them, you know, chair swivels, right? There's a lot of chair swivels where you don't have, you know, technology filling in, but they're also the areas where we tend to break as well, right? So I think the areas where I think Again, human intervention, I think, will always be key because— for sure, you know, but I think that there's some weaknesses in the way companies execute that definitely AI will take those, those chair swivels out and it'll be much more automated. And then people can be focused on, you know, working with the customer, solving the customer's needs, not so much fixing what didn't happen or what's broken.

Yeah, for sure. I'd like to, before we end, if you could talk a bit about Simplify, a bit about the business, what your goals are, who you serve, and, you know, what you guys are up to.

Yeah. So, so Simplify is really focused on, I would say, the medium-sized businesses, right? We've been in business about 15 years, and initially we were very much a geolocation type of company. We still are very focused on location. That, that's a key thing, AI-infused location and I think that it's to the next level though. You know, I don't know if you know this, but like 80% of purchases are still happening at a location versus online. So I think that's incredible that we still do think, you know, e-commerce still drives to the store. Yeah, still drive to the store.

So, you know, it's a form of entertainment. You know, it's actually a, it's actually a leisure exercise than just a shopping thing. People, people want to go to the store. They want to get the hell out of the house and go, you know, Yeah, yeah, you're right.

And so, so, you know, we meet with— we lead with really understanding location and we layer on there all kinds of analytics and understanding, you know, who the demographic is and who we're trying to get and making sure they're in market, right? All those types of things. And then we measure it and make sure that we're not just driving, you know, clicks and impressions, but we're, we're driving store visits, we're driving revenue, we're driving, you know, people ordering an additional hamburger, you know, when they go into adding to the check as well. And then, you know, and then we optimize all of that and we're really focused. One of the things that we've, we've done since I've been here and, you know, with Callie leadership and Michael's leadership as well, is we've been focusing on multi-location brands and really trying to help them, you know, focus that about that individual location and making sure it's really tailored around that. And then, you know, certain types of verticals, you know, making sure healthcare and legal and, and home services and restaurant and retail, right? Those are ones that jump to mind. So, you know, that, that's what we're doing. We're really trying to be out there serving that medium-sized business, making sure every advertising dollar they spend, you know, does result in an action that drives revenue for them. And, you know, really kind of trying to create that value off our platform, which is is, is what we're focused on right now.

Well, great. And, uh, thank you for having this, uh, conversation.

Thanks for having me.

I appreciate it.

Of course.

Thank you for listening to the CRO Spotlight podcast. The CRO Collective's mission is to help CROs succeed and help founders and CEOs build CRO-ready organizations. You can find out more information about our services at thecrocollective.com. That's thecrocollective.com.

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