Sales Leadership: Understanding the Shift from Head of Sales to Chief Revenue Officer

The CRO Spotlight Podcast, powered by the Growth Firm Production. 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 freeform 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. Thanks for listening. Now let's go mix it up. Hello and welcome to this episode of the CRO Spotlight Podcast. This is Warren Zenna, the founder of the CRO Collective and I'm excited to be here today with a great guest. We have Kevin Mulrain, who is the head of sales for Saster. So Kevin, welcome to the show.

Thanks Warren. Yeah, super excited to be here. Been a big follower of the podcast and so, yeah, very, very honored to be a part of it myself.

So tell me, if you don't mind a bit about what you're doing right now, your role is and where you're.

At, I guess to give you some context. So currently I'm running sales and sponsorships at Saster and I, I broke into sales back in 2007. Early in my career I knew I had a really kind of an aha moment where I knew I wanted to move more into a leadership role because I loved the mentorship, the coaching, like the development piece of sales. And so for about, I'd say 14 years now I've been in different sales leadership roles, was a CRO of a fintech company and also built out a lot of revenue organizations for early stage companies. And so I was usually a fairly early hire and it was really my priorities were to come in and basically build the revenue Org from scratch, whether that was account executives, SDRs, customer success, marketing ops, enablement, you name it. And so I've just been fortunate enough to be a part of some really cool early stage startups. I think the soft like the startup and the SaaS community, if you will, although seems really really big at times, is really, really quite small in the sense that you start to network and just like build connections with some really great people. And so I was fortunate enough to just build those relationships, learn from a lot of people who've done it before me.

Right.

Like I think even prior to my first CRO role and even while I was in sales Leadership roles. I was constantly trying to like learn like what did certain folks do to make that jump in their career? What were they doing that made them successful in their current roles? And so yeah, a lot of the, the building and scaling piece of, of early stage startups is I think where I started to fit in the most. Got it.

So talk a little about Saster. You know, because we talk so much about the SaaS business here and you know, it's a unique animal, particularly as it pertains to like the way a chief revenue officer would be deployed at a SaaS based company as opposed to like maybe a product company or maybe even like a service based companies. I have people right now that are working with me that are working for solar companies as CROs.

Right.

I mean everyone's now dipping into this thing. So walk me through in your view, you think about achieve rep first. Let's establish something here. Yeah, sorry, just curious, how do you define a CRO? What's your definition of one?

Yeah, that's a great question. I would say the CRO is responsible for aligning all of the processes, the departments that ultimately drive towards revenue outcomes. And so I think that for me a CRO is somebody who is focused on recruitment of their teams, collaborating, bringing sales, marketing, finance, product together to really hit the key business objectives pertaining to revenue and more, the financials of the business.

Great, great. So we're on the same page.

Yeah.

Okay. So you know, now my question, what's the, what's your perspective on CROs in SaaS based companies that have a very unique culture in the way that they go to market and the way they grow, the way they expand. And even something you alluded to before, which is interesting, is that it does seem like the SaaS business is so big because so much talk about it, but it actually is kind of small. And I think that's because. Why do you think it is there's all this focus on the SaaS business. It's like such a. Why do people look to that business so much as like a bellwether for things?

Yeah, I think it's because, I mean if you look at some of the most successful businesses, even if you look over the last like call it 5 to 10 years, SaaS had this explosive growth, right? And you saw a lot of companies hit the scene, got really impressive Series A fundraises were growing like weeds. So I think like when you just look at the, called the accolades or the highlight films, like I think a lot of it was pertaining to these high growth SaaS companies. And so it caught a lot of attention. It grew really, really fast. And I think that's where everyone started saying themselves, man, I want to be a part of SaaS. I want to be part of software. Like, how do I break into that category? And so I think, I think that was a big driver of it. And I think in a great way it created amazing opportunities, I know, for myself. Like I was able to get into SaaS sales earlier on in my career and caught, you know, caught some great opportunities with some great companies, was a major part of growing those companies, had amazing teams around me and just helped kind of catapult my career in a way.

Yeah, you said a couple things there that I want to touch on. So. Because it's sort of like part of the, say the foundational principles of some of the stuff we're doing here is based around the idea that the reason why companies need CROs that operate in the manner that you just said is because companies very quickly become siloed. You know, their operations start to work in separate streams and they're not managed properly and they're not like working as an engine, as we say. And you know, without that sort of alignment, both from a process and data and organizational, everything cultural perspective, companies just can't scale because they're going to just start to crumble with the weight of all these different disparate groups that are trying to serve the same thing. So the SaaS model is interesting to me because if I may, it sort of created most of these problems. And the reason is because the SaaS model is so growth oriented, it's almost like, you know, built for growth. You know, it's transactional, right? Subscription based. Close as many deals as possible, get people to sign up, get them on board.

Right?

Get that cadence going, right? Get their contract in play, collect those fees every month. The ARR, the mrr, all those things came from that business. And you said something that's really amazing. So talk about this how when you think about companies that are successful in the SaaS world, a success means we got an A round. Yeah, you announce it, you go to market, you go, we just got funding. And, and what you don't hear. And again, I want you to take this the right way. Cause it does go to. What I'm saying is that you never hear like, our customers are really happy. Yeah, that's not an accolade. You hear from SaaS companies, they hear like, we have the most satisfied customers. Like, no, we got the biggest A round, we got our next B round. And that's why people flock to these companies because that's the way that success is being like sort of touted in the marketplace. And so I'd like to get your thoughts on that because it is sort of colored the marketplace a lot, right? Investors love those kind of businesses, love to see that kind of growth, but they're not necessarily consumer or customer or client concentric businesses. And it sort of goes against a lot of the sort of principles that would go towards normal businesses, I'll say normal, wrong word. But traditional businesses, let's say where, you know, customer satisfaction is important, most important thing, because that's what's going to really help you kind of grow your market. So what are your thoughts on that, having worked in that for so long?

Yeah, it's, it's so interesting you say that because I can think of probably over the years, right, I've worked in a few companies where we secured a series A or we secured a series B and the number of emails I got from salespeople and the first line was congratulations on the series A. Congratulations. And it's this like, and it's almost this accomplishment. But in reality, I think if you kind of take a step back and you look macro over the last couple of years and then you kind of look at where we are today, it was almost this like assembly line, like marketing creates all this stuff and then sales closes it and we hit it off and it's. And it was all about that top line revenue growth. And then we started throwing tons and tons of headcount at the front end of that funnel, right? And it was let's hire tons of salespeople because we've got these five that are hitting quota, we can find five more to do the same, right? And there really wasn't this focus on how do we keep our customers happy, how do we continue to evolve to whether it's a product, it's our service, whatever it is, to continue to grow from the customer base. And I think it's interesting, I think today a lot of SaaS companies can probably learn a ton from these very, as we've said, traditional service based companies that have just. Oh absolutely. They put their customers first. And the way in which they grow their businesses is through really great quality work, through referrals, right, through testimonials, through all these different channels. But I think in a way like these accolades have almost kind of tainted the SaaS world in a way because it's funny, I had a previous CEO who, he got one of those Congrats on the Series A emails. And he was like, congrats on the Series A. He's like, our jobs just got tougher.

Right.

Like, we now have higher expectations now. You got to get a Series B now. Yeah, now it's. Now how do we get to the.

What have you done lately?

Yeah, exactly, exactly. So, yeah, it's, it's an interesting world. But, but I think you're right. I think if we looked at it differently and you thought, man, like, wow, we've got all these. And I've seen some. Actually some folks now are like, thank you to our customers. Thank you. You know, and like they kind of pay it forward to the customer base that got there. Which, which is really, really nice.

Yeah. I mean, I'm certainly painting maybe a bit more of a stark black and white sort of narrative here, but I think it speaks to this and here's some other things that I think about this. So why is it that a Series A or a funding round is congratulated? Well, obvious reasons, right? I mean, if you get capital, some other third party entity felt you were worthy of it, right? They looked at your business and they felt were willing to make an investment in you. So someone took a bet on you and they gave you an infusion of cash. And so in and of itself, right there, sort of, maybe they passing that milestone is congratulatory because it's hard to do. Not everybody gets it. Second part of it too is, you know, it's so weird, but you know, when a company goes to market and talks about how they just got a funding round, everyone thinks about, oh, good money to spend. I'm going to call these people, right? More people that are going to get hired, more vendors are going to get hired, more media is going to get bought, right? That's what everyone looks at. It's just like another pile of cash that's going to be spread around and everyone flocks over to that company now because now they have money to spend, right? I mean, how many emails do you get after a funding round from 20,000 vendors saying, hey, you probably can use X, Y and Z. Just another reason why people congratulated because there's sort of like this desire to keep the economy flowing and a rounds sort of keep that going. But I think what happened though, and I think this is where I think the wheels fell off. This, this is my opinion, this is sort of like why the CRO Collective was even started, is because as more and more companies went to like, let's call it like a SaaS based model or a growth models. You said it so eloquently before, just that top line growth. Throw more salespeople at something.

Right.

And with more and more salespeople you throw at a business, the more technologies that you need to support those salespeople and the more those technologies are developed that help those salespeople become more and more effective. And what does more effective mean? It means reach more people.

Right.

It's getting more attention, get more inbound.

Right.

And so what happened I think in the last four or five years is it's overload. There's just so much inbound like I'm receiving more and I'm not alone in this. It's not me, I'm not unique. But how many inbound you get like a day on a day to day basis and it's all driven by this same model that if you replicate it, I do think it cannibalizes itself. I think there's a point where how Many inbound software SaaS based email requests can I get in a day before they all look the same? I don't want to see them anymore. And I Now your job gets harder because the marketplace is kind of replicating what they perceive as success and success eats itself. So what are your thoughts on like what does a SaaS company do in this situation now where it's become almost, you know, growth at all costs and the customers are shutting off and they're shutting their ears and aren't listening anymore. And now at the same time too, that top line growth that you talked about resulted in all these unneeded salespeople that they have to let go of because that's what happens all the time. So this seems a cyclical thing that's going on. And given your experience working for particularly a company like Saster that's sort of at the seat of this thing, I'd be interested in your perspective on what you think is going to needs to happen in order for more of that integrated, more aligned revenue operations to occur at SaaS companies without that knee jerk reaction to try and go for more of that frontline growth.

Yeah, I think it's. Well, I think it starts with having a really honest look in the mirror around the value of what your product actually drives.

Right.

And are you a, especially I think in this particular year, are you a nice to have product or are you something that companies really, really need? Is it table stakes for them to operate and to grow and to really enable them to hit their key objectives?

Right.

And so I think that's the first thing because again, inboxes are flooded with very boilerplate. Nice to have messaging. It all kind of looks the same and after a while we all become a little bit numb to it. So I think you have to find ways to really ensure that your value prop stands out amongst a sea of pretty bland, terrible messaging. I think the other part is really looking into really. And again, you're going to derive a lot of this from your customers. What elements of your product do your customers love the most? Which will the ones they can't live without really understand what are you doing for your customers and what impact does that have on their business, on their daily lives, in their jobs, day to day, all of that sort of stuff. So I think that's, that's sort of where it starts. But the next is I think and again this, call me biased because Sasser, it is very community focused.

Right.

But a lot of founders and companies that I'm talking today are really looking at ways that they can, they can build their own community, right? Really build around their key Personas, around their customers. That's going to be a major part of I think, how companies continue to grow and thrive. And it's going to come from, it's going to come from the network, right? Like I think it's going to come from the network, it's going to come from referrals like we talked. Like think of how some of these like traditional businesses have grown and scaled their business, right? It's through great products, through quality service, it's through providing unparalleled value.

Right, right.

To your end customer. And if you can do that through partnerships, I think channel partnerships is going to be a really big thing to scale beyond the sales team as well. But I do think that sales has to. The best salespeople today are experts in their market, their category, experts in their Personas. They're more, I don't want to say consultants, but they're more finding ways in which they can help or can't help as opposed to trying to, you know, force or jam a product down somebody's throat, if that makes sense.

No doubt. I think there's no question I'm seeing a shift in, in sales strategies now. And I think everyone agrees that you sort of have to be more consultative even if you're selling something that people can sign up for online. I would say that the challenge on that is that a company that is, let's say subscription based and has a big tam, you know, where you can just keep on growing and growing and growing because there's like, you know, like Salesforce, right? Every company can buy Salesforce, technically. Yep, yep. Even though it probably doesn't make sense for them to sell Salesforce to a company that only makes a million dollars a year. They probably have a group for that. They probably do. They have resellers that do it. They probably figured out a way to just say, screw it, let's just get this thing in everybody's hands, right? Which they can. Any CRM would be sort of similar in that category, but I think Salesforce is uniquely sort of positioned that way. So if, you know, you have sort of a, let's say, relatively unlimited marketplace, you can sell your product to anybody, which, you know, let's face it, investors love those kind of products because they know sort of an endless spigot of people you can sell it to.

Right, exactly.

You become almost less specialized and just so big.

Right.

You can just throw more shit against the wall and get as much as business as you can, and there's plenty more room to keep throwing stuff at it. Whereas the other side of the coin is some subscription based business that's highly specialized, where it's really niche, where, you know, you service a very specific, carved out part of the marketplace, like let's say only, you know, hospital groups, you know, like just really a very finite certain market for you. You can't do the same thing. You have to be more finessed because you can't cannibalize the marketplace because there's a point where it ends, you know, it's finite. Now a company like that may not get a funding round because of that reason. They may say, you know, it's like this, too specialized for us. You know, we'd like to invest in companies that have a big upside, you know, and you can become a unicorn. So that's what I think happens though, and I'm bringing this to a point, is that, you know, I think that the investment or finance community tends to only want to reward companies that have a big enough marketplace that they want to get that scale. And as a result, it's the smaller companies that I think, in my view, they end up winning because if they don't have that money coming in, then they're forced to have to have business developed in different ways. They don't have the luxury of just spreading as much stuff around they can. And I think that's why the smaller companies are probably have an advantage in a weird way. Even though they can't get funding as easily, they're forced to have to do it in my view the normal way, which is meeting people and having conversations with them and building a marketplace in a different way because I don't have the benefit of that money. I'm just curious what you think about that as a way of looking at the world because I do see this is what's affecting Chief Revenue officer role today mostly.

Yeah, I, I, I definitely see that. And I think to your point, I think some of the, the best startups I'm seeing right now are those that are, they're, they are highly focused. I won't say specialized, I'll say focused on what they're building, what they're going to accomplish today. But they do have that path to, you know, this is our product roadmap for the next five years, which is going to open up the tam.

Right.

And so it's like, it's almost building blocks to that really, really large.

Right.

And so I mean I think if you look at, there's a, probably, there's, there's probably tons of great examples, but you look at like a Salesforce or Sales Loft as a good example of it.

Right.

They came out with a very basic cadence tool. Then it was analytics. Now it's conversational intelligence, it's forecasting, it's pipeline.

Like it's all these pretty big feature rich stack. They built those guys now for sure.

Yeah. You know, so you kind of start as that point solution where you're very focused on what you're building and then does kind of start to come out more end to end. But no, I think that's, but that's the way it has to be. It has to be built. And I think that's, but it's an interesting concept because I think that's the biggest challenge startups face in a way.

Right.

And CROs, especially when it comes to your go to market is what are you simply going to say no to?

Yeah.

And that can be your strategies, that can be the markets you're going to go after. It can be the, you know, aligning with your chief product officer on what, what's the next feature we're going to build.

Right.

Like, but I think that's, that's the biggest challenge that I've personally faced and seen. It's like what are we simply just gonna not do? And that sometimes too is, and I've had the conversation many times like are we gonna say no to this customer?

Right.

Because they want us to build X, Y and Z, which we don't have today. But this is the Revenue opportunity, and we gotta get to the number. And so it's interesting. Yeah, it's a really interesting challenge because.

The problem is you're sort of. If you're a CEO and you've been given some funding, you now serve two masters. You serve the customer and you serve the investor. And I think the investor wins almost all the time. I just do. And here's why I think so. Because if I have to make that decision.

Right.

And I think a lot of the examples you mentioned before are driven by this. So if I'm a CEO and I launched a product that I know has a very specific, focused marketplace, and I know that I can serve that marketplace, it's really very clear. And I do that, you know, yeah, sure. There's probably a point where I'll reach the end of that market and then I can do one or two things. I can figure out other ways to serve that same market, or I can try to replicate it into a new market.

Right.

These are all the kind of decisions. If I take on funding, there's no doubt that the people are going to want you to expand it to new markets. They're going to. They're going to say, okay, how can you replicate this to make your market bigger? It's always about size.

Right.

And so now that that CEO, who may have had a vision of serving this one marketplace, because that's their passion, is now sort of forced by virtue of this funding round to now think about ways to serve other markets because they have to satisfy the needs for growth. And I think that's the part that it gets interesting to me. It's like all of a sudden, now the culture of the company changes because money. And again, I got nothing against money. I'm saying it. Just the effect that it has. Okay. And so if you're managing a business, if you're a chief revenue officer and you're managing a business and you understand the dynamics of, okay, I got my CEO who has this vision and. And I've got this investment group who has these objectives. I'm stuck in the middle. All right, what is your perspective on that?

Right.

You're the CRO, and you're sandwiched in between financial goals and, let's say, customer goals. Like, I'm just curious what your thoughts are on how you speak to achieve revenue officer and managing that very precarious sort of relationship between those two things, you know?

Yeah. In a way, it's almost. It's kind of like being a mediator.

Right.

And trying to bring two parties that Very much not, I want to say disagree, but trying to find a common ground. And so the way I've kind of looked at it in the past is, you know, let's kind of take a quick pause and look back at, you know, especially to like, what are the major objectives and what are the major goals? And sometimes, you know, like for instance, right. Like sometimes there's a major focus around profitability and margins.

Right.

And so if you can use some sort of data point, something foundational to kind of pull the conversation back to and say, hey, look, we can go and we can either build this functionality for the current marketplace and, and this is what we think we can do from a growth perspective and because we're already there service costs.

Right.

Like you just have to kind of tie it back to a data point that's going to make both parties really happy and bring them back to like a semblance in a way. So that's, that's kind of how I've tackled it in the past. But it's, it's a tough place to be, right? Because you know, you are, you're serving two masters and you don't want to cross your CEO because they can easily be, you know, because that's the person you're dealing with day to day. And you have to have tight relationships at the same time, right. Like the investors are also folks that can take a look at you and say, you know what? This person doesn't believe in our vision, they're not aligned with what we want to do. Let's go find the person that does.

Right.

And so, so you have to kind of be that mediator. And again, I found if you can bring it back to some type of common goal which is not, it's not a story, it's not, it's something tangible, right. It has to be something tangible like a data point, a metric and a goal that you've wanted to achieve. Um, it's just helped bring, bring folks together and make more. And again, I think a major thing for CROs, make more data driven decisions as opposed to emotional gut, you know, that sort of a thing.

That's so great. Thank you for that. Because you're, I think you're, I agree with you, you know, doesn't make you or me right, but I agree with you. So I'm going to say so, you know, because we both agree you're right. Okay. So, so it's because I have a strong belief that if you think about the Chief Revenue Officer role, such a key component of that Role is the data, which is why that revops function is so critical to the role and the CRO's visibility into the data and the systems and the processes. Because every single decision you make, if you can substantiate it or rationalize it with data, it makes your life a lot easier.

Right.

But you have to know which data to show. Right. So here's what's interesting. So stick with this, because I think it's a really interesting sort of a conundrum that most of my clients find themselves in right now. So you've got this situation. You get hired by this visionary CEO, and he's like, we're going to, you know, serve this marketplace, and we're going to become the. We're going to. We're going to. We're going to make every. Every heart healthy in the world. Something like that. Yeah. And, okay, great. I'm on board. It's a wonderful thing. I want to do that. And then they get some of my money, because the money comes in from your success. And then investors are like, can you do that for kidneys? Can you do that for lungs? And all of a sudden the CEOs like, yeah, I really like hearts. That was my whole thing. My father died of a heart attack, and I'm really looking to do that. And I guess I could do that. And you could see the company go through a change based on this new sort of cash infusion and this sort of philosophical conundrum that your boss is in, and you're in the middle. So, you know, I've talked about this a lot with my. My clients is sort of almost mediating a middle ground. Yeah, right. Which is like, okay, look, guys, what got us here. What got us here was this amazing vision of helping a specific marketplace. And now I understand there's cash, and you guys want to use that cash and turn something bigger. How much do we want to stretch this thing out to the point where it doesn't look the same anymore? Like, what's the. What's the goal here so that I can be responsible for delivering those results, you know, because part of what got us here is the fact that we have really happy customers. Not just that we just had a marketplace. And I do think that there is this sort of thing where, again, you can bring data to support both scenarios.

Right.

So in other words, our attrition will go down, but our TAM will go up.

Right.

Or, you know, our churn will be worse. But, you know, stuff that I think, like, this is important, and I think that what Happens Too often is CROs don't have the access to the data or access to the, to the visibility into the data enough to be able to make these sort of calls. So I kind of want to just switch gears because I want to ask you a question which I was on my mind when you're talking before, which is you said you were a Chief Revenue officer, right? You were, you were one. So how did you, how did you find yourself in that position? Did you just get promoted? Did you ask for it? And how did you train yourself to do the job? What was the way that you kind of determined how to expand yourself from? I assume it was a sales position, right? You moved into it, right?

Yeah. So in my career, I went from, you know, individual contributing sales. Like I said, I knew I wanted to get into sales leadership fairly early on, so, you know, went from sales management to vp. But early on in my career, I was a VP of sales and we were bootstrap business, so we didn't have a lot of tools. And of course, like my CEO at the time was, you know, I remember saying we have no way to forecast. Like, can you build a forecasting model? Can you help us forecast more accurately? And so just in my career, I think naturally I was given the opportunity to dive into more revenue operational situations, and I just really took a liking to it. So revops, whether it's been myself trying to build things out, building a lean process like the data, the analytics, that has always been something I've been really passionate about. Don't get me wrong, I think I'm a pretty good salesperson, right in the front lines with customers, but where I think I really thrive and my passions are definitely more around the operational aspects of it and then the team and the people building. So I think because of those two things, I was able to do well as a VP of Sales. But I think my, my skill sets naturally gravitated more towards CRO, and not because it's like not a level or a hierarchy thing, but just more the operational piece, the talent piece, like attracting talent, building talent.

The role profile is more suitable for you as a. Your, your personality and your skill sets and your interests.

Yeah. And so what I. And I've always walked into every single situation, even to this day. Like, I, I never ever think I'm the smartest person in the room.

Right.

And so I've always wanted to go out and just learn. Like, learn from the people who have done it before me, look at people who I think are doing things the right way. And have been successful and just study what they do and understand it. And so, yeah, again, lucky and fortunate enough to have a really strong network of folks that I've been able to get access to. Years ago, I don't do it anymore, but I started a podcast because I just want to learn from like, what everyone else was doing out there. And I felt like at the time I was in a place where I'm like, man, a lot of people are looking at me for things and I don't have all the answers and I want to go learn, you know, and so I've always just tried to put myself out there just to learn from folks that have done a really great job themselves and see, you know, what can I emulate and how can I take the things that I think I'm good at and I'm passionate about and just continue to lean more into that?

Yeah, it's great. So you'd call, you're. You're what I call the, the organic Sierra, which means you're sort of homegrown, you know, wasn't like you sort of had this, let's say aspirational like, oh, I want another. I want to get promoted, or, you know, I want another level that was more like, this is just what I do. And it sort of resulted in you doing it just because it's what you were good at. You know, there's the people that find themselves in the role because they're personality and their profile and their skill sets lends itself well to doing it. And they, they just hand you the role, like, all right, you're the guy. You do this, you know?

Yeah.

And that's, that's. Those are the best situations. You don't have to sort of interview for the job. You just start doing it and then all of a sudden they give you the title because you're already doing the job, you know.

Exactly. Yeah, exactly, Exactly.

That's nice.

And I think, yeah, and it's been fun because I think for, for me too. Like, again, I've gone to spend, you know, like, for all of us. Right. There's elements of our jobs we love and we're passionate about, and there's also elements of the job you're just like, yeah, if I didn't have to do this anymore, I'd be totally cool with it. Like, I'm totally okay with that. And so with this, you know, kind of organic progression as you said, like, it's just allowed me to spend more time doing the things that I enjoy that I am passionate about. And the things I think I'm good at, right. It's like, it's tough sometimes doing things that you got to do. You don't think you're great at them.

Right.

So being able to lean more into the things I actually think I'm pretty good at has also been a ton of fun as well.

Yeah, it's great. So, question for you. So if you're talking to a aspiring chief revenue officer, someone who wants that job right now, whatever reason they want it, what would you say are some things that you think would be helpful for them to think about? Let's say they're head of sales right now, they run a sales organization and.

They'Re good at it.

You know, they're doing well, they're a successful sales leader recognized, and they're at a point in their career where they genuinely are, have enough experience where a CRO role would be appropriate thing for them to be thinking about. But they don't know kind of like what the next step is. What would you kind of offer them from your perspective of what way to do it?

Yeah, I think it's a really good question. I think the first question I would ask is why they want it. And again, anytime I've, even with sales reps I've mentored, I've hired, whenever they want that next progression and that next promotion, I've always just kind of asked why, why they want it and why they think they'd be good at it. Because I do think particularly that head of sales role to that CRO role to me are very, very different roles. Although kind of, you know, it seems like it's a linear progression and still obviously very revenue focused. But the, the CRO role, again, it's probably less of that Rainmaker salesperson, right? That's like leading the team in the deals, all single, every single day, closing deals with the team. Like, I think a CRO, you still have to be very customer facing, but you're less in the trenches of that sales motion day to day and you're making probably less decisions day to day, but bigger decisions.

Right.

So it's a little bit heavier from that side of things. But I would, I would also think about like, what's a, what's a gap analysis? Like, what do you think you're doing really well now and what are the things you think? Like, what's going to, how is it going to change for you in this role? How are the skill sets going to change? And again, if someone came to me and said, oh, you're going to have to be a lot more, you know, entrenched in revenue operations. You're going to have to align a lot more with marketing and with your product and your finance team. It's less about the actual pipeline, it's more about the team building and the recruitment. For me, that stuff got exciting, right. If someone I know, again, I'll just use the AE to sales manager because it's such a clear example. I know some AES who just love to focus on themselves and close the deals. There's nothing better than closing the deal. And all the stuff that comes with leadership, they just, they're not great at. They don't love.

Right.

And so sometimes they make that jump and they're like, oh, I made the wrong decision.

Right.

And so I do think that the roles are very differently and it's just. I think it's mapping out the differences, the skill sets where you're going to be spending your time. And is that what you really want to do?

Right.

Do you want to go learn those skills? Do you really want to spend the time there? Do you want to be doing these things? Do you want to be in front of the customer every single day closing deals or do you want to be in front of the board?

Right.

And sometimes things, you know, again, similar to the Series A.

Right.

Being in front of the board sounds cool and prestigious. Right. But it's not always great, right?

No, it's tough. You're like naked up there.

Yeah, exactly.

Well, it kind of great. I'm totally. My second question, which is, what then do you think are the core competencies that make great sieros?

Yeah, I think somebody who is, I'll say operationally minded, but when I say that, it's really understanding the financials of your revenue and the implications of your revenue. And an example of that is like, you know, the deal you take today for this much ARR. But what does that mean for retention and churn and expansion?

Right.

Making smart decisions around the numbers 2. I think a really good CRO is somebody who's a talent magnet, right. Someone that can recruit a lot of really great talent, can bring in a good team. I think if you're going to go in as a CRO role, you have to think about like, who within my network am I going to bring bring into this team? I think again, it's somebody that can manage all of the systems but how those interact between the different functionalities. Right. It's got to be somebody who can go with marketing to sales, to product, to finance, and somebody who can manage up really, really well.

Right.

To like to your CEO and to the board.

Right.

You have to have somebody that can really tell that narrative around the data what's really happening. And I think somebody that is a constant problem solver, I think is a good way of putting it.

Right?

Somebody who, because with, again, especially if you're going to be in SaaS, what you did this quarter means you got to do a lot more next quarter. And what you did this year means you got to do a lot more next year. So that curiosity, that problem solving. Okay, what's the strategy? How are we going to get from where we are today to where we are tomorrow?

Great, great, great stuff. And lastly, if you're a CEO, what advice would you give them to manage and make sure that your CRO succeeds?

Oh, that's a really, that's a really, really good question. I think that's probably one of the more important questions on this and I'm sure you ask quite a bit. So advice for a CEO managing a CRO? Well, I think to take even maybe a step prior. I think when you're, when you're hiring that CEO, that CRO, I think it's being really clear and understanding on what that person's priorities are. And again, why are you hiring CRO? Again, if it's, oh, we want to go close these deals up market, hire a senior ae, right? Like hire a salesperson for that. So I think one is understand those priorities and understand the profile of what you, what you really, really need versus what might be a nice to have. And then I think for managing that person is you have to give the CRO the room to go do what they do best.

Right.

And that may be, you know, again, if you're going to have a CRO who you're not going to allow them to invest within revenue operations, right, Then that's going to be a really, really tough job for that CRO. So I think it's like, give them the space and give them the grace to do what they do best. Of course, be very much aligned on the strategy, on the plan and how you're going to make those things happen. But you're hiring a CRO for the reason, so give them that, that space and the autonomy to do, do what they do best. And then, you know, I think the, the, the final piece is, you know, you have to support it. Then after that, like, you have to be in their corner, you have to support them, you have to enable them. And so I think that's, that's you know, I guess the advice I'd given and where I've seen it go really well or really, really wrong.

Yeah, that's great. So I'm in agreement with this. Like, this is one of my core tenets, is the upfront agreement is what makes the job successful. You know, the mistakes are made before the job is accepted.

Yeah.

And all the CROs I work with right now who are really having a difficult time, it was because they did a bad job of vetting the opportunity and they said yes to a lot of things that, without thinking it through. And they didn't make the right agreements. Yeah. With their boss, future boss, mainly because they were afraid that if they did, they wouldn't get the job, and they ended up getting a job they didn't want, you know?

Yeah.

So. So, you know, it's sort of like one of those sort of things. So you're 100% right. It's all about the two. Two people, this, these two key people agreeing on what the job is, what's required of it, and having a process in place for making sure that the CRO gets what I call the autonomy, the authority, the resources, and the Runway to do the job appropriately, or else you're kind of screwed, you know, and you have to be able to look under the hood too. I mean, that's a really important thing, you know, because every one of my clients goes, boy, I didn't know what I was getting myself into. You know, they don't have anything together. You know, they, they made, they thought they had everything all buttoned up. And I'm realizing that they didn't even know what button up meant, you know? Yeah, there's a lot of that.

Yeah. You know, there, there is, there is. And it's funny because I think one of the best things that CEOs, founders can do through the interview process is have that candidate present their strategy. And you can say, hey, here's where we're going to end by the end of the year. Here's what we want to accomplish next year or the next 12 months. And again, keep it open ended. But what's your strategy? How would you think about this? What are the things you would do or the things you need? And have a really honest conversation around that. And it's, it's funny, I think when I was, when I had those opportunities and interview processes, when I was early, earlier on in my career, I looked at it first, like, what do they want to hear?

Right.

And like, what do I think they want to hear? And I threw A lot of that kind of stuff in there. But then as I've kind of matured and with experience.

Right.

And all of that, and I'll never forget this, but maybe three years back or so, I was in this spot and I put together my very honest plan.

Right.

I kind of looked at it as like, okay, if this was my business, how would I go about this? And, you know, transparently, me and the CEO did not see eye to eye. We didn't. We didn't, you know, we didn't really, like, there wasn't great chemistry on it. We didn't see eye to eye on it. And it was the best thing that could have happened to me, I think, because I avoided a terrible car crash.

Right.

100, you're right. And it does take maturity to know, to do that. Because I interview people. People hire me to interview people, and one of the first things I look for is, are they telling me what I want to hear? Are they telling me the truth? Yeah, if they tell me what I want to hear, it's a big red flag to me because, you know, I'm never. I don't even really know what's going on with this person. All they want is to get the job as opposed to interview me. I should be being interviewed. When I'm interviewing somebody, you should be interviewing them. Person.

Right?

That's really, really good. Good stuff. Good shit. So I'd say, lastly, I would say, what. What are you up to right now? What are some. What are people? How can they get in touch with you? What is it you want them to know? Are you up to some things you're working on? And, you know, what are some ways that people can. Can speak to you or whatever you want to. You want to talk about that you're dealing with working well right now?

Yeah, no, absolutely. I. Yeah, I mean, definitely. I love connecting with folks, even if it's just to learn what they're up to, see what's going on in their world, see how I can help. Again, I just. Again, for me, it's kind of like I love paying it forward and just helping folks out. And I think I do a few of these kind of conversations week to week. And whether it's, you know, helping people through interview processes or trying to land their next job or things are going on, and so love doing all of that and always open to it. I'm on LinkedIn. It's an easy way to get in contact with me. I'm constantly on there. And so definitely, definitely would love to connect with anybody. Just if. If there's a way I can help, always like to pay it forward.

Great. Well, look, I want to thank you. This is a really great conversation. There's really good nuggets here. So appreciate you taking the time to speak with me. Bye. Bye.