Building Scalable Revenue Operations from the Ground Up with Jessica Robertson

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 B2 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. Welcome to the Cereal Spotlight Podcast. This is Warren Zenna. I am the founder of the Sierra Collective and today I'm real excited to welcome a guest that I met, Jess Robertson. I had a event on March 11th of this year as a Sero Roundtable, which they're great events, by the way, and I'm doing another one in June in New York. So anyone who's listening to this and wants to come to another CRO roundtable in New York, it's on June 2nd, you can just find me on LinkedIn and tell me you want to go. They're great. And Jess was one of the CROs that showed up. I met her for the first time and she was just one of the smartest people that I've met in a long time. Seriously, just like a sort of personality and just intelligence and insight and just incredible. And so we ended up getting together afterwards and having coffee and I just thought, my God, this person is so smart. We had a great conversation, very like minded, I thought just so much she has to say. I just want to bring her on the show and talk more to her here in this live setting because I think that stuff that we talked about would be interesting to a lot of other people. So you'll hear this great conversation we had. It could have gone on for three hours. We talked about so many things. Philosophy, business, sales. Just incredible. So today's guest is Jess Robertson and enjoy it. Thanks. I'm so glad you're here.

Thanks for having me. It's by nature we can't stop talking. Right. That's our job.

Thank you. Right, you're right. Well, you know, look, some people talk and they don't say anything, you know, but you say a lot, so it's a different thing. Yeah, so. So Jess is the CRO of a startup. But, you know, I got to know Jess. He's got a really cool history and some great track record and some interesting ideas. So you know Jess, why Don't you just introduce yourself a bit, tell everybody who you are, what you're doing now and then a little bit like sort of how you got here?

Yeah, sure. As Warren mentioned, I'm the CRO of a company called Orb and we believe that we're kind of redefining the sales process and bringing relationships back into it. We're kind of at, I'll use Warren's words here, peak noise in the AI world. And we're trying to find a way to become efficient and access our key accounts again when it's really hard to do these days and we feel like we've cracked that model in how to bring relationships back into it. So I started about six months ago. It's been an amazing ride so far. We are very young, we have about 50 customers under our belt today and looking forward for a big year of growth. But prior to this, very traditional sales upbringing. Started as an SDR when I was a kid, actually really at like 14 years old and kind of came up since then. I've been in sales leadership for about 10 years now all across industries, mainly focused on the SaaS industry in the last five to seven years I would say. And it's been a really fun run. I've been all over the place from an individual contributor in an enterprise world, 18 month sales cycles, lots of hard work going into each and every sale, to the VP of Sales doing 2,000 transactions a month at Accessibe, most recently at a $50 million org. So kind of all the way through the process. I love building and I love starting something and kind of watching my handprints build the walls and those sorts of things. So kind of been a startup girl and I've enjoyed every minute of it.

That's great. So why this? Of all the things we could do with our lives, what made you choose to get into selling and being part of companies and businesses? Like what do you think part of your personality is being activated there?

That's a good question. I think I would say creativity a little bit because I'm not a creative person in the sense of drawing or singing or arts or anything. But I do have a very like puzzle, puzzle brain, you know, like I want to fit the pieces together. I want to see how everything comes to fruition. I think sales in some ways is God given and like you just kind of were born with it. Now you can be taught some things and you can certainly get better and craft your skills and hone your skills, but I think that it's an outlet for my creativity Gives me the ability to talk to people and meet with really smart people and always be challenged. I think in any sort of revenue leadership role, you're never without a goal. Never. Not once. So I think always having something to strive for and drive to gives me that kind of north arrow, if you will. And I've enjoyed it.

I got it. I do. There is certainly a lot of creativity. People don't realize that it's really a creative undertaking when you're doing this sort of stuff, because, you know, if you're working for somebody, you're sort of given an assignment and you fulfill that assignment, and you're chosen for the competencies that fulfill that assignment. When you're running a business, you're building something, and that's a creative process. It's not really thought of that way. People think a business is money. You know, it's a money thing, but it. It isn't. It's building a machine, really, in a way. You're trying to take parts that work together and create an outcome, and. And it's always like a new thing. You bring similar principles to each endeavor, but it's new because the product's different, the audience is different. So, you know, people, I'd say, like us. Right. I'm. I'm certainly like you. I like. I like the building part better than the success part. I think it maybe reflects my bank account, but that's fine. You know, it's just. I do like to put things together and see that they can work, you know?

Yeah.

Would you say then, I mean, are you like more of a money or numbers or math or analytical person? Are you more of, like a strategic person? Are you more like a philosopher? What would you say or kind of profile your personality is?

I think it's changed a lot over the years. I think in the early days of the sales side of it, I was really into the emotional understanding of why people were doing what they were doing. How do you get people to buy? How to. Do you get people to like you while they're buying? How do you get people to trust you? How do you bring authenticity into the process while also achieving and meeting a certain outcome that's demanded of you? I think as I've, you know, ventured into higher levels of leadership, I've had to pull out the analytical side of my brain a lot more and trust the data and track the data and be the data and know my numbers and. And that's something that I don't think that I was, like, inherently given. And I've had To understand how all of these different factors play together. Certainly I would say that as I've gotten a little older, I've gone back in my shell a little bit and have become a little bit more analytical and I enjoy that part of it now. So I think it's changed over the course of the last 15 years.

Really interesting, isn't it? Because, you know, I'm probably a bit more like you. I'm definitely more of a psychological, human person. And you know, when I say that, I mean it like sort of in a wonky way. I mean like I, I like you. I'm really interested in why people do things and like what motivates them to do stuff and what they're really trying to solve. I tend to listen to people's subtext more than what they're saying, like what they're really saying. You know, I think my brain is more wired around that. And I too, right. When you're building a business, you sort of have to measure things and you know, build more mathematical, you know, metrics, biz driven systems. Or else you can't build a business. And it didn't come naturally to me either. I would say it's still not the strongest part of my, my skill sets. So it's kind of interesting thing. So I mean, here's the thing, it's interesting. Like, do you think, like businesses are different when they're run by different kinds of people like that? Like. So my point I'm making is like I know some people who are just numbers people.

Yeah.

Like they are good at looking at an opportunity and saying this thing, if it scaled, could make me this much money. So I'm going to build it this way and make this much money. And they do really well at it. They make a lot of money. I know a lot of people that think that way. And then there are people who think like, I just have a really good idea. And I know that if it's communicated properly and articulated properly, it'll totally attract people to it and they'll want it and they'll be persuaded to buy it and I can get them to do that and then we'll figure out the numbers later, you know.

Yeah.

You know, I don't know if there's a right thing because, you know, I look at it like my view is the companies that I tend to be most attracted to were driven by people who had really great ideas that they sort of figured out how to make work in the marketplace as opposed to people who just created a business because they knew it was a good opportunity. You know, there was something that was a money making opportunity. They're both good businesses, but I think they're different types of people. Right. I mean, I don't know.

I'll take it to an example, like a sales. You and I talked about this the last time we were together to think about a sales leadership role. Right. Not even the founder of a business. You have people who can create a system. These are operational leaders and the system is designed or let's go all the way to the outcome. The outcome is whatever the system was made to produce.

Yep.

So they typically you see these type of people in high volume inbound machines that can run like variant to who the human is. You don't have a lot of human skill set in those type of machines. And then you have leaders who are sellers. And sometimes those leaders really struggle, by the way, because it's like the best salesperson kind of just got there. And those people can create playbooks that work. Those people can build amazing cultural teams that row the boat in the same direction and take the company to the next level. And then you have kind of like these blended, which are like, in my opinion the most successful type of organizations is when you can mix the operations with the playbook and you can build the culture while doing so efficiently. And you and I talked about it and my God given gift is not teaching and yours is. But I would venture to guess that our sales organizations are run pretty similarly because you know that you have the operational background that you need and that has to be there. If not, you have a right hand to do it, which you and I spend a lot of time talking about that. So I think that those two things can project on the company as well. You have PLG companies and SLG companies and you have companies who focus on giving value upfront through free trials and high conversion rates of those free trials. And then you have really like intensive POC evaluation, trust driven processes. Those are different as well. So I think you have to match the style of your business to the style of the leader. Right. You can't put somebody or enterprise salesperson that's used to high touch, high trust into a high volume machine. They'll spin their wheels and they really won't know what to do. So I think it's, I think it's dependent on the company, who we're selling to, what we're selling, the value proposition of what we're selling and then you match the leaders to that.

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 Zero Spotlight podcast with any of your colleagues. We just think there's a great wealth of information here and we 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 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 these are great conversations. I facilitate them. The CRO Master's Councils, again, they're twice a month and they last for at least six 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. Yeah, it's such a good point. You know, it seems like so many companies that are successful seem sort of, in a weird way, happy accidents, right? That a person whom had a certain type of personality, had a certain type of idea, and through the sort of advanced competencies of their personality style, were able to kind of bundle together something that made it work, and then the company ends up looking differently. So, you know, the idea sort of being like. And I've had this situation where you hire somebody, you bring them into your company, you're sort of young enough that you don't really Know exactly what you want, but, you know, you need certain things. And so you bring in someone who's really good at that sort of thing, and you realize pretty quickly, well, they're almost only good at that thing, but they're really, really good at that thing, and we need that thing. So now we have to build a company around that person to compensate where they're not good. So that now, in a way, the company is being shaped around the people. Right. I've been this sort of person. I'm like the kind of person who comes in and I can sort of communicate with anybody, and I can convince people, do a lot of things, and I get pretty. Pretty persuasive and tell a good story. But because I'm sort of disorganized, and I'm not the kind of person gonna sit there all day and, like, put all my stuff into salesforce all day long, I'm just probably not going to do it that well. So, you know, it's like, well, you know, he's closing a lot of business for us. He's doing really well. Plus, he's kind of really done a good job of shaping the way we talk about things. We want to keep them here, but we sort of have to support him through these other systems. And then the culture of the company becomes changed because of that way you did that, you know, whereas if you have someone who's really methodical and really, really logical and really meticulous, then the company is going to look a bit differently. And as companies get bigger, they get more strict around the precise ways they need to hire people for. And I think this is where they miss out on other aspects of people's personalities, because they don't hire for them. So they're looking for people to have a repeatable skill. Right. As opposed to someone who may bring some unique magic to this table that they never know, because they're always looking for the same type of person. And I've had plenty of people I know who've not got. Not gotten jobs because they didn't fit this sort of such a precise profile. And I know that person would have been amazing at that job, but they missed out on it. So, you know, hiring is a really difficult thing for that reason. You know, earlier stage hiring is a bit more like. It's sort of like faith, you know, it's like, all right, well, we'll see if it works, you know, and you can get really lucky.

Yeah. Do you think, though, I'd love to tango with you on this one for a Second, because I struggle with the, the ideal that CROs specifically are stage people. I really struggle with this because I don't believe in it that you hire one person, one sales leader to go from 0 to 5 or 0 to 1 or 0, you know, whatever your mechanism or growth speed is, and then somebody else needs to come and run the machine from 5 to 50, and then somebody else should come in and run it from 50 to 100. And I see it a lot in like leadership hiring that, well, if you've been in startups like too early stage, you have no idea how to scale a company. And if you've scaled a company, you have no idea how to build a company. And I kind of think that this is a little bit farce. Like, I'd love to hear your opinion.

It's a really good question. I agree with you. There's no doubt that there's. I mean, it's kind of hard ones to say. There's some hard answer on this, but let's dig into it, right? So I think we'd agree with that. Zero to five requires a certain type of effort, right? And then five to 15, let's say, requires a different kind of effort, right? And then clearly, I think like, you know, 25 to 100 or even to 50 is a different. And then even like 150 to a billion is a completely different thing. And I think we both agree too, that while I know a couple people who've done that, like all the way through, there aren't that many. I think it's sort of like a rare thing that you have someone who's got such a nimble brain that they're able to adapt like that and bring things forth, or maybe it's because the position that they're in, where maybe they're an owner or they're a part owner, so they're able to maintain their hold on things and they have to figure it out and they come through it. Now, they might not have been the best person, but they managed to make it work. And so, you know, superficially it looks like, wow, what an amazing achievement. But it was like, well, we couldn't get rid of the guy, so we had no choice but to have make him go to the end. But I would say my experience with this is if I'm hiring, if I'm. If I'm advising, let's say a company that says, you know, we're looking for somebody to do X, Y or Z. A question I ask that's very much upfront, one of the first two questions is what stage are you at? And the reason I do is because I know there are, there's an environment associated with that stage and there are people who are more better suited for those stages. I mean the problem we have, I have an agency, it's a separate business and in our marketing agency our clients are pretty big clients. We have most only work with like, like enterprise sized clients. So I'm dealing with this all the time and what ends up happening. A lot of times I see that let's say smaller company will be very attracted to someone who came from like Salesforce, you know, or Adobe or Microsoft. Because there's a certain, I don't know, perception that because they came from an organization that that's successful that they must have gotten really well trained. And it's probably true. But you bring that person into a startup, most of them don't know what the hell to do there. You know, they worked in a company where everything was built for them. They come in and there's a whole machine around them and they perform this function. Plus they have a brand that gets them going every day and people listen to and people don't take into account that, you know, those things make people maybe not well suited for a place where none of that stuff exists. They don't know how to start something or fill in the gaps. And I would say, I think that someone whom, like, like you, you know, me maybe who are a little more scrappy, you know, and I can get into a smaller thing and I can put my fingers on a lot of stuff, would probably be better suited to work at a larger company than someone who's only worked at large companies to try and get them downstream and work at a smaller one. Because I think the requirements working at a startup are so different for someone like that's never done it before. They may just not know what it's like to be independent like that. So there is a different sort of thing. And then there are people like I say probably you are like this. Me too. I prefer working in smaller companies for that reason.

You nailed both of the things I was thinking it's like number one, what stage? It's not about the dollar because you can be high growth, 50 to 100. Right. The number doesn't matter or you are an efficient grower. Like this is a completely different mindset like PE run PE versus vc.

Okay.

And then I think the other side of the coin is what are you happiest doing? Yeah, one side is the company side, the other side is the the player side. Whereas I feel pretty confident that I could go into a big company and have.

You could.

And do it.

I don't think you'd like.

I think I would hate it.

You wouldn't like it. I know you wouldn't like it. Yeah, I don't like it. I was. I worked at a couple of big companies. I was an executive at two companies, and I didn't fit in well in that place. I was too entrepreneurial. I was trying to do a lot of things that the other executives are sort of like, you know, stay in your lane, you know, shut your mouth, you know, And. And I get it. I mean, I understand it. I'm not a child. But at the time, it felt so restrictive and political. And, you know, our earlier part of this conversation, it was like, zero creativity. I mean, it was none. Like, if I went with an idea, they were like, what? You know, it was like a committee, and everyone thought about it. There was no, like, ability to go, sure, Warren, go off and do it. You know, here's a budget. Go make it happen. And I probably would do it. Right. But. And so I found myself, a lot of times sort of fighting with everybody, and I realized it was just a. You know, it felt like high school in a way. Like, the group of kids that sat at the lunch table that I wanted to sit at, and every time I sat down there, they were looking at me like, when is this guy going to get out of here? Like, you know, kind of thing. And, you know, it was fine, you know, because there was the other, you know, sort of, like, misfit table that I belonged at, much better, and I ended up hanging out. And I think that's what it is, kind of. And so I do think, like, people like water sort of, in a way, sort of eventually find their level. You know, they get to a point where they're like, oh, I think I found where I'm comfortable. And I do think, if I may, that a lot of really successful entrepreneurs are basically unemployable. These are people who are just like, they're never going to get a job. You know, they're going to have to do this on their own because they're not suited for that sort of thing. And I think that the. The world we live in, particularly the SaaS world, which kind of exacerbated this whole thing. Right. Created a factory for this, built a lot of interesting environment for people whom can kind of build things all day.

Yeah, for sure. For sure.

So I got another point I want to ask you about this. So, you know, we talked a bit about doing things you like. Do you think it's the case that it's always the case that we're happiest doing the thing we're best at?

Oh, no. I actually think it depends on if you look at in the moment as happy, short term reward, like how do I feel right now or when you look back on it. Right. And there's a bias of looking back on things that you always see them a little prettier than they were. But I think I've been the happiest when I've been stretched the most, when I've been challenged, when I've been faced with something I didn't really know what the heck I was doing, but I was being driven to figure it out and I was trusted to figure it out and I had autonomy to figure it out. And I think that's when I look back on my career, when I'm. When I can say I was like, oh, I was in it, I was in my zone. I knew, I knew I didn't know what I was doing, but I had figured it out and tested and tried. I think that there has to be some sort of guardrail on that statement. Like it can't be completely outside of, you know, what you know and what you do. But I do think that, and it depends on the personality, I guess. Like some people really hate change and like don't like to roll with the punches. I would like to think I thrive in change. I think it's getting harder the older I get just because of life. But it, I, I really do think that for me in particularly it has come with some of the hardest fault battles or the most positive ones I look back on.

Yeah, I, you're probably right because looking back at my work history, I'm aware of the fact that the toughest things I had to go through were the things that made me better. Right. You do. You're forged through these sort of things. I can't necessarily say that. I, I guess in a way I do. I'm not saying I sort of like, I'm certainly not afraid of confrontation. I don't care. I'll do stuff I'm not good at, I'll try it. But it's more like the pain of feeling stupid, you know, and not knowing what you're doing and that sort of all the other shame and other stuff that goes with that feeling when you're trying to figure things out and then, you know, if it works out, it feels really miraculous. And sort of victorious. Like, wow, I was struggling and look at me. I figured it out. How amazing. And then there's times where you're trying to figure it out and you fail and you're like, I was an idiot. Why the hell did I try and do that in the first place? So, but, but both experiences certainly is what made me better. In fact, I started my whole business, the Serial Collective, because of a failure. What. That's what got me to do this. It wasn't because I succeeded at something. It was because something really like I had a really bad experience and I learned from. And I was like, okay, I, I'm going to see if I can make sure this never happens again. But I asked the question mainly because I'm battle with this philosophically. It's like, you know, telling people to, like to find the thing they're great at and pursue the thing they're great at.

Yeah.

Right. I mean, it seems like a logical thing to do.

Yeah. I think that is a career anecdote is like, I believe in staying in your lane from like, as you say, figure out what you're most productive in doing, figure out what makes you feel fulfilled, and then challenge yourself within that. Like, so it's like, like I said, the guardrails and then kind of bounce all over within something to find that place where. Because I think people are most satisfied and most happy when they're able to contribute. At least I'd like to think that. I think maybe that's, maybe that's a prolific statement.

No, no, I, I agree. I think that people ultimately want to feel like they're making a difference of some kind, that they're, they're, they're. It's more like, you know, the effort that I put in, there's some way in which it, it had an impact. And I can know that impact is. And if I don't feel that way, I feel like I'm sort of locked in a room just doing something, and it doesn't feel satisfying.

It's amazing. When I interview salespeople and hundreds in my career, I say, what do you want? Like, and they want a position where they have impact. And I always ask, what does it mean to you to have impact? Like, what is that thing? Like, what, what wakes you up in the morning? Because how I measure your impact is going to be percentage to goal. That's your impact when you work for. It's my impact when I work for a company, by the way. So deciding what that impact is and how you want to have it is also super important because it's not something a company can give you. You have to define for yourself what you think impact is. I've seen a lot of people struggle in their careers, in sales. Do I really want to do this? Am I any good at it? Is it the thing or is? And I say, well, what do you want? Like, do you want to win? Does winning bring you up? Does winning put that fire under you? Do you want to train people? If so, you probably should get into management. You probably shouldn't. Like, do you like what? Really? Do you have more of an analytical, operational brain, but still, like, the chase. Okay, rev op sounds good. Like, you have to define, because a company sees this as, like, flailing, right? When you don't really know what you want to do and you don't have an idea. Like, I think it's really good advice you give. Like, figure out what that impact means to you. Figure out what you enjoy being challenged by. Figure out where being challenged doesn't feel like failure, too. I think is very important. And then go and run.

Yeah, just great stuff, the way you articulated that. And, you know, when I run my courses, the first thing I ask people when they join, and hopefully you'll see that soon, is, yeah, what you're. You know, you hear this all the time. So I'm sure this sounds a little road, but you ask people what they think their superpower is, and I mean it. Like, you know, we watched how many. How many of these ridiculous superhero movies and other movies have come out in the last 20 years? And, you know, everyone looks at this thing like, well, what would I want? Could I. But I want to fly. Do I want to be able to be invisible? Right. It's an interesting thing, but in more grounded, like, what's your thing? What do you think the thing is? And I posed the question this way, is it's sort of a complicated way of asking it, but it's provocative. It's like you're in a room of 100 people that are your peers. What's the problem? If it were posed to those people, that you'd raise your hand knowing that if that problem were presented, you'd be the one to solve it better than anybody in that room. What's the thing that, you know that if someone said problem A, your hand would shoot up because you're confident that of all the hundred people, you're the person that should be asked to address this? What is that problem? Because if you look at it from that perspective, it's interesting. It's like, what's the thing that gets me off my chair right when that thing happens? Because I know, like, oh, like the, the God called me to do the thing I'm good at, I'm going to get up and do it right now, whatever that is, you know. And you know, it awakens something inside of people. They are like, oh, God, I know that thing. And I, I. And then, you know, the obvious thing when someone knows that is like, well, then that's probably something you should probably do as often as possible, right?

Yeah.

Right. You want to put yourself in a situation where that situation comes up enough that you're around, thank God, to do it right. And then that would be a really amazing life. Now, if it's something weird, you know, fine. But most people, it's not. Most people are like, you know, I'm an amazing communicator. I'm a really good listener mathematical problems. I can solve any math problem or I can fix anything. Right. It's not usually something like, you know, weird like I can play pinochle better. You know, they don't, people don't say that usually. It's an innate thing. And I think that, like, people who figure this out earlier in life have a better advantage than other people whom sort of are trying to figure that out later. I was a bit of a late bloomer because, if I may say, I just had a lot of things I like to do and I had a number of things I was pretty good at. So I didn't know which one was the one that I liked most. And it took me a real while to shut up and listen. To figure out that was really like, I just like to sort of like, help people figure out stuff. And once I figured that out, then it became easier for me to know where I need to be most of the time. How, how long did it take you to figure out what your like, let's say, thing is? And what is that thing if you were to articulate it?

I think probably to put words to it a lot longer than synthesizing the actions. I think I'm really good at understanding business and how to make money from business and where the opportunity lies. And I think that that's why I ended up in, in startup land is because I can see funnels. Sales funnels. Shall we? I can see them when I'm talking to somebody about any business and I'm like, why didn't you try this? Have you ever thought about doing this? Like, I see how to visualize how to make money. Like just when I'm talking to people about their go to market strategies or the lack thereof and I can see kind of like without being able to put a playbook to it, I can see how to play it out. And I think that that benefited me from the operational standpoint and really I was stretched at my job at accessibe to figure out the operational side. We were an operational nightmare. 2,000 transactions a month, high volume craziness, scaled growth, 10 to 50 million in three years. Like we were white knuckle in it sometimes. And so I think like being able to put those words to it, being a builder, being somebody who can envision how to make money and not only envision but synthesize something really complex into executable steps. And I think that's. If I could say one sentence is my thing.

Yeah, I get it completely. You see the end in mind and you know how to build the system to get there.

Yeah. And I think, I don't know that I could have said that 10 plus years ago for sure. Let me reword that. I know for sure I couldn't have said it 10 plus years ago. But I think that the, the innate skill in what I have always done is just a little bit like that, kind of like quick to act, understand how to execute, understand what the end goal or the outcome I want is and then figure out the path to get there. So I would say that's the skill synthesized but definitely not I think, I wouldn't say I have, I'm not like you, I don't have a ton of talents in, in that world. But most of my friends would say why do you always think and talk about money? Well it's because it's literally the way my brain works.

That's your thing. I'm kind of jealous because I don't think about that that much at all. And I, I know I should be. It's fine, it's not a self deprecative thing. It's just my brain is more, I think similarly I'm more interested in what's great is what you're saying is probably why you're so valuable in the marketplace. I mean that's usually the exact kind of person that a company wants to hire is because I'm thinking of it more about like what is it that I know people are going to respond to and that they're going to make a commitment to and secondarily is I weirdly know what it is that's in the way of somebody being able to be effective at Something I could see.

In two seconds, which is probably why, on your side, we talked about this, the sales training and the teaching people I teach best through just imitate what I do. I can't tell you how to do what I'm doing. I can show you what I do.

You're living by example. Yeah, no doubt.

I think that that's. It's a skill that I've always wanted to have more of, is how do I teach it? How do I give the part of me. Because I love being around salespeople and watching salespeople, like that light bulb moment where they just. They become a salesperson. I've had several salespeople in my career who didn't come from the background of sales, and they just kind of started anew and the light bulb went off and they realized they were a salesperson and they were doctors before art people before or whatever. And it's. It's really fun to watch that happen. But I have never had the skill of, like, let me really synthesize to you and tell you what I'm doing in a. In a theoretical way. That has been my.

Yeah, I get it. I do. I understand. It's sort of like I watched one time. I don't remember who it was a really brilliant woman who's an actress, incredible actress, and she was on some show or something, and she explained to the host how to act, which is a very difficult thing to explain to somebody. It's like, I don't get how do you explain that somebody. But she did. And he said, and I agreed. That was the most clear articulation of what acting is that I've ever heard before. And, you know, she obviously possessed this ability to break down something in a way that was easy to understand. Now, granted, still intellectual enterprise. It's not like I can't do it, but at least I now can put words together and I can see what it looks like. And I. I do. I do sort of enjoy unpacking that stuff, but I want to kind of switch gears because I want to talk a bit about. About what you're talking about more around operations and stuff, because we talk about this a lot. So thank you so much again for listening to the CRO Spotlight podcast. This podcast is an important plank in the zero collective communication strategy, and we're really thrilled to have such great guests on here. So listening and sharing the podcast with other people is really vital because we want to get as many people listening to this great stuff as possible. A couple things to note. If you're a aspiring CRO or a recently hired CRO or even a old salty CRO and you're looking to either become a chief revenue officer or improve your chops and gain some more insights and improve your competencies as a chief revenue officer. We offer the CRO Accelerator course. It's five years now. It's the first CRO focused course that was out there. It's a 15 week course that is populated by aspiring chief revenue officers and CROs. We're pretty selective in terms of who can be a member of the CRO Accelerator course. It's people who are probably like more like ready to be a CRO right now. They have number of years under their belt as a revenue leader, whether it be a sales leader or a marketing leader, or even rev ops leader. And they either want to move into the C suite or they're CROs that want to just make sure that they win in the role. The serial accelerator course, we kick off the next one in May, mid May 2025. 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. What you're. When you, when you're looking at an operational structure, you're building one from scratch, right? Someone says, jess, I want you to build my company. We have a product and you agree with it. You, you've already evaluated, you think this makes sense and you passed your own test around. Yep. This is sellable and the market needs it. Okay, I'll take this on. How do you start? What's your process for creating structure to get to that dollar? What do. What do you usually do in your philosophy around that?

Great question and a complex one. I think. I, I always start with top of funnel. Like I think the first thing and I'll get to the operation side in just a second. Good.

It's all part of it.

The, the top of funnel is like how do you get interest? Okay, there's a bunch of ways to get interest. Are you running something that's marketable, that people can understand, that people are largely educated on or can be educated on and 20 seconds or less and really get it? Are you a new market Leader, are you trying to build something that's never been built before, that people don't know, that people aren't aware of yet? Are you. Do you have the ability, in short form to access people, to access your buyer, to get to the places that they are? And so I think the first key that you have to answer is, who are you trying to sell to? Whose problem do you solve? And I think the first thing, and a lot of leaders miss this in the beginning, is who the heck is your customer? What's your icp? Who's your Persona within that icp? What are the levels of that Persona? Do you have more than one? Can you multi thread? Do you only have one? Then what's your tam? How big is it? Because all of these things is what, like, builds the operation for you. If your TAM is very small, you can't do high volume outbound. You'll burn all of your tam, total addressable market in a year. If you have hundreds of thousands of potential customers, you can't afford not to market and have high volume outbound. So I think the first thing that revenue leaders have to do is understand who the heck they're selling to, what problem are they solving, and how can they best deliver that problem. And then if you take it to like, a more technical start, like, yeah, okay, what's your CRM? If you're smart, you choose salesforce, and that's it. There's no other option because businesses grow and they demand more. There's a lot of other CRMs out there that are okay, that do the job. I'm not trying to say that, but if you're building for scale, you need options. So go with the big boys. Okay, so you put the, you put the puzzle pieces into place. And I think you start as simple as you can and you try to understand, okay, here's your center of truth. What are the stages of the sale? Okay, so how are we going to acquire leads? As I said before, how many of them are there? What pace are we going to go at? How are we going to triage them? What are our capacities? This is all stuff you have to think of before you even hire your first person, right? Like understanding how you will hold up the revenue organization. And then if you kind of go to the middle of the cycle, I would say, okay, build your stages. What does being interested mean? Okay, what does opening pipeline mean to you? How do you justify it? How do you stand behind it? How do you explain it? What are the stages of that pipeline? And I think it's really amazing. If you start with a map or a science of the revenue process from the beginning and then build into it, take away, put in as you need, as you see that you're missing a piece of data that you want to have and all of that. Like I haven't really said anything super crazy yet. Like there's not. These are all just the basics.

They are. It is. But I see how many companies don't do this that well.

Yeah. And it's funny, when I started here at Orb and late last year, it's something that I hit on with our founder, co founder Dean so much is we need to decide who we're going to sell to, who, what's the product made for, whose problems do we solve? And that's it. Because stretching a company in the early days is not a good thing. You need to go narrow. You need to find people that you can serve well and create customer cases for. And we were lucky that our total addressable market is still big even with a very narrow icp. So I think. And then as you have capacity from a product standpoint, you can add more layers to that ICP or as you have capacity from a sales team point of view. I was running the demos here for the first three and a half months solely. I would only take meetings with in ICP accounts with the exact Persona because my calendar was already six demos a day. What could I do? I couldn't do anymore.

Right.

So I think you only build capacity and feature functions as you can afford to. And this is where I think I can stop right there and say this is the foundation. This is where you start. A lot of companies start with money. They try to get to the dollar first. And I see this in founder led sales all the time. How quickly can you get to something that's viable, Right. Something that you can get. Raise your first round on that you can raise a little bit of excitement and that's great. And you have to do it. It's a part of the game. But how quickly you turn from something like that to really formalized process driven sales will determine how quickly you scale.

Yeah. So that's an interesting point. You're talking about the money thing. Right. And the other thing I want to ask you too is whether you sort of feel more comfortable with or you prefer like more transactional SaaS based type of businesses or more service? Like businesses like what's your, what's your thing? You know, if you were like to.

SaaS is I prefer as low touch as possible.

It's not why is that? Like what is why?

I like things that it's really clear what you're doing, what problem you're solving, what value you bring, because it makes selling it easier, frankly. I mean, the industry that I came from before was very litigious, but it was the law that you had to have something to make your website accessible to people with disabilities. It's the law. It's very easy to sell when you have the law behind you. And if you use that as an example, I don't need the law behind me at all times. Don't get me wrong.

I understand. I get it. Interesting.

When you have conviction over what you're doing and the problem that you're solving, that's when it's really fun to sell something. So I think SaaS that's like really, really problem oriented, meaning there's a very defined problem that you're solving. I think those are the most fun things to sell because when you have a switched on buyer, when you have somebody that can be educated, it's really fun and you like it's. The reason I love my job today is I get to sell to sellers all day long Y and meeting people, really smart people that I can learn from in my own demos of how to do and what to do is really a unique, you know, it's a, it's a unique thing for me.

It's fascinating. I, I totally get it. I mean, I know that like the SaaS model is predicated around this idea of being able to get somebody to press a button and make a purchase, right? Because it's immediately available for the interest and value and, and you know, it's funny because my entire career, I'd say like literally every single thing I've done was almost exclusively on longer term, complex consultative ideas. You know, selling intellectual properties or processes or you know, consulting engagements where we had a unique sort of point of view, you know, or a bundled expertise or we discovered some sort of process that was unique and all that. And you know, we'd have to have multiple meetings and multiple stakeholders and you know, these were huge deals, million dollars, sometimes more deals, you know, and there was something about this kind of weird boy, my brain works listening to you. And it's like somehow I ended up choosing the thing that's a lot more complicated to do, you know, and it's.

Like, why the hell you like to teach?

Yeah, I like the process of sort of figuring out how to solve, you.

Know, what it is.

I think it's a combination of that. Yes, it is. There is that. It's also, you know, the sort of stuff that we were doing and I still do is more like, you know, I'm selling ideas and transformations, and those are harder to implement, and they require people to think differently and change the way they operate, and they have to, like, think about the world for you differently and make big decisions and big commitments and make big investments. And it just feels sort of like, I don't know, it's. It's not probably not necessarily true, but it feels like it has, like, a level of significance to it that makes it kind of cool to pursue.

You know, Our people are magnetized to you, though. I mean, I think it's why you draw the crowd that you do is because you. These complex problems exist whether we like it or not. Right. Like, they.

Yeah, they most certainly do. And we make them more complicated. We over complicate them.

Yeah. And we're. We're all plagued by very similar problems. No matter what you sell. Right. The person that sells these big ideas and big services and complex, you know, solutions, and the person who sells a widget of any sort online, we have similar problems. I mean, we saw it in the collective room that we were in.

No, no doubt. All the same.

And these ideas, I think the way that you put them into the market transcend the type of business that you have.

Yep.

And they exploit the type of leader that you are.

Yeah, I get it. I mean, I certainly, like we said earlier in the conversation, I found the thing that suits me best, you know, but it isn't easier, you know, like, what you're saying I'm listening to. My God, man, this seems so much better. I should probably do that, you know, this seems so much smarter, you know, and, you know, I kind of tried to do it all the time, but it doesn't really work. I end up not really doing very well at it. But that doesn't matter. It's probably why you and I are going to probably start doing something together anyway. But that's a different conversation. But it's great. I. I totally love the way you're thinking about this because, you know, it's that understanding of those basic things. You know what I think? I think if you're a seller and you're a good one, you sort of know these things because you have to go through it all the time. You know, it's. It's. I think selling good sellers learned so much and like, they're pushing through this process enough times that they sort of understand it and they become good at Building it because they know the kind of environment that they have to create for themselves to be able to be successful. You know, I've done this so many times, and I think that that's an interesting thing that, you know, when I meet great sellers, you know, their brains are different. They sort of kind of know how to put all these pieces together because they're the ones who are quarterbacking it and they're like, no, nope. If I had this, this, this, and this in place, I'd be able to do this. And this is what you got to do. And yeah, they become really good. If they're good leaders and they can manage people and they can build systems and run operations, they become brilliant. You know, I know a lot of people that should just sell, you know, like, keep that person out of the kitchen. You know, I never want to make that person make pasta ever. You know. So tell me a little bit more if you. I want to hear a bit more about the business, about the orb and like, what it does and what you told me, what it solves. I want to hear more about, like, what specific way it does that because I, I'm. I'm intrigued by the idea of obviously relationships are becoming less and less valuable today and we need to do something about it. So talk more about that, if you don't mind.

Yeah, I'd love to. And first, I'll tell you how I got here, because I think it's a super important part of the story. Six months ago, I was looking at buying the solution in my VP of sales role. And I was again looking at ways, how do I create another funnel? How do I make my outbound more effective? How do I xyz? And the question we're always asking ourselves is, how do I make more money? And that's what all those other questions I just said ultimately reside in that business outcome. And I was evaluating a bunch of tools and our company was one of them. And I got into the process with Dean, our CEO, and eventually he coaxed me away. And I'll tell you, because I saw the data and the power of what we were doing. It was a very easy switch. And keep in mind, I went from a $50 million organization to a not 50 million or dollar organization. And it was the total start over. Build an office in the us build the team, some early success from the company, but certainly no official processes in place. And the opportunity that I saw is I've been an outbound girl my entire career. Whether, even if it was in my own IC processes, I was always the first one to pick up the phone phone to write the cold emails. And this stuff isn't working. Now, I'm not of the camp that it's going to die and nobody's going to ever sell via the phone or email anymore. I think that that's not going to happen. But I am realizing Superhuman drops a release where they move all pitches to a different inbox. Now we're not being seen, we're not being heard at the same rates. Today, the very best cold callers are getting a 10% connection rate. They're having one conversation for every 10 times they dial the phone. It's crazy. And a conversation isn't even that. It's a very, very low benchmark. It doesn't mean an interesting conversation. It just means they're getting a connect. And I think that because of this problem, you call it peak noise, I call it the lack of effectiveness, Outbound is becoming not effective. You can't even hire a whole gang of SDRs to do outbound anymore because you won't make enough money from it to do it. So when I saw Intel's kind of thesis about what we're doing, I challenged that thought, like, how are we going to do outbound in the future? And when I thought back to my very first early sales days, it all came from relationships. I did the cold call, I got through to that one person and then that one person introduced me to a couple other people or became my referral difference or my whatever into the next deal. And then I thought about the data problem that we've been talking about. Kind of the underlying thing throughout this entire call has been people don't know, they don't have good systems, they're not mapping their systems and they can't tell who their champions are, who they know, they have no idea who their investors or advisors know, they have no idea who their partners know. And everybody uses LinkedIn first degree connections today and how many times, Warren, you have a great LinkedIn following. If I called you tomorrow and I said, hey, Warren, I need help, I'm about to not make goal this month. Can you introduce me to this person? I see you're following them or you're connected to them on LinkedIn, you would say, I'd be happy to, Jess, But I don't know that person because most people don't know their LinkedIn connection.

That's true. That's true.

I went through and did a study on my LinkedIn. I knew 2%. We work with a lot of referral partners and people within our industry and I can tell you, I've run several studies with them. The most that people know is 4 to 5%. And these are the people who literally network for a living. People like you who do these CRO events and they really know the people that they're following.

Yeah.

And it's still not more than four.

I'm sure it's true. I'm sure it's true.

Yeah. And then when you take this and you try to establish how do I build a go to market function off of this? You can't build a go to market function bothering people for a 4% chance that they actually know the other person. They won't help you very long if they help you at all. So what intel does, the technical way we do it is from an org wide connection to your email and calendar metadata mixed with the public domain. Right. Identifying who people are and matching that to your front first party data from your CRM and your emailing calendar. So this surfaces. Who are your relationships actually with Warren? You wouldn't be in my CRM today because why would you? You're not going to buy intel tomorrow, but you're a fantastic person for me to utilize. I've talked with you a lot via email. We've, you know, we've had several meetings together that should be surfaced as somebody that you, you know, that you and I are close. But CRMs are structured databases that are not efficient at keeping in touch with who we know and how we can get into our next deal. So we're prioritizing everything from the people first perspective. Who do we know, where are they, what are their buying signals, what are they doing and who do they know. And we're doing it through what we call smart career overlaps. So we identify who you know based on who you've been an advisor to, who you've worked with in the past. And we're raising to the top only verified connections. And I hate to use the word connection because it's like practically owned by LinkedIn but there's not a better, better synonym for it.

It's become vernacular as opposed to just have meaning anymore. I get it.

Yeah, exactly. So through raising that we've been able to introduce which is new and it's something that we need to add, educate people on putting relationships back into your go to market strategy. And this is a new funnel, it's a new function. We can utilize some kind of commoditized things like champion tracking, but mixing it with this sort of thing to make it so Powerful that you all of a sudden have a new funnel, a new function to add to your company. And I can say from a buyer's perspective I vetted a lot of systems on the market when I was at my last company evaluating tools for this case. Nobody's data is as good as orbs data period. Like there just isn't. And it's been a lot of fun to be the person that I am dreaming about how to put this data into a go to market function in my role. It's what I get paid to do now. So I'm kind of at peak happiness I guess.

Awesome.

And trying to identify like I get to do it as my day job for a lot of, a lot of companies now.

So it's awesome. I love it. That's great. Well I agree. I mean I, I just had a conversation with the gentleman I had dinner with last night. We were talking, we were both old school dudes. You know, we're like probably, you know, he's in late 50s, I'm 60. We're talking about like how used to the only thing you got things anything done for most of my life was through relationships. There's no other option. You know, I was built on that. My dad too. My dad's 90 and he built his whole career with people, you know.

Yeah.

And you know I do think like one of the outcomes of all this technology is that it's going to force that to become a really valuable skill and if you can activate it, it's going to be a really big opportunity.

There's no question we don't want to get away from the technology. Right. Like we are still a tech first company driving teaching people how to put this into their go to market funnels. But it's still, it's something that technology has never been capable of mapping before because a human connection is really hard to map and identify.

Well, very cool. Well as I thought. You know I knew that we could probably talk for six hours and not stop so. But we'll have to get back to our respective regularly scheduled programming. So how do people reach you? I guess LinkedIn is probably the smartest way for me to get a hold of you.

I guess LinkedIn is easy. I'm Jessica Robertson at ORB and my email address is actually Jess J E S S@ORB AI O R B B A I feel free to hit me up anywhere. I am all over the place. You see me if you friend me on there. Beware content of full.

Got it. Well as I suspected this was great. Thank you so much for doing this and I look forward to our continued conversations. Jess so much.

Looking forward to it. Warren, thanks so much for having me today. I really enjoyed it.

Thank you for listening to the CRO Spotlight Podcast. The CRO Collective's mission is to help CRO succeed and help founders and CEOs build CRO ready organizations. You can find out more information about our services@the crocollective.com that's thecrocollective.com and we look forward to having you join us next time. RA.