Latest / Rev-n-u Unplugged / "AI Brought Sean Foster Out of Retirement: A CRO's Comeback Story"

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"AI Brought Sean Foster Out of Retirement: A CRO's Comeback Story" · Rev-n-u Unplugged

• james: Welcome to Rev-n-u Unplugged, the show where we sit down with CROs and senior revenue leaders to unpack what it really takes to lead go to market at the highest level. The wins, the mistakes, and the lessons you can only get from having done the job. Today's guest is the one and only Sean Foster, a 27-year cybersecurity sales veteran who has held the CRO seat at Force Point, IronNet, and Anomaly. And now leads revenue at high trust. We get into his own learning curve stepping into the CRO role, why the CFO relationship matters more than most sales leaders realize, the shift from chasing deals to building process and whether AI will ever replace the art of closing deals. If you're a sales or revenue leader looking to level up, this one is for you. Before we get into it, if you are enjoying the show, please hit like and subscribe. It genuinely helps us keep bringing on guests like Sean. But if you're ready, sit back. Let's get into it. This is Rev-n-u Unplugged with Sean Foster. Sean, welcome to Rev-n-u Unplugged. Excited to have you on the show and hear everything you have to say from the wisdoms of years as a sales leader. I always get my guests as a way of starting to give a bit of background themselves who Sean Foster is. So Sean, please give a bit of intro on yourself. Sean Foster: Yeah, thanks for having me, James. good to talk to you again. yeah, look, I I hate to say this sometimes I kinda cringe when I say it, but I've been in cybersecurity for twenty-seven years now. I started my career back in nineteen ninety-nine at Symantec. I kinda grew up at Symantec fifteen years there. I went on to another big company, Hewlett Packard HP, and was running the America Sales Organization and then took over. Global operation until we sold that business to MicroFocus. And then I made the switch over to startups. So in the last 10 plus years, have been CRO at a couple different startups out there. Some bigger ones as Force Point, some very small ones, such as Sienna Group. But have been involved in you know being acquired. I've taken a company public, also have divested business units. So I feel like I've been around the horn quite a bit in my career and currently I am the CRO at High Trust. So that's just started about six months ago. So just well on my journey now with with the High Trust organization, which is about a $50 million assurance company, insurance and trust organization, a framework, and we're about 150 people. james: we've got some great topics we're going to dive into. We've got your learning curve into the CRO seat, the CRO and the RevOps partnership and the importance of that. And then we're going to finish with you giving some advice for VPs of sales aspiring to be a future CRO. Before we get started, I'd love for you to share with our audience why you came back and took this role. because you've been there, done it, you've got the t-shirt, worked a lot of time. What made you come back? Sean Foster: That's a great question. So I I did. I for my CRO role at Anomaly. I took some time off. two and a half years. So not not a couple of weeks. and and I was enjoying that time. but I was I was missing it too. And there was a couple things to trigger. One, I my children got older, so that was you know, not I didn't didn't need dad quite as much, so that was an easy one. but I did miss the camaraderie, I missed the people, I missed building. I felt like just even though I was doing some advisory work, I felt like, you know, not owning it, I never really gave that up. you know, it's great to give advice, but then when you see it not being followed, I had an issue with that. And and so I wanted to kinda to jump back in. And the other thing, just coincidentally, when I decided to step down and and kind of do an early retirement, that's really when AI exploded. And james: Hmm. Sean Foster: I felt like I definitely had, you know, FOMO or fear of missing out. I I saw what was happening in the market and I was just amazed of what was happening and and actually d experienced it myself. and I felt like, wow, this is not the time to be sitting on sidelines. I need to be part of this. I feel I felt like it was back in ninety nine when I was at Symantec and security was just starting 'cause james: Yeah. Sean Foster: back then it was just antivirus was really the only security tool around. And and I felt like the same thing now. It's like this is a new wave of something being AI, which it's proven to be that that case for sure. james: Awesome. So let's, when we were doing the prep call for this, you were interested to talk about your own learning curve into the CRO seat. Is there anything that kind of sticks out to mind to you? What were the key kind of learns that you had on the way? Sean Foster: Yeah, I learned a lot by making a lot of mistakes. I'll tell you that, James. but no, look, I think you know, I what I didn't mention is, you know, my first CRO role was was actually a pretty fairly decent sized organization. It was at Force Point, which is the time I went there, you know, it was eight hundred people, half a billion dollars. So it was it was not a startup. It was definitely a larger organization. But You know, when you're a CRO you realize that you know, it it's much more about scale and it's much more about you know, placing your bets or or playing chess, if you will, than you know, than checkers or doing deals and and do and and caring about deals and revenue. That's obviously still important. You still have to you know have your your finger on the tr on the pulse of what's going on. But much more you need to really understand, hey, what levers can I pull that may not change the direction the next month or even quarter, but a year from now it's gonna make a major difference. Things like channel organization, streamlining the process you know, of customer adoption, things along those lines that I kind of figured that out maybe too late. and you know really, you know, that was that was a a key learning for me. Also having a good mentor. You know, a you james: Hmm. Sean Foster: know it's key to have a great mentor that's been there, done that. ideally someone that, you know, maybe is on your board. or or is you know been there are on different boards that can kind of coach you as a new CRO about the do's and don'ts sort of thing. And and I did have that. you know again I figured out I needed that very, very quickly. And that I was very fortunate to have some great mentors in that space too. But but that was my first kind of go into it. you know what I would say is that you have to think much more strategically than tactically going at CRO. james: So you kind of came up in the era of when the whole CRO title, I guess, was invented. Parking that to one side, was there a role, it new, was there a change? What happened around that time when people started getting, being called a CRO and was their role being changed at all or was it just a VP of sales that had a C title? Sean Foster: Yeah, that's a great question. yeah, I did I did live that. I think in the beginning it's it was more of the latter. It's like, hey, we need to give these folks, if you will, the you know, these these sales guys and gals, you know, a proper title, and that's kind of what it was, but you were still doing the same job, right? and then I think it morphed. I think you gotta see that the board, you know, you're a part of that conversation. you are being looked at and viewed at, hey. you not only need to bring the numbers in, you need to open up new areas of opportunity for the company, right? And we're counting on you to form new partnerships, form new ways of go to market, expand geographically. I think that was kind of sometimes played out more on a on a COO, even CFO level, and then as a sales leader you would go execute on someone else's plan. And I think it changed that they're very much looking at you now to you know, write the plan, execute the plan and and be accountable for those results of that. james: What skills did you have to build from scratch once you became a CRO that your VP of sales experience hadn't actually prepared you for? Sean Foster: Yeah, I think there's a couple of things there. I think, you know, even as VP of sales, I worked with some big companies, you had to have cross-functional alignment. but when you're CRO, I mean, you you've certainly, you know, you need to have everybody working in the same rhythm, right? And so you've got to be in lockstep with your CMO, certainly, you know, your COO, your CFO. you know, for sure, I think that is paramount. I mean, you need to spend as much time there, even then, even as much. much time with that sort of relationships than with your your troops in the field, so to speak. But the the one I'd key on the most that for was probably the biggest jump for me is the CFO. And truly again you think sales, you know the numbers, you you know the numbers coal, but but there's a different way a CFO looks at the number, right? And, james: Yeah. Sean Foster: you know, depending, you know, if you were in that chasm where you're trying to go from on prem to SaaS and and now SAS to AI, you know, what those effects are from the CFO's lens. you know, how they thinks about, you know, budgeting. they're always, you know, thinking twelve months ahead as well and and what bets are we going to make. but but really pull your seat what I I what I for me anyway, it was pulling my seat around from my end of the table in onto his or her end of the table to see if I was in the table and saying, okay, how are we gonna do this together? And and not be an an adversary at all. It was very much a a collaboration. And I got a lot more, you know, doing that once I figured that out than just you know being your typical you know sales leader which is like hey I've hit the numbers then you gotta give me more and that wasn't the case I think you know finding out when I've sat in that seat that hey this is a this is a partnership you guys work together you get a lot more working together and to grow the business quicker by doing that. james: we're going to move on to process over deal chasing, which I think is a super relevant topic right now. You see it a lot in the startup world. Firstly, I'd love to understand when did you first realize that chasing deals doesn't help you scale? Was that in the larger businesses or in the startup world? Sean Foster: Yeah, it's a great question. it's a l a little bit of both. I think you know, when you're in a larger organization, I mean y you just don't have the time, right? It's just you you're pulled in so many different areas all over the world. you know, and you try to jump in or or you know, you might have to be there at the end of a deal or to try to save a deal. but again, you you know, you need to hire really good people, right? You need to hire really good people that you trust. can do that job for you. but then like I'd say where it's more pronounced is certainly in the smaller organizations. when you may only have a couple salespeople starting out. I I had that case where I only had two or three salespeople. So I was involved a lot more, but you still don't scale, right? It is still your job to grow the organization, not win deals. Right. And so it's much more of like, hey, we need to figure out the playbook, right? And and how we can all Make sure we're saying the same thing. We've we've won a few things, we've lost a few things. Let's understand why that is and let's pull that together so we can all follow the same script. Now you can begin to scale. because that is how as a CRO you add value, not jumping in and being the super salesperson and you know, ringing the bell. because again, you don't scale. Maybe it works a quarter or two, but then you get to a point where you've you're you're winning so much and you're scale and you're growing as an organization. You certainly can't scale. That's not going to work. And if you haven't taught those people in your org and given them the playbook to be successful, you know, you're gonna you're just gonna fall. You're just gonna flatten out at that point and you know, you're never gonna grow at the rate that you you wanna grow. james: So how important is it for a VP of sales to be not looking in the, I guess get caught up in the weeds of trying to get deals done and win revenue and actually focus on process and I guess the right client. Sean Foster: Yeah, I I think I'm gonna change that question a little bit, James, because I think you need to be able to CRO, you need to come with a plan and a point of view of that whatever that process you're trying to bring, whatever's worked, you know, again every company's a little different, but you should have some building blocks of what's worked for you. And why I say I'm changing the question because you gotta make sure that your if you're in startup, that your founder or whoever the CEO is is on board with that. because I can't tell you how many interviews that I've had that I've said no to. Even though I like the technology, I like the company, but you know, the founder or CEO, all they want is someone who's going to come here and be the super salesperson and win all these deals for me. And I've heard great things about you, Sean. I I I've seen you won all these awards for selling, and I'm like, yeah, but that's that's not what this job is, right? james: Yeah. Sean Foster: at least that's not what the job description said. You said you wanted a CRO, and and that's not what a CRO, you know, its only job is. And so I think it's very important to go in and say, Here's, you know, again, everything I've learned about your organization. Here's how I plan to run the business. Of course, you're gonna be involved. You know, you'll do your forecast calls and things like that. And again, it's given the size, you you'll probably be involved in some of the largest deals, but it's not gonna be your number one job, right? Your number one job is to figure out how to grow you know, responsibly and as fast as possible, you know, with the limited resources that you have. but I think you've gotta take that extra step, especially if you're a first-time CRO. And make sure you're on the same page with that founder and CEO about how you how you want to run the playbook. james: And from your experience, particularly if you're going into somewhere new, you mentioned there you've turned down opportunities where I guess those, the board and the founders were looking for quick revenue wins and to build that pipe as quickly as possible. How do you bring a founder or CEO around to being on your side and your way of thinking? Sean Foster: Yeah, I think I'm kind of a a picture says a thousand words. I I'm big on, you know, showing them, hey, this this is this is my playbook, right? This is why I've I've been successful. Even though some of these things might be from big company, other things been from small companies, this is why I would think it'd be successful in your company. And by the way, it's a it's a conversation. It's not a my way or the highway type james: Yeah. Sean Foster: of thing. It's like change what you what you feel like wouldn't work here. You know, and let's let's have that discussion. but, you know, a lot of times honestly it it's I get two different camps. I get the board who's like, I love this, it makes sense, I get it. And then typically the founder is like, No, no, no, I we gotta grow at all costs, right? And so a lot of times it's those guys going behind the scenes and having the conversation, say, Okay, is Sean the right fit for this or not? and and I'd be the first to say, Hey, if you guys don't want to do it this way. I'm probably not the right fit. I'm not the type of CEO or sorry, CRO that you're looking for you know, at this time. Maybe a year from now, two years now, you'll realize it and you'll you'll figure it out. But right now, it's just not the great time. james: you've had a huge amount of exit success in your time in all different shapes and sizes, which shows a real depth of experience. There's another CRO that I know really well. And one of the things that's similar to what you just mentioned there, when he's at a job offer, he does a presentation to the board and the founder, which effectively says, I'm not going to move the needle for 12 months. And this is why you happy with that. You still want to hire me. which basically goes through the same bit. When did you realize that that was more important than the product, the company, because a lot of people will move for technology? Sean Foster: Hmm. You mean, sorry, I just want to make sure I clarify that question that making sure that you have the board and the s and the CEO on the same page with you? james: Yeah, so once you realized that the process and everything and how you're going to do this was more important than the product and what the board and everybody was thinking, because I say most people at the moment, particularly, I guess, sales leaders that I speak to where it hasn't worked out, and they're like, it's a shame because it's such a great product. And I thought it would do really well. So when did you realize that putting all the products and people to one side and knowing that people need to be on board with the process? be able to do it. Sean Foster: Yeah, I I think just by trial and error. I mean, I've I've been in those situations where you know, the i I always say it's a cop out for any CEO or board to say, hey, it's just sales execution, right? And james: Yeah. Sean Foster: and that's that's such an easy an easy out. well, you know, narrow that down. What part of sales execution? We didn't get enough deals done. I mean, is that is that the the recipe for sales execution? because look, I'll be first to admit There's probably sales execution things that could be better, but there's a hundred things in that statement. So let's let's clarify it. so for me, I guess I'd say first of all, that's a red flag, right? If if someone got rid of a former CRO and is trying to hire me because sales execution, I I dig into that number one. I tell me why. What does that mean to you? You know, and if they go back to saying, Well, the product's great and you know, this thing sells itself, we barely need a sales force, I mean, run. is what I would say because they're james: Yeah. Sean Foster: you know, no product is perfect. and if it was and it was selling itself, then they would have a you know a a credit card kind of stripe on their on their website and they wouldn't need any anybody, they wouldn't be talking to you. So just, you know, be aware of those situations for sure. But I look I I think you it's a business discussion, you know, back to your your question, you james: Hmm. Sean Foster: you have to say, guys, what's your vision? You know, and if the vision is to exit the business and in three years or five years or you know hopefully that's you know somewhere the case if they're a startup. you know I I like to bring the perspective like you mentioned I've I've I've been acquired I've taken company public and and there's a very two different very different things but you have to have a clean process in both in both respects. You have to have hopefully clean books, clean contracts, business done right. A well-oiled pipeline machine, Salesforce hygiene, all that kind of stuff. Because when you know, I always say you think you know your business until you got 20 bankers looking over your shoulder and digging through, you know, every every line of spreadsheet and realize how much you don't know about your business. and so it's gotta be clean, it's gotta be accurate. You have to have a motion and a method of yes, we're at 50 million now, but this is exactly why I think we get to 75 million next james: you Sean Foster: year. Here's all the deals that make that up in our Salesforce. Here's our partner community and our pipeline there. And be able to show all those things and paint that picture because they're not buying you for the revenue you have today. They're buying you for the next 12 months revenue that's coming. Or again, even going public, right? You know, james: Hmm. Sean Foster: like I said, if you're going public, you've got to have the next two to three quarters in the bag already, right? you know, that's that's gotta be a given. and so that's a I think that's a key piece as well. james: how do you get your reps to be accountable for process, particularly without feeling like they're being micromanaged, Sean Foster: Yeah, great question. I mean, I believe in scorecarding. I try not to boil the ocean. it's the vital few, not the trivial many. So I mean I'm doing it right now. I I don't think you can do it on day one unless it's a very mature organization. But that you know, give you an example of the organization that I walked into, you know, they got the fifty million, but it was kind of on the backs of the founder. whereas but there wasn't a lot of process. Right. And it wasn't like, okay, so why do we win? Right. And now none of that was really documented. And so after six months now, just to give an example, I've kind of gone in and and asked the question, okay, what do we do that w that makes us successful on a weekly basis? Right. And then on a on a monthly basis, and then on a quarterly basis. And like we have three different lines of business here. And so I asked those three groups independently. And then, you know, inevitably they come back with. Well, this is what makes me successful, not successful. And we kind of agree on those things. So it's not me pushing down what I think is successful. It's really what they've kind of came back to me, is what made them successful. And I try to bring some synergies to that. And it could be on a weekly basis, I make at least you know eight sales, you know, calls in person or on Zoom a week or a day or whatever it may be. It doesn't matter. But I then scorecard that. So okay, well, here's how you get an A. Every day you wake up, I think a sales rep needs to understand how to get an A. And it's like, okay, well, here's what we need to do on a weekly basis. Maybe it's one or two things. Here's what we do on a monthly basis. Here's on a quarterly basis. And then we score it, right? We score those saying, you know, if it was a number of meetings, or if it was you know, obviously pipeline generation, how much pipeline generation we have to have each month, or you know, quota, obviously quota attainment. You know, we we certainly score those things, but what are the things that would act ultimately get you to those outcomes? It makes it simple. I get sales ops involved. w it's you know, now it's a lot easier with AI. It just does it a lot of that work for me because everything is recorded, whether it be in Gong or Salesforce or whatever. So it's much easier these days than it used to be. and it comes out with a scorecard. You know, like, hey, this is what A looks like, this is what a B looks like, C looks like, and and I publish that and everyone knows where they stand and you know, it's it's working, you know, it's worked out so far. you know, certainly at this company, it's worked for me in the past too. james: how often are you reviewing these scorecards? How often are you giving out the marks? Sean Foster: Yeah. Well, I mean, weekly, monthly, and quarterly. Just like I said. I mean, there's a james: Yeah. Sean Foster: a weekly card that rolls into a monthly and then rolls into a quarterly. So on a weekly basis, you know, we're sending out, you know, their their marks. And then a monthly, we aggregate, you know, all that together and let them know where they stand on a monthly and then on a quarterly. And then ultimately, I have the leadership also have a leader scorecard based on their people. Yeah. james: and do you have any straight A students that aren't hitting quota? Sean Foster: No, not typically. it's a pretty good indication. Now, I'll say I have the opposite. I have some really bad actors who are hitting quota. james: Yeah. Sean Foster: You got you got those lone wolves out there james: Yeah. Sean Foster: that do that. It take a it takes a while, right? And you realize when james: Yeah. Sean Foster: you start digging into like, yeah, I'm not the best at Salesforce. I didn't update this stuff, and so that's why I got these marks. But again, those excuses, James, are they're not they're kind of few and far between these days because james: Yeah. Sean Foster: AI is doing so much that work. We like for here at High Trust, for instance, we we put Gong on every call. Gong updates Salesforce for us, records how many meetings obviously we were having and good, bad, the ugly. And so it's a lot easier and you get a lot less pushback these days. and it's a lot easier by the way to manage remote employees that way too, you know, james: Yeah. Sean Foster: because you don't see them in the office, you don't know how effective they're being. and are they doing the right things for you? but when you have those scorecards and again, it's not 20 things a week, it's two to three things a week. You know, it's not 10 to 15 things a month, it's three to five things a month. So it's those sort of things. james: I think a scorecard is super effective. People know what good looks like and what great looks like and what they need to do to get a layer on the journey, I think is exactly the right thing to be doing. We're gonna move on to another really important topic at the moment, the CRO and rev ops partnerships. The first bit I guess I'd like to understand it from your point of view, what does that rev ops relationship actually look like on a week to week? basis. So is it standing one to ones? Is it just looking at shared dashboards? How do you work with your rev ops on a week to week basis? If you do Sean Foster: I do, I do. And again, I'll give you an example of where I am right now. I'm I think it might have been the first place I've I've been where I did not have a dedicated REMOPS person that came in the door. and and again, you could probably tell from our conversation already, I'm very operationally focused. I'm more of an operational type CRO than a like said a super sales CRO. so that was a challenge for me. I we had operations, but they were more CFO operations, if you will, right? And And that didn't that that didn't do it for me and and I kinda uncovered that pretty quickly with with my CEO. It's like, hey, here's what I'm missing. We're trying, but you know, we you can't serve two masters, so to speak. We need to have a dedicated person and here's why. And so to answer your question more directly, so now I do have a a a dedicated sales ops person. and yes, we meet I mean I it Definitely on a you we have a a standing one-on-one, but it's probably me on a daily basis, to be honest with you. when I came in, I'm like, hey, here are the views that I want to see of the business. Here's the views I want to see in Salesforce, here's the views I want to see my business, here's the views I want to see on my people. and just setting it up, right? and the data was in like three different places. I was like, I I don't care where you get it, because that's what was happening before I was going, having to go be taught all these different areas of where the data was. And I think I I don't need to do that. I just want it. Here's what I want to see, and here's how I want to see it. Go make that happen. And that person, you know, is doing that. So I think it's good to set a cadence. Certainly, absolutely, if you're not talking to yourselves that person once a week, I would try to say it's probably once a day. because they're gonna get you the big picture of what you need at your fingertips at any times, you know, where you stand in the business and different lines of business, how do your rep stand? what's the pipeline look like? You're gonna want to see all that at any point in time. but then You the other piece james: you. Sean Foster: is more strategic piece is when they're looking at all the data and the history of the trends, you know, what are they seeing that that maybe I'm not I'm not seeing, right? Because I'm not in it all day long like they are. So, you know, what are they gleaning from that information that they could say, Hey, you know what you may want to look at this. I've done the analysis. Here's what I've come up with. I think we can go faster in this particular area. You got to make a decision, or here's james: you Sean Foster: the trade-off. And you're just making decisions at that point. You know, you're not You're not having to do all that research yourself or or guess at it. The data's presented, you've gotten some options. You're hopefully your sales ops person's you know you know more s you know skilled enough to give you those those sort of options and then you go from there. james: What, I guess you went into this role knowing that they didn't have that person in play. Your experience will tell you that you need that person and luckily you uncovered it and the CEO granted you the hire. What, just to get more detailed, what did you find was missing which doesn't just help you as help the business as a whole by now having that person in play? Sean Foster: Yeah, again, I I think it was just a sales focus, right? So that james: Yeah. Sean Foster: the I didn't have a sales focus. I had a finance focus, which was fine. And again, any of the data I just talked about I could get over time. It wasn't, you know, at my fingertips, but now you know, I have a sales focused person that is I love doing sales plays. So I find a niche, we found a way that we've worked, how to repeat that. So we build a list of here's our target, you know, prospects. Here's here's we're gonna train a team on the sales play. We're gonna run the play. We're gonna measure the play, how well it's effective. Sales ops person does all that, right? The sales james: Yeah. Sean Foster: ops person is doing all that measurement, you know, all that review work. you know, and and revs isn't gonna do that, right? Your typical RevOps person, they they just don't know, right? They they don't they don't understand that. you know, things like just again, I'll go back to simple things like when you're doing a forecast, you know. Well, we use this commit best case pipeline, right? And and how do you quantify those? you know, you can pull it out of Salesforce, of course, but building those reports or or calling BS, you know, to your rep saying, Hey, you've got this, you know, you've overrid in a sync commit, but you know, you haven't talked to this customer in 30 days. Or you know, you're you you've skipped some gates that that you overrode the, you know, so the we're gonna have a conversation on that. But your sales ops person. should be to fill your shoes when you're out on PTO or a customer call and and host forecast calls, pipeline calls, and be your proxy, right? And you're not, you know, and again, no offense to the rev the revenue people. That's just not their thing, right? They don't they're just not james: Yeah. Sean Foster: in deals all day long. But your your sales ops person is and should be experienced in that and should not have a problem filling those shoes. james: A question you may not want to answer, so feel free to say pass. Once you uncovered that it was necessary to have that person and you went to the board and said you needed to hire this person, if they said no, would that have ended your journey with these guys or would you have found a way to do it? Sean Foster: would have found a way into and again I'm just gonna say this particular situation. james: Yeah. Sean Foster: you know it wasn't a hard no. It was like we hear you, we need to figure it out. we're on a limited budget. So what do we maybe not do or beg, borrow and steal from other places to get you what you need. so it was never like I said it was never a hard no here, but like I say if they said it, I know that they from the beginning that they've been very willing to work with me, very open and saying, hey, again, I I'm certainly not perfect, but I I got a a a resume that I think can it's not my first time doing this. And so I know james: Yeah. Sean Foster: what I need and when I need it and what's key. And and I think, you know, that's what I would probably go back with and if they were to say no and say, guys, look, this is how important and key this is and this is how we're gonna go so much faster. and again they so here they were willing to to do it. But if I did again role play this, if it was A hard no and we just don't believe in the value of this and the people, the guys that we have are the right guys. You know, I I'd probably it would be at least a red flag for me. I'm not saying I'd take my ball and go home right there, but it'd be a red flag that that, you james: Yeah. Yeah. Yeah. Sean Foster: know, I'd I'd probably approach it, James, a different way. I would probably make sure I brought that up in a board meeting and say, hey, I think we could go faster if I had this and james: Yeah. Sean Foster: see if that would change the perspective. But you know, it would certainly be a red flag. and one that I'd start be watching if there was another one that popped up, then maybe it it's time to to look elsewhere. james: So an important question here for you, for anybody who is a sales leader who is making this type of hire, how do you pick the right revops partner? What do you actually look for beyond someone who is effectively just good with data? Sean Foster: Yeah. so again, I I'll go back to what I said earlier. I think you have to some have to have somebody who could step in your shoes when you're not there. They don't have to be a certainly a CRO type person. They would have to be a great salesperson, but they have to be able to be able to prosecute a deal. So it's not, you know, i it's so when that person shows up, the sales reps know and sort of show up on a forecast called the sales reps know, Hey, I'm gonna get grilled just as hard, if not harder, by this person than I was with Sean. Right? That's important. someone that is able to diagnose the pipeline, I think very well, and not just produce the pipeline, but diagnose, hey, where are what's you know, geographically are we doing well somewhere or bad somewhere? Why? is it, you know, large enterprise, enterprise or or small, medium business that we're starting to excel at or not? And why? I think those are are certainly key areas. And and now I say more than ever, I would never hire a sales person that that doesn't work in AI. And I know it's james: Yeah. Sean Foster: you would think everybody does, but I have found that it's not. I mean, I just went through this process. james: Yeah. Sean Foster: I have some people like, Yeah, you know, I I don't really mess with it and I'm like, pass, hard pass. james: Yeah, yeah, yeah. Sean Foster: you know, people that have leaned in and says, Hey, I'm able I was working sixty hours anyway, but now I'm working like I'm a hundred hours a week because, you know, I have AI, I have Claude doing these seven skills for me that I no longer have to do. I mean, that is a To me, someone you want to gravitate towards for sure. james: Makes sense. So you've worked in companies that hit IPO and you've worked in the startup world. Where does someone need a RevOps? When does RevOps become most valuable? Should you have them in from the get go or is that just a nice to have? Sean Foster: Yeah, it's a good question. Yeah, yeah, I'm trying to think how to answer. I think it depends the volume that you have. I mean, look, if you're trying to find product market fit, probably not, right? You probably don't need a revos person at that point. There's probably a you know, de facto finance person that's good enough. but you're starting to scale. you're starting to move into other markets or different verticals or the geos and things like that, maybe getting in you you got product market fit down, you passed a couple of million. maybe a couple of hundred customers, I'd say at that point, hey, you know, it's gonna get overwhelming quickly. you want someone in there to I would say a couple of things. One is everything I just mentioned before, but you also want someone to set up the the data and the processes and everything else james: you Sean Foster: and make sure everything is done correctly. Because now you're about ready to take off probably and you've got to make sure that your your house is in order in order to take off. and so I think at that point you definitely want to have someone in place. But you know, there there can be too soon, but again, given my background, like I said, I'm I like to I'm I'm I share more on the opposite. I I I steer more that way. I'd like to have it sooner than later. james: I just think in today's world, you can collect so much data in so many different ways. That it seems mad if you're collecting data that you're not understanding what the data is saying and then how to act I really appreciate your time on that. So the last the topic we're going to talk about is advice to VPs of sales who are aspiring to be a CRO. There's a lot of people out there that want to do that. First question I'll hit with you on this one is, what's the biggest misconception a VP sales has about what the CRO seat actually involves before they get there? Sean Foster: I think it's everything we're talking about. I think the biggest misconception james: Hehehe. Sean Foster: is they think it's like I'm just gonna keep doing what I've been doing and I'm gonna be successful. Because again, if they got to a VP sales role and depend on the size of the company, they'd probably be very successful as a rep manager director, and now they're VP. And so they've moved up and they've been successful, typically selling, and you know, depending on the size of the company, maybe the at in the VP role, then they got an idea. If they're for instance, a VP of America's. They understand the importance of working cross functionally, they understand the importance of operations, understand, you know, those other nuances outside of just hitting numbers. so I think that's probably the biggest misconception because it's a very different job as a CRO role than just a VP of sales. james: And you mentioned yourself that you're very operationally focused. How would you advise the standard VP sales coming through to really fall in love with that operational side? When in advance of wanting to become a CRO. Sean Foster: Yeah, so I mean I'm breaking up in just a second there, but you said how would I advise a VP of sales to fall in love with the the data side of the equation or the process side? james: Yeah, operational side of it, because I think that is one of the key differences that I think, you know, I'll ask you towards the end of this about whether RevOps guys will end up being the new CRO. But, you know, if you go through it, a good VP sales is normally at the moment just someone who knows where the deal is. They can get things done. They know how to hit a revenue target. That is not a skill set. I'll discuss with the CEO. a P board about a CRO. So how would you get them to really fall in love with that operational stuff, which they tend to leave to Sean Foster: Yeah. james: someone else? Sean Foster: Yeah, look, I I would say that the data will set you free. And I I think for a new CRO coming in, I I would say get get curious on on what the data tells you, right? And you'll see that and I'll give an example. I I was at a a company, the CRO of an organization that we kept having, you know, we were mainly in the U we're a global company, but we're mainly in the US. we kept having these great wins in the Middle East. Like, why is that happening? You know, and I just got curious about it. Looking at the data, the pipeline kept growing, that you know, the deals kept kept growing. They were, you know, not much smaller than they were in in the US. And I was like, I gotta go see this just for myself and realized that you know our technology wasn't certainly cutting edge in the US, but it was cutting edge in the Middle East. Middle East is always a little bit of a lagger. we played particularly well in the energy sectors, and which have a lot of obviously oil and gas there. And we just We just had some really good people too. but it was a small amount of the business, but I felt like if we could pour more gas on the fire there and, you know, give them more resources, you know, increase our our awareness locally, then you know, it could be a big win for us. and I can tell you, I know before I left that that business quadrupled in about a year and a half that I that I was there. And I know it still grows probably now probably the as big as the US. and it's just because I looked at the data, right? And I looked at, you know, what's happening, got curious, got on a plane and went there. but if I wouldn't have done that, I would have left that to you know to operations or, you james: Hmm. Sean Foster: know, I don't know if that ever would have came to light. Or if I would have been like, you know what? I'm just gonna do a bunch of deals and, you know, do what I do and not really think about that. I never would have quadrupled the business. I mean, I can tell you that. Maybe james: Yeah. Sean Foster: I maybe I would have, you know, won a couple extra deals or maybe even double the business, but you know, by getting curious, you know, understanding what was going on there, finding out why we were different and then getting, you know, funneling money there to help them grow. I mean, that opened the floodgates for those guys. james: And if there's a couple of aspiring VP sales who look at this, want to, I think a lot of VP sales want to make it to the CRO position. What questions would you recommend they ask themselves about their character and whether actually it's the right thing for them? And that's a true CRO, not just a CRO title, which I mentioned on a podcast I did last week. think the title CRO has given out like business cards at the moment. But what For being a true CRO, to be a Sean Foster CRO, what questions should they be asking themselves about their character and whether they have the right character to actually fulfill that seat? Sean Foster: Yeah, it it's it's a really good question. you know, and I just there's a there's a couple of things, right? It's not wrong when people say it's lonely at the top. you know, a are you do you have that intestinal fortitude to take the heat, right? you know, you have to ask yourself, right? And this is kind of a a little bit of a lone time whether you go on a walk or do a run or however you had that internal talk with yourself. am I okay, you know? Taking that heat. Am I okay being lonely in this organization? Because there's gonna be a lot of time that it's gonna feel like you're on an island, right? And you don't have anybody to talk to, right? There's no, there's no peer. You're certainly not gonna talk to your boss. you've got to make sure that you are steadfast in the plan that you have. Maybe you have a mentor. Hopefully, you have a mentor that you could you could speak to. But I think that's you know, number one that you've you've got to ask yourself. And then number two is again, whatever your personal situation is. most CRO jobs, if not all of them, are global jobs. and that's a whole nother element. Are you prepared to do what it takes to be a global CRO? You know, it's not just the travel, you know, and that's obviously a big part of it, but the sacrifices at home. You know, a lot of those travel, you're you're missing weekends, right? You're certainly james: Hmm. Sean Foster: missing family. you know, you're y you have to show up, you know, in these particular areas. Are you prepared to, you know, you know, again if you're a US CRO, are you prepared to go and learn all the customs that you need to learn you know in other places around the world? Do you know what it takes to open an entity, you know, in those places around the world? You know what the tax situation is? you can't just willy-nilly go and decide to do business somewhere. Do you know it takes to hire and fire in places like you know, in Germany and Spain and France? And it's a it's it can be a bit tricky, especially for a US company. So so I think asking yourself those sort of things too, are you really willing to be all in? Because it's an all in. type of role, right? I mean it's you know next to the CEO, I'd say you're probably the most all in. You're you're always on in this job. And, you know, if you're willing to do that and you know what you're walking into and you're okay in your own skin and you have a confidence in your own skin, then I'd say you go for it. You know, but if you're not and you question it, then, you know, do some soul searching, you know, james: Yeah. Sean Foster: or or or pick up the phone, call me, call s call another james: Yeah. Sean Foster: CRO who's done it a few times, you know. So james: I have some great advice there. Before I let you go, because I appreciate all the time you've given us so far, you mentioned when we were talking about the rev ops, how your rev ops leaders should be able to jump onto forecasting calls when you're out on PCO and things like that. Putting you on the spot, in the next five to 10 years, do you see more rev ops leaders moving into the CRO role? And that being the route into the CRO and less pure sales routine. Sean Foster: I don't know. I've seen it happen already. I will tell you that. there's a person that used to be my sales ops leader is now sales ops converted now to CRO at a at a company local here in in Tampa, Florida. And she's doing a really good job. and so so yeah, I could see that happening. I definitely could. I think the data is the key, right? The data is just what sets you free. And now with AI, it will tell you what to do with the data, what not to do with the data, right? Where to where to go. And so you know, I think it could absolutely be that. I think you have to have sales ops people that get curious and and you know, want james: Yeah. Sean Foster: to be able to lean in. but if you have that right sort of DNA, you know, as a sales ops person, I don't think there's any reason why you couldn't go be the CRO again, as long as you're comfortable doing the things I just talked about, you know, you know, in front of customers and things like that. But yeah, I look I've already had an example of it happening here locally once and I don't see why it couldn't continue to happen, to be honest, James. james: It's a super interesting point because also the talk with AI and automating things and whether it's going to replace humans and a lot of conversations I've had is that it's not necessarily that there may be certain roles that go, but, for instance, a salesperson can be an SDR and customer success around everything with in time with the data and the technology is there. If you've got a really good Rev Ops person that can do a CRO role. Do you need a coo Sean Foster: A C O O james: Yeah. Sean Foster: you know, I think Potential I mean like different reasons, right? I think COO depends on the size of the company. I mean I think smaller companies typically don't have COOs, but when you get when you get bigger you do. And because then you're working you're thinking about, you know, facilities and you know, all that kind of stuff that goes along with it. So I don't know. I know it's a it's a good question. you know, I think james: We'll see you with time. Sean Foster: yeah, I I I I don't I don't have a great answer to that. I've not played in a COO role. I do see more CRO is moving to C R O slash C O overall. james: Yeah. Sean Foster: you know, so I have seen that more consolidation lately than than I had in the past too. I don't know if you've you're seeing that too. james: I haven't seen too much of it, but just with this talk that your individuals are able to do more because of the technology, it just looks like there may be one there where that role could combine in time or the COO reinvents themselves and there's other stuff that comes out of the wheelhouse off the back of this AI journey. Sean Foster: Yeah, it it it again, I'm that's one of the reasons I came back. I'm fascinated james: Yeah. Sean Foster: with it. you know, one thing I'll tell you that just as a side note I'm finding is that we're we're I don't think sales will be replaced or CROs will be replaced. I you give you a quick example of you know, the company I'm in right now, we have a couple really good subject matter experts that that are in sales, but they're probably more subject matter experts. I've joined some calls with them recently. The relationship's unbelievable. ciso so down, great. They know what they're talking about. They're super advocates, well respected, but they can't close a deal, right? And what I mean james: Yeah. Sean Foster: by that, I'm not not it's just like they're figuring out they when to offer something and get something in return, how to create urgency, how to build that urgency, make sure that the urgency is met on the other end, the matched energy. And I'm gonna do this for you, but I expect you do this for me by this date. That piece was missing. And I think it potentially could still be missing even in the AI era. You know, how are you going to hear the the tone of that voice or the body language? And that's why I love you know Zoom, because you can see body language when you're talking to people and you realize, can I push here or should I back off? you know, inflection in the voice. I not that we can't get there eventually, but I can see even in my own organization right now that my team still needs needs help in that area. I don't know if AI would potentially help there right now. james: Yeah, love that. Well, Sean, taking up so much of your time already. I really appreciate everything you've done to help get this episode recorded. I'll let you get back to the rest of your day. Sean Foster: Perfect. Thank you, James. Really appreciate it. Nice talking to you. Yep. Bye-bye. james: Thanks a lot. Cool, right.