CROs: When Growth Stalls, Change the Rules

Speaker A: Foreign. Welcome everyone to the C Suite Sales and Marketing Perspectives podcast. I'm Steve McDonald, the host and today we've got a super interesting conversation lined up. Jordan Bulkowski. Now, Jordan, you're the Chief Revenue officer at Jeeves, and that's, uh, an international fintech company. And that only begins to talk about the success you've had there. You've been there over a year. You've been an instrumental part of growing revenue 4x. You just landed last week, 110 million round. So congratulations, you've got something really good going on there and hopefully we can learn a lot from what you're doing. But you kind of even you were talking to me. You've always put yourself into, in a competitive environment, even growing up as a kid, lots of board games and card games. It was like good competitive fun in the family. And that's really going to come through in our conversation because when you and I talked before, you just had such a really incredible, practical, pragmatic way of looking at things. And what we're going to talk today about is if growth stalls, just change the rules, right? And we're living in a day and age today where, boy with AI and all the disruptions and we're ripping up playbooks left and right. We're trying to really figure out like how do we carve out our success in this kind of a market. And so I really looking forward to our conversation. But before I ask the first question, I'd love just to give you an opportunity to explain a little bit more about your background and Jeeves and what you're doing there.

Speaker B: Sure. Thanks for having me on, Steve, and thank you for the kind words. I definitely can't take all the credit myself. I think any fantastic company that does fantastic things is made up of fantastic people. So it's really a team effort there. A little bit about myself, as mentioned personally, I grew up in a very small town in Ravenna, Ohio. We didn't have cable TV or video games or any of that fun stuff. So we got our competition fixed from family board games and card games. And let's say I didn't come from a family of sore losers. I came from a family of great winners so that no one had to worry about losing a little bit about me personally. And then professionally, I started my tech career at SAP, obviously just an awesome place to learn what great looks like and truly best practices in enterprise selling from there. I moved to Koopa shortly after they IPO'd, so I'd say they were more mid stage. Koopa is really where I began my value selling journey. I think the CEO there coined the term value as a service or VAS. At the time that SaaS was really popular and it was well put also, right? You couldn't rely necessarily on having a big brand name of SAP behind you. You really had to dig in with the clients, understand what their business cared about and what the actual outcomes were that you could drive for them, not about you or your product that you're selling. And then from there joined Brex right about the time that they introduced more of this kind of SaaS go to market motion and marrying that together with the issuance of credit which is now very popular in fintechs. Right? We see it from M Brex to Ram to GS where I am currently. And I brought with me a lot of these ideas of spend management that I learned at Koopa which are then very applicable to the fintech space now. And then Dalip who is the CEO of Jeeves, he slid into my DMs personally on LinkedIn and reached out to me and told me a lot about his vision and what they were building on a global scale. Which was personally interesting to me because going back to my university years I majored in international business. And so I wanted to have more of this global scope in nature and global approach to things. And so currently CRO of GS we operate in almost every continent in the world. We've got a very good sized go to market organization made up of sales, marketing, Rev ops, partnerships, SDRs and just an awesome team. And that's what led us to the recent announcement of the 110 million raised.

Speaker A: So I'd love to start unpacking the conversation we had before. It was just phenomenal. We all know at a root level that high performance companies have high performance teams, right? It's about the people. Like we do have the best products in the world but if you don't have the right people your go to market's just not going to work. So tell me a little bit about. You have this idea of creating predictable team performance, even designing around humans who are unpredictable, right?

Speaker B: That's right.

Speaker A: Tell us a little bit about that.

Speaker B: When you think about the various types of businesses that are out there in the world, there are people based businesses and then in some cases there might be widget based businesses. Think like manufacturing where you have a uh, just a clear cost, inputs, equal outputs. Now with people based businesses which are often an underlying component of a tech company which is not technically selling services, they are selling A product, but it's powered by people. Everyone desires that same structure of inputs equaling outputs. But the question is, how do you get there? Because you're dealing with people who are unpredictable. And that is even compounded in even more greatly in an international business where you're dealing with many different cultures, many different approaches, many different thoughts. There's a whole extra layer of complexity there too. And so when I think about structuring a, uh, go to market organization or a team in a way that delivers the results that we want, there are of course the components of, like, how do you build the organization, what are the types of people that you need, what on average do each of these people produce? And then you have your standard revenue operations or mathematical approach that everyone applies. Math is not enough. Not by any means. Right. Because there's also different people on the other side on, um, the buyer components. And there's many different rules and different markets as well. And you have a bit of a multi layered approach where you have your mathematical structure, you have your organizational structure, and then you ultimately have to have trust in people too. Right. It's definitely not me by myself, Jordan, who quadruple revenue at Jeeves. That's not by any means what happened. Right. And so at the executive level, you have to have a lot of trust in your peers and the team that you're going to war with. Right. In Jeeves, for instance, we obviously sell the product, but there's a whole other team who has to go build that product. There's another team in finance who has to do underwriting and risk to approve the deals that we bring in. There's an operational team that actually has to make sure we deliver a premium customer experience every single time, so that it's not just deals in the door and those same deals turn around and leave and go somewhere else. We want to be able to retain those people. And then there's the people component internally, like from the HR team. And how do you source really great talent? How do you retain that talent? How do you make that talent want to work together, together? And so there has to be a lot of trust at the executive level. And then all of us following the vision, uh, of the CEO and the board as well. And then there has to be trust within my organization. And so I never, ever want to do everyone's jobs for them. I would always prefer to hire and work with people who are far more intelligent than I am and really are experts at their craft in exactly what they do. And then I need to trust my People as well with how they run the team, be able to take their feedback as I provide them with my vision, that is a shared vision of my peers and of the board and where the company needs to go and then put, um, that in place and let people do their thing in partnership with them.

Speaker A: So this idea of trust is really interesting. So I started about a year and a half ago, maybe a little bit longer than that at the beginning, like the call to proceed to this call where we were preparing for this. I asked you a question. What are your two greatest challenges for creating long term sustainable growth? The number three answer on that, and we're going to get to number one and number two in our questions here was building trust internally and externally. Right. And so obviously external trust building. We thought a lot about. You just spoke very eloquently about internal trust. What is it about internal trust that's such an important part of all of this? And then how do you foster that? How do you develop internal trust?

Speaker B: Yeah, I think there's many fantastic books on the topic, whether it's on EQ or radical transparency or radical candor. Right. Uh, there's many great authors on the topic. I think what's interesting about your question is when you're separating this dichotomy of internal and external trust is really a reflection of internal trust. If you think about the description of everything that I went through about how much I need to trust my peers, the leaders within my organization, the individual contributors, all of our cross functional partners, the entire purpose of all of us trusting each other and working in unison is to deliver a phenomenal experience for the clients externally.

Speaker A: Yes.

Speaker B: And so

Speaker A: if

Speaker B: we aren't operating the right way internally, that will quickly be exposed and then affect the external trust. And so I believe when you and I had chatted first, that was one of the items that you had brought up from other leaders that is really important and they might struggle with is that external, uh, component. I believe it's a reflection of internally how well your teams are working together.

Speaker A: And you know what's really interesting is so this whole thing is an ecosystem together. Right. And so the number one challenge across all C suite executives, and by a large margin, I mean, like the largest is internal alignment. Right. And so there's these components of trust and alignment that are necessary to have high performance teams. Right. And how do trust and alignment work together? And then how do you actually create alignment amongst the teams?

Speaker B: Yeah, it's a great question because things move very fast, particularly at cheese. We just talked about quadruple revenue and barely over a year, very fast. Everything's moving at light speed. And so when things are moving very quickly and everyone has to move within their various organizations, it's easy to not be aligned because things are moving so fast. And so you do have to have initial alignment, right? You have to have lots of conversations, you have to speak quite often as a team and be genuinely interested in what other parts of the organization are doing, not just in your own organization, so that you can make equivalent decisions based off of what the team is doing. But then you need to trust that post these alignment conversations, your peers and their orgs are aligned and they're also going to continue moving forward. It's a lot about just having the right team. I think when I made the decision to come to Jeeves, I had a lot of really great mentors, very successful CROs and other executive leaders that are out there in the space and have done just amazing things in the tech world. And one of the really great pieces of advice that I received when looking and making a decision to join a company was look at the team. Number one, make sure you have some sort of a common language that you speak with the CEO, right? Because you're going to be focusing on go to market things, he's going to be focusing on company things. So make sure you have something even outside of business that keeps you aligned personally. And then look at the team that you work with every single day. Because not every day is going to be perfect, right? There will be bumps in the road, there will be disagreements, right? And so ask yourself, are those people that you can get through that with and that can be aligned on the same long term goal for the company and for the company's customers. And so that was something I was very selective about before coming here.

Speaker A: So this whole alignment, I love that you threw in alignment for the company's customers. Right? So the top three answers to that long term sustainable growth question, the challenge is number one, internal alignment. Number three, trust internally, externally. Number two was as a challenge, a lack of a deep understanding of the voice of the customer. Right. And I had this woman on, there's some interviews. You're just like, oh dang, that was like good, right? And so she's a three time B2B CMO. She's now a partner at a go to market mid market go to market consulting company. And she said, yeah, A, everybody has misalignment, everybody. And so that's the number one thing that they go in to fix. Okay, so the number one change Agent in order to create that alignment is the voice of the customer. Because everybody will listen to the voice of the customer. It's not our star. Right. It's our highest authority.

Speaker B: Businesses only exist to serve the customer. Otherwise it's not a purpose in the business being there.

Speaker A: So how does the customer come into building trust internally, externally, building alignment? Right. And how proactive do you have to be in order to do that?

Speaker B: As a leader of a go to market organization, we are the front line, right. Every single day we are interacting with existing customers, with new prospects, with potential prospects, partners, active evaluations. We are the feet on the street. And so what happens at scale is then the more people that you grow within this go to market organization, how do you make sure that all that really important information its way up to the executive team and that you can act upon it? Right. And so you really have to remove as many barriers as possible. We're a very flat organization. At Jeeves, anyone at any time can reach out to anybody on the executive team. The CEO himself sets the pace in that and he's very good. Uh, he will handle the most minute customer service issue personally because he, he is maniacal about customer success. Right. And he wants that to show and to shine through the rest of the organization and within our executive team. One of the very first things I did was develop really close relationships, particularly with product, finance and operations. Right. And so that way we are able to exchange on a weekly basis exactly what we're hearing from the street and from the clients, feed that back into a full 360 degree loop with products so that what we're actually creating in product is not just our own ideas, but it's what our customers actually want. And then same thing on the operational side, when we're getting feedback about things that are working really well, let's do more of that. When things aren't working well, let's go do a root cause analysis, fix that, make sure that works better moving forward. And so we do that across the board. And then we also utilize different AI technologies which helps operate at scale. And note, takers are very common nowadays on all calls. Right. Uh, there's many different, there's Gong and Do and Fireflies and many different technologies out there that we can then plug in to the various cloud agents that we built across Go to market and across Jeeves that essentially can be our eyes and ears in all places at all times. And then aggregate that data, pull that up and then use that as a contextual layer to make decisions across the Business. That's what's really amazing about being a leader now in 2026 is that before you kind of had to filter as much depth and information up to you and then try to make a directionally accurate, good decision about long term vision setting for the business as well as handling the day to day fires. And now you really can be a little closer to omnipresence, um, in the business and be all places at all times to be very keyed in on what decisions are really important to make

Speaker A: and you know what you're talking about here. Maybe this stat has changed in the last couple of years, but there was a McKinsey study that came out that said that only 15% of companies use the voice of the customer to make strategic decisions. And what I love about what you were saying there is we have such an ability today to take all voices of the customer from all corners and all conversations and analyze that and really understand what they're saying. Instead of Jordan having some really important conversations, Steve's having some really important conversations other people are having and everybody's kind of having to translate that. It's like that cup game where the you whisper and you go around and by the time you get to the end of the circle it's completely different. Right. We have an amazing ability to understand our customer's voice and act on it in a way that we haven't before. And so I love that you're using all the right agents and cloud and everything. And my nephew is a software engineer at Anthropic. He'll be happy to hear you're making good use out of it.

Speaker B: That's awesome. I had my AI awakening, if you will, right after my son was born because I spent a lot of time nights awake, not sleeping. And so that was when I was able to dive in initially with Claude and it really took off. Yeah. Just to expand on your point a little bit, there are so many tools out there now. There is so much AI, uh, there's such a greater ability now. How you use it all in your role is really important because that I don't believe is necessarily ubiquitous across all leaders and all companies. My personal take on AI is that AI gives us more time to be human. And so, you know, when you think about what each one of our personal skill sets or talents may be in whatever role that we have within the organization or in life, to be the best and most effective version of ourselves, we should have as much time as possible to really lean into that particular skillset. Now if we spend A bunch of time sifting through data or in the old days before we had AI, if I would have to spend a lot of time talking to various people, maybe only getting partial information or the cup game version of the information that you're mentioning, make decisions, then my time to actually do what, uh, I'm effective at doing and building these predictable systems that have delivered repeatable, predictable results is significantly reduced. And so if I can use AI to do all of those kind of move the cheese type items, so then enable me to have better bandwidth to use strategy and thought and clarity and decision making to make great long term decisions for the business, then I am more effective as a human.

Speaker A: We all have a proactive list of things that we want to get to that we never really seem to that are the things that we know we're going to actually move the business if we can get to them. We got to take those humans on the team and not give them more efficiency so that they can spend a little bit more time kind of relaxing. Right. Like that's obviously there's a balance there. Right.

Speaker B: Same advice I give to my salespeople, I interview every single person who joins our go to market team. And I get asked that question a lot by interviewees. Right. As a salesperson, how do you see AI affecting me or my career? Salesperson's innate ability is to sell and to have conversations. That's your skill set. And so the time spent finding deals or researching deals or updating your sales force or all these other things that are required to do your job, if you can automate those things and spend more time selling than your effectiveness as a salesperson goes way up.

Speaker A: I, uh, want to make sure the number one thing that I took away from our previous conversation was your idea of just changing the rules. If the game isn't going the way that you want, change the way the rule, then the way the players play the rule. Now you couldn't do that growing up with your family. Like the rules of the game were set. Right. But you're the CRO, right? You get to establish the rules of the game. Tell me a little bit about what you mean by all that.

Speaker B: Yeah. So I think this is applicable, um, in many different roles, likely even outside of sales or go to market. But most of us in our day to day careers or whatever we're trying to accomplish, we feel constraints, right? We're trying to operate within a certain box of whatever it is that's been put around us, whether it's time or money or investment or strategic Direction or number of people or whatever. There's always tons and tons of constraints. And so oftentimes people may be frustrated by those constraints and say, hey, I'm doing literally everything that I can do, which they probably are within the rules of the game that you're playing. But if you don't like that game and change the game, change the rules, right? And I say that a bit facetiously because everyone might say, yeah, of course, Jordan, we would if we could. You can't. There's a trade off. Changing the rules of the game or making extreme decisions may cause friction that may be unexpected, that may not be the obvious choice, but then it creates a new reality that everyone's operating within. Right. And particularly when you put it in the context of being a CRO. Right. Or a lot of what we do is we are. We're looking at the company goals, we're looking at the markets that we're operating within. Right. We're looking at the people that we have. We're looking at, uh, compensation structures and incentives and those types of things which then drive behaviors that are ideally aligned with the company and where the company is going to. And so I actually did this very recently, so it's quite applicable time into the conversation. But when you're seeing particular outcomes not being achieved that you want to be achieving, you need to make critical changes in the business. And so even if we think of some of the things I just listed off, let's say we were operating within core markets where we've always done the best and we've had the best branding and we're dumping tons of money and people and investment into those regions and we're just, I don't know, our revenue stalling. And it's not just to be clear, but as an analogy or story, everyone could get very upset and say, hey, why is this thing not working? Or we could change the game. We could go into a totally new market, we could start a totally different product that has nothing to do with the products that our company has ever ran at before. I could throw out the entire compensation plan and have the comp plan drive in a completely different direction that reps have never chased before. Now, are those things easy? No. But do they change the game? Absolutely. And so you can either exist within your box and die within your box, or if you need to break free and go out, then just go build a different box.

Speaker A: You know what's amazing about this? So I'm going to go back to those answers, to those. What are your top challenge Questions. If I looked across the whole top 10, not one of them is external. Every single C Suite executive only talked about, and I didn't say I did, there was no limitations. Right. What do you see as your two greatest challenges to long term sustainable growth? When I started asking that question, I was thinking about people are going to be talking about competition and where the market's going and tariffs and whatever. Right. Nobody talked about that. Every single challenge was an internal. We are our own greatest challenge to creating long term sustainable growth until we start thinking differently about maybe changing the rules of the game. Right. You just put such a great wrapper on top of this. I never thought about it that way. But really, nobody's telling us how to do our own go to market. Nobody's telling us the product we have to create. Nobody's telling us our compensation structures, who to hire. Right. We get to define all that. Right.

Speaker B: That's part of being a leader, is you should lead. Part of leading doesn't always mean taking the easy path or doing what others have done before you.

Speaker A: Little bit of risk with that. Where there's risk, there's reward. Right.

Speaker B: There's also risk of not doing anything.

Speaker A: Yes.

Speaker B: And dying within your box.

Speaker A: So I've got one last question that I really want to make sure we have time for. And we've talked about so much here, literally proven our human brains can't retain all this information. We're going to take away two, maybe three things, Mac. Right. So what I'd love to know is, for the C Suite executives that are watching today, what do you want them to have as the number one takeaway from our conversation? If there's one thing to remember, what would it be?

Speaker B: I've used this analogy of if you don't like the game you're playing, change the game. My entire career, even before being a CRO. So even if I think about, and I'll extend it to your audience of no, uh, matter where you are in your career, if you don't like the role you're in, go get a different role. If you don't like the company you're in, go to a different company. Right. If you don't like being in sales, go be a chef. Right. You are in control of your own destiny at all times, whether you are in the C Suite or whether you're in any type of position. Like you are the master of your own destiny. Now your responsibility level grows significantly as a leader and as your teams grow. And then you're thinking about the destiny of your teams. And people and the company, but you can change that, too. That's part of being a leader, right? And, um, don't always just count the constraints and say, this is the lesser of the evils. There is always a way to change the game. You may not see it yet, but there's always a way.

Speaker A: That's a wonderful takeaway. And I got to tell you, the mission of our whole podcast here is to talk to C Suite executives from around the world, right? CEOs, CROs, CGOs, CMOs, about the experiences they've had, how they've carved out, how, uh, they pick themselves back up when the cards have gone down on the table, right? What have we all learned and how can we share with each other? And if we can, that literally is the rising tide that lifts all boats. You were amazing. Part of that rising tide today. Uh, Jordan, thank you so much for coming onto the podcast.

Speaker B: Thanks for having me, Steve. It's been a real pleasure.