Sailing Through B2B Challenges Holly Rollo on Leadership and Innovation

Episode Overview

Holly Rollo is the CEO and principal of Surge Strategies, a strategic advisory firm dedicated to transforming the go-to-market (GTM) engines of B2B software companies. With over three decades of experience in the technology sector, Holly is a recognized leader in marketing strategy, business transformation, and digital innovation. Before founding Surge Strategies, Holly served as the Senior Vice President and Chief Marketing Officer at RSA, where she spearheaded the company’s digital transformation and successful carve-out from Dell Technologies. She also held significant leadership roles at major tech companies like Fortinet, Cisco, FireEye, and SAP, playing key parts in driving growth, market repositioning, and strategic acquisition. Throughout her career, Holly has been an influential force in cybersecurity, risk management, and digital transformation. She has helped numerous companies navigate challenging market environments, delivering impactful marketing strategies that align with business objectives. Her work has been recognized with multiple awards, including accolades for operational transformation and global customer demand center improvements. Holly is also an advocate for women in technology, mentoring aspiring leaders and contributing to initiatives that foster diversity and inclusion within the tech industry​.In addition to her professional achievements, Holly is a passionate sailor and a dedicated advocate for work-life balance. She has a personal love for sailing and is currently completing a circumnavigation on her sailboat, drawing parallels between navigating the seas and steering businesses through periods of growth and transformation. Her book, Power Surge: Five Ways to Supercharge Your B2B Software Business and Unleash Hidden Value, shares valuable insights from her experiences, providing a playbook for CEOs and investors to accelerate growth and adapt to the rapid pace of the digital era​

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Episode Transcript

Holly Rollo: You haven’t figured out. Like where your product market fits exactly. What are the segments with the biggest propensity? Okay, here’s the segments. Okay. What are the beachheads you need to win that are going to give you past these other segments? And then how are you going to go after those segments with use cases with the right pricing and packaging, with the right messaging, you know, with the right.

Kevin Rosenquist: Hey, welcome to Pay Pod, where we bring you conversations with the trailblazers shaping the future of payments and fintech. My name is Kevin Rosenquist, and thanks for listening. Holly Rollo has over 30 years of experience in the technology industry with a focus on B2B software company value creation and growth. She’s a best selling author and CEO of Surge Strategies, a strategic advisory firm that helps executives, boards and investors lead through major transformations. She has an understanding of B2B tech marketing that, in my opinion, is unparalleled. If you’re in the tech sector, which you probably are if you’re listening to this and are not sure of what your marketing strategy is, or if you even have one, this is one of the most valuable episodes of Pay Pod you’ll hear. So please welcome Holly Rollo. So your LinkedIn profile says you’re a strategic GTM advisor, a best selling author, a board member, and a sailor.

Holly Rollo: Yes.

Kevin Rosenquist: When did you get into sailing?

Holly Rollo: Gosh, my husband and I started talking about it when we first met for coffee. So that was probably 15 or 16 years ago.

Kevin Rosenquist: You talked about your first date?

Holly Rollo: Yeah, our first date. Awesome.

Kevin Rosenquist: I love it.

Holly Rollo: Because he’s a recovering sailboat racer, and he and he had this dream to sail around the world. And, you know, back then I thought, well, that sounds interesting and romantic and wonderful. Sure. , and so we started learning how to sail, and he had a little sailboat. And , there was a point where He. We were next to Alcatraz in the San Francisco Bay. And there’s currents and tides and fog and everything. And at one point I realized, okay, so if I fall off, he can come and get me. But if he falls off, we both die. So I thought it would be a good idea to learn how to sail. So actually, it’s interesting because we’re in the process of completing a circumnavigation on our sailboat right now. This past season, we sailed across the Atlantic. So, , you know, it’s interesting, like even in the book I wrote, Power Surge, I use a lot of sailing analogies because it’s near to my heart. But there’s so much to learn in business from sailing. So. Yeah, that’s my little sailing story.

Kevin Rosenquist: I noticed on your website, too, there’s a lot of nautical themes going on there.

Holly Rollo: Yeah, I’m.

Holly Rollo: Going for it.

Kevin Rosenquist: Yeah, yeah. Hey, I love it. You gotta have a theme. Did you have an interest in sailing before you met your husband, or did he kind of spark that? Yeah.

Holly Rollo: So? So he said, oh, I’d love to do a circumnavigation one day. And I said, well, I like camping and I like boating. I mean, I water ski and stuff and you know. And so that’s how it started. And , but then as we were sort of, you know, he said he had done some races, the trans PAC and the Pac Cup on a more 24, which is, which is a 24 foot boat, which is tiny. And when you’re actually sailing on the boat, it’s so thin because it’s a racing boat that you can see the water ripple rippling, the light from the water rippling on the side of the boat from the inside of the boat. And so as we started sailing, more and more, you know, it dawned on me, this is kind of dangerous. You know, should we actually be doing this?

Kevin Rosenquist: That’s the time you finally realize it was dangerous? Yeah. Yeah, yeah.

Holly Rollo: Because, you know, you think, you know, it’s very it’s very romanticized, you know?

Kevin Rosenquist: Absolutely.

Holly Rollo: Except for the pirate movies, I suppose.

Kevin Rosenquist: But, yeah, the pirate.

Kevin Rosenquist: Movies, there was that one where Robert Redford was all by himself. That was kind of creepy, too. I don’t know if you saw that one. That was a little creepy.

Kevin Rosenquist: But it was a good movie.

Kevin Rosenquist: But a little. A little creepy for sure.

Holly Rollo: Yeah.

Kevin Rosenquist: So your experience is incredible. You’ve worked for some big companies and you’ve held some impressive titles. You’re a best selling author, as I mentioned, and a thought leader on national security, cyber threats, workforce trends, digital transformation and risk management. Who inspires you? What thought leaders give you motivation?

Holly Rollo: That’s a great question, and it’s so hard to answer because there’s so many people in my life that have had an impression on me. Most of them are not famous. , the obvious one, I think, is, you know, inspired by my own children. I think when you see your children grow up and become adults, , you know, you kind of can look back and say to yourself, wow, what, what would I do if I were in their shoes starting all over again? , so that’s a great source of inspiration for me. I’ve also been really inspired by other women in technology. There’s too many to name, but you know, it’s such an insular industry in many ways, not so much as bad as it used to be anymore. It’s gotten better and better. But I think early in those years, especially, a lot of women helped me along the way and, you know, helped me kind of navigate.

Kevin Rosenquist: What do you think makes a good thought leader?

Holly Rollo: Oh, I just.

Holly Rollo: Think someone who has some strong points of view that that truly wants to help people, , that’s who I get inspired by when I see people, you know, communicate or write books, you know, that they have just this enduring passion to want to actually, , make people’s lives better in some way. Yeah, that are authentic. And so that’s, that’s what I kind of stay focused on as well, is what can I share with people that would inspire them to think differently about something or do something different or help them. And I think that’s the best ingredient, probably for success.

Kevin Rosenquist: You mentioned following women that helped motivate you. And, you know, I’ve talked to other women on this show before about the male dominated, male dominated, uh, fintech world, the finance world.

Holly Rollo: And all that. Probably exactly the same. Yeah.

Kevin Rosenquist: Yeah, it seems like it seems like it might be getting better in the fintech space. I mean, do you see that in what you do. Is it, is it more, is it getting more diverse?

Holly Rollo: I mean, it’s a lot like, uh, cybersecurity has kind of similar.

Kevin Rosenquist: Yeah. Yeah. For sure. You know for sure. Yeah.

Holly Rollo: Because the industries start very, , same word, very insular, you know, and then as the, as the technology or as the company scales, , or as the marketplace matures, you have to bring in much more diversity because you need talent from everywhere, right? And so that’s when you kind of start to see companies grow up or industries go up. That’s certainly been the case with cybersecurity. When I first got into it about a decade ago, uh, you know, it was great because I’d go to trade shows and there was no line at the girls bathroom, so that was awesome.

Kevin Rosenquist: Half a cup.

Kevin Rosenquist: Half full attitude right there. Awesome.

Holly Rollo: , but I think over the years, you know, more and more people get in it. And, and certainly, you know, this goes without saying, but I’ll say it anyway, is across all of these industries B2B, technology, fintech, health tech, cybersecurity, business, AI, you name it, there’s a talent shortage all over the place because software companies are eating the world. So, you know, what we really need to do is pull up and create our bench, you know? And that’s a really, really important thing. Something I’m really passionate about. And I’m, I’m actually working on something to kind of help address that in my little space. , because we just need to get people, you know, up to speed and, and able to lean into some big, hard problems because the scale, scope and speed of digital with, with AI and everything is just really fueling growth and nine zillion directions. So we have to really develop talent as quickly as we can.

Kevin Rosenquist: Yeah, that’s definitely something that’s come up about cybersecurity and and government is that it’s really hard to get the tech people into those worlds because they’re chasing, you know, they’re they’re getting wooed by the the sexy new AI products and the Googles and the and the OpenAI’s and all that. And it’s hard, it’s hard to lure them into something that some may see as boring, like cybersecurity.

Holly Rollo: Yeah.

Holly Rollo: Well, I don’t know. I think if you ask most people in cybersecurity, if it’s boring, they will say no.

Kevin Rosenquist: Yeah that’s true.

Holly Rollo: But what I’ll also say is I do some work with the, , with the federal government. And, you know, I don’t think anybody that joins the federal government says in certain agencies or areas. Right. I don’t think they join it for the money. You know, they join it for the mission and the purpose. And honestly, some of the things that are being worked on are things that you would never have an opportunity to work on in the private sector. So I think there’s a lot of really exciting things to do and a lot of really interesting developments on the text, the cyber side, the AI side, the intelligence side, etc.. So I think the mission is really what drives people. And frankly, I’ve done quite a bit of work just understanding workforce trends and, and what’s going on, the general generational differences, because I think that’s something all cultures are struggling with in tech in general. And I think more and more the younger generation, and I certainly see it in my two adult kids, you know, the mission, the purpose, you know, can they have an impact? Can they drive change? Can they participate in creating the big idea and be successful? You know, every night when they put their head on, head on the pillow, you know, can they say I did something good today? I think that’s what motivates people. I think it’s moving away from, you know, the the perks and benefits and the, you know, free ice cream and stuff. You know, foosball.

Kevin Rosenquist: Table for the most.

Holly Rollo: Part. Yeah. I mean, I really think people want a purpose.

Speaker3: Yeah.

Holly Rollo: At least that’s what I’m seeing.

Kevin Rosenquist: Well, that’s.

Kevin Rosenquist: It’s interesting that you say that because. Yeah, I think about how I grew up and, and, you know, my parents were boomers or our boomers and, and. Yeah, I was taught to, you know, you got to go to college, you got to make money. You have to buy a house, you have to have 2.3 children. You have to like, you know what I mean? Like it was very ingrained in our culture. And yeah, I think maybe all those parents like me are like teaching their kids, hey, do what moves you do what makes you happy. Yeah. And that is kind of helping, I think, to fuel that.

Holly Rollo: I also.

Holly Rollo: I also think, and this is not an anecdote of one, I’ve heard this from my other peers who have adult children now, you know, they’re looking at us and saying, I see all the trade offs and sacrifices you made, and I may not want what you.

Holly Rollo: Have, you know.

Holly Rollo: And so and so I think that’s also a good thing to think about. And, you know, as I’ve gotten older and, you know, on the back nine in some sense of the word, you know, finding ways to let go of some of that too, is, is important to have more balance.

Kevin Rosenquist: Yeah. Yeah. That’s a good point. That’s a really good point. Yeah. They see you know, I mean how many times have you talked to some super successful founder or tech person business person. And if you ask them what regret they have, it’s not spending enough time with their family or with their kids.

Kevin Rosenquist: Or.

Kevin Rosenquist: Spending too much time at work or whatever. I mean, you hear that story a lot, so you got to believe that it resonates with the younger generation now.

Holly Rollo: For sure. For sure. And achieving personal, you know, goals. Or maybe you have things on your bucket list, you know, like circumnavigating or something that you need to sort of start working on.

Kevin Rosenquist: It’s not on mine. I would throw up the first day.

Speaker3: .

Kevin Rosenquist: So a saying in marketing is you can’t sell a secret no matter how good your product is. People need to know about it for it to be successful. And you work with a lot of startups, do they generally know that they need marketing and just don’t know how to get there, or are they more like, oh, we need to market this product. Like, was there or is it a combination? Maybe.

Holly Rollo: That’s such an interesting question. And there’s so many ways, there’s so many answers. So there’s I think a camp of people who are born in the cloud. So they are taking a full product led growth approach to how they think about their product. So the engineers, the founders, the developers have sort of embraced this. It’s all about putting it in the product and making the product, you know, be so great. It just sells itself. Sure. Now that mentality, by the way, even though Plug is considered a new term, that mentality has been around since my first job at a semiconductor company out of college, which was if we just build the best chip, it doesn’t need sales and marketing, it’ll just sell itself. So nothing has changed in the last 35 years.

Holly Rollo: I actually had one of.

Kevin Rosenquist: My co-hosts of my first podcast say that to me. Oh, as long as we’re good and funny, then our personalities will sell this thing. I’m like, I don’t think that’s right.

Holly Rollo: It doesn’t work that way.

Holly Rollo: I would say, and I think to that point, I mean, truly, every tech company needs to be a product led, you know, have a product led orientation because ultimately, your customer experience and how the value your customer gets out of the product is what makes the product right. Now that’s very different from having the best features. That’s a very different idea, right? And what I mean by that is, is, you know, the buyers, the technology buyers are getting younger and younger. They’re, you know, they’re in their 40s now right. Late 30s, mid 30s, 40s. So they had more of a digital experience than I did when I grew up. They have a consumer expectation with how to use and interact with technology, how to find it, how to research it, how to talk to people about it. And by the way, they actually don’t want to talk to people unless they absolutely have to.

Kevin Rosenquist: Absolutely. Yeah.

Holly Rollo: So that’s a very different way of thinking about, you know, having a product that sells itself, you know, versus thinking about having the best product for, you know, all the features and functions and innovations and bells and whistles and shiny objects, you know. That’s a very different idea.

Holly Rollo: , and it sounds so simple but it’s so hard to do. And so, you know, when you go back to your question about companies not knowing they, they need marketing. There’s some people that you know have an orientation like that. But even if you take a startup who’s doing a plug model, people still have to know about it. Like they still have to be able to find it. And so that’s one challenge. The second one is, and this is what I see a lot more of, is companies that have been maybe around a little while, a lot of this, uh, growth and mid-size companies I work with, you know, they’re owned by private equity firms and there’s a resistance to lean into the marketing problem until it’s acute, and then it becomes an emergency. It’s like it’s such a problem that everybody believes that marketing. Marketing is the biggest problem because we’ve solved the product problem, We’ve solved the sales execution problem and it’s just our marketing is really broken. And by the time you’re at that point, it’s already too late. And so what I try to explain to companies is when you’re thinking about maybe replatforming the product or, you know, turning it into a more integrated, you know, set of use cases or whatever it is you’re doing to your product. , or when you’re thinking about restructuring your sales model, because that’s the second thing that they think about. You have to think about marketing, too, because in today’s world, with the AI initiatives and what I’ll call this next AI fueled wave of transformation, you can’t take advantage of the benefits of AI by just piling on top of sort of bad strategy and shaky foundation, you know, from a from a tech standpoint.

Holly Rollo: And that really matters because functionally, sales, marketing and customer support have kind of grown up in silos. So they have siloed functions, they have siloed workflow, they have siloed process, they have siloed systems. So then people want to like pile on all this AI and like get cool stuff. But because the functions are are converging, you have to completely rethink the model and ask yourself, do I really if it’s all digital first, like, can I do more of this digitally and using the technology where I don’t need as many salespeople or, you know, maybe I don’t, I need I need more marketing resources, not necessarily people, because more of it’s happening out there versus one on one face to face. And what would that look like? And then there are things your customer success teams are doing to expand accounts that your sales team used to do, or that can be enabled by AI, for example. So everybody just sort of needs to rethink this model. And I think I think that’s where companies then, you know, kind of go back from going, oh, I have a marketing problem. And now I need to market stuff to, I actually need to rethink this whole thing. So I think that’s where a lot of companies are.

Kevin Rosenquist: So you’re saying when you said earlier, you know, by the time you realize you have a problem, it’s too late. Is it the only choice at that point to sort of completely reframe the entire thing? Is that kind of what you’re saying? Like, you can’t just go, all right, well, we got a marketing blitz, you know, like like you.

Holly Rollo: Well, that’s that.

Holly Rollo: That’s that’s the first, you know, I mean, I can’t tell you how many calls I get. I get called and I would say 80% of the calls go like this. A CEO calls me and he says, I have a marketing problem, or my CMO isn’t that good? Or maybe I need the first time CMO. I have two too many junior people in there, and I dig underneath it. And actually it’s not the marketing that’s the problem. I ask them, what’s your business strategy? And they say, my business strategy is growth. And I’m like, well, that’s an outcome. So what’s the strategy for that? You know. And so.

Holly Rollo: Then I know like growth more.

Kevin Rosenquist: So.

Holly Rollo: Because.

Holly Rollo: Just to say grow means you can sail in any sail in any direction. You can market in any direction like it means activities. You’re doing a lot of activities you haven’t figured out, like where’s your product market fit exactly. What are the segments with the biggest propensity? Okay, here’s the segments okay. What are the beachheads you need to win that are going to give you pass these other segments? And then how are you going to go after those segments with use cases with the right pricing and packaging, with the right messaging, you know, with the right precision targeting. And so that part of the work hasn’t been done, which is really the meat of what my book is about. And without that, you can’t be successful. So you know, the problem? Someone comes in and goes, I have this problem. There’s a short term set of needs that can be fulfilled, but getting the Strat the strategic foundation right and it doesn’t take that long, but you need to do it. And the reason why I say it’s too late is because in Bain and Company just recently released their 2024 Technology report. You might want to check that out. I just saw it for the first time about a few days ago.

Kevin Rosenquist: Yeah.

Holly Rollo: It’s focused on the impact of AI, and their conclusion was that AI initiatives are worth up to about 20% of EBITDA. So early movers who are already kind of adopting this kind of technology are seeing those kind of gains 20% of value in 18 to 36 months. So if you’re looking around and your competitors have the strategy right, the org structure right, the tech foundation. Right. And they’re and then they’re just like pushing on the gas with AI you’re going to be completely left behind.

Kevin Rosenquist: Yeah for.

Holly Rollo: So it’s like you have to work on it like it was yesterday. And the comment I made about private equity is sometimes it’s some of them are starting to see this. But to do that kind of transformation creates a double bubble, right? Because you’re paying for what you have and your legacy to kind of keep the plane in the air while you’re also building for the new thing. And so I think there’s an investment discussion that needs to happen. But, you know, that’s how companies really drive value is getting over that hp.

Kevin Rosenquist: Yeah, yeah. And fintech startups are pretty plentiful right now.

Kevin Rosenquist: You know, between between.

Kevin Rosenquist: Ai, Web3 and other advancements in technology. It’s just opening a lot of doors for a lot of new products and services. And I mean, it’s such a crowded landscape. I mean, how is it? I know, like the tools that we have are awesome and the structure and we’re doing better with strategy and all that is it. But is it becoming harder and harder to stand out because of that?

Holly Rollo: It’s so hard.

Holly Rollo: To stand out. And fintechs. One of those places, HR technology is one of those places in cyber certainly is in the same, you know, in the same camp, right, where it’s so frothy. There’s brand new companies coming out.

Kevin Rosenquist: I like that, I like that I’m gonna steal that.

Holly Rollo: There’s, , you know, the market leaders that you can’t touch that are kind of consolidating. There’s the people in the middle that are trying to figure out what they need to do. And so what I’m seeing more and more, and actually working with clients now to focus on is really, really focusing on a niche. And a lot of salespeople don’t like that, you know, like sometimes I have to talk them into it because the problem is it’s all about relevance. You know, people want to know that. You see what they see. You think of the world the way they see the world that you trust you to understand their set of problems. Right. And so having a focus say I’m working with a client right now who is an HR platform. And those have been around a while. Right. , but they’re focusing on construction, commercial construction. And it’s very interesting because commercial construction, even infrastructure, roads, bridges, that sort of thing haven’t had an influx of funding because of the infrastructure bill. Right. And they’re having the same talent challenges, but they’re having to hire up like 2 or 3000 people for these big projects. And they’re going from paper. So a very immature market, , ripe for disruption and everybody knows it. And a huge talent problem. And they’re having to like to lean in. So if a company can really has experience in that and knows best practices and that knows how to deal with unions and compliance and regulations and different things like that, You’re on to something special.

Holly Rollo: Right. And? And you’ll beat your competition all day long at another similar company is it was a major service provider and they had all of their customer base. I wouldn’t say all I would say 70% of our customer base came from what I would call health and wellness. For some reason, the customers that they have in their customer base just happened to be, you know, like doctor’s offices, hospitals, medical insurance companies, you know, things like this. And they wanted to get into retail and manufacturing and some of these other industries. And I said, but you can still get into those industries if you focus on health and wellness, like your brand can be about that, you know. And so those are examples, I think, where you can break out of the noise by being hyper relevant. So not just hyper relevant. And in the technical bits of go to market and marketing about targeting, but hyper relevant in terms of how you offer your product to people and what you focus on and how you think about the features, or the best practices, or the use cases that you can deliver to people that no one else can.

Kevin Rosenquist: Yeah. You talked a little bit about speaking the language of the customer and all that stuff and kind of connecting in that way. We hear a lot about story when it comes to marketing. What’s your story. Is that something that is still important to tell your story and to tell it well?

Holly Rollo: Yeah.

Holly Rollo: So it’s kind of funny because the story came up, I think about five years ago it was hot.

Kevin Rosenquist: Seems about right. Yeah. Is that.

Holly Rollo: About right? Yeah. And so for me, it’s always just been about positioning, you know, so whether it’s the story, your narrative, your uvp, whatever people want to call it, it’s really about knowing what your market positioning is and how you differentiate. And to me that’s the story and that’s the relevance. That’s where you can say, are you using my construction example? Like, you know, we’ve been doing this for 20 years, you know, for construction builders and contractors. We speak your language. We get it, you know, like, this is all we do. And then and then suddenly and by the way, we’re going to make it simple for you because we know this industry so well. We know the people to bring to the table to get this solution successful for you, because your head’s probably exploding, because this is your first big technology purchase, right?

Kevin Rosenquist: And they know the pain points. They know the struggles. They know. Yeah for sure. That makes sense.

Holly Rollo: 100%.

Holly Rollo: Yeah.

Kevin Rosenquist: Yeah, yeah. It’s interesting because like you think about, you know, somebody like I always like to use the example of Patagonia, like because they have that they have that, that eco story. They have that desire to help the planet. They have cool, like, you know, founding story and all that stuff. And, you know, that’s one thing. It’s sure you can tell a great story with Patagonia, but when you’re some small but powerful payment processor that lives in the background of other software, it’s like, how are you telling that story? Right? Like, And I don’t want to sound mean to any of those payment processing companies, but, like, who cares in some way? Yeah. Is there a way that you can spin it when you’re in a company like that where you can connect with the right people?

Holly Rollo: Again, I think you have to just really, uh, pick some market segments that are niche. You have to think of them as niches. And the reason why that scares people, especially salespeople, is they say, but I have a number to make. I want to go out and market to the world. Well, sure you can. You know you can. You can close any deal you want. You know, but in terms of where you’re going to put all your wood behind your arrow, you have to put it somewhere. And what used to be in technology 20 years ago, niches are actually big. And , here’s a great example: Amazon. So this is one everybody can relate to. Remember back in the day like the only thing you can buy on Amazon was books. Yeah.

Kevin Rosenquist: Yeah.

Holly Rollo: Okay.

Holly Rollo: Well like I’m sure that wasn’t Jeff Bezos vision. Like, I’m sure he had some grander plan.

Kevin Rosenquist: Yeah, you’d think so.

Holly Rollo: You have to start somewhere, right? So if you start there and then you can build out it’s it’s better than being everything to everybody and then you can’t break through the noise. You have no differentiator. And honest to God, this is the truth. If you look at any one of these industries, the products are kind of the same. You know, like the tech people will argue with me about that. But, you know, there’s a whole lot of products that are absolutely driving leading edge, innovative features like, can they do one thing really, really well that is very attractive to a certain set of customers? There’s companies that struggle to just do the basics right, but the grand group in the middle are sort of good enough. Right. And so, , what’s going to make you different is how you, how you differentiate and where you target and who your value proposition is for. Specifically in a given cyber, Southwest Airlines is another one. Like it doesn’t mean business class fliers don’t go on their airplanes. You know who want like this because business fliers need to get to different places. But they’ve marketed themselves early on, you know, as cheap like no frills like get on the bus and, and, you know, taking your flight. , and so it’s that kind of thinking we need to kind of bring, bring back. , I feel pretty strongly about that. And it’s always been something me and my peers and everybody in marketing have been talking about for years and years, I think. I think it’s just getting harder and harder to compete because there’s so much more competition.

Kevin Rosenquist:  That is for sure. Yeah. Yeah. Especially now. Yeah. Yeah. You, you I read a recent blog of yours. I think it was an excerpt from your book. , the blog was titled an I ready GTM Requires Radical What do you mean by radical unity?

Holly Rollo: Yeah.

Holly Rollo: So it’s a little bit of kind of what I was saying earlier on, but I’ll expand on it. So as marketing, sales and customer success kind of grew up, , they grew in silos. So they’re, they’re led by different leaders and, , they have different KPIs. They have the same goals.

Kevin Rosenquist: Sure. But they’re actual.

Holly Rollo: Objectives, you know, are different. Sure. And, , they’ve they’ve accidentally sometimes not always purposely added a bunch of stuff to their tech stack that they’ve been able to control. So they have these little control points in their workflow and process and how they do the digital things that they do, which worked fine to a point. And and now what’s happened is because the customer experience and the customer and the buyer doesn’t care about the silos. You know, the handoffs between the silos is where customers go to die, right? Like like leads just get stuck, you know, opportunities get stuck and everything gets, like, overcomplicated. Because then people are reengineering how to get things from one hand off to the other, versus having radical unity about what matters to the customer and a tight set of aligned targets across the entire go to market. So I have this and it’s in the book. I have this like smart of the opportunity modeling, which basically says every single function in the organization in the marketing, sales, and customer success organization, including the partners, how they’re going to drive, you know, the outcomes in net new net new deals or expansion deals. So everybody knows their piece of it. Because what happens between sales and marketing sometimes is like marketing is like, I met my target and sales is like, well, I don’t have enough pipeline. And and you know, I’m not getting qualified pipeline and leads and marketing saying. But I met my target. What happened? And there’s a lot of finger pointing.

Kevin Rosenquist: I did my.

Kevin Rosenquist: Part, you know.

Kevin Rosenquist: Yeah, yeah, yeah, yeah.

Holly Rollo: And it’s like it’s like that doesn’t work. It doesn’t work. Because, , you know, as I said, the roles are converging because of the speed that we need to get customers through. We can’t any longer have these complicated funnel models and all this waterfall kind of stuff.

Kevin Rosenquist: You talk about it being.

Kevin Rosenquist: A non-linear journey. Right?

Kevin Rosenquist: Is that it’s not.

Holly Rollo: It’s a complex system. It’s like the weather you know like.

Holly Rollo: It’s.

Holly Rollo: Not like you know sales people are like well here’s the sales process. No, there’s no sales process. There’s a buying process. That’s all there is. Yeah. And it’s not you don’t own it. The buyer owns it. So you have to kind of think that way. Like how do you manage in a complex system. And so the radical unity has to start like from the top, I would say the trap, which in my book I call one of the dead reckonings is thinking that you can put a chief revenue officer in a role and say, okay, the chief revenue officer, the chief customer officer is going to own sales, marketing and customer success, and that’s going to make it all better, because that may be true in a large company, but in small to mid-sized companies, they don’t have the luxury of then also hiring a CMO and these other roles. Right. So they say, well, I’m going to promote a sales rock star to lead this effort because that’s typically how they grow up. And then give them junior people and they’ll know what to do. And that’s proven to be a huge failure on many, many companies to do it that way. So, you know, you definitely need to, need to put the right talent together so that it’s complementary. But having a unified approach for how to do that is really important.

Kevin Rosenquist: You, your book, The Power of Surge five Ways to Supercharge Your B2B Software Business and unleash hidden value. Who? Who did you write this book for specifically?

Kevin Rosenquist: Talk about.

Kevin Rosenquist: Your niche.

Holly Rollo: Yeah.

Holly Rollo: So I wrote it. So here’s what happened. I’ll tell you my story. So the last company I was at was a carve out, and we spent four and a half years carving it out from a very big, very big corporation. And we got it sold off. And then I was like, you know what? I’m going to take a sabbatical. I’m going to do some sailing. And so I was out on the sailboat and I thought to myself, what have I learned in the last 30 years? Like, if I were to say to someone, you know how to make this world better. Like, what would that be? And the thing is, is I got really frustrated because I was like, you know, I feel like we’ve been debating the same things over and over again internally across sales, marketing and services of what to do. We’re kind of to the point where we’re debating best practices like these are known things to go do. And so we’ve gotten in the way of our own ability to execute just by simply having these debates. That shouldn’t be a debate. And they’re debates because I think , not everybody’s on the same page with how the engine works anymore. Right? So as people within these organizations go up higher and higher and become CEOs, you know, they’re 55, 60 years old. And what happened at their last job at Cisco maybe ten years ago isn’t what works anymore. And so I said to myself, well, if I could give a gift to the CEOs in my life, and also, by the way, the investors. So private equity firms, you know, who are on these boards for these companies, if I could give them a gift that would suddenly make them look at the problem differently and be able to kind of overcome the debates because they shouldn’t be debates. It’s like debating facts, you know, or debating ideas versus debating facts.

Speaker3: Yeah.

Holly Rollo: That we could get out of our way. And, you know, because I am exposed to a lot of things on the national security front and on the cybersecurity front, we have so much bigger problems to solve, and it’s going to move so fast in the next ten years. We don’t have time. And so actually I got the first draft of the book back. I don’t tell the story a lot, but I got the first draft of the book back, and my editor was like, you sound kind of angry. And I said, oh, no, that’s not what I’m meant to do. So I rewrote the book and it’s much nicer, but I think I had to get it out. You know, it’s.

Holly Rollo: Like, gosh, you gotta.

Kevin Rosenquist: Stop swearing so much, Holly. Way too many F-bombs.

Holly Rollo: If we could just get out of our own way, like, let’s do it. So the way I structured it was just a very logical, practical approach to like, okay, if this then that, if that, then this. So it’s kind of like Chutes and Ladders. Like if you’re in this kind of company with this kind of situation, with this kind of problem, you know, this is how you kind of go down this playbook and then here’s how to look at your playbook after that. So you can kind of just plug your own company in. So that’s kind of how it started. And then I got really excited because the feedback I started to get was, wow, you know, can you show my team how to do this? Also was talking to some private equity firms who are trying to figure, because they typically have very junior level marketing talent, high potential. Totally. But they just don’t have the experience. And also the marketing roles I think for people recently have focused on specialization. So if you’re always a specialist, how are you ever going to get the whole picture and the strategic view. Right. So I actually as we speak right now building that into an eight week challenge so people can take their own business situation and turn it into, like, apply it to the principles and then turn it into a more unified strategy. And there’s tools and playbooks and all that thing. So I’m really excited about that because that’s that goes back to helping the next generation. Yeah.

Holly Rollo: You know yeah.

Holly Rollo: Getting people.

Kevin Rosenquist: Getting to your point, it’s going to.

Kevin Rosenquist: Change a lot in a very short amount of time. So you have to be prepared for that.

Holly Rollo: Yeah for sure. Yeah.

Kevin Rosenquist: Do you think that some of that like I don’t know when you were talking about debating ideas versus facts, obviously you can’t help but go in just to a societal kind of viewpoint. Does that like does do you think that plays into it? Is there like an overall attitude where, hey, this works really well, like this whole idea that we have to, like, not stick with the facts, not believe the facts, or maybe a desire to disrupt in every situation. Could that play into why people are trying to argue things they shouldn’t be arguing?

Holly Rollo: Well, I.

Holly Rollo: Think when it comes to development, It’s a very binary conversation, right? It’s very ones and zeros when it comes to dollars, you know, in finance. It’s very clear when it comes to sales and quotas. It’s very clear when it comes to marketing. It’s sort of a black box. Yeah. And so therefore I think there’s a lot of different ideas about how marketing is supposed to work. And , it’s probably in tech, it’s probably the only vocation where everybody thinks they know how to do the job, you know? And I think that’s another part of just, you know, marketing has a branding problem. I think in tech in general.

Kevin Rosenquist: It’s funny.

Kevin Rosenquist: Marketing has a branding.

Kevin Rosenquist: Problem like that.

Holly Rollo: So I think I think that’s some of it. I also think, as I said, sometimes it’s small to mid-sized companies. You get executives who come from larger organizations and a larger organization does things very differently than smaller mid-size.

Holly Rollo: Companies.

Holly Rollo: Or turnaround companies, or transformational companies or startups like you. Do things differently. And so I can’t tell you how many times I’ve had conversations with, well, we need to do this because that’s what we did at Oracle or that’s what we did at whatever company. And it’s like, oh no, like we’re not even there yet. Like we need to do these things. And so I think that’s part of it is, you know, because everybody thinks they have a handle on what good looks like and because they’ve seen things work at other companies, they go on to plug those in. And it’s kind of a process of explaining, like there’s a certain baseline set of things you need to do first and then you get to do these other things. You know, you can’t do these other things or expect these other things when you haven’t, like the basics, like your website doesn’t work. Like there’s some.

Holly Rollo: Kind of, you know, I’m being.

Holly Rollo: I’m being facetious, but.

Kevin Rosenquist: Yeah, yeah, but like start, start.

Kevin Rosenquist: Start at the beginning and work.

Holly Rollo: Your way up. Yeah.

Holly Rollo: And sometimes, you know, this is this is the call as well. You know, my marketing person doesn’t know how to do this or that and it’s like, oh, okay. So have have you set up this and how is this working? And do you have these operations. Right. And you know, how’s the reporting. And they’re like, uh, no, we don’t have any of that. And it’s like, well, it’s not your marketing person. You know, it’s like you have to kind of understand what needs to get built first and how that works. And with the modernization activities and a lot of these systems, swap outs, you know, uh, it’s a really interesting time. It’s an interesting time for Salesforce. I’ll be really interested to see what happens, because I used to be at SAP back in the day and, you know, Salesforce came, came up and completely disrupted everything because they were cloud based and easy to use and this and that. And now they’ve become the monolithic system, right? That everybody’s frankensteined and there’s multiple instances. And then you acquire a couple companies and the whole thing’s a mess.

Holly Rollo: So people are trying to figure out what to do with this. The core CRM at this point. And it’s really interesting. And what sometimes I like to remind people is there’s three tech stacks or three platforms you have in your organization that you rely on. One is the technology you build, like, so that’s the thing that you actually sell people. The second is your back office system. So your finance systems and your HR systems and to a large degree your CRM. And then there’s your customer experience platform. And I’m using that term not in a specific, you know, name a technology term or category. I’m meaning like the thing you use to engage digitally with your prospects and customers. With this one, there’s no roadmap. No one owns the budget. No one’s looking at security of it across the entire flow, typically, and no one actually knows where the data is. So this is crazy. And so, you know, as people are then like trying to bolt on all these AI tools and whatnot. It’s just chaos right now.

Kevin Rosenquist: Yeah. So that’s a good point. You know, it’s.

Kevin Rosenquist: A good point.

Holly Rollo: Yeah. People really need to look at that as a core system. You know, if you were looking at it as a core system, would you treat it differently? And I think that’s where we’re at.

Kevin Rosenquist: Are you saying like they kind of treat it more like an add on.

Holly Rollo: No, no, no to think of your customer experience platform. Right. Which typically this day and age, I think the last number I saw was the typical midsize company has 94 tools.

Kevin Rosenquist: Oh, wow. So it’s 94.

Holly Rollo: Tools that make up this. It’s not , it’s kind of like a virtual infrastructure.

Kevin Rosenquist: Yeah. Most of them are cloud.

Holly Rollo: Based tools.

Kevin Rosenquist: Right? Sure. Yeah, yeah.

Holly Rollo: And you know, as a cyber professional, I freak out because like, you know, it’s not it’s not this cloud vendor or that cloud vendor. It’s the APIs. It’s the thing that stick it together, you know, and it’s the security protocols that keep access controlled. So, you know, that whole thing is just, uh, you know, the third party risk is huge. So, yeah. So I think if people looked at instead of looking at it as tools and looked at it as a virtual infrastructure, they would think really differently about how they needed to resource it and how it needed to pull together the whole experience, not just solve this one reporting problem.

Kevin Rosenquist: That’s a really good point. Calling them tools rather than a whole overall system in place to handle this part of your business. That makes a lot of sense.

Kevin Rosenquist: Yeah. Yeah.

Kevin Rosenquist: All right. Well, the book is Power of Surge five Ways to Supercharge your B2B Software Business and Unleash Hidden Value. Holly Rollo, thanks so much for being here. I really appreciate your time.

Holly Rollo: Thanks so much for your time. You take care. Thanks for having me.