Well, hello, and welcome back everyone to another leadership author series episode. Extremely excited today to welcome someone that I think has not only some amazing content a great book, but some fantastic ideas and theories and concepts around.
Leadership in general.
Where we are today, where we're going, what we need, and I'm excited to have this conversation.
So welcome to the show.
We have Holly Rolo here B to B marketing and transformation expert and author. So welcome to the show, Holly, and tell us a little bit about yourself.
Thank you so much for having me. Yeah, I've been around about three decades and B to B tech, and I've seen a lot and over the years, I've gotten very attracted to and good at helping companies go through major transformation periods or major transitions, whether it's transforming to a platform company, transforming into a new customer base or
market area, or even turnarounds. So I've been involved in quite a few transactions and so that's that's what I focus on, and I help cmos, CROs CEOs help kind of position their company for you know, what they're trying to do next. And most of the people that come to me are organizations where either what they were doing no longer works, or they've had a change in how their investors think about their business. So maybe they've been purchased by private equity and there's a new a new
orientation around the business. Or they come to me and say, you know, do I have the right CMO, Do I have the right cr do I have the right head of sales? Like why aren't things working anymore? And so these are these are the clients I help most of the time.
Yeah, no, I love that.
And you know what's what's interesting is when I at first look at the title of the book Power Surge Five Ways of Supercharge your B two B software business and at least hidden value, I was like, okay, And then I started to read a little bit more into it and then talk about some of the concepts in there when we talk about bridging generational skill gaps and understanding, you know, how to have a future ready workforce, and
I was like, these are the things to me. I'm not in marketing, I'm not into B to B software sales, but these things I think have a big chunk of how to actually, you know, supercharge of business, how to resolve some of the things that you just talked about
in the calls that you get. So I'd love to start there, like unpack a little bit around maybe what you're seeing currently in the industry, where we're going, or where do you feel the time has to be spent to really you know, prepare organizations to be completely supercharged and to really unleash all of the hidden value, including the human capital piece.
Yeah, I mean, it's one hundred percent all about getting the best out of the people at the end of the day, and a lot of the concepts in the book really start with having a sound business strategy that everybody understands and everybody sees their part in. And it sounds so simple, yet it can get so convoluted as leadership kind of turns over, as people come and go,
as investors come and go. It can get really focused on the tactics and the programs and you know, functional silos that are hindering people who want to come to work every day and just do their best work. That's what people want to do, So you have to arm them with an appropriate strategy, help them see their part in it, and then give them the tools and enable them to you know, do the best possible thing they
can by their customers. And if you have incredibly motivated, highly focused employees, you're going to have a successful business.
And that's the I mean, that's the simplest way to put it.
I love that.
And when you're thinking about finding them most highly motivated and kind of driven and excited employees from a workforce standpoint, and you're talking to also about you know, CEOs and cmos and these types of decisions, let's unpack that a little bit. What are you see or what are we looking for or what you know? What should companies be really considering to stand out in this space?
Well, first, there is a convergence happening across various roles due to AI and the speed, scope and scale of digital. So it used to be the various functions could be successful in their own silo. And so the conversations over the last ten years have been about alignment and handovers and workflow and aligned KPIs and those kinds of things. And it still doesn't work because the actual customer experience is completely changing and the tools and technology.
Is completely changing.
So in terms of talent, you ca wean't hire for traditionally, how you may have seen the business paradigm, because the business paradigm is changing, So that's number one. Number two, you should be hiring for a set of skills, experience, or more importantly in my view, is mindset.
That you want to add to your.
Team to get the kind of change you want. You don't want to hire a bunch of people that are the same, which is very easy to do because you know, people on the interview teams want to work with people
that are like them. And I've always you know, stressed to my leadership teams, we need to hire for the best combination of people, which means diverse ideas, diverse backgrounds, people that are willing to challenge the status quo, Like we want a range of viewpoints to come to the table to come up with the best possible solution.
And you can't do that.
If everybody sees things the same way. And then and then third, you know, there's certain things the company needs to do. As I mentioned the business strategy. So if you're a turnaround you're going to have a different set of challenges in front of you than you are if you are a super high growth, you know, super innovative
company with one product. It's a, it's a different DNA, and oftentimes people want to hire you know, oh well, I think this is this is what good experience for this function is, which may not actually be what you need. You may need better leadership versus functional experience, or better uh, transformational leadership versus management, and those are different types of things that people need to think about when they're interviewing for the right group of people to work together.
Yeah, I love that.
I think that every data point will tell you that having, you know, diverse leadership teams, diverse teams in general, will always lead to like larger elements of innovation because many times the best idea when not necessarily the loudest voice, especially when you create an environment and a community where people are are very open to debates and healthy debate and that type of thing. I think it's so critical. You mentioned mindset in the selection process, which I love.
I it's it's the first time that I've heard that. I left a litle little bit more about that. When you're when you're assessing for mindset or you're considering mindset, what are maybe the questions that you're asking, what are you looking for? How are you feeling like okay, this is this is good from a mindset that we need when it comes to adding to our team.
Yeah, so I can just speak for you know, my practices. Everybody might have different viewpoints, but I really look for
people over experience. I look for people who've had to overcome something really really hard and impossible, even if they failed, because to me, people who tend to be faced with really big challenges and it could be in their personal life, it could be you know, a medical condition, it could be something like this, you know, where they've been faced they they have to be resilient and they have to
continue to work through it right. And to me, those people are really great problem solvers and can drive to a result.
And that's what I've found to be true.
And those are the types of people, you know, I've I've wanted to hire for even if there's someone who comes from maybe a big brand, you know, who's had more experiencer and an Ivy League school, like I would rather have someone who's streets smart and scrappy and resilient than someone with multiple degrees personally.
Yeah, I love that.
It's it's because it reminded me of a question that I like to ask, which is like, tell me about a time when you, you know, achieved a goal that you surprise yourself with, that you weren't sure that you'd be able to achieve, and that you felt, you know, you almost exceeded your own expectations and you felt, you know, you felt amazed at yourself for achieving it. And I think it's it's in that same kind of breath of that idea, because what I hear many times is everything
from like, I really had to get scrappy. I had to persevere. I had to you know, get myself through this thing, whether it be a health challenge, a school challenge, you know, a financial challenge. Like you you said, you tend to hear these real stories from people that help you to kind of you know, see maybe the the
challenges that they've had, how they've had to persevere. And I think you're you're so spot on, like that's such an important piece of somebody who's going to really hold on to and commit to and stand on you know what they're looking to accomplish and achieve, and they're gonna learn and they're gonna you know, they're they're gonna adjust as needed, but they're not gonna give up and that's kind of what we're looking for.
I think it's such a great call out, right.
Yeah, that's for sure. And I think people who are also have different ways that looking at problems. That goes back to your diversity thing. I mean, for one hundred years, I was the only female at the table half the.
Time in B to B tech.
It's changing a bit, but you know, we'd like it to be a little further along on that spectrum. And sometimes, you know, you just have to take you have to be courageous and brave to bring up what you're thinking, and people will look at you crazy, like you're like like they don't like you're speaking a different language kind of.
But then ten minutes later someone will bring up the same idea using different words and it sticks, and you know it, it's hard sometimes to swallow that, but the point is somewhere you triggered the thought and it can often lead to other ideas or even the same idea. And what matters is the forward progress, not the initial reaction.
And I think I think that's an important thing, you know, as executive kind of come up through their journey, you know, just to be really courageous with your convictions because it's likely that a few other people at the table see what you see but can't put it into words.
I want to ask you, Holly, a little bit more about that kind of the gap of grief concept that you have and talking about the importance of building trust within relationships, and maybe even going a little bit further.
You mentioned this earlier, but like.
This important piece of the evolution of something like sales and marketing. What are we seeing in the industry and why this is something we want to talk about from a leadership standpoint, Why this is really important to how you know how and where this will impact your organizations from a success standpoint.
Yeah, So, the best way to articulate the problem is there is a tendency for CEOs to not always understand what their head of marketing is trying to do. And a lot of it the root cause, nine times out of ten is the understanding that marketing and sales can't actually execute well if there isn't a business strategy. So oftentimes I'll get calls by clients and they'll say, oh,
you know, I don't have the right CMO. You know, my CMO is terrible, and you know, and they'll literally use those words, and I'll say, well, what's your business strategy and they'll say growth, and I'll say, growth is not a strategy, let's start over. And it really takes time for them to understand they actually don't have a strategy, and a business strategy like a growth plan on a spreadsheet,
you know, where all the numbers show. Growth is not a strategy, right, it's a spreadsheet and growth is an outcome of having a good strategy. So this is the number one root cause I see of this gap of grief where the CMO or the head of sales is like, I want to do X, Y Z, and the CEO is like, well, you know, I don't understand how this aligns and why aren't the KPIs adding up?
Why can't I get the ROI why can't I do these things?
And it's because sometimes these functional leaders are trying to do so much of everything in the name of growth that they're not actually doing anything well, and so it causes a lot of bad expectations I think across the board, and once the expectation conversation goes sideways, you lose trust. So, you know, the CEO no longer trust the marketing or sales executive to execute because they can't actually understand what they're trying to get done.
And it's a fascinating thing to watch.
It's happened to me a few times. And you know, I remember the first few times that happened in my career, I was like, what is going on? It's like, I'm
explaining it, but it's not getting through. And you know, oftentimes, especially in tech in my in my world, in cybersecurity in particular, you know, the CEOs are technologists, right, so they tend to even have a different orientation from a sales and marketing executive who's thinking about the narrative, you know, the relationship, the storyline, you know, the messaging, the market segments and things like this that don't necessarily translate. So
I think it's a two part problem. You know, it's a root cause of not having a business strategy you're relying to, and it's also just different sides of the brain, you know, trying to communicate.
Yeah, No, it's a great call out, and I think it's you know, there's always been I believe a maybe tension between sales and marketing, right because it's kind of like that we just want to sell things we're trying to, to your point, have a narrative and spend money in getting this out there, and then it's kind of like who gets the credit for what type of thing? And I think most in all really successful businesses understand that
both are needed. But to your point, that business strategy piece the actual thing to point to and say this is the plan and we all have a part to play in this plan, I think is.
Something that that's very needed.
So what happens if somebody, you know, reading the book, listening to this podcast, is like, Hey, I'm in this space right now, or I see that we have this in our organization where there's either that element of a gap of grief or we're seeing where we're kind of combining these roles in our organization. You know, talk to us a little bit about like what you do in those instances, what you would suggest for them to go do, how they would be able to work through these situations.
Right.
Well, the book I put together specifically for marketing leaders.
But what I do is I coach for.
Modern go to market transformations across the board, so CMO CROs and heads of customer success and support, and the first order of business is really to determine what quadrant your business is in. You know, are you a market leader. If you are, you probably don't need help. You know, if you're a startup or early innovator, that solves it.
You have to you're you don't have really a lot of customers, yet you're focused on actually just landing and breaking through the noise quite frankly, because a lot of these these types of industries are really frothy. And then the other two quadrants are really you're transitioning or you're going through a transformation to go from you know, your
current state to a future state. So the most common one I hear all the time is we're going from a product company to a platform company that would be an example, or or from a set of features and use cases to a set of services. You know, there's like a different orientation on that. And then the fourth quadrant is really you're retrenching, you're losing your customer base. You've been around a long time, super legacy and it's
a turnaround. And I've seen a lot of companies honestly try to compete in their go to market as a market leader or as an innovator, when really they're a turnaround, or maybe they think they're a transformational company when they're actually a turnaround and so their go to market strategy and their narrative isn't aligned to the actual business situation. So the customers get confused, you know, because you're sort of saying, oh, well, we have all these innovative solutions.
So your customers like, seriously, you can't even support my support, you know, like a I have five tickets into you that you ever responded to. So it has to match, you know, to have integrity. And so in the book, I kind of outline some very practical steps to do this, you know if you're a head of marketing.
But I have taken it one step.
Further to offer a go to market challenge across the board, because, as I mentioned before, I see the roles converging with AI and a digital first customer experience, and so that whole model needs to change. So the search challenge is really an attempt to get more high potential talent in whether you're from sales marketing or customer success and formulate a more modern way your company can be fully customer obsessed around the customer experience and delivering that digital first.
So it's meant my goal in life is really to just get people into the modern age and start thinking differently and helping people, you know, really accelerate their experience level. As I mentioned to you I offline as we were sort of getting ready for the call, I have thirty years of experience, but we don't have time for the person with ten years of experience. We have twenty more years to get them up to speed. Like we need
so many good go to market leaders. We need to build a bench and really accelerate this thing.
So that's that's the hope.
Yeah, I love that, And it's a there's so many things in there that I think, uh, you know, really resonate with leaders kind of at all levels in regards to just the the understanding of what where we are.
Today, where we're going, and what's needed.
And I think you just spoke about that, like the the need for new ideas kind of you know, fearless innovators coming into the space. But then also to have a winning strategy, you have to have current leaders that are open to that and that are creating the space for those to kind of come in there.
So if if if you've got let's.
Say that I'm a leader and I see some of these struggles in my own business right now, what would be maybe the one or two things that you would suggest that I do to number one maybe better self assess am I you know, I love you talked about kind of like you think you're this, but really you're probably that, and did these things type of match Like, what would you say that I need to do to
really self assess maybe where my business is? And then what's something maybe a couple things I should do as a leader if I really want to help to move my business forward in how I show up as a leader of people in my own business.
Yeah, I mean, I think the first question is really understanding the condition of the business and on the marketing and sometimes the customer's success side. And I'm generalizing and everybody's different. There's not always a deep dive that they've done into the condition of the business from the perspective of the investor, right, so let me just dig into that.
So for example, everybody will be saying grow, grow, grow, but then there's just this myopic focus on ebadah and cash flow and there isn't an understanding of how overleveraged the business is. To be able to actually invest in growth, and so the executive team will be saying grow, grow, grow, but there's actually no way to make the changes is
to enable that to happen. So if you understand the condition of the business from an investor perspective and dig into that with the CFO, ask as many questions as possible to understand, I think there would there would be a good context for why it's so hard to get.
Some things done sometimes. So that's kind of point number one.
Point number two is this generational thing is fascinating both my kids. I have kids now in their late twenties and they're in tech and they're they're on their own journey, but they completely look at problems differently because they're digital native, right, and.
A lot of us are gonna want to go at.
Some point retire, you know, and these people are coming in, but we need them up to speed quicker, and we need them to be we need to be able to give them a really long long leash, you know, like go for it. And because they completely look at.
You know, the.
Customer experience differently and see things that aren't encumbered by you know, our legacy views of what we think works or doesn't work or did work or didn't work or used to work at some big company but won't work here. You know, like we need to like give them the ability to own a problem and solve it their way, because the customers and buyers are actually more like them than.
They are like us.
So I really really think it's important to bring in high potentials, give them a problem to solve, and give them the decision authority to get it done. And it also helps the rest of the organization and the culture understand that age isn't an issue, like the problem and the solution are the issue, and I think that that builds a really healthy environment.
There's one client I'm working with.
They were using language like you know, the old guard and the new guard, and I was like, you have to stop because you're creating camps, right, And it's good. I mean, it's great that you recognize it, but it's not in us versus them. It's you know, solving the problem looking at it through a different lens, and this is where we need to get to.
Yep. I love that.
Well, Holly, please let our listeners know like where we're going to get more information kind of about you, about the book and especially those that might be listening they're like, hey, I could use some help here.
What are the best ways for them to get in touch with you?
Yes's great.
Well, visit my website at www dot Surge dash Strategies dot com and you can learn more about what I do, more about the book, but most importantly, I think check out the Surge Go to Market Challenge. I would love for high potentials to you know, take a look at that and join. It's cohort based online challenge that is I think packed with very short challenges that are really in line with I think the parts of the book
that are most important. But I designed it so it was very good for people whose time is really valuable.
So I'd love to invite people to join that.
Awesome.
Well, thank you so much again, Holly. We appreciate you for taking the time and talking to us today. Again, please check the links in the podcast description here we can get you right to Holly's website, to the book itself, to the challenge all that will be listed below. Thank you all for checking us out, and we'll talk to you all next time.