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Today’s show featured Holly Rollo, the author of The Power of Surge. We also featured John Shrader, Chief Revenue Officer at construction software company Arcoro.
Find Holly on LinkedIn. Find John on LinkedIn.
HOLLY’S TIP: “The real thing that’s going to differentiate you is a frictionless customer experience. That customer experience can’t be managed if it’s in bits and pieces all over the place. Then sales, marketing and customer success aren’t radically aligned, which is what I’m a big advocate of. Priorities become really, really clear when you figure out where’s the friction in that customer experience and how can you properly set goals, which I think would help align CEO expectations, not just on marketing, but on the investments and attention spent across the go-to-market roles that remove that friction and make the experience stronger.”
JOHN’S TIP: “What are those things that you’re doing on a regular basis that cover three things? You’re always prospecting, you’re selling, and you’re closing. There’s different times in your day, your month, your week that the amount of time you spend between those three things shifts. The beginning of a month, you’re going to be spending more probably on prospecting. The bottom end of a month you’re doing more on closing. But that balance of how you do that in a day matters.”
THE PODCAST BEGINS HERE
Fred Diamond: Holly, it’s great to see you here. It’s great to see you, John, also. Holly, before we begin, I just want to acknowledge you on the book. I published two books in 2022, one on sales and one on Lyme disease awareness. Your book, I recommend to anyone who is a technology marketer or a technology CEO for that matter. I was a CMO for two companies in the early part of this millennium, and they were highly funded companies. The challenges that you talk about in the first 10 chapters of the book were things that I could definitely relate to. The last part of the book is something that we’re going to get into detail here. Where does sales fall into this equation for B2B SaaS companies? We’re going to talk to you about what the content is, your positioning, and then get some of John’s perspective as a sales leader.
Holly, give us a brief intro.
Holly Rollo: My name’s Holly Rollo, and I’m the CEO of Surge Strategies. I help companies with the strategic advisory to help get them mostly unstuck. The clients that come to me, come to me in a situation where either what they were doing before for a go-to market has stopped working and they need to regroup and understand. It’s very much a transformational type of moment. I’ve spent over 30 years in B2B technology since the dawn of time, and I’ve seen a lot of best practices evolve. I think what’s really exciting about now is with the AI fueled wave of digital transformation, it’s really forcing companies to think much more different than they have in the past, because everything’s changing.
We said this around digital transformation in the beginning, but this has scale, scope, and speed that is completely unprecedented. Some things are becoming much more important, like focus on strategy, focus on the customer experience, and with the roles blending across sales, marketing, and customer success, companies are really needing to rethink everything. It’s an exciting time and I’m really happy to be a part of it.
Fred Diamond: One thing we talk a lot about at the Institute for Excellence in Sales and on the Sales Game Changers Podcast is the evolving role of sales. Of course, the evolving role of marketing too. But how has everything affected the sales profession and how has everything affected sales professionals?
I’m glad that you brought on John Shrader as well. John, give us an introduction as well. Then I’m just going to ask you what is the state of sales. Holly and her book goes deep into the state of sales as well, but mainly from a digital marketing, customer experience perspective. She does talk a lot about the evolution. As a CRO, give us your state of sales. Introduce yourself and give us a state of sales.
John Shrader: John Shrader, I’m CRO at a company in the construction technology space called Arcoro. I’ve been in the sales space for about 24 years now. Been in that from startups to larger enterprise companies to mid-level working with both venture to the last 15 years have been with private equity portfolio companies and have seen a lot of change. I’ll echo Holly’s comments. Also, as you see from the sales standpoint, the things I see really are around speed. I talk a lot with my teams, we have a phrase about adapt and adjust. There is a living mantra around things are moving as quickly as they can be, especially if you see things with AI that are coming out right now. How do you continue to stay relevant? What is it that I can stay in front of people that makes it interesting and relevant? Because that buyer is so tech savvy, their attention span and what they’re looking for is coming in at a much higher level than where we were before. But that challenge is also an opportunity for us, but it definitely lends itself around when I see this speed and your ability to adapt and adjust.
Fred Diamond: In your book, Holly, you use a lot of good sailing analogies. I’m not a sailor but I have a lot of friends who are. The acronym for surge, strategy, unity, reputation, gains, and efficiency. That was really well done. I just want to applaud you on that. I’m based here in Northern Virginia, so Chesapeake Bay isn’t too far. I have a bunch of friends who are sailors and I’m sure they would definitely appreciate the sailing analogies.
Why do B2B software companies struggle to break out and how can they turn the tide? I’m just curious, is it a sales problem? Is it a management problem? Is it a marketing problem? Is it an experience problem? Give us some of your insights.
Holly Rollo: What I see is when people come to me, they come to me with symptoms, and it typically falls in three buckets. One bucket is my sales team is having trouble executing. We have seen the execution in the past in pockets, but that has stalled. The second issue is my CMO isn’t the right fit. I don’t have the right CMO, they don’t have the right skillset, or the marketing is broken, and maybe it’s time to rethink marketing. That’s the second symptom. The third symptom is what we’ve been doing hasn’t been working generally, so maybe it’s a product market fit problem.
The follow up question I always ask them is, what is your business strategy? The business strategy, I would say 9 times out of 10, B2B companies, and I typically work with small to midsize companies, not the big, big sales forces of the world that are already public and all that. Many of them are late stage or private equity owned, maybe had gone through a couple different things. What they’ll say their business strategy is, is they’ll say growth. I’ll have to remind them that growth is not a strategy. It’s a measure of how well you’re doing at a certain point in time.
Just to use a sailing analogy, it’s like getting in a sailboat and going around in circles and convincing everybody that you’re getting somewhere. That’s not really the case. You have to have a destination in mind, a specific continent, a specific timeline that you want to achieve, and you have the resources you have. A big boat, a little boat, a lot of gear, not a lot of gear, whatever it is, but you still have to get there.
This is the number one thing I think that is really hindering companies, is they’re stuck on the quarter-quarter mentality of growth as a strategy, but it’s not a strategy. What the result is, all these activities go in a bunch of different places. They’re measuring the activities, but they’re not measuring the distances they’re traveling to get to their destination. Are they making the milestones? Because I think the priorities aren’t shared across the whole go-to-market, again, marketing, sales, and customer success.
Just quick three things. One is the business strategy has to fit the business situation. For example, I’ll have companies that come and say, “Growth is my strategy. We have an innovative solution. We’re competing with startups who maybe are taking our customer base, we’re seeing a lot of churn.” I’ll have to say, “Well, you’re actually not an innovator in terms of a go-to-market motion. You really need to focus on expanding and protecting your installed base.” In the four models I outlined, that’s one of the other two. You have to balance the priorities on expanding and protecting your base versus driving net new logos solely. That’s one thing.
The second thing is the segmentation. The maturity of the segmentation model really needs to get much more precise on the needs of the customers. The problems, the pain points, the motivations they have in a very segmented way. You’re focusing on the biggest beachheads that matter. We can talk more about segmentation, but that’s another big problem I see, or opportunity.
Then the third thing really is a very clearly defined positioning strategy. You can talk about positioning as Simon Sinek uses the why. Some of us call it positioning, some of us call it UVP, some of us call it different things, but it’s that unique space in someone’s brain that you camp out on and then jackhammer their brain all the time on that’s what you stand for. I think we’ve lost the ability to do that over the last 10 or 15 years.
We have to get back to that because I think the technical buyer, as John said, they’re getting younger. They have the attention spans of hummingbirds. If they have one bad interaction, they have expectations of a consumer-like engagement experience, and you can lose them in any moment. That customer experience needs to be very clear and seamless, that the branding is becoming much more important because to my delight, they’re focusing less on industry analyst reports and more on how their peers see the problem or how they’re discovering and dealing with the brand. We can come back to that topic, but I think that’s a big one.
Fred Diamond: John, from a sales perspective then, Holly threw out a whole bunch of things. Actually, as Holly’s answering that question, I was the CMO heavily invested in firms. It’s been 25 years, which is incredible, the beginning of the 2000s. But we had so many challenges. As you’re talking now, I’m thinking about all these challenges.
One, for instance, is we had the only product that did what it did, and we charged a lot of money for it. Then I went to a trade show, and then I saw that one of the biggest tech companies in the world was now selling the same thing for one tenth the cost. Then I realized that I was going to be out of a job in a very short amount of time once the investors figured that out. It’s not just sales, marketing, strategy, and timing, there’s so many other factors that come in.
John, talk about sales. Where does sales fit into this? Where does this lead or participate in this struggle?
John Shrader: I’ll call out the word that Holly has in surge around unity, and there really has to be this unity between sales and marketing. I would say I attribute some of my success, much of it to that collaboration working with marketing, because as you’re looking at this, and to Holly’s points around this business strategy, you’ve got to have a strategy that’s going to be long term that says, “Why are we here? What is the value? What is it we’re bringing to our clients?” Then there’s the sales hat, which is I have monthly, quarterly targets that I have to hit, and there’s a ton of metrics around how I’m doing that. But they have to continue to be aligned to the business strategy, which is the long term around why we’re here. What is unique about us that’s in this space?
When we talk about growth or sales, at the end of the day, everybody in the organization is interested in attracting and acquiring clients. Then I would say then hanging on to them. Making them raving fans of yours, but call it sales, call it whatever you will, but we all have that role that we work together and how we bring them to us, and there’s a reason why they’re coming to us, and that is grounded on our business strategy. Where are we going? Then how are we going to get there? How we’re going to get there, those are those steps that I see as we adapt and adjust as we’re going, that we can still be hitting milestones along the way. But the how we go about doing that, we have to be very clear and aware of how we’re doing that. Because to Holly’s point, that buyer we have today, they’re looking for easy to use, speed, and personalized.
I see that as well around how am I making this relevant to them right now? Relevant along the lines of this business strategy that’s long term, they’re looking to us, I want them to look to us as a trusted advisor. That they see our brand as, “That is something I can trust and go to.” Because if I go to that and I know that’s our core brand, or whatever company you’re with brand, then those other items that I’m looking for, I’m going to just go, “Yes, those make sense to me because it’s with that trusted brand.” That takes time. That doesn’t happen overnight. That’s part of that business strategy that you can show yourself as being proven and an impact player that’s within your space.
Fred Diamond: One thing you talk a lot about, Holly, in the book is the common disconnects between CEOs and CMOs, chief marketing officers, that undermine execution. I want to talk about why that happens. What are they? Then, John, I want to talk about where does the CRO come in. You lead a function, you have people reporting to you inside, outside, whatever it might be, partnerships possibly, how do you maintain the stake of your departments and your organization to be successful here?
Holly, what are some of these common disconnects and why do they happen? Then let’s have John answer the question and then maybe we’ll go back and figure out ways to solve that problem.
Holly Rollo: The thing about the CMO and CEO disconnect is if you ask any CEO, what’s a tech company that does marketing really, really well? They’ll typically say Apple, maybe they’ll say Adobe, maybe they’ll say ServiceNow, maybe they’ll say Cisco or Salesforce, and all those companies prioritize marketing, and it’s part of their business strategy. That’s point number one.
Point number two is, and you ask any CMO this, because I did my own survey of 100 B2B software CMOs as well, and they validated this as the key point, it’s the expectations. Any CEO will say, “Do what they do, but apply these kinds of constraints.” The constraints might be, and I’m not going to go into budget and investment because that’s a red herring conversation that I don’t think is the point, is you still have all these priorities and look entirely short term, and you’re measured based on the what’s going on in quarter versus measuring a more broader set of aspirations that help the company get to where it goes.
In the book, I talk a lot about transactions, that we’re in the valley of transactions. Most of these companies get bought and sold. It’s all about the transactions at the end of the day, truthfully. There’s people that make it over the chasm and become public companies and all that, but most companies are on the other side. It’s not having alignment on the priorities, which causes this expectation gap. Why aren’t we getting 4X pipeline after spending X amount of dollars in one quarter? The timing thing doesn’t work because there’s certain things that take longer, number one.
Number two, marketing and sales is no longer linear. It’s more of a complex system like the weather. There’s all of these other factors because the tech-sumer is going to 95 other places before they even talk to you. That’s much more of a set of engagements and information and positioning and thought leadership that needs to happen all over the place. I think that’s the other thing.
Then the thing I’ll really stress, and this comes back to expectations, is there’s three fundamental tech platforms that any B2B software has. One is the product they sell or the platform they sell. The second is either back-office system, so their ERP, accounting, billing, and payroll, all that stuff. The third one is their customer experience tech platform. In the olden days, we just called that CRM. In the new days, that’s 90 plus tools and applications that nobody has a budget for, nobody is accountable for, and nobody actually knows where the data is. That’s a big problem because, back to your point about you’re always going to have a company that has the same set of features, there’s so many software companies, many of them are very much the same.
The real thing that’s going to differentiate you is a frictionless customer experience. That customer experience can’t be managed if it’s in bits and pieces all over the place. Then sales, marketing and customer success aren’t radically aligned, which is what I’m a big advocate of. Priorities become really, really clear when you figure out where’s the friction in that customer experience and how can you properly set goals, which I think would help align CEO expectations, not just on marketing, but on the investments and attention spent across the go-to-market roles that remove that friction and make the experience stronger.
Fred Diamond: I’m flashing back to a moment in 2000 when my CEO, and I was a CMO, came into my office, threw down a stack of collateral from, not a competitor, but a very successful company. He said, “Take this and make it blue.” I was like, “Okay, sounds great.” We took their stack of collateral and we made it blue.
John, I want to ask you a different question based on Holly’s excellent answer. What do you want from marketing? Again, you’re a CRO, you’re responsible for all revenue and sales. What do you want marketing to do? What do you want them to do for you? What do you need as a sales leader? What does your team need from marketing? You go through the book in great detail about how things aren’t linear anymore. We have to be flexible and come in at the end of the day, but at the end of the day, John, they’re looking at that revenue number and they’re saying, did you make it or not? What do you want from marketing?
John Shrader: As I mentioned even at the beginning, it’s partnership. It starts with the partnership. From there, then we can create the business strategy around what it is that we’re trying to accomplish and recognize that there’s a blend of these things. I love how you’re comparing it with the weather. Because there’s going to be all sorts of different things. But as long as we’re both on the same page, I identify with my head of marketing, what’s our KPIs? How do we know that we’re on track to where we want to go? Some of those are very tactical. How many SQLs? What’s our conversion rate? How many logos? Those types of things. But others are around say brand, and where are we placing our bets, for instance, around a geography that, I’ll use the example of where we are in the construction space. There are some areas that have more construction going on around the US than there are in other spaces, like in the south, in California, there’s more that’s happening there.
Working together around we need to get in front of our clients and how we go about doing that, what do we see as the best path for us to do that? That has to be an open conversation around, “Where’s the weather sunny? We’re going to move there because that’s where the dollars are going right now.” That partnership is key guided by shared and agreed upon KPIs, which I show as being expectations. We have the same expectations. I look at it as a shared budget to some degree. These are some things that we’re spending together around how we are acquiring, attracting, and keeping our clients. But that conversation, Fred, is ongoing. It’s a constant conversation around where we’re deploying resources, people, tools, and how we’re using that to grow the business.
Fred Diamond: What do you expect out of your salespeople now? I ask that question a lot, because typically I just interview BSLs for the Sales Game Changers Podcast. John, you manage, I presume, salespeople, or you have those who you mentor, et cetera. What are your expectations of them right now? We’re doing today’s interview in the fall of 2024, if you’re listening sometime in the future.
John Shrader: I look for my team to know your business, and we talk a lot about knowing your business. What are those things that you’re doing on a regular basis that cover three things? You’re always prospecting, you’re selling, and you’re closing. There’s different times in your day, your month, your week that the amount of time you spend between those three things shifts. The beginning of a month, you’re going to be spending more probably on prospecting. The bottom end of a month you’re doing more on closing. But that balance of how you do that in a day matters.
The second to that is their metrics. I’m a very metric-driven individual and I want them to be aware of what are their own conversion rates? Where are they spending time? Talking about AI, we use a great tool called Gong. Gong is game film. I love having the game film to go in, that I can go in, they can go in and utilize to see how much time am I speaking versus how is the client speaking? Those metrics sometimes are just hard, easy, did you hit this number pipeline dollars, or it’s also game film. Where do you find that you need to be working and growing with this?
I talk to folks about words matter. In sales, the words matter. Sometimes it’s just the subtleties of that. I always talk with my reps about there’s seven words that they’re not allowed to use with me. Those words are would, could, should, maybe, might, hope, and think, because those seven words mean you don’t know. In sales, you need to know, even if it’s the next step. When they speak with me, they catch themselves. What I want it to is it relates to their clients and their prospects, when they hear those words, maybe I have the wrong person, maybe I’m at the wrong stage, I need to ask more. We talk about words matter. I capture all those together, but it all is grounded on prospect, sell, and close.
Fred Diamond: Holly’s book is called Power of Surge: Five Ways to Supercharge Your B2B Software Business and Unleash Hidden Value. I recommended it. It literally was an MBA class. Holly, I hope you get a lot of attention from the book. Having been a CMO in a company that you talk about here, there’s so many great things.
I want to ask you a different question than what I was planning on asking you. Holly, if you could have one message to CMOs, what would it be? If you could have one message to CEOs, what would it be?
Holly Rollo: I think it would be the same message to both, because we’re in a really interesting time. I do some advisory for VC firms and early firms with startups. Startups are going to eat people’s lunch because they’re able to set up their customer experience and their go-to-market functions in a way that is completely future ready and integrated with AI engagements. That is a new change. We’ve been evolving over the years, but then AI came along and it really does change the game. That’s the first point.
The second point is we have so many software companies dropping from the sky, just coming into being, and not enough talent. I see a lot of high potentials or VPs of marketing or VPs of sales who are being asked to get into these roles, and they’re trying to figure out how to do their job using best practices. But the best practices, to my first point, are changing rapidly. What the message would be is to make sure your go-to market is future ready. Don’t rely on best practices that worked 10 years ago at Cisco or Dell. You have to use best practices that your competition, which is going to be these startups, are going to be using. Otherwise, they’re going to blow past you with a good enough product.
We’ve all been in this business for decades. Everybody thinks they have a better product, and that’s never been the case. The best products haven’t been the products that have won mostly. There are those, but most of the time it’s good enough, but got the go-to-market right. I think that’s a really important thing to consider. You have to really change your perspective on how you think about the go-to-market, because it’s not linear. It’s more of a complex system that is completely centered on this customer experience. These startups are building from the ground up and they’re building it right. It’s all AI ready and it’s fast, it’s sleek, it’s very much focused on the buyer that’s 35 to 40 years old, not our age. That’s going to be more and more the case because those are the people that are in the industry now.
Fred Diamond: We end our show with a final action step, something concise and specific. You both have given us so many great ideas, but something specific people should do right now after reading the transcript or listening to the show to take their career to the next level. John, why don’t you go first, something nice, crisp, specific that people should know to take their career to the next level.
John Shrader: Go listen to your clients. Holly talks about this AI driven, everything’s changing, moving, you can learn so much as to why clients buy from you. What is it about you? To keep yourself fresh on, why are we relevant? What is it that makes us unique and special in this industry? Go listen to your clients. Find two to three clients and go talk to them. Because I would imagine you’ll be surprised that they will find something that you didn’t think about that say it’s because of this, and sometimes it’s not always the technology.
Fred Diamond: It always happens that way. Holly, give us a final thought here.
Holly Rollo: I’m absolutely aligned with John. You have to find product market fit, and you can’t be all things to all people. You have to really focus. The smaller the needs-based segment, the better, because you’re going to get better traction with your customer base. The S in surge, the strategy component, is where companies really need to take another look. I would invite people to come to surge-strategies.com and check out the Surge Go-To-Market Challenge, because I actually step people through all of the aspects. But the strategy part is really, really important and needs its focus.
Transcribed by Mariana Badillo