On this week’s episode of Digital Conversations, Billy Bateman is joined by Courtney Wilson, VP of Global Marketing at Cloud Academy. He gives his insights on how to lead a growth team to success during these troubling times.
Guest: Courtney Wilson has been in marketing leadership for over a decade. He has extensive experience in growth marketing, and managing teams located around the world. Talk to him on LinkedIn here!
Billy: Alright everyone, welcome to the show today. I am your host, Billy Bateman. And today I am joined by Courtney Wilson, VP of Global Marketing at Cloud Academy. Courtney, thank you for joining me today.
Courtney: Absolutely. It’s great to be here.
Billy: Yeah, I’m excited for this conversation. We’ve got a couple different topics we’re gonna hit. But before we get into it, will you just tell everyone a little bit about yourself?
Introduction to Courtney
Courtney: Yeah, so as you said, I am currently VP of Global Marketing at Cloud Academy where I’ve been for about four months. So, it’s kind of a new adventure for me. Before that, I’ve been in tech marketing for a while, 12 years straight. Done a couple startups, my most recent one was a company called Cloud Factory, where I was for about six years and helped build up the marketing team there and get them to a point of scaling and raising a significant amount of money and having hundreds of customers around the globe. So that’s, that was great. But I was ready for a new challenge. And I’m really excited to be at a Cloud Academy now.
Billy: Awesome. And tell us a little bit about Cloud Academy and what you guys do?
Courtney: Yeah, so we are an E-learning platform for cloud and tech skills. We do both sides of the markets. We’ve got a lot, thousands of individual subscribers, people who are signing up, usually to get certified on one of the big cloud platforms. We cover just about every one of the certifications across Google Cloud, AWS and Azure and also things related to Kubernetes and everything. Everything cloud you can think of, we pretty much cover with hands on learning and thousands of courses and learning paths that are dedicated for specific, specific roles, and the like.
So, we do that. But we also, a lot of our business actually comes from large teams. So we work very closely with Fortune 500 companies, helping them to scale really effective training programs for multi cloud and pretty sophisticated environments where they’re needing to maintain certain levels of certifications. There’s containers and everything else, and they’re doing all kinds of things. And we’re helping them really kind of provide that operational backbone as the software for helping us scale that training.
Billy: Cool. Awesome, awesome. Good stuff. So before we hop into our topic, which we’re going to talk about leadership and marketing growth. But I always ask everybody this question, so I’m not going to let you off the hook. If we’re going to look you up on social, whether that’s Facebook or LinkedIn or Instagram and try to figure out who’s this Courtney guy and what is he like and what does he like and not like? What is one thing we wouldn’t be able to figure out about you?
Courtney: That’s a good question. Well, I do keep it pretty close to the best. I think when it comes to social, I’m not really engaged much on Facebook these days. And, I might tweet something every now and then. But not all that often. I need to get a little bit more engaged. LinkedIn is definitely the platform of choice for me. I do enjoy LinkedIn quite a bit.
What would you not find out about me? I actually don’t talk all that much about my family on social which is kind of, which is kind of odd. So I am a proud father of two daughters who are 10 and 7. And they are the light of my life, but I don’t really talk all that much about them on social media now that I think about it. So that would be one thing that may be hard to tell unless you just kind of looked at my bio and just happen to see it there.
Billy: Awesome, man. Awesome. Okay, well, let’s get into it then. So, we first engaged and start talking about doing a podcast together, one of the ideas that you had, that I really loved was talking about the confluence of leadership and growth, and a few different things about that. But, before we hop into it, what are your thoughts on just the overall topic there?
Courtney: Yeah, no, it’s, something I’m, two things I’m really passionate about. So, I think one of the things that I have been most proud of, I think, in my relatively short career, but, over the past, 10 to 12 years in the tech space is kind of the building of teams and the relationships that come along with that, and really, finding people’s strengths and working with them and figured out, kind of, what does the business need to really grow?
And what do we have in terms of knowledge, skills and abilities that we can match to that, and then, providing the environment where people can grow into their roles and really, make a significant contribution. And, basically kind of creating that space for them to do that, and helping them along the way. So, it’s something that I really, really love doing.
And they have a pretty strong point of view that, that is also what helps scale growth. You need to get the right people on the bus and then you need to basically put a put a lot of trust in them. And they put a lot of trust in you and you’re there to guide and help and provide the vision and the leadership and the strategy. But they are the ones that are kind of the heroes of the story in my book.
Billy: Yeah, no, I think you’re right, especially, whether you build a team or inherited team. You got to find everyone’s strengths. And that is a skill in itself. So let’s start with building a team. What are some things that you’ve found as you’ve been building out marketing teams to help find people and get them in the right seat on the bus?
Courtney: Yeah, I think one of the things that I learned very early on. Particularly at Cloud Factory, which was, kind of my biggest building project. I would say so far is that, talent is all over the place. And we a lot of times we tend to think that. It should be in our backyard or that’s where it’s going to show up. But, some of the most talented people I had on my team were actually in Katmandu, Nepal. Where we had a pretty big operation there. Which is where the company was founded.
So for the first three years, I was there, my entire marketing team was. Myself and about four other people were all they were all based in Nepal. And I learned early on that, they were every bit as smart and dedicated and talented as somebody would have found here in the triangle area in North Carolina where I’m located. So, I think, particularly, as we’re kind of getting used to a little bit of a new world. Where more and more people are remote. I’ve encouraged people to really think about that. Kind of assess talent based on, not on where they are, but what they can bring to the table.
Adapting To A New Team
Billy: Yeah, so you had a pretty remote team then and, I mean, I’ve never dealt with having most of my team not in the office with me. What kind of challenges did you encounter with that? And then, how’d you overcome them?
Courtney: Yeah, no, I think, there were definitely several, the first one was just, the ability to kind of build trust. Yeah, when I first started my role there at Cloud Factory, within two weeks, I was on a plane to Nepal with the CEO and another colleague of mine, and it was, one of the most memorable trips I’ve ever been on. But, I basically had one person on the team at that point, somebody who had been there for a few years. And, he was really just kind of building that from scratch.
And we hired our second person while I was there, and we got built from there. I think, particularly when people are remote and they’re on the other side of the world, it creates a lot more challenges, right? There’s a certain level of cultural intelligence I think people need to have, where, you really need to kind of dig a little bit deeper and understand their culture, understand the things that make them tick. The things that are sources of pride, sources of shame, which sounds like a heavy word, but it’s something you need to understand and then how to relate to them.
And I had to kind of learn my way through that for sure. I think, the other thing is, you got to have some late nights and some early mornings, particularly if you’re in the states and you’re working with teammates in Asia or what have you. That’s a pretty big time difference. We had weekly team meetings that were, sometimes at 11 o’clock, Eastern Standard Time, which was tough, particularly at a time when I had two pretty young kids and, life that was very, very flexible, very nice to me about it. But that was that was a challenge, too. But we did a good job of leveraging technology.
At the time, I don’t think Slack existed. Yeah, back when I started in 2014. Or if it did, it was early on, we were using Skype, everybody uses Zoom. Now, we’re using Skype for meetings and all that kind of stuff. So, there were definitely tools involved in helping to bridge that gap. But I think the biggest thing really was that cultural intelligence piece and being able to understand, where people were coming from, what drove them and how to just how to relate and how to be the best manager I could possibly be from halfway across the world.
Billy: There have to be some good stories about either putting your foot in your mouth culturally and not knowing it or something like that. Do you have anything you want to share with us?
Courtney: You know, so there were definitely times I did a pretty good job, I think of being very self-deprecating, maybe to a fault. I never took myself too seriously. I always felt like I stood out a little bit and, sometimes falling over myself to be genial and nice. One, funny story, I guess I was my second day and Cloud Factory and they would have lunch on the rooftop of the building every day.
It was amazing. It would be sometimes close to 100 people, and they cook food every day for everybody. Best food you can imagine, all these great curries and just amazing food, Dalbat, which is the rice and lentils, national dish.
And I remember grabbing one of these little red peppers that were sitting out by the food I just kind of grabbed, whatever I think as interesting. And somebody who wasn’t on my team at the time, but wound up being on my team, said you like you like hot, you like spicy stuff? I said, Yeah, you should try that pepper. And I did I took I was like, alright, everybody’s kind of looking at me and I took a little bite of this pepper and I blew up. I mean, it was the hottest thing.
And then while I’m while my face is you know red and I’m sitting there and I’m like having a hard time breathing and I’m choking out water. I rub my face with my fingers. So I got into my skin. So my skin started burning ,and man, did I talk about feeling like a fool I did you know that saying something embarrassing, but doing something embarrassing. It was pretty funny. It was it was even funny at the time, but it’s really funny to look back on now.
Billy: I’m sure. Oh man. Yeah, I, I actually have a pepper I’m due to eat because the engineering team met a goal and they wanted me to eat, I think it’s a ghost pepper. Yeah, I told them after I do that I am out the rest of the day. So maybe the next day, so? So, with building the team, like, that’s got its own unique set of challenges. When you inherit a team, like, I think you have, like at Cloud Academy? What are the different challenges that you have when you’ve already got a team in place and, and figuring out how to best lead them and utilize them?
Courtney: Yeah, I think obviously, it’s, it’s very different in the sense that, you’ve got Cloud Academy has done a fantastic job hiring very talented people across the organization. And that is very much true in marketing as well. So, I think the challenge for me there was to say, Okay, what strategically do we need to do here in order to drive growth for the business. So it was a little bit of, really just kind of coming in and trying to really understand the business as best I could from a go to market standpoint.
And, say okay, well, we’ve got a product like growth strategy for our individual subscribers where it’s. We’re trying to get them into free trials and convert them into paying customers. And then we’ve got, our sales like growth strategy. Which is very much enterprise that’s sales and product marketing and demand gen. All the things that go into that. So, basically being able to kind of establish those things and of course. We’ve got to kind of maintain our customer base and market to our customers. And build a brand. Those are kind of the four key pillars of the marketing strategy. What you need to do is kind of figure out okay, well, who can contribute best to what?
And who likes doing what, right? I’ve got some people on the team that I, came in and there was a team of five or now together a team of seven. So we’ve added one, but, is really kind of digging deep with people getting to know them build some of those relationships, and you’ve had to do that, obviously over Zoom because I came in on March 23rd. Right, as things were going a little crazy with lockdowns and everything else. So I have yet to actually meet a single person on my team in person, which adds to the to the fun. But, really, dig deep and figure out what they like, what are their strengths, and how do we kind of deploy those strengths and talents, against that strategy to help support it?
Billy: Yeah, so you’ve never met any of your team members in person. So, how are you utilizing Zoom to, to build those relationships?
Courtney: Heavily. Now to me, I do want to make a bit of a distinction. I think between kind of leadership and management for that. But from a management standpoint, I truly believe the most important tool for anybody is to really get solid on one on ones. It is the best tool that any manager has to. Really kind of build those relationships and whether it’s over a screen or if it’s in person. You still got to do it. And that that’s been the most effective thing is just having conversations, talking, listening, kind of trying to explain. The vision and kind of where I think we need to go and having them kind of tell me. Hey, look, I love working on this. I’m so thrilled about this.
And, you say, great, you’re talented over here and maybe don’t have the experience over here. So that’s, that’s fine. Yeah, let’s, let’s figure that out and start to kind of shape jobs a little bit more, more closely to that strategy. Right. So, in any startup and Cloud Academy is still relatively early on. But, you need to really kind of figure out what those things are that need to be done, what are those jobs that need to be done and start to really, rather than people wearing a lot of hats and trying to do too many things, try to get people a little bit more focused on, specific areas of marketing.
Billy: Yeah. So, I got two more questions on your one on ones before we move on. Are you on like a weekly cadence, a monthly cadence? And then the follow up to that is, are you more of the, very formal one on one or the informal type of one on one?
Courtney: Yeah, good question. So, so I am much more on the weekly end. Certainly with the direct reports and team that that I think is really necessary. I think I have had times where maybe it’s been bi-weekly. I think that that really just depends, but right now, it’s definitely weekly. And what I do is, basically say, Hey, look, this is your time, you can grab 30 minutes, 45 minutes or an hour. If we need more than that, yeah, you just let me know.
And we’ll figure it out. But, and each of my teammates did that, some are a little bit more like, Hey, I can we can get in and out in half an hour, that’s fine for me, other folks, want to take the full hour or beyond that at times, and that’s fine. So I kind of put that in their hands. And then in terms of the nature of the one on ones I am definitely much more of a casual person. We all have agendas. We have kind of an agenda doc. Some people follow there’s a little bit more closely than others and that’s fine, but to me, it’s an opportunity just to continue to kind of build that relationship.
I don’t necessarily always like getting into a meeting where it’s kind of like, hey, let’s, chop chop, let’s kind of get right to it. Sometimes that’s necessary, and that’s fine. And particularly when you’re, dealing with executives and things like that, where they’ve got a million meetings and, yeah, we don’t have time to, to chit chat too much. But I really do like to get the space for, to talk a little talk about some things that are outside of work, we’re not robots and we all have lives and I’d like to know what people’s lives are like outside of work.
Billy: Yeah, no, I agree. I like to keep it more casual myself as well. I think it’s, I think it’s a little more productive and building that relationship with your team. So okay, so I want to before we let you go, we want to talk about engaging the two different personas that you guys sell to. Because you have product lead growth and then sales lead growth. And then, what are the differences and as a marketing team trying to support both of those things. So with your messaging, on your website and in your marketing materials, what kind of challenges and opportunities does that present to you?
Challenges Of Growth Marketing
Courtney: Yeah, I think the biggest challenge is threading the needle between the two. That’s really difficult and, as a company, we’ve gone back and forth a little bit in terms of, kind of who were who we’re focusing on and the answer, unfortunately is not, and or it’s yes and, right. It’s, we need to, we need to be able to do both. a product like growth is a little bit more is a little bit newer to me.
My background has been, much more focused on growth around kind of, sales like growth and demand gen and fill in the pipeline and nurturing and all those great things and engaging people on the website and everything else. So, learning a little bit more about product like growth has been, fascinating. And, a lot of that really does come out of product, it truly, is we’re building a growth team now.
That growth team is led by product. Product kind of owns that, the revenue, and they own everything else on that side of the business. And marketing works very closely with them as the CS but, they’re really in there, running the experiments. And that’s the biggest thing, right? It’s a lot of, it’s a lot of small experiments. It’s a lot of like, hey, let’s, let’s digital first, obviously, and get people into the funnel. What do we need to do once they’re kind of in that free trial. To make sure they experience value as quickly as possible. So they get that time to value really fast. And we’re able to convince them within that seven days that hey, you should you should sign up and be a customer.
And that’s a very different thing than on the sales lead side. Which is, obviously we’re trying to penetrate bank accounts. Because we are really focused on enterprise. So, there’s an account-based marketing aspect to that, that we need to get in place. And there’s also the inbound, flywheel and content marketing and the product marketing and sales enablement. Everything else that goes along with that to drive that kind of growth. And that’s what we’re kind of building right now. We’re probably actually a little bit more suited to the product lead growth side than we are currently to the enterprise side. But, we’re, building that out fast and we’re. We’ll be able to support everything as we go forward.
Billy: Awesome, awesome. So what tools are you guys using for that ABM strategy?
Courtney: That’s definitely TBD. Right now, we’re actually evaluating an intent data platform as kind of one of the first things actually we’re going to do just largely because we need to enable our sales team, our sales team can’t necessarily wait for, for us to catch up. So we will get there but ABM requires a level of sophistication and I think talent on board in order to really do it well.
So we’re, early on in that in that journey. But right now our core stack is really it’s HubSpot, Salesforce. Our website is hosted on WordPress, and we’re engaging in conversational now and we’re just getting a lot of that stuff set up. And really, focus now and really maximizing the use of the technology that we have before we start kind of bolting new things onto the stack.
Billy: Awesome. Okay, man. Okay, so the next thing I want to hit is when you’re creating buyer journeys, I mean, obviously your growth team is doing that on the product side. But I’d imagine you guys are probably owning that on the on the sales led side. How do you strike the balance there on the website for them?
Courtney: Yeah, it’s a good question. I mean, a lot of times what we’re, we really are, an operating system for tech skills internally. So what we want to say on the on the product lead side and what a lot of the value that we bring to the table, I believe our individual subscribers is, hey, this is the platform that’s trusted by Fortune 500 companies.
And if you’re going to be training and getting certifications and putting your time into something, and your passion into something, you may as well be using the platform that’s trusted by these guys. So we need to kind of strike that balance and kind of get people to the right spot on the website, which a lot of instances our pricing page. And kind of getting them there so they can kind of assess, Okay, what are these two different plans? What am I getting?
And we’ve got ways for them to kind of get into the funnel on the sales side via landing pages or conversationally getting them in and engaging them via chat, or, on the other side is, hey, sign up for a free trial and give us a shot and kind of running automation off of that to make sure that, we’re keeping in touch with everybody as they go through that process that they’re, that they understand how to use the platform and to get value out of it, and convince them to convert.
Billy: Yeah, and using chat going for you guys?
Integrating Conversational Marketing
Courtney: It is super early on, it is very early. So, I helped along with my demand gen leader at Cloud Factory. We used it kind of on and off and had some pretty good success with it from time to time. But it was, always a challenge to kind of get aligned. I think with, with our sales team. And particularly our SDRs to just kind of make sure people could really man it that we were doing it right.
As I was leaving we had spent about four months selling drift internally, and getting that stood up. I know they’re having a ton of success. With that, at the moment, because I keep pretty close touch with those guys. For us, we’re actually using the HubSpot chat, kind of out of the box. Building out some initial chat flows, particularly, we’re starting with our pricing page.
And the idea there is to, just start collecting data, just start trying it. We opted not to do live chat to start. So it’s pure kind of just, chat flows right now, just to kind of collect that data. See how people are engaging. And once we get a better handle on it, we’ll start to kind of, include either. CS people potentially on the product lead side or SDRs, on the enterprise side.
Billy: Awesome, you make a good point about getting an alignment with sales with chat. What do you think companies can do to get that alignment?
Courtney: Yeah, it’s tough because a lot of times, what you don’t have is data. So you’re kind of, you’re left to fend for yourself in terms of finding external validation. For what you’re trying to do. The way that that we tried to do it at Cloud Factory in particular was. Because we’re selling Drift, we kind of leaned on those guys quite a bit, to provide some of that. Validation and the data that they had with different customers that were, like us, and certain aspects.
Really engaging with our SDR leader with our sales leaders, saying. Hey, this is, that people don’t want to just fill out forms anymore. And just, kind of wait for you to get back in touch with them. Yeah, we got all these people coming to the website, and we’re not engaging. We’re absolutely losing deals, and I think there’s probably an aspect of making the pain real. To say, Hey, look traffic on the websites going up, leads are going up, right. We’ve got more people kind of downloading things, whatever it is. But we’re having a harder time, converting them in the pipeline. And, if you’ve got somebody coming to your store. You don’t hide behind the counter, because brick and mortar store, right.
So, it stands to reason that on your website, if you got somebody there. Particularly if they’re on a high intent page, like a pricing page or a case study page or a landing page where they got there through. Let’s say, pay per click or something like that. It makes sense that you would want to engage them rather than just kind of let them poke around and then just kind of bounce out without getting any help.
Billy: Yeah, I agree with you on, on you got to be there and willing to engage, and available to engage people. Just like you said with this with the brick and mortar store example. On the website, more and more the research shows that people want answers now. They don’t want to fill out a form and wait for you to call them back, you know.
So the quicker you can engage people, the more deals you’re going to get in your pipeline and have the ability to close. So, okay, Courtney, it’s been a great conversation, man. If people want to reach out to you and continue the conversation or learn more about Cloud Academy, what’s the best way for them to contact you?
Courtney: Yeah, no, absolutely. I think LinkedIn is, as I said before, definitely my platform of choice. So feel free to shoot me a message if anybody’s got a question. If I can help you in any way. You can always go to CloudAcademy.com we got, tons of information there on the website, too, if you’re curious about that. So those are probably the two best places to find me these days.
Billy: All right. Thanks, man. And we’ll chat later.
Courtney: Absolutely. Billy, thank you so much.