Mind The Gap, with Kristina Libby

Will devlin

How do you bridge the gap when it’s just two people? In this episode, Nick sits down with Will Devlin, head of marketing at MessageGears, to talk through life as a marketing team of one, and how to work with sales as you scale.


In our first episode of 2022, Will Devlin brings his experience in growing from a one-person marketing team to a full organization to the table, as he discusses what it’s like to fuel sales in a smaller, personal team. Key points Nick and Will discuss are:

  • When you’re the only marketer, it’s important to focus on what you can do well and control, but don’t let yourself get spread too thin. Things like marketing automation can wait – find your core competency and nail it.
  • In a small environment, you may not be able to project how many MQL’s or interested leads you can deliver to sales. It’s important to try and prove out a case by experimenting and seeing which things move the needle for sales
  • Marketing always has a seat at the table. If you don’t understand why sales, or the organization as a whole, are doing something – it’s important to speak up and be heard, because you can’t effectively bridge the gap if you aren’t in lock step


Nick: Welcome to Mind the Gap,  Enablix’s only podcast about closing the gap between sales and marketing. My name is Nick Ziech-Lopez, and I’m in marketing at Enablix. And today, I’m joined with Will Devlin, SVP of marketing at MessageGears. How’s it going, Will?

Will: Nick, it’s great to be here on the only Enablix podcast- you guys used to have like four or five…and this is the only one left? 

Nick: Yeah, I think we were flooding the market. I think we had upwards of like 70 or 80 at one point, but we decided to hold it back now. Will, you’re a household name- everybody knows Will Devlin, but for those that don’t, Will, tell us your story. 

Will: I am the head of marketing at MessageGears. I have been there for a little over seven years now. I’ve seen the company grow quite a bit. And prior to that, I was with another software company in marketing. I’ve been in the B2B, SAS marketing side for a little over a decade now. Before that, I cut my teeth on the retail side running e-commerce for a couple of brands- Overton’s, which is a boating accessories company and Gander Mountain, which was an outdoor retailer based in the Midwest.

Nick: So you went from very outdoorsy and boating straight into SAS and multi-channel marketing.

Will: The natural path, right? Overton’s corporate was a catalog company for boating accessories and water sports equipment. I went to school at East Carolina, and Overton’s corporate center was based in the same town as East Carolina. A lot of people that didn’t want to go work retail, or in a restaurant would work in Overton’s call center during the summer, because their big season was obviously in the spring and summer. That’s how I got my foot in the door there.

Nick: You are at MessageGears now, you said you’ve been there for seven years. What is MessageGears, what do you do there?

Will: MessageGears is a customer marketing platform, which essentially means we deliver marketing software to really big, consumer facing brands. If you get marketing emails from brands like BestBuy, Home Depot, Chick-Fil-A, Expedia, et cetera, or if you have their app and you get push notifications or text messages, there’s a good chance that’s coming through our software. MessageGears is powering that. We have a unique solution that’s built specifically for that really large, really high volume, really data-mature brand.

I’m the head of marketing. I’ve always been the head of marketing. I started in 2014 as the first marketing hire. It was a few engineers and one salesperson that they had hired a couple of months prior, and they needed some marketing help. That was why they hired me- they knew nothing about marketing and knew nothing about how to get the word out, and that’s where I came in.

Nick: That’s where I want to spend a lot of time talking today. You came in as the first marketing person, and like you said, there was a marketing person and a salesperson. What do you do in that kind of environment? How do you decide what to do? How do you work with sales? Is it a push? Is it a poll? When you’re that small- before you even bring anybody in and it’s just maybe the two of you or the three of you- what is it like?

Will: You know, I focused on what I knew that I could do well and could control. At the time, our CEO was very tech focused and a co-founder, so he didn’t have a lot of experience in building businesses. Fighting for a budget for marketing was difficult. I knew that I was going to be Hacking together a lot of stuff too- the “fake it til you make it” model of making MessageGears, look, feel, and sound bigger than we were. Nobody needed to know that we were six people that didn’t really know what we were doing. Nobody needed to know that in those early days, so it was a very collaborative relationship with the sales leader because it had to be. We were the only two people that really spoke a lot of the same language and were really tasked with bringing revenue into this organization. 

I came in and focused on output and deliverables. I focused on things like making sure that the website had a bunch of stuff on it, making sure we had a blog and were posting on social media, as well as doing events that we can afford. There was not a lot of sophistication beyond that, it was a lot of hacking things together and learning. We had to learn how to use Adobe’s Creative Suite, and create one-sheeters and case studies. It was a lot of my own writing and going to Shutterstock to find stock photography and trying to make it look like we had a whole team of people doing it. There wasn’t any real sophistication in how we generated demand, in marketing automation, branding, product marketing. I focused specifically on assets and content at the time, and then paired with our sales lead on how to get it in front of the right people, how to tell the right story, and how to get people excited. 

Nick: It’s funny because it was almost like you were ahead of time with that because at the time, five years ago to seven years ago, it was very much automation, chat bots. Now, the pendulum is swinging back to just make and distribute content- if you just focus on content, that’s the important part.

My question for you is, when you’re that small and you’re focusing on content, at that point, are you held to KPIs? Because you only have- like you said- a limited amount of time. 

You’re learning Adobe Suite to get as much stuff as you can out there. How do you project either to your sales team or to your boss who might not know sales and marketing, what you’re going to do? Or, is it just trying to convince them that this is the thing to do right now and the results will come in, but you’re not sure what they are?

Will: Yeah. In those early days it was very much the latter. It was very much, we’re going to put this stuff out here, we think this is going to work, and we have no history to go off of, so we don’t know how successful it’s going to be. It was very much, let’s try these things and see if anything happens positive or negative, and we can learn from it.

It was more of building a story to then fight for more resources- we either need more budget or we need more bodies, because we can find success only if we could do more of these things. Early on, it was trying to prove a case for budget and resources. As we got bigger over the next couple of years and as we brought in a more seasoned executive, that changed into trying to grow by X percent each year, honing in on what works versus what doesn’t, and investing in those good areas.

Nick: I think that’s a struggle that I feel, and I think a lot of people feel too. Marketing experimentation is so important, but when you’re one of one or one of two or three, how much time can you really spend on experimentation versus just getting something out the door and not being able to A/B test, or experiment, or see if it’s the right thing- you’re almost caught in a tension between two different ways of trying to find the best thing and going out with the thing that.

Will: In email and marketing automation, the content we were writing was all about test and measure, and yet we were really just pushing a bunch of stuff out there early on to see what worked, because that was literally the capacity we had- that was all of it.

Nick: So obviously, you did pretty well. You guys are growing, you’re much bigger than you were six, seven years ago. Along the way, how did you grow with sales? Tell me about where you are now and then walk me there. How did you grow? What were some missteps you made? What were some good decisions that you think you would do again?

Will: I think big lessons learned for me was managing up and speaking up. Managing up is making sure that my boss, the CEO, knew of all the things that I was learning, that my team was learning, that we were working on. Sometimes when you’re in the trenches and you’re just trying to get things done, you forget not everybody has that context and visibility. Providing that update to my boss and the rest of the executive team on a regular basis took me a long time to figure out how to do that properly. I always felt unqualified to weigh-in on sales processes, especially because I’ve never been in sales, I’ve always been in marketing. Even if I didn’t understand or didn’t necessarily agree, I would bite my tongue because, as marketers, we know everybody has an opinion on what we do. You put something out there that you spent months planning for, and somebody asks why you chose that color font, and you’re thinking, there’s so much more that went into this, thanks for your input. I didn’t want to be that guy for sales and I now know that I should speak up- it’s a key part of marketing success to be in line and lockstep with sales.

Nick: I mean, it’s funny because that right there is the gap. That right there is you feeling like marketing shouldn’t comment on sales, but it’s, it’s the same thing, right?

Will: It is exactly the same thing. Yeah.

Nick: Okay, so, you had to do it again, right? You have a marketing person and a sales person, let’s say you’re talking to two teams of one. How do you bridge that?

Will: I think I would do it very similarly to how we did it- joining forces the way we did and just looking at each other and saying, how are we going to do this? Recognizing that marketing is going to be responsible for giving a storyline, and building a deck, and having some supporting content, and sales is going to be responsible for getting in that meeting and knowing when to bob and weave and strike. It was that collaboration that was really good upfront. I’ve been fortunate enough to stick around for seven years at MessageGears. We’ve cycled through a lot of sales leaders in that amount of time, so I haven’t had the same luxury of having two people grow and grow their teams together. Somebody is going to end up leaving and then you have to start from scratch on building a relationship, but I do think we’re trying to do the same thing. My success is their success and vice versa.

Nick: It is interesting, especially when you come to talking about what to focus on. We recently had Christina Libby on the podcast, she’s the CMO to HyperGiant. She had said that the company is a brand, and the brand is not defined by marketing. The brand is the company- in her case, it came from the CEO- but I think that it can come from marketing, it can come from a lot of places. What you’re really doing as sales and marketing is you’re trying to live that brand in different ways. As silly as it sounds, it sounds super high minded. It’s like, you’re reflecting what our values are, what we do, the way that we are in the world, and I’m going to be covering you from a different way. 

What are your thoughts on how you measure- especially when you’re that small- marketing’s abilities and the things that marketing is contributing versus sales. Do you draw a line? How do you draw that line? 

Will: Early on, especially, it was not very territorial because it was collaborative. I think it gets territorial as you scale and as teams get bigger and incentives may be disaligned. People’s behavior is definitely driven by incentive, so if the sales group is compensated one way and marketing is compensated in a different way, that doesn’t align- maybe they should be compensated differently, but they’re not, it’s not in alignment. Then, there is this jockeying for who had a bigger impact on revenue and who should get the credit. This is why there are attribution, you know, software companies out there because everybody’s asking these questions, right? Everybody is trying to figure that out. I think early on it was very much like, “we got this,” and it is hard to maintain that spirit as you scale from two people trying to do it to a hundred people trying to do it, that’s a tough task.

Nick: To that point, I want to transition here into looking forward and some of the current trends about how to bridge that gap. I’m seeing companies hire a chief revenue officer, or you could call it a chief commercial officer, basically a single person who owns all of marketing and sales and it’s their job to make sure that incentives don’t get misaligned. What do you think about the idea of combined sales and marketing organizations? Do you think that’s going to be a thing going forward?

Will: I think the spirit of having a chief revenue officer or a revenue leader is the right spirit. In practice, it’s more complicated because there are things in marketing that don’t directly tie to revenue, that are a bit more flowery, or loose, and then there’s other areas within the org that are definitely revenue focused like CS, and retention, and growing your teams, and things like that. I do see more teams trying to have a leader focused on revenue and from an executive standpoint and a board standpoint, it’s one throat to choke. It’s definitely hard to do that in practice. Look at MessageGears right now, we have sales and partnerships under the CRO, but marketing is separate even though marketing owns a lot of the demand gen practices that feed the sales team, it’s difficult.

Nick: You had mentioned the “flowery” parts of marketing. I was in a panel the other day where someone had mentioned that they feel it’s a struggle to convince their CEO to build brand. That kind of struck me with the question of, why are you building a brand if you don’t think it’s going to make more revenue, right? I don’t think we’re doing it because it’s fun, even if it might be fun. Say you’re going to redesign your website. How would you, and do you pin that in any way to revenue? Or, do you just simply say, I get a certain amount of resources that I think is going to raise the tides and is unattributable. 

Will: Everything you do should tie back to trying to grow this company and grow revenue. It is hard to tie back things like doing a new website or even, internally, corporate culture things  like going to a brewery or to an ax throwing thing as a company. The goal is to make people happy or make the path easier, but the end result is still trying to make more money, so you can’t tie  every individual dollar at that point because it’s very difficult. So, if we’re going to redo the website, that’s not coming from a budget that is demand gen focused. It is a cost of doing business and marketing focused. 

Nick: Let’s talk about another couple of the trends going forward. I’m seeing a huge spike right now in revenue operations, rev ops, and everybody is talking about it- is that going to stick around? Why or why not?

Will: Yeah, I think it is. I think as businesses get more mature and get more data savvy/data centric, whatever buzzword you want to say, I think having a department, a function, focused on all the tools working together and all the data moving back and forth is really important. I don’t see that going away, we’re investing in that and it also prevents different teams from going and buying their own tools. And then nobody knows, oh, that tool exists, how does that play with this other thing? There’s one department focused on making it happen.

Nick: Recently, we had Nelson Gilliat on the podcast who very strongly felt that the SDR function should go away and that sales will stop having commissions or quotas in favor of salary plus bonus. Thoughts? 

Will: Ah, it’s interesting. You know, we’ll have a number, I think demand gen should have a number, right? If we’re again holding other teams accountable, demand gen is part of that. I go back to it’s tricky, right? If that comp is misaligned, then there’s a lot of people- and we’ve seen this before- where there’s multiple paths that person took and that spans partners, and sales, and marketing, and customers, and everything, so who gets credit for what? There’s a lot of what our revenue leader calls, ambulance chasing, which I tend to agree with, you know, it’s a lot of that. I think it’s an interesting thought. I do think demand gen should have a number and be held accountable for that and rewarded for beating it, just like other teams.

Nick: Let’s talk demand gen. How is demand gen different than sales?  I see the demand for demand gen is incredible right now. Is that not just sales, though? How is it different?

Will: I see it in two ways. It is the filling the top of the funnel and then setting sales up with the- and when I say sales, I mean account executives, closers. It is our job as a demand gen org- and that spans marketing, that spans business development, sales development, that also spans partners at some level- to make sure we’re getting the message in front of what we think are the right people at the right time. It is then getting those signals converted into if it is a real sales opportunity. If this person is browsing on our website or coming to our webinars, is that a real opportunity or are they just learning? Once we’re convinced that there’s a real sales opportunity, then it’s great and we’ve done our job. Now, we’re a supporting role where we’re helping to close that, but it’s then being led by sales. That’s how I view it. I view demand gen as very much top of the funnel and sales as very much closing that. 

Nick: Any other thoughts, anything to plug, anything to talk about as we wrap up here?

Will: Look, I’m a big fan of Enablix. Is that good? 

Nick: I think so. I think some of the listeners would say gratuitous.

Will: We benefit greatly from Enablix from an organizational standpoint. And, Nick’s old podcast, In Gear, which is a MessageGears produced podcast, will be starting back up in January and I will be leading executive one-to-one conversations with marketers, learning about their jobs, learning about what their day-to-day is like, learning about how they learn about their customers. I find it very fascinating when we get to talk to marketers and leaders in different organizations about how they approach their jobs, and I think other people will also find it fascinating. So, look for that-  In Gear, a play on words, which, I’m not sure I can take credit for, but I will.

Nick: I mean, you can, you’re the only one here. Thank you so much for joining me today, ladies and gentlemen, Will Devlin.

Will: Thank you, Nick. This was a pleasure. I Appreciate it.

Nick: This has been Mind the Gap, a podcast about sales and marketing alignment put on by Enablix. My name is Nich-Ziech Lopez. Thanks for listening.