CMO Chats with Tyler Lessard, CMO of TechnologyAdvice

Hi everyone. My name is Tyler Lessard. I’m the Chief Marketing Officer here at TechnologyAdvice.

Tyler, can you tell us a bit about your journey and what sparked your interest in marketing?

I actually joined the business about six months ago after spending ten years at a SaaS startup called Vidyard as the Head of Marketing. My career actually began as an engineering graduate. I started in software development but quickly found that I was much better at explaining technology to others than actually coding and building software. So I slowly moved into more and more communications, partnership, and product marketing roles. And here I am today, with a huge passion for storytelling, for connecting with audiences, and for helping businesses really differentiate themselves in crowded markets.

Can you tell us a bit more about what your company does?

Sure. TechnologyAdvice is a B2B media publisher. We own and operate more than 30 different tech media sites, newsletters, and social media channels like TechnologyAdvice.com, as well as TechRepublic, EWeek, SecurityPlanet, and many other properties that appeal to very specific types of B2B tech audiences. As our business, we work with B2B tech providers to help connect them with those audiences of in-market researchers and buyers. We do that through digital advertising and integrated demand-gen programs, where we help get their content, their message, and their ideas in front of the right people at the right time. It’s a lot of fun for me, being a marketing leader with a huge passion for demand-gen, to be able to market to and partner with those demand-gen leaders out there in the market.

And as a CMO in your company, Tyler, what is your current main marketing focus?

It’s a little bit of everything these days, especially with being about six months into the business. But there are a couple of things that are really standing out as big priorities for myself and, I think, for our business overall. First and foremost is building our unique brand within our community. I emphasise the word unique because we do have a good, well-known brand within our audience, but we’re in a very crowded space where differentiating from many of the other vendors has become increasingly difficult in recent years. I’m sure many of you can relate to that, being in crowded markets with lots of new entrants. We’re all seeing it as the barriers to entry in lots of different spaces are dropping. So, more and more, we need to be conscious of how we create a unique perspective in the market, how we differentiate from others, and how we create a unique feeling in our audience—our customers—about why they should think about working with us as opposed to others in the space.

Another big priority for us is pipeline generation. We all think about it; we all know it. I’m really focused on not just how we generate more pipelines but how we partner closely with our sales team to find those opportunities, to not only find new leads for them to work with but, equally importantly, to collaborate with them on helping them be more successful in their own outbound efforts, generating new opportunities in their current accounts. Those types of things are increasingly important in the market and something that I think a lot about as well.

Can you tell me about a particularly innovative or successful marketing campaign your team has recently executed?

Being relatively new to the business, we’re still in the process of building out some of the big programs we’re working on. But one thing that we have done—and that I’ve found a lot of success with in my previous roles—is launching a fresh new thought leadership brand that’s really oriented around helping us build a highly engaged audience of B2B marketing and demand-gen professionals. We’re trying to cater not only to those who are ready to do business with us today but also to build an audience of folks who will follow along with us over time and come to us when they’re ready to run new demand-gen or advertising programs.

So, we did that by taking somewhat of a unique approach. I’ve spent a lot of time in recent years understanding how social media audiences engage with brands and how people are transitioning into the types of content they really associate with. We decided to launch a thought leadership brand called The Marketing Insiders at TA. The idea behind that was to really create a more personal and human-centric social media and thought leadership brand that our audience could connect with. Rather than trying to publish brand-centric content on our social channels, blog, or research coming from, say, Technology Advice, we’re taking a very person-centric approach, introducing the market to “the marketing insiders at Technology Advice.” It’s myself and seven or eight other people on our team who are all bringing insights to the community, working on our research reports, and creating video content for our audience.

By creating that horizontal thought leadership brand, it now gives us a platform for a new newsletter, podcast, and social channels where we can create an audience who’s connecting with the real people here at Technology Advice, not just following a brand. More and more, I think it’s important for all of us to be thinking about how we’re creating those more human connections. People want to connect with the real people—”influencers,” both inside and outside your company—more than they want to connect with corporate brands.

What would you say is your biggest marketing challenge at the moment?

Our biggest marketing challenge right now is standing out in a sea of more and more competitive companies in our space. As part of standing out, it’s not only about speaking a little bit louder or being a little bit different but also about finding new ways to get our voice heard. It’s not just about brand awareness; it’s about how we create unique brand affinity and ongoing brand engagement with our community in a way that helps them understand how we’re different from all the others in our space they could be considering.

It’s a big challenge today with the increasing volume of competition. More and more, people are offering the same features. Many of us in B2B tech companies, particularly with the rise of AI and automation, are finding it increasingly difficult to differentiate on features alone. Competitors can quickly catch up with new capabilities, new plugins, and new partnerships faster than ever before. So, we need to think about how we create that unique brand affinity with our audience, connect with them as real people, and make it clear that not only do we have the best products and services in the market, but we also have the strongest and most reputable customer service. We care about our customers and are invested in their success, not just ours. These are the things we’re thinking a lot about as we build our brand in the market to uniquely position ourselves with our buyers.

What do you believe is the biggest opportunity for CMOs today that might not have been available in the past?

I think one of the big changes in buying audiences—and this is always how I tend to think about the life of a CMO—is how our buyers are changing and how we align with that. Over the last ten, five, even two to three years, there’s been a rapidly changing set of preferences, expectations, and behaviors among tech buyers. The biggest part of that change is the extent to which the buying journey happens self-service online before they ever reach out to their shortlist of companies. In a lot of markets, it’s becoming close to 100% of the buying journey, with companies offering freemium products, free trials, and other ways to get started without any friction.

As CMOs, we have to embrace that shift, no matter what industry we’re in or our starting price point. More and more, buyers are actively researching on their own time, on third-party properties, following influencers, podcasts, and YouTube channels, and reading product reviews, comparisons, and other information sources. As CMOs, we need to think about how to become a part of that buying journey—not just the one we’re trying to create. If we spend all our time thinking about conversion rates once someone arrives at our website, we’re missing out on a large part of the community who may never come to our site if they don’t find out about us through our thought leadership and media programs, an owned media strategy, or partnerships with demand-gen providers and media publishers who reach those audiences daily.

In your opinion, Tyler, what does the future of marketing look like to you?

Well, it’s complicated. The world of marketing has gotten simpler in some ways but much more complicated in others. Going back to the world of aligning with our buyers, the way people are researching, buying, and making decisions keeps changing—and at an increasingly faster pace. We’re all thinking about the impacts on SEO and inbound strategies with the rise of AI and AI recommendations. More and more, people searching for a topic might just get served information from Google or other engines rather than being pushed to different websites.

Not only are platform dynamics changing, but buyer behaviour is shifting further away from “I’m going to your site, requesting a demo, and talking to sales” to a more self-service, hyper-transparent online approach. So, the future of marketing, in my view, is being ready to serve buyers on the channels they prefer, in the formats they prefer, and in a much more timely and personalised way than ever before. It’s very difficult to do that in a scalable way, but it’s something we need to focus on as marketing teams, leveraging the right tools to help us get there.

What would you say is the role of the CMO in one word, and why?

Vision is the most important—of course, it’s just one of many—but vision is increasingly critical as we think about delivering buyer and customer experiences. CMOs need to be in tune with the changing dynamics of the market, understand the competitive landscape, and help set a course not only for marketing strategy but also for the broader go-to-market and business strategy. This is happening more and more, where CMOs are becoming more strategic, focusing on vision rather than just tactics and execution. With buyers so digital-focused and self-service-oriented, marketing needs to play a bigger role in company strategy, ensuring we serve our customers in ways that stand out in the market and foster the best possible relationships. Vision at the CMO level is essential to creating the best possible buying experiences.

What’s a piece of traditional leadership advice that you believe doesn’t apply to modern CMOs?

I remember being told multiple times, “If you can’t measure it, it’s not worth doing.” While I believe that’s valuable in terms of forcing us to think about measuring program success, it can also put us at risk of not investing in programs that we intuitively know are important for building high resonance with our audience and creating the relationships we’re looking for. I think we need a balance. We should invest in programs where we can test, measure, iterate, and optimise, but we shouldn’t shy away from programs that might be harder to measure directly but are likely to move the market and build relationships with buyers, increasing brand affinity.

And my last question for you, Tyler: what career advice would you like to share with other marketing leaders?

Now is the time for marketing leaders to establish a strategic presence within their organisations. Going back to my one-word description of CMOs—vision—is so critical. I encourage you to think about and contribute strategic ideas, not just within marketing but across go-to-market functions. How can we adapt, grow, and advance the overall function? How can we bring our understanding of buyers and customers into product strategy? I approach my role as an executive of the company, not just as a marketing leader, because more and more, marketers need that voice to help drive strategy across the trifecta of product, sales, and marketing. This alignment is more important than ever due to the evolving expectations of buyers and customers.

As VP of revenue marketing, what is currently your marketing focus?

My main focus is two things: at the simplest level, it’s acquiring new customers and then growing existing customers. On the acquisition side, we do that through demand generation, other acquisition channels, advertising, paid media, and such. The website, our SEO, and the self-serve funnel, as well as field marketing and events, are all focused on bringing in new customers into the funnel.

On the growing existing customer side, this is more of your growth marketing process. We’re testing and iterating across onboarding and lifecycle marketing, working with sales, and trying to create opportunities for self-serve accounts that are coming in with the opportunity to grow. I also oversee the marketing tech stack and all of our marketing operations and systems. What I try to do is get these things working in harmony. Because all of these are kind of squarely placed against the customer life cycle where we’re bringing them in, we’re nurturing and onboarding them all digitally, and then as they adopt the product and as they use more of the product, we try to grow those customers and introduce other features and products to them.

Can you tell us about a particularly memorable marketing campaign, whether it was particularly challenging or especially successful that you’ve executed recently?

Prior to DigitalOcean, I was at Google for seven years, and one of the things that really has stuck with me in, really, my whole career was during COVID when I was on Google Workspace. Team workspace is, you know, Gmail, Calendar, Doc, Slides, Meet, etc. This was when Zoom and the surge of video communication began; all of us were locked at home, and all of the chaos was going on. It was a great opportunity for Google to strategically bring Google Meet into that conversation. At the time, I was leading growth marketing for the workspace team, and we created a master class on how to get a team focused, mobilise that team, give them strategy, give them structure, and ultimately execute a really big vision.

We had maybe 50 people coming in and out of this work, streaming across daily stand-ups, regular syncs from a program management perspective, looking at metrics and reporting to leadership, and a full project scope. We had people from brand, media, the UX team, research, product, product marketing, growth marketing, sales, and even engineering sometimes. What was really, really amazing to me was that it could have been utter chaos. It could have been a complete disaster, right? You have that many people that many opinions, and that many agendas, and it wasn’t. It was just that everybody was so focused on what we were trying to do. Each person was completely content with their work stream, their tasks, and what they needed to do, and everyone had the autonomy to sort of own their own lane in the pool. That, in itself, was just amazing to be a part of. I’ve taken that with me and thought through it whenever I’m building a project team.

But the thing I was most personally proud of was on the growth side. What we did was figure out how to introduce Google Meet to existing workspace customers. So these were customers that were heavy users of probably Gmail and Calendar, maybe even docs and slides, and some of the collaborative document types. What we figured out was a way to extract some of the signals of what these customers were doing in these apps and then feed that into a predictive formula that would then introduce Google Meet at the right time. An example of this I’ll share is: let’s say you and two other folks in your workspace account are all in a document at the same time. Maybe you’re editing; you’re sort of interacting with each other. That’s a great opportunity to say, “Hey, did you know you can actually take this document and share it directly and meet and have a quick huddle? ”You can see each other. You can have a conversation. Maybe that makes your collaboration a little bit easier. There were dozens and dozens of these experiments. But it was new. It was the beginning of what would later become a more solidified, cross-functional growth process. It was just a really profound opportunity to be a part of that when the world wasn’t at its best. We all found some solitude in that process.

What are your biggest marketing challenges at the moment?

I’ll share something I think is kind of general for the industry because I think that might be more relevant. I certainly face some of these, and I think a lot of them. When I talk to friends and colleagues in marketing positions, we’re all kind of hearing and saying the same thing. But I think what’s happened is that, particularly in B2B, the buyers that we’re trying to market to are extremely fatigued. In some cases, they’re annoyed, right? They’re tuning out our marketing. I think you see that in the data. You see website traffic start to go down, and you see impressions go down. You see advertising costs go up. It’s ultimately just harder to get in front of our buyers, on top of even just understanding who our buyers are.

The second thing is that I think over the last few years we, as marketers, really kind of overdid it. We had this surplus of budget and desire to grow during COVID. And so, what did we do? We did tons and tons of webinars, tons of digital content, tons of digital media, and tons of messages nonstop. We were able to distribute this on a scale we never had. Unfortunately, what we did was just saturate the market, and now, as a result, we’ve got these buyers who are engaging less with marketing, and I think, ultimately taking the sales process into their own hands. You see all these stats where the average sales deal the buyer has already completed, like 60% of the process before they even talk to a salesperson. In some cases, they want to do it all themselves. They want to go to a review site, they want to talk to peers, they may join a community, they look at social media, and they’re already formulating their opinion before they even talk to you. That’s a key sort of risk for marketing, where we typically try to influence that thought process before they talk to sales.

On top of that, you see budgets are down. Marketers are facing lower budgets, and they’re trying to do more with less. But also, for the companies that we’re selling to, their budgets are down, right? They might be investing less in certain types of software or certain types of processes. And so, all of these things happening at once kind of create this perfect storm where it’s just become a lot harder to market, is what I think. As a result of that, I believe it’s forcing the marketers to get back to some of the basics. We need to understand who our customers are and what pain points they’re trying to solve, and then creatively explain what our product or solution does to them. This is where you’ve got to find something unique and just simply use the channels that every other one of your competitors is using in a kind of mundane way. It’s just not going to cut it, right? You really have to focus on the customer and what they’re looking for, and then build around that.

What are some common trends that you have noticed different companies capitalise on to stay ahead of their competitors in terms of marketing?

Right now, I see two things really growing: One is the rise of the B2B social influencer. You go on LinkedIn now, and it is, it’s all; it’s either founders, CEOs, CMOs, or some sort of C-level that is positioning themselves as an influencer in their industry.

Then the second is communities. You can see how these things can actually work well together. But a lot of companies are investing in the community. I think the ones that had this sort of strategy in their DNA as a company before are doing really well because they’ve already got this built-in audience. And so, as I mentioned before, it’s getting a lot harder to reach that audience through media, essentially renting it from LinkedIn, Facebook, Google, or whatever you’re using as an ad platform. If you have that built-in community, you now have a leg up. You have a community of, hopefully, your prospects and customers that you can learn from. You can do research, understand what their pain points are and what they’re looking for, and then design products, solutions, and marketing around that. So, I think influencers and communities are really important right now.

But I think the catch here is that it’s like content. Simply creating content doesn’t drive growth or performance—it has to be good content. And so, on the influencer side, I think you see some who have kind of stumbled into this, and their posts just look like promotions for their company or their product, not really creating any value. You have to be a part of the conversation; you have to join the conversation and add value to it. It’s the same thing with communities, right? If you build up a community and all you do is advertise your product to them, you’ll likely not have a community very soon. I think it’s all about how you create value across these two channels and, ultimately, how you build and win the trust of your customers and position them to consider doing business with you.

In your opinion, what does the future of marketing look like?

Oh, I love this question. I think the answer is that it’s different. It’s going to look different. I’ve already made some, like, I guess, predictions you could call them from, say, six months ago, that are stale already. I think the big thing is that AI is obviously going to change a lot of marketing. But what I’m excited about is where AI strategically gets placed in your marketing supply chain. If you think about the entire marketing process across brand, creative, demand, generation, and operations, and how you’re showing up to meet buyers in their hypothetical journey, I think that’s the key. There are so many places where it can be valuable. And what you see now is kind of the first foray into AI, which was messaging and creative. You can now build content and copy and visuals and videos and audio just super, super easy—almost too easy—to an extent, where we really do run this risk of over-saturating and already saturated market content is just becoming a lot easier to create, but also harder to find and harder to consume.

The second area is workflow management with AI agents. This is where I’m really excited because you think about all of the mundane commodity tasks that a marketer might do, even just preparing a social post. They historically, maybe, went to a copywriter to get the copy, they went to a designer to get the design, and then they went to maybe a channel owner who’s going to craft all that together and put it into the channel, click Post, and then you’ve got a person who’s going to report on that. You’ve got agents now that can do most of that, and then you’re sort of managing these agents. I think that’s really cool. It also comes with some responsibility, right? If you’re sort of hyper-accelerating with crappy messages, it’s not going to do you well, right? You still need to be creative, but what you can do is speed up the delivery process.

Then the third one I think I’m particularly fond of, and I’m really keen to learn more about, is just predictive analytics and better insight creation through AI. In my career, a kind of pre-chat GPT coming up with insights requires a data scientist. Building a predictive model required a data engineer, a data analyst, and a lot of resources, and the results were great, right? You can really understand a lot about your customers by looking at that data, but I think I imagine a world where a lot of that is automated and streamlined. As you launch a campaign, you basically feed that campaign into some machine learning or predictive model, and it’s now looking for all the things that you’ve trained it to look for. As a result, it’s giving you much faster, more real-time insights that you can take action on. It could be simple things like changing creative or changing messaging, or it might be something more along the lines of, “Hey, your most valuable customers are doing X, Y, and Z before they take that action.” And so, it’s starting now to help you understand what the buyer journey is and doing that at a way more granular level. All customers are created equal; they’re all very, very, very different. Now you have this proliferation of buyer journeys that are driven by insights, and then you can take action on that, personalize messaging, and do all that fun stuff.

If you could describe the role of a CMO in one word, what would that word be? and why?

I love this one. I think I just sort of came across this as an aha moment, but the word is servant. There’s a common description of servant leadership. As a leader, are you serving? I really want to understand what this means. There’s the leadership side, but even as a marketing team, you have to think about your role of serving customers, those on your team, your organisation, and then other areas in the company, right? Most businesses don’t succeed just because of marketing. I think you really need to be okay with that; you need to be humble that your role is to work with products, to work with product, marketing, sales, engineering, operations teams, and strategy teams, to bring the brand to life in the market, or to bring those products and solutions to market in a creative way. For me, the times where I felt the most successful are when I’ve been really tuned in to these other teams and really understand what they’re working on and what their goals are, and then I can bring that marketing perspective. Whatever it is, whether it’s from a creative side or it’s from more of an operational and growth side, either way, you know the value that you bring, and you’re working with these teams to execute.

What career advice would you like to share with other marketing leaders out there?

I thought about this one a bit, and where I landed was to control what you can control. Thinking about where I’ve been successful or felt the most successful is in the places where I didn’t get caught up in either politics, drama, changes in the organisation, or things that I just couldn’t control, right? Like, maybe the market’s down. I can’t really control that, right? But what I can control is my little slice of marketing, my team, and the people I work with.

In some cases, as I’ve personally grown through my career, most of my role changes were the result of reorganisation and new organisational design, which most people kind of commiserate around. “Oh, I don’t want this change. I don’t want to do that and this and that.” You can’t control the fact that it changed. But what you can control is how you show up, how you work with your new leader, and how you transition from the old leader. If you’re getting a new team or joining a new team, you can control how you show up there, and you can control your personality and your outlook. Those types of things, I think, go a really, really long way. I’ve tried to think about this and even the day-to-day. You can very quickly at work; just get thrown into a bunch of things that you realise you really have no control over. But find the thing you can control and just run with it. Do what you can do as well as you can, and block out what others are doing and the things that are out of your control.