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.