Drive Digital Commerce With Content Marketing

Now more than ever, content is the heart of your business. It’s what drives people to your products and keeps them coming back for more.

Recently, WordPress VIP gathered a panel of ecommerce and content marketing experts from Square, PHLEARN, and Craftpeak who shared tips for using content to fuel high-growth digital commerce channels.

This conversation originally took place as a live virtual event. The comments have been edited for length and clarity. The panel was moderated by WordPress VIP’s Chief Revenue Officer, Jary Carter.


Mallory Russell, Head of Content, Square

Mallory Russell is the Head of Content Marketing at Square, overseeing both the Editorial and Lead Generation functions. In her role, she grows Square’s brand and customer base by creating content that aid and inspires businesses of all sizes.

She previously led content marketing at where she used social and editorial channels to tell stories of people making change all over the world. Before working in tech, Mallory reported on the world of marketing at Advertising Age and Business Insider and worked at some of San Francisco’s most storied ad agencies.

Mallory holds a B.A. in Communication from the University of Southern California and an M.A. in Business and Economic Journalism from New York University.

Seth Kravitz, CEO, PHLEARN

Founder. Writer. Collector of interesting people. 3x founder with 2 exits to public cos.

Specialties: launching startups, SaaS, journalism, photography, branding, big events.

John Kelley, CEO, Craftpeak

Craft beer drinker. Problem solver. Builder of things. With a degree in mechanical engineering and a penchant for fostering and accelerating startups, John is equal parts cowboy visionary and pragmatic business director.

While John’s early career was spent in a suit as a technology consultant for Accenture, he’s devoted the past 15 years to working with other entrepreneurs, designing and pioneering new kick-ass products and solutions to market in the hi-tech, non-profit, and real estate industries.  His startup experience traverses the spectrum of bootstrapping innovations from his kitchen table while pounding coffee to working sales for the world’s largest venture capital firm.

Before we jump into the questions, please introduce yourself briefly and share a little bit about your background.

Mallory Russell: Hi, everyone. I’m Mallory. I am based in San Francisco, California. I’ve been working for Square for about four years, and grew the content marketing team from just me to a pretty multifaceted team. I’ve done really traditional B2B content marketing, I spent some time doing B2C content marketing at as their first content marketing hire.

And then, Square is a bit in the middle, which is a really interesting and exciting space to work.

Seth Kravitz: Hi, I’m Seth Kravitz. I’m from Chicago, Illinois. I got my start in tech when I started a company in the insurance business, scaled it up to about 65 employees, and sold it to Bank Raid. About four years ago, I came in to run PHLEARN.

PHLEARN is a 10 year old company that teaches Photoshop and photography online. We’re a very large online platform for the photography community to learn those skills.

John Kelley: My name is John Kelley. I’m the CEO of Craftpeak. Craftpeak is based in Asheville, North Carolina, and we align ourselves with great beverage companies, typically craft breweries. Our goal is to understand their business challenges and develop solutions and technology to help. There’s many opportunities on the digital commerce side for breweries. It’s been an exciting time to see that shift.

Great. Let’s dive in. How do you approach the proliferation of video content hitting the market?

Mallory Russell: We’ve always done a lot of advertising work around video. It’s probably our most common tactic in terms of traditional ad campaigns. We’ve recently decided we’re going to make our YouTube channel an editorial channel, which means thinking about the purpose of the video along the entire funnel: how you bring in people at top of funnel with things that are more brand-focused, and then pull them down, but also cross- link with your site to increase visibility in terms of search.

Seth Kravitz: When I joined PHLEARN the marketing I had done was maybe 1% video. I didn’t really believe in it. Then I come to PHLEARN, and I mean, we sell people video education.

So being a video-forward company made it easier for me to jump into video marketing, way outside of my comfort zone, using tools I had never touched before.

What I discovered though, after about two months, was it was nowhere near as intimidating or difficult as I thought it would be. A lot of the videos that are doing incredibly well, shared on Instagram or Facebook or Snap or Tik Tok or anything, they’re usually very low budget.

People don’t mind homemade-looking videos because a homemade video actually looks pretty good these days. Going forward, any company I work with or start, I’m going to go video-first on all of our marketing.

John Kelley: You have to be willing to push forward without it being perfect. As I look at our customers and the engagement rates they’re getting on social media and other platforms, anytime they’re putting a video out there, no matter how simple it is, the engagement rates are off the chart compared to anything else they’re doing. If a picture is worth 1,000 words, video is more important. There’s just something about the story and our human connection to that, that we’re drawn to. It’s definitely here to stay.

“Creating a high-quality knowledge base empowers customers to solve their own problems, and positions your brand as one that genuinely cares about the success of their customers.”

Seth Kravitz, CEO, PHLEARN

Podcasting has come up for a lot of companies. How are you thinking about that?

Mallory Russell: It’s funny—I’ve been at Square for four years and we’ve been talking about doing the podcast for four years. The biggest thing was finding the right idea that made sense strategically, and not just doing a podcast because podcasting is cool right now, but because it ladders back to our editorial strategy, our brand strategy, and serves a purpose for us.

Our social team had been doing very short audio stories on their channels and getting amazing engagement. They were really moving, and they were filling this need during COVID. We can’t give people all the answers we usually give them because things are changing so rapidly and people have to adapt and pivot and come up with what works for them. Everything’s different. And so, I saw the engagement and said, “I think we should do a podcast. I know we say that all the time, but this actually makes sense.” We got together with our agency, talked through it, and figured out that it really did. We didn’t say, “we have to get this perfect on the first episode.” You see a TV show with a pilot, and the pilot’s often very different from the later episodes. “Let’s do the first episode, see what works and iterate as we go.” We’ve definitely seen changes over the episodes. It’s really exciting to find our stride.

Can you talk about how thought leadership plays into your customer acquisition strategy?

Seth Kravitz: This is the second time I realized writing a book could be really valuable. The first time, our customers were insurance agents; people weren’t writing very interesting content. We decided to write something that was more fun and less dry than they were used to, and we gave it away free to all of our new customers, and we sold copies of it as well, for a very low price. It made a difference. It immediately separated us from our competitors; nobody else was doing anything like that.

At PHLEARN, I was inspired to try again [but] I didn’t want to publish a book unless we had distribution figured out first. We partnered with Flickr and SmugMug, two of the biggest names in photography, to co author the book with us. So they’re also distributing it to their entire user base. Now, the book has been emailed out to 10 million plus photographers and hopefully that’ll continue to trickle in.

It’s very much a top-of-the-funnel thing. We get on their radar as someone they can trust, who’s giving out free information and wants them to be successful photographers. And then, we hope that goodwill will pay off in the future.

“Businesses can’t operate the way that they used to. They have to do things in a more digital environment. Everything has to be content.”

Mallory Russell, Head of Content, Square

Mallory Russell: With content marketing, you have to think about the entire funnel all the time. You can’t just be producing for one piece of it; you have to think about how those pieces connect together. There’s going to be a finite group of content that really converts. They’re like your work horses, but you have to get people to them, and that’s how you build a funnel from the top, to the middle phase, to the bottom. The podcast, which I’m going to plug, is called Talking Squarely.

That’s a thought leadership type of content. It’s being used as part of our brand campaign, so we’re driving people in that way, and then we’re linking them out to other types of content. Thought leadership is how we bring people in and start forming the relationship. It’s how we let them know what we’re all about, and why they should trust us, and why we’re credible.

Our goal from there is to think about what would be interesting for them next, and create a web of content they can get pulled into, potentially leading to email capture where I’m going to deliver content to your inbox. Thought leadership for me is always the first step.

How do you measure the effectiveness of content as you take it through the funnel to conversion?

Mallory Russell: It’s such a hard question for every content marketer. I have ongoing debates with people about this. A lot of places want you to measure everything by conversion. As a program, we look at really high level business metrics.

We have a lead generation team within content marketing; we are looking at leads into sales, we’re looking at what money is actually coming out of the work that we do.

When you’re looking at individual pieces of content, judge it by the purpose it was created for, as opposed to one metric for every single piece. One piece of content could be used for a campaign that’s driving awareness, and another type maybe you really want to look at engagement.

That means reporting on these things is actually quite complicated. I’ve found most measurement systems, even within marketing organizations, aren’t specific to content.

For example, I know a lot of site pages, they measure by bounce. Well, sometimes with content, you don’t need someone to go to the next page; you need them to sign up for your newsletter or you need them to just read it because you’re expecting them to come back later when they have the next question, because it was so top of funnel.

My experience is that you really have to be your own advocate in terms of measurement and what that means, because it is a different way to think about it than traditional advertising and traditional digital marketing.

Whenever someone starts talking to me about content, I say, “what’s the distribution strategy?” to the point where someone made me a sticker that’s on my computer.”

Mallory Russell, Head of Content ,Square

John Kelley: Top of the funnel is exceedingly important. Buyers are becoming more educated on their own, so content needs to exist out there as part of that buyer’s journey. The statistics say 67% of people are making a decision prior to talking to somebody directly from your company. The second piece is if you’ve got good intentions, lead with them.

We work in a market where there’s a lot of change right now; things are going through some dynamic shifts in both the market and the businesses. What we want to do is serve, to be a guide or a source of information, and not necessarily always think about it in terms of direct acquisition or conversion. The education phase, that awareness phase, gives us the ability to begin that conversation, to begin building that relationship.

Certainly, there is a business and transactional element associated with it, but just expecting that people are going to be making those decisions much more frequently on their own, it’s important to meet them where they’re beginning
to get educated.

Mallory Russell: What I always tell my team is, your ultimate goal is to provide value because nothing is going to happen after that if you’re not providing actual true value to the person on the other end. You think part like a publisher and part like a marketer in that respect.

John Kelley: Yeah, absolutely. I would consider Square and other strategic partners that we have relationships with, an important part of that equation. It’s not only about the content we can provide, but also, how can we leverage our relationships to bring the right skill sets and the right thought leaders to the table to educate our market?

Seth Kravitz: As far as content marketing goes, it just takes a lot longer than anyone in performance marketing is used to. Like, you want to build a knowledge base of 100 articles that cover all of the most common questions. That takes a lot of work, a lot of time, and a pretty good investment, and then it’s going to take a while before you see the results that you want to drive. It’s not like, we create a viral video on the first try and just magically, that was content marketing.

“Going forward, any company I work with or start, I’m going to go video-first on all of our marketing.

Seth Kravitz, CEO, PHLEARN

The pandemic has accelerated the planning and thinking and execution of digital transformation. How does content fit into that?

John Kelley: Everybody we work with is going through that digital transformation right now. Breweries are typically great at creating the real world experience, the tap rooms and tasting rooms. Now that taprooms and tasting rooms are closed or at least have a limited capacity, how do we extract and extend that brand experience into the online world? How do we create that same sense of engagement online?

We use technology to point people to those products, and ultimately what we’re trying to do is connect the story closer to the transaction. We think it’s an opportunity for businesses to differentiate themselves by the experiences they’re creating online. What is the ultimate customer experience you’re trying to create and how do you leverage technology to do that?

What other types of content allow us to create that experience online?

Mallory Russell: Since March, content has become so much more important across everything because businesses, in some cases, can’t operate the way that they used to, and they have to do things in a more digital environment. Everything has to be content. How do you communicate with your customers now? How are you telling your own story? How are you communicating what you’re offering and how you’re offering it? In every piece of this, content plays a role, mostly because we can’t interact in person as much as we did before.

Seth Kravitz: Now is the time you can get away with the most bare bones things possible. There’s this local bakery about three, four blocks away that we used to go to all the time and they put up this just awful checkout experience to try to pre-order their stuff and you could stop by and grab and go. I put up with just this horrible checkout experience because I want to buy their goods.

A lot of excuses anyone had before where, oh, we can’t roll out our site and sell online until it’s perfect, until it’s amazing, the excuses are now just completely out the window. Now, it’s just time to get it live and benefit from the fact that customers are willing to put up with things they never would have before.

Mallory Russell: Yeah. It’s interesting. We talk to small business owners all the time, and that’s what they started doing at the beginning of all of this. They came up with really creative ways to get people; restaurants doing cooking classes on their Instagram accounts and things that they weren’t doing before, but it gave them a lot of room to experiment and try things and see how their audience reacts. And in talking to them, it’s things they wouldn’t have done before, but necessity dictated that they try something.

“It’s not only about the content we can provide, but how can we leverage our relationships to bring the right thought leaders to the table to educate our market?”

John Kelley, CEO, Craftpeak

Many businesses have had to change during COVID-19, but with reduced staff and change in the facilities, many ran into roadblocks to generate content. What tips would you suggest to enhance the online ecommerce experience?

Mallory Russell: I get asked a lot, “How do we do more, faster?” I never think that’s the right question. It’s figuring out the one thing that’s going to work, concentrating, and doing that well. Because quite honestly, you could produce 10 articles that have the same results as one that really took the time to research, what keywords are people searching for? Where’s there an opportunity to win on search? The foundation of any good content program is organic search and really building that up is going to set you up for success. You can actually do a lot more with fewer pieces of content as long as you’re doing your strategy and research in depth.

John Kelley: Right now what we’re recognizing is people just want the information. They want to know how they can get their hands most conveniently on your products. Seth, like your example with the bakery in your neighborhood, what we see our brands doing is adapting and hustling. Their business doesn’t look anything like it did six months ago, but they’re fine with that because they’re pushing forward and they’re letting people know, here’s how you get your hands on our beer, here’s when we’re releasing things, here’s how we can make it convenient for you.

The second thing is that consumers are being very, very flexible right now. Absolutely. Hopefully, that remains for a while. At the same time, we’re also really discerning. If you look over the last 10 to 15 years, we as consumers really care about not only the products we’re buying, but the companies and people that are behind these things. It’s a combination of both: reminding people about the ethos and the personality and the people and the spirit behind the brand, while at the same time, making it easy to get their hands on the products.

“There’s an opportunity for businesses to differentiate themselves by the experiences they’re creating online. What is the ultimate customer experience you’re trying to create and how do you leverage technology to do that?”

John Kelley, CEO, Craftpeak

How do you prove the value of top of funnel efforts to stakeholders who want to focus on tactics directly connected to revenue?

Seth Kravitz: We hired an editor-in-chief, a full-time salaried person in charge of pretty much all the content marketing. We take marketing seriously enough that we’re like, you know what, we should treat it like its own publication. It has its own separate editorial process. That has helped me not ruin it by being like, okay, under this first paragraph, I want a buy button, and then on the third paragraph, I want another buy button… our editor-in-chief, she stops me and says, “No, we need to deliver a great piece of content first. If they really engage with it, enjoy it, we will win. I promise, we’ll win.”

Mallory Russell: My first piece of advice would be, you can’t do by yourself. That philosophy has to be consistent across the entire marketing org. If you’re investing in brand and awareness for your other marketing tactics, you should be doing it with content, too. It’s about showing people that this stuff isn’t just to get people into the site and it’s just traffic. You’re creating journeys from the top of the funnel to the bottom of the funnel, through links in your content, through recommended articles, maybe an email capture where you actually get to serve that information through CTAs, through surfacing that content on other parts of your site. So, you have to paint that picture that it’s not any one piece of content, it’s the sum of all the parts, and by building the top of the funnel, you’re actually creating something that grows much more quickly. You invest a lot less over time if you’re building the entire funnel versus just the bottom.

John Kelley: We think about the content ecosystem more than any one specific piece of content. Just about everything can be measured at this point, but that doesn’t mean those measurements are meaningful. Focus on the areas that need some adjustments or enhancements, measure those things, make improvements there, knowing that the health of the ecosystem is going to drive overall results, but it’s not necessarily a direct line between a single piece of content and a sales number.

How do you identify channels to drive visibility beyond your brand’s owned properties?

Seth Kravitz: Everyone wants to control the content, have everyone come to their own property, but that’s just completely unrealistic today. Everything we do is about syndicating our content out to as many places as possible. So, if we create a video, a video is going to go native to YouTube, it’s going to be natively posted to Facebook as well, we’re going to natively post it on Instagram, everywhere. We’re not going to try to link all of them to go to one place, we’re not going to try to drive back to our site. We want people to consume our content on the platform that’s most comfortable for them.

Mallory Russell: Whenever someone starts talking to me about content, I say, “what’s the distribution strategy?” to the point where someone made me a sticker that’s on my computer. I think about distribution a lot. The content we produce gets pushed out through our social channels, through our different email channels, we cross-link with our YouTube channel a lot. The way we’ve put together our content strategy though, we do it pretty holistically. We are always thinking about the multiple use cases of any piece of content we produce, and it’s proved quite effective for us. We also do some syndication partners. We do a lot of branded content now with publishers, so we are producing things where people can find them.

My big thing, once we’re talking about our own channels, is not creating islands of that content. Make sure they can find content in one place, because otherwise, you’re really doing a disservice.

Getting a lot of traffic to a channel is difficult. And so, if you put it all in one place, you’re going to continue building that traffic faster. Get really creative, though, with your distribution. I’m doing some tests right now around earned media with the podcast that I’m pretty excited to see how they go.

“I get asked a lot, ‘How do we do more, faster?’ I never think that’s the right question.”

Mallory Russell, Head of Content, Square

Bonus: Audience Q&A

These questions were submitted by audience members throughout the discussion and addressed by our panelists via email after the event.

How do amplification partners play a role in your content strategy to bridge the gap between the creation of content that lives on your dot com or blog, to actually driving those low-funnel conversion activities?

Mallory Russell: Like the content itself, amplification partners play a part at every point in the funnel. Without amplification partners, content marketers must rely heavily on SEO to build traffic. SEO is critical, but a mix of traffic types to your content is moreso. The thing about SEO is that someone has to know what they’re looking for to find your content. Amplification partners give you a chance to tell people what they should be looking for.

Amplification partners are particularly important at the top of funnel, to create awareness. You can do anything from programmatic native and paid social to branded content or article swaps with brands. The important thing in doing amplification of ToF content is to ensure the audience is broad enough to build a sustainable funnel, but specific enough in targeting that people will also want to move through whatever journey you create for them (whether that’s through CTA, recommended content, lead capture, etc.). You can also use amplification partners to drive more directly into conversion content, but you need to be really specific with your targeting or, more likely, retargeting.

What should be the split for our content strategy in terms of educational-based content vs. product/sales content?

Seth Kravitz: I would always vote for educational content to get priority first as it serves the dual purpose of keeping existing customers happy and engaged, plus it’s used for closing and onboarding potential customers as well through thought leadership. Creating a high-quality knowledge base can take quite a bit of time, but I’ve found it pays dividends for years going forward through SEO benefits, empowering customers to solve their own problems, and positioning your brand as one that genuinely cares about the success of their customers.

John Kelley: I would say about 50/50. Knowledge/educational based content should include a teaser for product/sales content (for example, having CTAs to schedule a demo or purchase at the end of an educational piece), but not be pushy about it. Once people are educated, they start looking for solutions—that’s where your product/sales content comes into play. While amateur video has greatly improved the past few years, our organization has just awful photography (because of low funding and a lack of skills), limiting our use of that medium. Do you have recommendations for how to work around that, on the web or social media, for example?

Seth Kravitz: If the product is something that can be shipped and isn’t exceptionally expensive, use services like The H Hub to get professional photos taken of your product for a low cost. If it’s neither, you can still use a service like that to book a local photographer, as I can’t stress enough how helpful it is to have good photos of your product. In 2020, I consider it a requirement, no longer a “nice to have” item. Also, if you can get photos from your customers using your product, those don’t need to be exceptional, they just need to look genuine. They can easily be used in marketing campaigns on social with no expectation from potential customers that they need to look professional.

What are your suggestions on content distribution? What channel(s) do you use to make sure that your content is reaching out to people that you’ve made it for (social media, ads, SEO)? Thanks!

John Kelley: Content distribution should include as many channels as possible–however, think about where your customers are the most active. Is it LinkedIn, Facebook/ Instagram, Google, certain websites? Develop a media strategy tied to the personas that you’re targeting with your content. Also, think about how you can team up with partner brands with co-developed content, such as a webinar, guest blog post, etc. to tap into partner companies’ audiences, as well.

I’d love to hear more about how the team at Square is working through evolving YouTube to more of an editorial platform. This “re-org” feels like a massive effort for us. Are you organizing content around persona? Product or solution? Biz issue?

Mallory Russell: We think of our YT channel the same way
we think of our editorial channels. We’re building from the same strategy, using the same personas. This allows us to build funnels for those personas both on YT and between YT and our owned website. A YT audience, of course, has specific wants and expectations and those should be taken into account when developing what the content actually looks like. A few other thoughts on why I think there’s value in syncing strategies this way:

  • Content Marketing is a long term game and you need repeat messaging for it to be effective. Consistency across channels helps with that.
  • If your strategies are aligned, you’ll be more efficient with production. You’ll be better able to cut up your content and use it across all your channels.
  • Strategically aligned channels can aid each other in terms of search visibility. (Remember YT is the second biggest search engine in the world.)

But how you organize your content is really dependent on the type of business you work for. My experience has been that you’re going to get better results starting with persona rather than focusing on product/solution or issue. The persona should outline the issues that person faces and the products/solutions that can solve it. So by addressing personas, you’ll likely do a better job of creating content for each stage of the funnel that appeals to your audience.

Key takeaways

  1. Video is here to stay. But don’t get intimidated by the need for big budgets or complicated editing software. Often, the best performing videos are those that feel unpolished, because they build a more authentic connection with the viewer.
  1. Thought leadership belongs at the top of the funnel. Start building your brand as one your audience can trust, one genuinely interested in their success. That early relationship requires an investment but will pay dividends.
  2. Buyers want to be educated. Invest in quality content that is genuinely helpful to your audience.
  3. Leverage your existing partnerships. What companies in your sphere can you collaborate with to share workload and extend the distribution of your efforts?
  4. Avoid “islands of content.” It’s hard to build traffic! So make sure once your prospect is interacting with your content, you’re serving up links to other content pieces that are catered to their particular stage in the buying journey.
  5. Get creative with your distribution strategies. In fact, start thinking about distribution even before developing your content. Figure out where your target audience is natively consuming content, and work backward from there.
  6. Invest in content workhorses. One thoughtful, valuable, well researched content piece ultimately brings more value than 10 lesser pieces. Always emphasize quality over quantity, at every stage of the funnel.