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How Jess Cook Turns Content and PR into a Power Couple at Island (Interview)

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We’ll need new ways to reach people if an exponential increase in copycat content makes existing channels less effective (thanks, AI).

PR could be one of those ways. Not necessarily in the traditional sense like getting your brand on TV or in national newspapers, but by getting your content placed in newsletters and your team on podcasts.

Jess Cook is creating this playbook at Island, where she’s the Head of Content and Comms. She shared four great lessons about intertwining content and PR on LinkedIn, which inspired this interview to learn more about her approach.

Jess explains how she uses both disciplines to tell stories across owned, earned, and paid media. She goes into the role of brand, how she measures the effectiveness of PR and content, her thoughts on the future of content marketing, and much more.

Editor’s note: We’ve lightly edited this interview for clarity and readability.

Tim: Can you tell us about your background and how you came to oversee both content and communications at Island?

Jess: My background is actually in copywriting on the B2C side. I was working at ad agencies for a long time, doing consumer packaged goods like cereal and toilet paper. Then, in 2019, I made a complete shift to B2B content marketing. This newest role at Island — Head of Content and Comms — has brought on a whole new level of communications experience, which is really exciting.

What was the biggest surprise in taking on comms responsibilities in addition to content?

Just how intertwined content and PR are. In my past experience, I sometimes found it difficult to work with the comms team. The content team was no stranger to storytelling, but with comms, there’s less room for story. A press release is very structured: this thing happened, these are the people involved, here’s a quote, here’s the boilerplate. It felt almost devoid of story.

Coming to Island, content and PR are very intertwined, which I really like and appreciate. We’re all telling the same story; we’re just telling it in different places. And we’re not afraid of using paid PR because that’s where the model has shifted.

PR used to rely very heavily on earned media. If you had a good story, it would get printed. Now, it’s so much about clicks, eyeballs, impressions, and paying to play. You have to have a truly groundbreaking story for it to be earned nowadays. You basically have to break the Internet with your story to not have to pay for placement.

How do you approach paid PR opportunities?

It’s about looking for opportunities where your audience overlaps in paid and earned channels. Not everyone can afford something like Ad Age or Adweek, but there are so many resources out there where you can find places where your audience aligns.

We do have a [PR] agency, which I think is a must-have. You need a group of folks who are entrenched in PR, who can make connections for you, reach out to the press, understand the opportunities out there, and be very honest with you about whether your story is rich enough or has the right angle.

I would also say to look to your customers as a resource. If you can get a customer who just happens to really like your product and is using it for a really interesting use case onto a podcast or doing a byline in some sort of publication, that delivers a level of credibility that would feel like selling if it came from someone at Island, but feels like social proof of the highest form coming from a customer.

It’s been a really nice playbook for us. Customers get to talk about what they’re doing. We’re helping them promote their personal brand, but then they’re also talking about how Island is helping their company. It’s a one-two punch.

Can you talk more about featuring customers in your PR efforts? That sounds really interesting, but also like a challenging pitch.

There’s a lot of digging and research to be done, and then there is the hurdle of getting that person to say yes.

It’s like sales — I get a lot of no’s for various reasons. “We don’t endorse any vendors at all,” or “I’m just too busy at this time.” We get lots of no’s like that. So you have to keep going to get to a yes. It is difficult, but when you get there, it is well worth it.

Can you share an example of a successful customer story placement?

We just had two customers on a podcast called CXOTalk. It has a far-reaching, large listenership where the host brings C-level executives on to talk about how they’re solving their problems, modernizing their companies, becoming more secure and efficient.

One of our customers who went on the podcast is the head of IT for Hendrick Motorsports, one of the winningest NASCAR teams. He talks about how they’re out there on the track, and they have to figure out how to download 7,000 images each race in real time.

He’s talking about how he’s built the infrastructure to do that, and part of that is Island, but it’s just part of it. There’s a bigger story there in terms of modernization, and we get to go along for the ride, which is great.

What can other content teams learn from how content and PR work together at Island?

The synergy between PR and content is absolutely underutilized, and there’s a really nice opportunity that people can capitalize on if they realize how closely these two can be interlinked.

It starts with having the right team and a very defined approach. Laying out the stories you plan to tell, the pillars, what you’re going to talk about, and what you’re not going to talk about is an important first step to getting it right.

We have a handful of stories we play out in press interviews, across the blog, social media, and even at events. It all has to start with story at the very top, and it has to filter down into the different ways you’re going to pick that story and put it into all of these different places.

At Island, I am overseeing both content and comms underneath someone who understands and fully values both. The two of us together are coming up with the stories and work with leadership and SMEs to decide how they’re going to be told in both channels.

How do you measure the success of your PR and content efforts?

For PR, we’re looking at share of voice. So, over the quarter, how many mentions were there about us versus competitors? For our Series D raise, for example, we did an entire readout at the end of the week of all the press and traction we got, including some of the best headlines.

For content, I oversee social and editorial. I’m specifically looking at not only social followers but also the makeup of our social following. Are the right people following us? We want a large makeup of IT and security professionals.

For editorial, I’m looking at branded and unbranded clicks and impressions. I want to see how those are growing relative to each other.

I really want the unbranded number to grow because I want to measure myself on how many new potential buyers I was able to bring into the fold with content. That’s a big one for me.

Another metric I track is what I call the “repurposing multiplier.” It measures how many more people we reach by repurposing our original content in different ways.

For example, let’s say our original piece got X impressions. Then, we create four social posts based on that piece, which collectively get Y impressions. If Y is 12 times greater than X, we achieved a 12x repurposing multiplier.

This metric helps people internally understand that you don’t always need brand new content; you can continue to tell the story you’ve already told in a different way.

How important is brand in the context of content and PR?

At Island, we’re very intentional about branding. Their first marketing hire was a Head of Brand, and he’s still here.

He, myself, and my manager make up the comms and brand team. It’s really important to us because we know that part of what makes Island so different is the brand — how we talk about ourselves, how we present ourselves, the tone, voice, and imagery.

My hope is people start to realize that if you don’t have a good brand foundation built, nothing else matters. The content doesn’t really matter, the demand gen efforts don’t matter. If you’re putting out a bunch of ads focused on conversions and leads but don’t have a brand to back it up, people just aren’t going to be interested for long.

With the uncertainty around SEO because of AI-generated content and results, do you see elements of PR becoming more important in content marketing?

Absolutely. The lines are blurring. If we can’t fully rely on SEO — we’re still investing in it because it’s still important, but it’s going to change — we have to keep that in mind. As a content marketer focused on brand awareness, I’m going to rely more on third parties who have credibility and an audience that aligns with mine.

What else? How else do you see AI impacting content marketing?

We’re finally figuring out the right ways to use AI. When it first came out in November 2022, everyone thought, “We’re going to write blog posts this way.” But we’ve come to realize that’s probably not the best use.

Yesterday, I had an interview with an SME. I took the transcript, dropped it into ChatGPT, and asked it to break it down for me — give me a good summary and the key takeaways. It did a really good job of that.

AI has removed the time-consuming part of summarizing and synthesizing data. Now we need people who can take that and strategically understand what to do with it, where it should live, and who else in marketing can use this story.

Any final thoughts on the future of content marketing?

People are realizing content marketing is just marketing. You have to have content in order to go out and do anything. It’s funny to have that label of “content marketer,” but really, a customer marketer is a content marketer. Demand gen still requires content to be successful. It’s a weird blurriness, and I think it’s just going to get even weirder and blurrier in the next few years.


You can find Jess on LinkedIn.
She’s also the co-host of That’s Marketing, Baby.


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