Next Stop: Your Magazine Dream Job

Q&A with Kate Rockwood, founder of Rock Top Media 

The Talent Fairy chats with people who hire content people 

The best part of my role as Talent Fairy is that I talk to people constantly. I talk to folks who still work in traditional publishing and want to ride it out. I talk to folks who have successfully transitioned to new or adjacent fields. And I talk to lots of people who are trying to pivot and need the tools to do so. But what I’ve found is that those three groups don’t necessarily talk to each other. There is a knowledge gap between those who are looking for content jobs and those who are hiring for them. In my series of posts, Chatting With People Who Hire Content People, I bridge that gap, and answer questions that career pivotors might have about roles and organizations outside of traditional media. I talk to folks who have content backgrounds and “get it” and those who don’t, but they will all have one thing in common: They hire content people, people like you. 

My interview today is with Kate Rockwood. Until our chat, I have admired Kate only from afar. As a new business owner myself, I was impressed with her ability to segue her magazine skills to building her own content agency. A former editor at O, the Oprah Magazine and Fast Company, Kate now runs Rock Top Media, a Chicago-based content agency that serves up editorial-like copy for brands and content marketing agencies in the business, tech, and healthcare space. I love her tagline: Magazine-Quality Content. By Journalists, For Brands. In our Q&A, we talk about when she saw the writing on the wall for print magazines, her personalized approach to business development, and why she believes that not every editor has to be a strategist, too. Here is an edited version of our conversation.

The Talent Fairy: You had a pretty good job at Oprah. Why the move to Chicago? 

Kate Rockwood: My wife and I were living in New York for six years — I was a senior editor at Fast Company and then O, The Oprah Magazine, when I got pregnant. That’s when the flip switched for me: It was so expensive, we had no family in New York, and the hours at magazine jobs can be nuts. The entire time I felt like there was an ax hanging over our heads as editors. I realized there just aren’t that many women in their 40s and 50s in consumer magazines. Where do we go? And I thought, I might not be one of the ones who make it! So my wife and I started applying for jobs across the country. I got an offer first at a content marketing agency in Chicago. That’s what helped me make the transition out of traditional media. I moved there as a content director. Moving into content marketing was seamless. There’s a new lexicon to learn—conversion funnel, content audits, lead generation—but so much of it translates easily. I just had to learn the new phrases. I was at the agency for a few years and got pregnant with my second kid and wanted more autonomy. There was a lot of travel and I wanted to have more control over my schedule, so I decided to start my own thing. Rock Top Media has now been around 5 years!

That takes a lot of guts! How did you get your first clients? 

KR: The agency that I left couldn’t hire me right away to be an IC or contractor. Which was a blessing because it meant I couldn’t rely on them for work. So I just made a giant spreadsheet of every editor person I had ever worked with. I reached out to them and said I was open for business. Like a former coworker, who had been a fact-checker, moved to an insurance brand. When I reached out, he immediately had work for me. Eventually he was like, We’d like you to write this one product page, but we actually need 10 of them. Do you know of other writers just like you? 

I was happy to make referrals, but I also wanted them to come back to me for the next assignment. Initially I partnered with a friend and we had an informal agreement that I would toss her stuff, but I wanted to be the primary person doing the communication. Now she does steady work for Rock Top Media. That was my early model, to outsource to one person. And it gave me the confidence, to say: Hey, we are a team of 2, 3, and now 5 writers. What do you need? And those companies that I did one-offs for before, now we can do content programs that span entire branded magazines or 12 case studies or 80 digital pieces to launch a new site vertical. I can split that up among our writers and get it done. And from the client’s POV there is a consistency to the content they are creating.  

Who are your clients? And how many client programs are you juggling at any one time?

KR: We typically juggle between 20 and 30 content programs in any given month. Sometimes that’s a one-off content deliverable, like a ghostwritten thought leadership piece for an executive. And sometimes that one program might be 250 content pieces for a new app that a company is developing. It really runs the gamut.

One of our clients is TrustWave, an IT data security firm. Another is Rally which is part of United Healthcare. We do a lot of work with business, health, and finance. We also do a lot of work for content marketing agencies, which then white label our work. We don’t do the strategy, just the content creation. I will refer clients to agencies for strategy work and then the agencies reach out to us when they are ready for us to write those 8 e-books or 12 product pages or whatever. I don’t think that everyone needs to be everything. We don’t have an SEO specialist for instance. I can recommend an SEO specialist to a client if they need one, and then incorporate what the SEO recommends into the content. It’s a nice ecosystem. 

How did you make those contacts with the content agencies and the SEO specialists? 

KR: I’m in some content marketing Facebook groups. If you are deeply part of those communities, they can be helpful. I love the Freelance Content Marketing Writer. It has about 4,000 members. The group is nice because they are making a real living from content marketing. 

I find it’s hard coming from a background as an editor to be a sales person, yet it’s such a big part of running and growing your own business. How did you crack that nut?  

KR: Last Friday I had my Q1 marketing push and told myself that I’d send 40 cold emails to new agencies. I’ll write to them asking, Do you use freelance writers? Here are five links that are examples of my work. I keep it short: Three paragraphs with five hyperlinks to, say, a cool ebook we did or a long form article we wrote. I sent five out today and one content director wrote back and said, “We do need more content marketing writers. What has the team worked on in the mar-comm space?” There is an appetite for people who can write well. If we send 50 targeted emails we might get two gigs out of it.  

How do you set your rates with clients? 

KR: $1/word is a great place to start. I do the quick math based on if there’s no interviews or research. Sometimes they’ll say that they have the copy already, such as a report that needs to be rewritten and given the magazine treatment. So it’s about crunching a time estimate of how long it’ll take to write internally and if the margin seems decent. I don’t charge an hourly rate to the client though; we provide project fees. 

Can you give me an example of a program/campaign you have worked on recently that you were really proud of?  

KR: Yes, I actually have two examples. A content marketing agency had a new high-level healthcare client coming in. They wanted to create a magazine, and the first issue had a two month turnaround. The content director from the agency said, How much of this can you do? We did half of the magazine and [the agency] did the other half. It was a lot of interesting and varied articles, like one on senior citizens and the opioid crisis, and another on the business case for value-based care. Very journalistic stories. The agency was over the moon and the client signed a two-year contract. 

Another was a direct brand that was putting together an app for people going through surgery. The patients got a piece of content every day. The client had a team of clinicians working on the content, but they didn’t have an internal writer to translate that clinical speak to editorial. We had to make it engaging for someone to continue using the app on Day 26, 27, and 28. I love those bigger projects where we are getting in there and doing deep content for one brand. 

How much are you writing yourself?
KR: About 50 percent of my job is writing. The paperwork does seem to be a time suck and takes up the rest of that. We have 7-10 steady freelance writers we assign about 4-7 stories to a month. We also have a senior editor, who does quite a bit of writing and manages all the freelancers. We have an assistant editorial manager who does a ton of writing and a lot of special projects, and then an office manager. 

Wow! That’s a decent sized team! How did you get the confidence to bring folks on full time?

I joined a mastermind group for female business owners in Chicago. That was back when I just had one independent contractor. I was overwhelmed by the volume of work, and I joined this group because it was all women. And none were in my industry. They were all small business owners who had between 1 and 20 employees. I realized handling all the projects was just too much work for me, but how do I afford to hire someone else? Those meetings helped a lot: I could copy and paste a lot from what the women in the mastermind said.  

How did you find this mastermind group? I want to join one of those!

It was a word-of-mouth thing. A friend who had a photography business told me about it. The way this one was structured was a small group of 10 Chicago-based businesses would meet once a month, for about five hours each time. Two people would take turns presenting their challenges. One woman was a manufacturer of furniture and was thinking of opening a second location, and asked the group, “What are the holes I’m not seeing?” Another wanted to rebrand, but had so much equity in her current branding she wanted to know how to do it right. We took turns facilitating and there was a one year commitment to be a part of the group. It was pivotal for me. You want to present as an expert to your clients, but the truth is we are building something that has never been done before. 

Goldman Sachs also has a small business program called 10,000 Small Businesses that I applied to and joined as well. It met every Friday for months and was incredibly rigorous. You are with people of all industries and also see people who have run their business for 20 years who don’t know anything more than you know! Most people are doing it with intuition and a bit of luck.

One of the issues I have to deal with is doing my own content marketing, which takes a lot of time, but I don’t get paid for those hours. Do you content market yourself?

I send out emails [as noted above]. You see a lot of agencies do newsletters with tips on how to do content marketing well. But for me it’s more personalized, I just reach out to clients directly and it’s more one-off emails. I joke that the cobbler’s kids have no shoes [when it comes to content marketing]. But we are not an SEO play. People aren’t looking online and finding us. It’s about relationship building.

So true and such good advice. Speaking of content marketing (!), you may have seen that I have a quote series called “Why Editors Make the Best Hires.” What unique skills do you believe that editors have to offer the world?

The appetite is out there for good writing and for knowing how to package content well. I think as editors we have a knack for packaging; that is what sets us apart. We understand how readers approach the page and the screen. We consider everything—the headline, the text, the pull quote, the call-to-action, the related pieces—and we know how to draw the reader in and sustain their interest. That’s a real skill that not everyone has, not even every storyteller has.

Such a nice thought to end on. Thanks so much for your time today, Kate!

KR: Thanks, Chandra! You’re the best—it’s my total treat to chat with you.


Chandra Turner is founder and CEO of Ed2010 and Talent Fairy. She is a talent recruiter specializing in the content and media space. She also offers personalized career coaching for media professionals at all stages of their career. 



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