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How to Craft a Winning Content Strategy with Column Five’s Ross Crooks

Gray MacKenzie
Gray MacKenzie is a true operations nerd who has spent the past decade helping hundreds of agencies build more productive, profitable, and healthy teams by solving the core issues plaguing their project management.

To chat with Gray and have ZenPilot lead your team through the last project management implementation you'll ever need, schedule a quick call here.
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Ross Crooks is one of the Co-founders of Column Five, a creative agency specializing in brand development and storytelling. There, he oversees creative operations, working with a group of wonderful humans to craft content strategy for some of the most forward-looking companies. He is passionate about building a thriving culture based on transparency, trust, and having a good time.


Topics discussed in the episode:

  • The Importance of Crafting a Content Strategy
  • Marketing Content Strategy Best Practices shared by Ross Crooks
  • The Evolution of Column Five’s Content Strategy
  • Career Opportunities with Column Five

Presenting Sponsor: ZenPilot


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Episode Transcript:



Gray MacKenzie

All right. Welcome back to Agency Journey this week. I’ve got the pleasure of bringing on Ross Crooks from Column Five. columnfivemedia.com. Ross, thanks for making time and joining me today.

Ross Crooks

Yeah. Thanks for having me. I appreciate it.

Gray MacKenzie

So we got a chance to meet earlier this year. You got a really cool story. And I want to dig into a couple of similarities in your journey and some of what we’ve been through. But first, could you give us maybe 32nd minute-long kind of overview of Column Five and your role at column five?

Ross Crooks

Yeah, sure. So column five is a creative agency. We do a lot of marketing work for brands, and in more recent years, that means kind of working with them from anywhere in the brand strategy, content strategy, and then into content production. So we’ve done a lot of creative content production in a variety of forms over the years. And our client base looks like a lot of tech brands, but we have a pretty diverse array of clients in the education and nonprofit space as well. So it’s spread around quite a bit.

Ross Crooks

And then my role with the company, I’m a co-founder. I have two partners that I started qualified with about twelve years ago, and I oversee our creative teams and our kind of operations teams were there three cofounders when you started as well. That’s kind of a trick question. There were five originally, but we actually sort of separated from the other two pretty early on. So it’s been three for most of the ride.

Gray MacKenzie

We started. Andrew, my current business partner. He and I, along with two other good friends out of our College dorm room back in 2011, started our first agency. I went and met with a friend. Totally different. He’s a big pole barn builder, so totally different industry, and had lunch with him like my senior year. And he said, So you’re starting a business. How many founders? I said four. He’s like a year from now when we’re talking, there’s not going to be four of you. It was like a rude thing to say.

Gray MacKenzie

It never works out. Don’t take it personally when it happens, you guys probably won’t be in business together for the whole time. A couple of years later, it was the two of us who still have a great relationship. It’s just hard to get. A business is a big undertaking, and not everyone is a fit. And you don’t know all that stuff going in.

Ross Crooks

Yes, it really has to be kind of a perfect balance of equal contribution and skill sets that work well together and personalities that work well together.

Gray MacKenzie

Right.

Ross Crooks

We still give each other a hard time about ownership jokes.

Gray MacKenzie

It’s classic. So I was doing some digging through some of your backgrounds. This theme of, like, data design or data visualization came up. You are an author. We didn’t mention that at all, but you’ve written a book on infographics, content strategy. You started a software that looks like it was around infographics. Where did that focus? Maybe tell us a little bit, I guess, to set the stage on what that background looks like. But where does that come from?

Ross Crooks

Yeah. Good question. It’s a bit of a long story and a little bit of an accident. But what happened, essentially, was my cofounders and I were all kind of working in different businesses. We were all working in the clothing industry. I had started clothing recommendations clothing brands with one of my partners, and our other partner was doing the clothing boutique. And so we’re all kind of working together in the space, trying to make our first companies work. And we started a blog that was sort of like an art, music, fashion, lifestyle type blog to be able to cross-promote and create a content strategy for our own brands, but also, like, develops a content strategy, bring partners in and build relationships.

Ross Crooks

And that sort of thing if you only create something of value, basically through sharing and giving media. And as we got into developing a content strategy and started creating content for this thing, we started to get pretty good at crafting a great content strategy resulting in creating and promoting content and getting it popular, having to go viral. And that sort of thing, this is like 2007 2008. And what happened is a lot of brands started to see us have success in that. And some of the early startups that we’re getting into kind of content marketing and trying to stretch their marketing dollars a little bit further.

Ross Crooks

And so they started hitting us up to create and promote content for their blogs. So Mint dot com was a really early one that was a client of ours that was kind of a startup at the time. And we started creating content for them. And how the data visualization and infographics focus came was really what was happening is we were creating, promoting content and a lot of the social news sites at the time, which was like the Redditbid. Com stumble upon. And what we were seeing was a lot of people really geeking out on old infographics, like scanning them out encyclopedias, looking at them in old newspaper clippings.

Ross Crooks

But no one was really creating new, contemporary infographics outside of, like a few news outlets, like The New York Times at a very high level. So as we were writing articles for these startups, we started to kind of piece together, hey, we can use this data from these startups and visualize it and use contemporary kind of graphic design to make a more visual artifact. And that was kind of how we made a name for ourselves was in kind of pioneering those common. Now it’s kind of a mainstay in the marketing ecosystem, but it’s kind of long, skinny blog infographics kind of develop organically like that.

Gray MacKenzie

That’s wild. Remember Noah Kagan, was it meant back in the day right before our time, I guess. Okay. And that’s kind of a wilderness. At what point then does the agency become, like, was that. Did you just get enough traction on that side that that was the evolution of, hey, we want to start? We might as well do this for now as an agency or what’s the story?

Ross Crooks

We were just trying to figure out a way to work together and do something that was fun and creative and make some money. And yeah, that started to get traction. And so we sort of slow over the next year or so kind of shuttered our other businesses and develop something together. And it started growing really quickly.

Gray MacKenzie

So we kind of put all the eggs in that basket and then so you want to build out a software. But my impression is it’s an infographic generator, right?

Ross Crooks

Yeah. Kind of a web-based design tool that was meant for.

Gray MacKenzie

Like, Canva for infographics, basically. Yeah.

Ross Crooks

I think there is a lot of similar stuff.

Gray MacKenzie

Okay. Makes sense. And then is that still active?

Ross Crooks

There are a few clients that we’re still working actively with, but we’re not actively marketing at our selling yet.

Gray MacKenzie

Makes sense. How was that? I assume at that point, the agency already had legs. Was that the I mean, I feel like every agency goes through at some point in time. They’re like, we’re going to build the software on the side. We’ve got these extra development hours and resources that we can do and build it out. And some of them take and some of them don’t take as much. Yeah, there’s a range. But with the agency, the main thing the whole time and software was that side business or what’s your yeah.

Ross Crooks

We started the agency in 2009 and kind of properly started it. And then we started incubating the software may be in 2012 or 13 and then spun it out into a separate company in 13 or 14 and raised some venture capital or speed ground for it. And kind of made it split off the company and made a separate go of it with a separate team. And we did that for three or four years. And we have a lot of good traction but didn’t get quite the traction that we needed to have it survive on its own.

Ross Crooks

And so we ultimately pulled it back into the agency and kind of kept focusing on that.

Gray MacKenzie

I can 100% relate. I mean, we a project management tool. Starting in 2013, House spun it out as its own business, took all the best people from the agency, and moved over to the software. And ultimately, we weren’t that good at software and consulting and had a choice to make between one or the other and went down the road that we were better at the less lucrative path from an evaluation perspective.

Ross Crooks

It’s hard work. It’s a competitive area, especially when you’re in something like project management or the market. It’s like just in this family-busy ecosystem.

Gray MacKenzie

That’s awesome. And then so for a little while, you were also teaching at Columbia, and you were writing and you’re building an agency and you had a fashion manual. I’ll back up. I’ll start with the book here. What was the journey to say? Hey, I need to write a book. And then was it worth the effort that it took?

Ross Crooks

Yeah. Good question. You make it sound like everything happened at once, and it kind of did. It was like, I think 2012 ish, but yeah, we had the opportunity to widely approach us, book publisher, to write a book on infographics, and we were kind of the leaders in that space and had done a lot of thinking around it and developed more practices and things like that. Other people were creating infographics for sure. But I think we were the first people to start to do it at scale and really commercialize it.

Ross Crooks

That was like an exciting opportunity for all of us to be able to put our name on something and share what we knew and also a good kind of marketing tool to have to say that we wrote a book on the topic. And yeah, I think it was the exact same week that Columbia University approached us to write to do a course on visualization of information, so we couldn’t really say no to either. And so we were developing the course and writing the book at the same time.

Ross Crooks

And I was on my honeymoon for some of it and moving into a new office and building it out and that sort of thing. So it was a very crazy time. But I think looking back, certainly, I think it was worth the time and effort to be able to write the book and the experience of teaching as well. I kind of wish I had more time to dedicate to it and obviously thinking of philosophy and all those things have evolved quite a bit over the years from those early days.

Ross Crooks

So I think I’d love to be able to update it sometime or to do a follow-up.

Gray MacKenzie

Right. Well, I wanted to bring it up because you’re saying Wiley approached us and Columbia approached us. And then if you go to columnfivemedia.com for anybody who’s looking at the site, you can see a bunch of logos. You guys have worked with LinkedIn and Uber and Netflix and Dropbox, and you’ve got all these big household names in the tech space. But those connections obviously don’t come to most four-year-old agencies or real estate agencies. Is this largely a product of networking or I mean, the combination of you guys were super early on, a trend that stuck as well.

Gray MacKenzie

And so you got a chance to be first movers and benefit from that advantage. But you’re saying things that most agency owners don’t get to live through early on in their career, which is why I wanted to have you on, because it’s a fascinating story. Where did those connections come from?

Ross Crooks

Yeah, I think a lot of it did come from being kind of a first mover in that space. So we were able to be found when people were looking for execution on that. The other piece was we were working with a lot of these kinds of scrappy early-stage startups. So as these people got acquired, we kind of came into their mother company, right. So into acquired men. So we work with Turbocharc and we work with QuickBooks and these sorts of things. We work with LinkedIn and Microsoft, and they came together and GitHub and things like that.

Ross Crooks

So I think some of that just happened naturally through this sort of M and a cycle. We had a lot of really good clients early on that we were friends with and that was really helpful to us and just making introductions. And those people went places. I think a lot of that is just sort of the organic things that happen when people move from company to company and clients acquire each other. But I think the nature of our work has always been pretty visible because early on it was like the goal was to create an effective content strategy and for the content to always to go viral.

Ross Crooks

So we had a lot of viral content thru an effective content strategy. And we had contributions, a lot of our graphics were created by column five. And so a lot of people would find us through those sorts of things. And now that’s shifted away from the novelty of the format, and it shifted away from being able to get credit on everything we do. It’s much more about our own content strategy. So creating useful resources on our blog and kind of pulling people into that blog outside of being beautifully designed.

Gray MacKenzie

You guys produce a ton of content on all these different topics. I definitely recommend looking at the blog if you’re listening for inspiration as well as the resources themselves. So that piece hasn’t, even though infographics they zoomed up in terms of a trend and then maybe have cooled off a little bit. The dedication of content hasn’t changed at all, which is cool to see from the story. One of the things that a lot of early-stage agencies struggle with agencies in general struggle with is, who’s my market?

Gray MacKenzie

What are we doing for them? What’s the fit between what we’re good at and what the market needs and how do we get in front of people? Was the tech ecosystem? Was that an intentional decision or was that kind of an accident of, hey, there are early adopters, and you guys are early adopters.

Ross Crooks

I think it was more just the coincidence of that. And even over time, we’ve asked ourselves the question of, like, do we need to narrow our focus because we work on with a lot of different companies, maybe 100 plus companies in any given year, and those are all across different industries and vertical. So I think there tends to be a tech focus just because those are people that have pretty well-established digital marketing practices and so it tends to be a good fit, but we’ve never been exclusive in that way.

Gray MacKenzie

Right. That makes sense how scaled out and are servicing the volume of clients that you are. What does that look like? Scaling client services to support that kind of growth?

Ross Crooks

Yeah. It’s always a work in progress. I think we’ve been experimenting a lot even this year just with reorganizing our teams and working in different ways that might better serve our clients. I think that what I noticed there, I guess, is that there’s always this balance between the flexibility of staffing, anyone on anything at any time with the focus of having a dedicated team that works really well together and has clearly established ways of working and that sort of thing. So there are pluses and minuses about those things.

Ross Crooks

And I think we’re trying to figure out what’s the balance of the most pro.

Gray MacKenzie

Right. Looking forward, I was just mentioning, this is a great time to grow. We’re coming up on the fourth consecutive quarter of the best growth across the board for agencies that I’ve seen in the last ten years being in this space. But staffing for that is a challenge at the same time. That’s part of where you’re spending some of your time now, but kind of inclusive of that and other priorities you’re looking forward to what is the end of 2021 look like? What does 2022 look like for the agency?

Gray MacKenzie

What are some of the big targets that you guys have as a firm?

Ross Crooks

Yeah. I think recruiting has definitely been a big one for most of this year. I think coming out of last year, that was pretty uncertain. We were sort of hunkered down and just making do with what we had and figuring it out. And then the beginning of the year hit and felt like we needed to grow by 25% overnight. And so that’s been a longer than usual cycle to get new people in the door. But we’ve just had maybe five or six new people start in the last month or so, which is really exciting to have some new faces and to be growing again.

Ross Crooks

I think what that looks like is we’re really trying to I think we’ve been behind in some of the things that we’ve been doing just because we haven’t had the staff to be able to be really Proactive in some of those ways. So I think it’s getting more intentional and more Proactive with each of our clients to be able to look forward to what needs are not being met. What opportunities are there to grow with those people now that we have the capacity to do it?

Ross Crooks

And one of our big focuses and sort of one of our this might be going back to your other question about the evolution, as well as one of the more intentional shifts that we’ve made in the last couple of years was to start to move upstream from just a lot of creative content production into the strategy realm. And so we’ve really built out that practice and those roles on our team to be able to build the foundation that’s needed to create content and any marketing down the road, any sort of communication and understanding at the core of the brand, what’s their sort of purpose and values, and then flowing that into a strong content strategy and then being able to actually create content strategy for them.

Ross Crooks

So some of the roles that we’re hiring for right now, we’re hiring a couple of strategist roles. We’re hiring for a new account director or maybe two and a new video producer as well.

Gray MacKenzie

So what is that when you say staffing up and kind of going upstream and you mentioned Strategist roles, I’m assuming that that’s maybe strategy roles. What’s the correlation or how is you guys are scaling up? How does that set up from an org chart perspective, I guess. Do you have because typically, you’ll see, like an account manager or Strategist is kind of lead of X many accounts, and they either work in pods or shared resources underneath them. But you mentioned account directors. So is a strategist working across more accounts to your accounts.

Gray MacKenzie

What’s an account director’s role? How do you kind of break down those distinctions?

Ross Crooks

Yeah. Our account directors are kind of responsible for growth in the relationship. So they’re maintaining the relationship and doing some planning and budgeting and things like that. But they’re also really responsible for finding new opportunities and understanding what else clients I need. Our strategies are really focused on actually just building out the strategy in any given engagement. So understanding where a brand is at the time, what gaps might need to be filled in their strategy and being able to do the research and make recommendations on that.

Ross Crooks

But then we can go and kind of execute on downstream and who coordinates an execution, usually a producer role on our team. So that’s sort of our creative project manager. It looks a little bit different on different work types. Some people are very tactical project managers, and some are getting much more into the creativity and helping to guide the team in that. But, yeah, they kind of help run the show.

Gray MacKenzie

That’s awesome. Ross. I’ll look this up real quick. The careers page. I’m trying to remember, but I think there’s a link from the footer that takes you to the careers page on the site.

Ross Crooks

Yeah. ColumnFiveMedia.com/Jobs

Gray MacKenzie

Cool.

Ross Crooks

Okay.

Gray MacKenzie

That’s even easier. Awesome. So if anyone’s interested in opportunities with column five actually just saw one person who you just hired is from Erie, Pennsylvania.

Ross Crooks

Yeah.

Gray MacKenzie

So that’s where I grew up.

Ross Crooks

I think we just hired two Pennsylvania people.

Gray MacKenzie

Okay. We’re infiltrating Column Five! So that’s really happening. That’s awesome. Well, this has been really fun to dig into the Column Five story.

I think as you look at the kind of closing out this year, one question I’ve just started asking people, I did not prepare you for this at all, but this is just kind of a fun question. Is around kind of year-end expenses or like write-offs running to a lot of agencies.

This has come up a handful of times here recently in conversations with folks, “I have made more money than I’ve ever made this year. What are we writing off?”

Do you have any fun end-of-year write-offs that you’ll be paying for this year or past stories?

Ross Crooks

I don’t think so. Usually, it’s a balance because we have clients that are trying to get rid of their budgets. But sometimes we’re playing the bank in that where we might take it on the nose from the tax bill. But we’ll take your money and work through next year, right? But, yes, sometimes we’re also trying not to cash the checks until the first of the year, for sure.

Gray MacKenzie

Yeah.

Ross Crooks

Nothing big. We started doing a little more just in terms of we just got everyone their own credit card. So we’re having a lot more kind of put a lot more toward kind of connection and communication events. So a lot of times we’ll all order lunch from our own respective places while we do our town hall meeting, or we’ll have different celebratory type events where everyone can just kind of spend their own meal budget or that sort of thing. That’s cool.

Gray MacKenzie

I’m obviously a tool nerd. Are you guys using do you run your credit card through Brex through Ramp or are you using something else?

Ross Crooks

We’re using Divvy.

Gray MacKenzie

Okay. Yeah.

Ross Crooks

We just switched over to them earlier this year.

Gray MacKenzie

Makes sense. That’s awesome. It’s been cool to see that just the business credit card space changed the last couple of years. It was like Brex kind of burst on the scene, and then all of a sudden, Divvy was the next big one, and Ramp is just raising an absurd amount of money right now. So interesting to watch that space evolve.

Ross Crooks

Yes, it definitely seems like a good evolution because I think it’s been messy for a while or a hard thing to do.

Gray MacKenzie

That’s awesome, Ross. For folks who want to connect with you or follow you online outside of the column five site, is there anywhere else we should point people to?

Ross Crooks

I don’t think so. I’m not active early on social media, which is strange for a person in my position, but I have a couple of accounts but don’t use much, but everything’s really through. It’s kind of my focus. Awesome.

Gray MacKenzie

Cool. We’ll make sure all that stuff is in the show notes, but I appreciate you coming on. Being generous with your time. This was a fun conversation. Thanks, Ross.

Ross Crooks

Thanks, Gray. Appreciate it.


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