Debra B. McCraw’s Career Journey from IC to Content Director

This story is part of our guest post series on career journeys in content marketing. This series focuses on big career changes and includes insights and advice to help guide others who want to make a career change in content. You can read the first, second, and third career transitions posts for more inspiration.

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Meet Debra B. McCraw, Senior Director of Content Strategy at CompTIA. After several years at the company, Debra went from being an individual contributor (IC) to a director with several direct reports. You can follow Debra on LinkedIn here.

1. When and how did you get started working as the Senior Director of Content Strategy at CompTIA?

I've been with CompTIA for seven years now. I had been freelancing for a long time, writing and editing for organizations including Goodwill Industries International, Northwestern Mutual and LinkedIn. In 2016 I saw a job posting for a Writer and Editor at CompTIA and I was intrigued. I was at a point in freelancing where I either had to step up and grow my business—or figure something else out. It's that tipping point a lot of freelancers get to, where if you want to grow, you've got to find a way to scale. So I decided to give CompTIA a chance.

When I interviewed for the position, it checked all the boxes of things I was looking for. I considered myself more of a content specialist who was focused on the content creation side of things—less so on the strategic side of it. And that's what I was hired to do. At that time my company had a fairly simple content strategy, and there wasn’t a content career path. There was just one other content marketer in the organization, and we had the same responsibilities but were supporting different business units.

As I learned more about the organization and its goals, I thought about where the opportunities might be and what we could do. It started with learning about SEO and understanding how it could attract a new audience to further drive our business. We had really strong branded SEO, but we hadn't really explored the unbranded side. So that's an area I dove into. Over time through attending conferences and doing my own learning, I studied content strategy and what it meant, and developed a content strategy for CompTIA.

2. List out your job titles with years for as long as you've worked in content marketing

• 2009 to 2017 - Freelance Writer and Editor
• 2018 - Manager of Editorial B2C Marketing 
• 2019 - Senior Manager of Content Marketing Strategy 
• 2020 - Director of Content Strategy 
• 2022 - Senior Director of Content Strategy

3. As a Sr. Director of Content Strategy, what does a day in your life look like?

It's a little bit all over the place. The difference I've found between being a manager and a director is a lot more people want time with me. I get pulled into a lot of meetings to provide the content strategy perspective. For example, in any branding discussions or whenever we go through any sort of website redesign overhaul, I have a seat at the table.

I have a lot of standing meetings with marketing leadership too. We have an internal research team that I meet with regularly, and I have regular meetings with the web development and social media teams. As a supervisor, I also have a weekly one on one with each of my staff members as well as some of the primary contractors that heavily support us and are sort of extensions of our team.

It’s much more thinking and talking versus actually doing. Every day involves a lot of conversations, ideating, and providing guidance and direction on projects. Whether it's in terms of prioritizing what's most important, making sure my team understands the goals and objectives that we're trying to meet, or our messaging/value propositions—I make sure everyone's on the same page and has everything they need to do a really good job. 

Sometimes on Fridays, I'll look at the week ahead. If I have any blocks of time that aren't filled with meetings, I'll build in two-hour chunks of focus time. I use that time to evolve our strategy and our processes. When I'm in meetings all the time, it’s hard to find quiet time to think and innovate.

4. What was your biggest career pivot & the motivator behind it?

Going from an individual contributor to a leadership role was the biggest pivot. When I went from freelance to full-time, there was an adjustment to no longer being my own boss, but the work I was doing was pretty similar.

When it comes to managing a team and being a leader in an organization, there's a lot that comes with it in terms of mentorship, guidance, and motivating people. You don't want to micromanage, but you want to make sure things are getting done, so finding the balance is important.

As far as motivation, being in a leadership role was something I had been wanting for a long time. When I started at CompTIA, I had to pave my own path, and it took time for those opportunities to come to fruition. But last summer, our marketing department went through a reorg that merged multiple content teams, positioning me as a leader in our organization. 

5. Were there skills that carried over from your last role to your current one?

You certainly could lead a content team if you haven't been a writer-editor before. But knowing what it takes to produce content makes me a better leader. I understand where my staff is coming from. I understand the challenges that they're facing, so I look for ways to help alleviate that.

Part of the reason that I got to where I am today is because I’m a very good writer and a very good editor. I produce high-quality work. So I can also offer the editorial perspective of asking questions or identifying holes in a story. To offer that kind of guidance it really helps to have that background.

6. What new skills have you learned in your role that have helped you succeed?

People skills definitely come into play. I am someone who’s always been very direct and forward. I tend not to beat around the bush and sugarcoat things. When you are in a leadership position, you have to recognize how that comes across on the other side. 

So I've learned to be more thoughtful in the timing of providing directives or feedback and how I communicate with people. It's easy to just send a Slack message, but I think okay, if I were to get a Slack from my manager, that was just very quick and direct and didn't have any context or anything, it could be nerve-wracking. So I make an effort to just say, like, hey, can we hop on a huddle? Don't worry. It's good news. I try to preface what we're about to talk about. 

I've had really amazing managers and I've had some not-so-amazing experiences. So I try to remember what that's like and be direct and transparent with people as best I can while still trying to choose my words and tone carefully.  I try to understand each individual—what works for them, how they digest things and how they react to things.

7. What advice would you give to someone who wants to pivot from an IC to a leadership role?

One is to look for opportunities to be a leader before you have the title. Speak up when you have something to say. Take the lead on projects or help mentor junior staff. Manage a project, do anything that you can do to show that you have an interest in this and that you are taking the initiative to move your career forward.

Two, think about the leaders, whether in your organization or elsewhere, that you admire. What qualities do you admire in them? What do you think makes them a great leader? If it's someone you have a relationship with, take them for coffee. Ask them, how did you get to where you are? What advice would you have? How do you handle XYZ situation? Try and learn from what they've experienced to figure out what kind of a leader you want to be. 

And then my last piece of advice is really just in general for careers—I'm a big proponent of just saying Yes. If there's an opportunity there, even if it seems scary, even if it seems like something that you're not quite qualified to do, just try it. Say yes. Give it a try. See what happens.