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Content Strategy

Hiring My Own Boss Made Me a Better Marketer

January 29, 2016

I’m not a “Director-level” marketing professional. At least, not yet. I’m currently Head of Content Marketing at ReviewTrackers, a SaaS in Chicago. My boss is the CEO and founder, and he’s a former marketer. A damn good one, too. But he needs to focus on CEO things, and we are looking for a VP of Marketing to help him make decisions, be my boss and shape the rest of the marketing team. 

TL;DR – Because I work at a startup, I’m hiring my own boss and it’s a little strange, but good.

I currently work with a few great marketers, and for the first time in my career, I love coming to work. I will gladly put our marketing strategy toe-to-toe with any Fortune 100 marketing plan you can find. I feel comfortable with my assessment of our small team’s marketing prowess, but we desperately need to hire a VP of Marketing; for the sake of the company, my boss, and my career.

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What We’re Looking For

In the past 6 months, we’ve gotten close. This is an important hire, possibly one of the most important in the history of the company, and can have tremendous effect on every aspect of the organization. Knowing the right mix of strategies, the right tactics, and implementing them at the right time is crucial. We know we need someone with years of marketing strategy experience across different industries. After all, online reviews transcend industry verticals, and we need a marketer who can adapt their strategies to best communicate to hospitals, hotels, strip clubs and morgues.

At the same time, we need a hands-on, swiss-army knife. They can’t sit back and strategize all day, they must contribute to the marketing efforts. (This is usually when marketers’ eyes glaze over.)

What I’ve learned

Okay, it’s probably not as complicated as I’ve made out to be. We’ve interviewed over 300 applicants. To say we’re being picky would be an understatement. But it hasn’t been a waste. I’ve become a better marketer because of it.


As I focus on traits I’m seeking in a potential mentor, I’m learning which of those traits I already possess. And, more importantly, where I need to improve. These marketers all have double the amount of experience I have, and I am constantly evaluating what I’m seeking in a mentor.


I’m studying their storytelling, their focus on audience, and ability to empathize. I’m learning, first hand, the value of audience information in marketing. All these great marketers are asking about me and my background first, and shaping their message to help me understand.  

Specific Tools and Tactics

I’m picking the brains of the most successful marketers in Chicago; their favorite tools, their best experiences, and their opinions on the future of marketing. There are obvious ones, like Hubspot, but a lot of less obvious ones like Buzzstream, Screaming Frog, and Moz. I can pick their brains, getting in depth, asking for specific examples of success with each, helping me prioritize my strategy, giving me creative ideas for new channels.

Interviewing Skills

I’m gaining valuable interview experience. Now I know the core thirty questions I want to ask any employer before I accept an offer. Even better, I can avoid hiring issues for my own company when I start one later down the road.

Why We’re Having A Hard time

Marketers (with the experience we’re looking for) don’t usually want to roll up their sleeves. Sure, they’ll develop the content strategy — once. And, sure, they’ll pull analytics — but they’ll have to outsource it. After all, they’re the ones making the big bucks, why waste time performing menial marketing tasks? There are only 5 marketers on the team but we’re already doing the work of 10. If you’re a marketer, but you don’t want pull reports or coordinate a guest post, this probably isn’t the job for you. I can hear myself now, “Yes, that funnel is a great idea. I’ll take care of it when I can, but it would be much more productive if you set it up.”

Another aspect of the role is the organizational structure of the marketing department. This person should not only be able to pick some low-hanging fruit on day 1 and plan a road-map to get us to day 180, but along the way, we’re going to be hiring like crazy. They’ll be spending a lot of their time working with our CEO and the rest of the executive team to plan a course of action for the entire company. They’ll decide budgets, how many interns to hire in the summer, which automation software to implement, and the roadmap of scaling the team. There are a lot of decisions to be made, so we need someone who can execute.

In fact, if you know someone who would like to apply, please send them our awesome new recruiting video or a link to our jobs page.

A Growing Trend

I want to point something out that a lot of entrepreneurs may not realize. Hiring is really, really hard. Finding people who are good at their jobs, for a price your business can afford, and who happen to be looking for a new job is rare. In the “startup” world, the right candidate is the real “unicorn.” This is also why a lot of startup employees end up interviewing their own boss.

The bare minimum metric for success is a business which has put extra care into hiring the right people from the start. You always want what is best for your business, but you really get whatever is best for your business at rate you can afford. Hiring great employees means you must pay above market rates. Unless you are VC-funded and have room in your budget to hire all-stars, it can be a very difficult task. Combined with the zero-bandwidth and I’d be willing to bet that talent acquisition is one of main causes of startup failures.

Impact on Business

Obviously, this VP of Marketing will have a serious impact on my company. Some of these traits and skills can can take a profitable business and make it even more successful. At the same time, this person will take a lot of work off of my boss’s plate. This means more time wearing his CEO hat. More time to make company-changing decisions, or perhaps even a weekend afternoon off to relax. This hire will change his life. Almost as much as it has changed mine.

No pressure.

Chances are, the person we hire won’t be perfect. That’s fine, I’m not perfect either. I’m not looking for perfection, I’m just looking for someone with integrity. A marketer with integrity, how hard can it possibly be?