Why is hiring a great content marketing specialist so difficult?

Like finding a needle in a haystack, except you’re looking for a specific pine needle in a big stack of pine needles.

Perhaps many marketing managers can relate — as someone who is responsible for keeping the Help Scout blog moving along, there is no question I receive more than “How do we hire a great content person?” It seems to be on the mind of growing companies everywhere.

Since we’ve begun hiring for this position at Help Scout, however, I’m starting to see why nabbing an effective content marketer is so difficult.

It isn’t the lack of hungry, hard-working candidates, the trouble comes in finding a myriad of specific skills under one umbrella; manifest in a single person, so to speak.

This is new frontier for me personally, so I figured we’d start this re-cap off with some third-party feedback.

What you should look for

To get a better grasp on the challenges to come and what Ivana and I should really be looking for, I reached out to my network and received some valuable responses.

I’ll share a few below (thanks Mark, Georgiana, and Will for the feedback).

Mark Hayes, Head of Communications at Shopify

Boy, oh boy hiring a good content person is tough. I find they’re either experts at ecommerce and marketing but struggle with writing, or they are awesome writers but don’t know much about the subject matter. Finding a happy middle ground is difficult.

In general I look for: history of success, resourcefulness, and a balance between writing and ecommerce skills.

Our most recent hire was Richard Lazazzera. I knew I wanted him because he was already writing the type of content we want at his own site, A Better Lemonade Stand. He was an easy choice… having a history of successfully published content is important for me. People don’t just become good at this stuff overnight — there’s a trend.

With Mark, I actually hired him as our social media manager even though he had no experience with social. His history of success was a site (and apps) called Toronto Food Trucks which be built from scratch by himself. That showed a huge amount of resourcefulness, I knew he wouldn’t be someone whose hand I would have to hold — I could point somewhere on a map and he’d find a way to get there.


My big takeaway from this was that having an existing audience (“platform”) might be the most important asset of all.

Even if it isn’t all that big, it shows that this person is familiar with and passionate about helping people solve problems. And that they enjoy building communities around interesting topics.

If you’re hiring, I recommend you visit Richard’s site in particular. It jumped out at me like “Wow, if only I could find a person building an audience like this in the customer experience space.”

Focus on the quality of the platform they’ve built, not on the sheer size; be more concerned with where they can go from here.

Georgiana Laudi, Director of Marketing at Unbounce

One of the things we do differently at Unbounce is that we don’t accept resumes.

In order to apply for a job you have to build a landing page.

This helps the evaluation process in a big way. It takes a little longer to receive and analyze applications, but those we do get are of much higher quality.

Obviously from a content perspective, writing and tone are huge. I also need to see published writing and have someone else who I trust with that stuff (often Oli) read it to confirm it’s quality.

If all that is gold then I do an interview and gauge if the candidate shares similar core values with the Unbounce team.

Once this is obvious, especially with more junior positions, I’ll hire for personality and “fit” over experience.


The idea that the application process should be more of an “audition” is one that I love.

Unbounce is conversion software, so the landing page idea is gold — it will qualify domain expertise and interest in the topic very quickly.

We have not implemented anything like this quite yet (our search is just beginning), but the idea that potential hires should execute on some small project before they are further evaluated makes a lot of sense.

I also thought the mention of a cultural fit was important and highly underrated. In fact, I’d argue a culture fit will generally result in the person already having the right tone and voice for your content.

Will Hoekenga, Content Marketing Strategist at LeadPages

As someone who was a “writer” before I had anything close to a clue about marketing, here’s what I’ve realized: most people who identify purely as writers are grossly unaware of marketing… which is a damn shame.

Many of them see writing as more of a lifestyle than a highly valuable skill. It is rare to find marketers who were writers first. It’s usually the other way around.

This is one of the reasons why it can be difficult to find people who can create exceptional content — if they’re industry experts, they often don’t have a ton of experience writing; if they’re great writers, they often don’t have a ton of industry experience.

So yes, obsessively or narrowly focusing on finding “good writers” for content marketing and/or copywriting positions can be a mistake. As a former English major, it’s a little tough for me to admit this, but I actually think it’s easier to turn a merely adequate writer into a good writer than it is to turn someone with little to no marketing skills into a good marketer.

If you’re looking for a “great writer” to hire for a content marketing and/or copywriting position, look for people who have built an email list around written content they’ve created. It’s nearly impossible to pull that off without having some degree of “good” in both the writing and the marketing categories.


I also wanted to get the opinion of someone who is head’s down writing great stuff, and Will offered up an analysis that mirrors my own.

Writing creates “lift” for other skills and interests; the most important thing in content marketing is actually customer success, or more specifically, creating ideas and tactics that help customers succeed.

The ability to write allows you to express your ideas clearly, but being a writer is obviously not enough.

Much to Will’s chagrin, he feels that writing is the easier skill to teach — I would agree.

The content marketing trifecta

Content marketers, in general, benefit from being renaissance women/men.

There are so many extra skills that can come into play.

If I had to boil things down to a “Big 3,” however, this is what my content marketing trifecta would look like:

This belies the importance of other abilities like: everything SEO related, copywriting, email marketing, conversions, etc etc etc… but this is definitely the starting point, in my opinion.

Let’s break it down:

  1. Networking skills. Although some might call these “promotional skills” or what have you, good content marketers only become great when they have the drive, ability, and interest in connecting with other smart people. Industry leaders in any topic all know and regularly chat with each other; content marketers should know how to connect with up-and-comers and bigger players.
  2. Domain expertise. With the Help Scout job posting, we placed emphasis on a passion for the “user experience.” This was key for us. Just because someone can write about sports, fashion, or traveling doesn’t mean they have the chops to succeed in this space. You shouldn’t judge people too harshly (I mostly learned about customer service as I went), but they need to have some relevant experience and interest here.
  3. Writing ability. Not spinning pretty prose, but crafting clear, concise writing that is a fit for educating customers. Flowery writing would actually be a detriment. You should also look for an understanding of web formatting, and a general knowledge of writing for the web (ie, they break up long paragraphs into a bullet-point list without being asked). Lastly, personality is big: adding enough to be interesting, but not so much that you’ll end up with an angry mob.

I jokingly refer to this as my triad of frustration because not only is it hard to find all three traits, there is a secret fourth problem — availability.

People who are great at all of these things “get” how to build an audience; they often understand it so well that they’re already making a living from doing it. Or, they’re working as a freelancer (which they might prefer).

So, the search doesn’t end simply by finding someone who has these traits, you also need to hope that they’re available for work.

You can get around this by hiring diamonds in the rough, but then you’ll have a harder time identifying “Can they actually do this?”

It’s a tough process, to be sure.

One way that you can better qualify candidates is by trying to strategically intimidate people with your job posting.

Using your job posting to “intimidate”

I personally wrote the job description for the position, which we featured on our site and on Inbound.org.

Below I’ll explain the language I used, and why I used it.

You know that your job is just getting started once you’ve hit “Publish.” You’re a marketer with an uncommon talent for writing—you’re not a writer with a passing interest in marketing. You’ll be teaming up with our marketing department to create industry-leading content that helps online businesses provide outstanding customer experiences.

I really wanted to emphasize that this is not a writing position where your work ends once the article hits the CMS.

Read the New York Times leak and you’ll see that the web of today is ruled by “platform people,” not writers:

Contrastingly, when the Times published Invisible Child, the story of Dasani, not only was marketing not alerted in time to come up with a promotional strategy, “the reporter didn’t tweet about it for two days.” Overall, less than 10 percent of Times traffic comes from social, compared to 60 percent at BuzzFeed.

I love the New York Times, but even their editorial team admits they need to be better at getting their exceptional stories in front of the right people.

Once I’ve written something, my 2nd job begins: showing it to people who care. Whether that means hustling to find unique ways to promote it on social sites.

Front page of Reddit

Or, working with other smart people to get it in front of new audiences (Entrepreneur, Inc., FastCompany, TheNextWeb, etc.), I wanted people applying to realize that this job is half writing, half hustle.

I also emphasize the importance of being a marketer; do you know how to write articles that educate and convert paying customers, or do you just know how to write? Do you care about customer success? You should.

You understand that great output requires great input—much of your day will be spent reading, researching, and analyzing topics in order to find original, thoughtful ways to help our readers succeed. You’re not scared of crafting long-form resources, video scripts, or writing for presentations.

Great creative output requires quality input, so we want to guarantee this hire is someone who reads above their level.

A lifelong passion for learning is so important in keeping your ideas “fresh,” and in keeping writer’s block at bay.

I started off knowing only a little about customer service, but I was willing to watch videos, read hundreds of articles (and dozens of books), listen to podcasts, and even read boring industry research, all in the name of getting more familiar with the space.

If you don’t have passion for the topic already (ideal), you should at least be the kind of person who loves learning new things; especially when those new things help you educate customers.

You’ll base all of your decisions on utility over virality—we want well researched advice that is built around customer success. You don’t write for entertainment, you write to help customers be a little better at their jobs than they were yesterday.

We’re a B2B company, not a niche BuzzFeed. We get results when readers see results from our education, so we put entertainment on the backburner.

I don’t mean this in a preachy way. Perhaps your industry benefits from “You Won’t Believe What Happened Next!” headlines and buzzworthy writing.  No judgement from me.

But that isn’t what we’re looking for, so I wanted to make that obvious. Marketing on our team really only on focuses on “Did customers get a lot out of this?”, we don’t care all that much about things going viral.

You recognize that “content” is a crowded space—that it’s going to be your job to make sure that any exceptional piece of writing gets in front of the right people. You aren’t intimidated by networking, friendly outreach emails, and working with others to promote your ideas.

This was my “poke” to encourage applicants to highlight their networking ability.

Can you get on major media? Can you guest post on highly selective blogs? Have you appeared on cool podcasts? What sort of genuine connections have you made?

All of that is relevant, and all of it matters.

We love that you have a strong personal brand. We think a rising tide raises all ships, and we’ll encourage and support your personal platform! Ask Gregory Ciotti.

This was just a small reminder that we want to help your personal brand succeed.

We also assume that you have (or are working on) a personal platform, because someone operating in this space really isn’t a fit if they don’t like putting themselves out there.

It doesn’t have to be a blog, but a key trait in standing out is highlighting how you’ve already built a small following somewhere on the web.

You are adept at exploring the technical aspects of building an exceptional user experience. Topics like onboarding, customer success/development, and user retention get you fired up.

Ah, here’s the interesting one: we decided that one way we could improve education for customers was to bridge the gap between the “customer experience” and the “user experience,” with a specific focus on web apps and software, since that makes up a fair amount of Help Scout’s current customers.

This is the big hurdle for us, and for most other companies as well: genuine domain expertise. At the very least, applicants should have a passing familiarity with a topic and the motivation to learn a whole lot more.

About the author: Gregory Ciotti is a marketer and (embarrassingly infrequent) writer. Previously, he led content marketing on Shopify’s growth team and was executive editor on the communications team.