Gregory Ciotti

Writing / Content Strategy

Why is Hiring a Great Content Marketer 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.


(Clark Valberg from InVision. I don’t know if they’re currently hiring, but it’s an awesome company.)

The results some companies have seen with content is likely spurring on the demand.

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. I count Buffer’s recent hires, Courtney and Kevan, as good examples of the gold standard.

This is new frontier for me personally, so I figured we’d start this “current lessons learned” analysis 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 butMark 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.Georgiana

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 whoWill 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:

Content Marketing Trifecta

Also known as “Greg’s triad of frustration.”

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

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…

Reddit Front Page

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.

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20 Replies

  1. Jen

    The part about spending much of the day reading, researching, analyzing resonated with me. To do this kind of thing you’ve got to be passionate about always learning and pushing the boundaries of your knowledge base. If not, it’s tough to make any kind of name for yourself. Plus, you do need to be willing to reach out to the big guys – ask questions and get your content in front of them.

    I don’t envy you. Finding the right person who has the combination of writing ability, personality, and passion may not be easy. Good luck!

    1. Appreciate that!

      I like Buffer’s policy: the company gives an (unlimited?) allowance for self-education through books.

      I think that encourages the team to really expand their horizons and take learning seriously; I’d say that is a superb policy to have for the content team at the very least.

  2. Ross Beard

    Loved this read Gregory.

    When hiring paid writers I’ve found that domain expertise is the most important skill.

    The ability to draw on personal experiences and confidently explain an opinion, idea, or concept is essential.

    My advice: look for someone who has worked or had experience within your industry.

    For example, I do some work with an IT and Cloud Services firm. The first few ‘writers’ I hired wrote engaging articles but lacked that deeper knowledge when it came to structuring and linking their ideas together.

    Now, I’ve found someone who previously worked as an IT technician. Although his writing can be a bit rough around the edges (getting better), his ability to bring together past experiences and opinions makes the content far more valuable to our audience.

    Over time, I’ve found you can teach someone how to write, but you can’t teach them real-world experience.

    1. Thanks Ross!

      The note about personal experiences is smart, as some of the most captivating writing you’ll read obviously comes from stories.

      I had an easy time of that with Help Scout, given that almost everyone has a story of great/bad service to share.

      In other industries though, that places even more emphasis on domain expertise; hard to share what you’ve done, learned, or experienced in a certain space if you’ve never lived it.

  3. Vinay

    I love this article it embodies many of the same problems we have had trying to find a content marketer for Process Street. After about 6 months of searching I have put that on hold and committed to work on the blog myself until it gets some more traction. I think the more traction your blog/product has the easier it is to find a solid content marketer.

    Interested to see his your search goes.

  4. Matt Gratt

    Great post Greg! We were just discussing this yesterday.

    I think the key is exactly what you say – you need someone who’s as much a thought leader and marketer as a writer/video producer/artist/etc.

    I think the advice of “Hire a journalist to do your content marketing and have them interview people” or “hire a 22 year old English major for $30K a year and have them interview product managers and write stories” is frankly, terrible.

    The biggest challenge we’ve found in staffing these roles is you need someone who:
    – Has something to say your customers find interesting
    – Can say it effectively in writing
    – Has the marketing skills to get that content out there
    – And has the business skills to solve business problems (AARRR, etc) with content.
    – Ideally knows something about digital marketing, web production, design, driving traffic & SEO, psychology, and the list goes on.

    These people are reasonably uncommon – and the biggest issue is that the people who already do it often are already in places they’re happy about.

  5. Will Hoekenga

    All great points here, Greg. This is outstanding and I’m honored to be included.

    That secret fourth problem you referenced is the one I find to be most challenging. When you finally find a unicorn, the unicorn is already off doing really cool unicorn things…which can make hiring difficult.

  6. Megan

    I couldn’t help but feel flattered and left a bit confused after reading this.

    If you’re one of those people who have industry experience and can write (I consider myself to be a bit of one), what’s the best way to get your name out there in an industry that is lagging behind in its use of content?

    I have an MBA, 12 years industry experience and 10 writing content (blogs, building mailing lists, etc.) and am still not sure of the best way to “sell” myself. Thanks!

  7. Ashir Badami

    Expectations have a big part to play here. I’ve been a writer, a content strategist, a strategist and now direct marketing efforts (whatever that means). I still consider myself a content specialist, because the sensibility that goes into producing content is very unique. Sadly, I’ve spent more time on the sites and activities of clients and employers than I have on my own site and ‘brand.’ I’m sure that impacts my visibility and reputation when it comes to people looking for a ‘content person,’ but that’s okay. I don’t belong in organizations where people want a ‘content’ person, because that term itself is a flag. A content person doesn’t exist. There are content specialists of so many different flavors across the inbound spectrum from engagement (social and content development), to demand generation (SEO strategists), experience (content strategists). The pursuit of a ‘good content person’ is often replaced by the desire to produce a good content operation within companies who realize that in order to utilize content for marketing — effectively — you need more than one person. Don’t get me wrong: I find a lot of good candidates who understand how to leverage SEO, analytics and propagation techniques to inform and evolve content operations — but they’re not schooled in the ways of brand, user experience or customer experience. And that’s okay, because the teams I build are based on what the overarching goals of the organization. This is why I think Unbounce is the most ‘correct’ in their approach. You should hire to your goal and needs of the organization, but to get there you need a clear understanding of what ‘content’ means in terms of your operations and goals. What are you trying to build? Once you do that the search for candidates — and the wealth of good candidates also becomes apparent. Good topic, great post.

  8. Melinda B

    Before I started my own company I applied for a number of content marketing roles. As a generalist with a number of years of experience and an insatiable need for knowledge, I thought it would be the perfect job. I’m also a data driven marketer so I get social media AND measuring things. I was also very interested in and taught myself how to code in HTML and CSS and now do my own video editing. I found that the companies I applied to were very hung up on my having either a journalism background or a video production/design background.

    Before I went to business school I went to theatre school where I learned how to coordinate a team of experts to tell a story. So much of what you write here truly resonates with me. They need to start with story telling skills first. Then focus on execution–because that is just the means to the end and it can be learned or outsourced. What cannot be outsourced is the creativity, the ability to assimilate hundreds if not thousands of pieces of information daily; and to organize all of it into a cohesive narrative.

    If my startup doesn’t fly for some reason I now know where to look for my perfect content marketing job. 😀

  9. Eli Overbey

    Great Post Greg!

    How do you hire humility? Or does that come into play? I’ve run into quite a few awesome content marketers applying for a job – who are – for a lack of a better word – arrogant.

    I’ve found many content marketers are extremely quiet or extremely vocal about their “awesomeness”.

    If their networking skills, domain, and writing abilities are top notch, but are arrogant (lack some teachability), is that a deal breaker?

    1. I’ll take this as a subtle poke that I should reel in the self-congratulatory language a bit 😉

      But seriously, I think hiring for humility really just depends on deciding where confidence turns into arrogance.

      Confidence is necessary in online publishing because when you put an article out and then promote it, you’re essentially saying “This deserves to be read.” You can only feel that way if you’re confident in your work.

      Arrogance is demanding that people laud your work. It generally results in thinking that you have nothing left to learn; a death toll to a content creator. As a personality trait, changing it is quite difficult and would require behavior modification, which is “training” and not “teaching” — at a business, you want to teach.

      So yes, if someone is too arrogant about a job that really revolves around helping people, it is a deal breaker.

      Thanks for your thoughts bud!

      1. Eli Overbey

        No subtle poke at all. I think you and your writing are very humble.

  10. Radford Castro

    I have people like this at LTG Media whom understand this. They are really good at content creation and marketing. They know their audience. One of of them is the complete package who continuously expands his domain. He’s left for a Fortune 500 company but still participates in a part-time basis to hone his craft. The other guy is also really good and is working on expanding his domain. Both put themselves out there and connect with their readers. On the other end of the spectrum I also have a video and sound guy who are also content creators who are incredible workers and expand our site’s reach outside of writing – particularly podcasts. My video guy now works with a well known podcasting network while my sound guy is produces and records professionally. I agree with the many points the article states. I don’t think finding a good content guy is hard to find, it’s holding on to one. My best advice is to find people who are thought leaders who bring with them quality and work ethic to the table. However, I agree with Ross Beard that domain expertise weighs more. Audiences resonate with those who can connect at a professional level while having the ability to break down those concepts into something that’s personable and interesting. When well-known and knowledgeable experts agree with your content creator, you’re definitely in the right direction.

  11. Emma Siemasko

    Great insights, Greg. Thanks for posting this.

    I love your trifecta (of frustration, as you call it). It represents (EXACTLY!) the skills necessary to hire a great content marketer.

    Curiosity plays a huge part. It’s not just that the person has to have the writing and marketing skills, but they also have to be curious about learning and discovering more. That’s why it doesn’t matter (necessarily) if someone has written much about customer service before. As long as they’re willing to read voraciously, go out and talk to real people about their customer service issues, and internalize experiences they have in their every day lives, they’ll be able to create content about the subject if they’re any good.

    In terms of Ross’s comment about industry expertise: this depends on your industry. Some industries are more “teachable” than others. My boyfriend’s startup company sells mathematical programming software, and I’ve had conversations with their COO and marketing VIP about how to hire a writer. They could probably hire anyone and teach them about the product, the community, etc., but the amount of time it would take to do so would be rather astronomical (and real world examples are tough in this field!)

    I think the best content marketers have a genuine need/desire to help others. They create content with a “helping hand” in mind, always.


    1. Beautifully put; this was a divide that I don’t think I made clear enough, but you summed it up quite well: “Some industries are more “teachable” than others.”

      Really, domain expertise is on a sliding scale of importance, I would say the ‘Trifecta’ is one I concocted based on the general requirements.

      I guess now I need to decide where the “user experience” falls on that scale. 🙂

  12. Neil Addison

    That’s an excellent overview of a problem that isn’t going away any time soon. Returning to what Emma said in her comment above – that “The best content marketers have a genuine need/desire to help others. They create content with a “helping hand” in mind.” I’d echo that and make a big claim for cognitive empathy as a key trait. Not only the ability to put yourself in other people’s shoes – both customers AND co-workers – but also to walk a mile in their footsteps. If you have this ability – to be agile in terms of emotional intelligence – then it becomes less important or necessary to operate inside a single content domain. I acknowledge this might sound idealistic, but it’s highly pragmatic also, as the ability to identify with other people’s problems gives you a head start in proposing interesting solutions to them (a form of content which is worth its weight in gold).

    1. Emma Siemasko

      Yes! Empathy. Walking in someone else’s shoes. Getting people to confess their biggest issues to you. If you’re the sort of person people come to with their issues, solving problems and helping via content is a cinch.

  13. Hudson

    Good points and fair enough, but I would argue that the marketing is the easy lesson, and networking can be taught, but the hard part is finding the person who can learn, is willing to learn, and can write engagingly but _for a blog_. The growing trend is to scan, not peruse, so blogging is definitely a different bag than writing an essay. A track record of blogging in different styles would be key for me, with some good HTML and CSS knowledge, just for SEO purposes.

  14. Arshad

    I read this article in like 3 hours, not because I have poor comprehension skills but because I have been doing things in the middle of reading, I just couldn’t close the tab, because I thought I might miss something interesting and honestly this article has provided me new insight on Content Marketers, thanks Greg!