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How to Pitch Job Board Ads (with a Freelancer Hiring Pro)

Every Friday I host (and record) a live Blab with a fellow freelancer. For those of you who can’t catch it live, want a review or just prefer reading a blog post to watching a video, here’s a recap of my recent chat with Kevin Fleming, the founder of Contena – a service that helps freelance writers find the best paid gigs.
Many of you reading want to find writing jobs to pitch. And Kevin saw the need for a service that helps freelancers find writing jobs faster – by searching the internet for leads in one fell swoop. So he created Contena to collect all the good writing jobs in one place, for easier access and less time spent on wild-Google-goose-chases.

What was your MVP (minimum viable product) when you started Contena?

There are a lot of job boards out there, maybe too many. I didn’t want to build another job board.

I wanted to build a way to parse that information for the average person to digest. So our minimum viable product was building a tool that would let you search all of the great resources that are out there.

A common misconception is that we built it because there aren’t a lot of good job boards out there. But that’s not true. The problem is finding them.

Your wife’s a journalist and you’ve worked in the industry hiring a lot of writershow did that play into you wanting to bring this product to market?

When I sold my previous business, I needed to find something to do.

I used to own a network of financial websites, and we hired a lot of writers. The first thing I had to do was help the buyer of my business hire writers. I was amazed that the process hadn’t progressed since the 5-6 years that I was involved in it.

The way that you found writers remained the same.

For writers, this was a massive pain point. They had to go to these archaic job boards that were created 10+ years ago that didn’t cater to remote work.

I thought that was a problem I could solve.

And if it’s a problem for writers, I thought it was probably a problem for other remote workers too.

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Do you write for the Contena blog and the newsletters?

Everything is done by myself and my brother, Ryan. I also have a blog about startups with evergreen content. So I do have experience blogging too.

Reader question: How do you pitch within a niche that you want to write for when you don’t have any samples in that niche?

(Thanks for the question, Joe Dyton!)

Answer: Start your own blog in that niche.

When I started Contena, I thought that the people who would get the jobs would be the people with the most experience.

But that was not the case, judging from the success story emails that we get.

Find creative ways to develop a relationship with the clients.

[Tweet “If you want to get the job, go above and beyond what everybody else does. “]

If you want to get the job, go above and beyond what everybody else does.

Write a sample post. A lot of the successful writers that I know offer to write a sample and end up getting paid for it. That’s a great way to initiate a relationship with the client you’re trying to court.

Don’t just send your resume and expect to be hired.

Find creative ways to get the conversation started. Once you hook them, you can then reel them in.

How to Pitch Job Board AdsOne of the most creative pitches I heard about was for a ProBlogger ad that was asking for unique, creative and personalized pitches. The writer who landed the gig crafted her pitch as a blog post.

Yes, most people just copy/paste an email. It doesn’t take a long time to craft a personalized email.

Doing so will put you in the top 10 percent.

Do you have any subject line advice especially for cold pitches?


It has such a high open rate.

Probably people think it comes from someone they know.

There’s such a wall when you meet someone online. Your mission is to break through that wall in a creative way. I got a lot of people to respond with exactly this simple subject line“Hey” People don’t feel that they’re being sold on something.

Gina’s Tip: The intro is also important to craft so that it doesn’t feel like spam. I’ve been successful using the first line to make some kind of connection with a prospective client, maybe citing a specific pin or blog post they’ve written. Read a company’s about page and their mission. That will help you start the conversation.

How does a simple subject line like “Hey” get through spam filters?

I think it’s less likely to get flagged because it’s short and it doesn’t use special characters. I used to run a startup incubator, and invited a different startup founder to come and speak every week. Some of these people were heading billion dollar companies.

Every week, I sent emails with the subject line Hey and it got through. Every. Time.

But if the job post requires you to use something else in the subject line, please do that.

What are your thoughts on following up on pitches?

Continuing to build that relationship is never a bad thing.

There’s an awesome plugin called Streak. (It’s a chrome extension for Gmail like Sidekick.) You can get a reminder to follow up again.

Gina’s Tip: Following up is key. As Joe would say, pitching 10 people 10 times is WAY more effective than pitching 100 people once.

Do you have a magic number for how many pitches a person should send in order to get results?

I don’t have a magic number. But when you’re first starting out, and don’t have any clients, you should spend 80 percent of your time on marketing.

Gina’s Tip: Spend whatever time you have set aside to write and complete client work on pitching in the beginning. It’s WAY more important than perfecting your blog or even writing samples.

Any thoughts on rates? What’s too cheap to work for?

The difference in rates out there is incredible. That’s one of the reasons why I created Contena. There was not a lot of transparency. Some people were making two cents a word while others were making five dollars a word.

We wanted to create a service that would give writers an idea of what others were making and paying. I don’t know if there is a magic number. It depends on the niche, the type of job and whether you’re working for an agency or for the client directly.

Gina’s Tip: I’m currently at 25-30 cents a word myself. Overbid – most of us underbid and work for too little!

Thanks for joining us, Kevin!

Check out Kevin’s guest post on Fully Booked VA for more tips on how to find writing jobs faster and how to successfully pitch job board ads.

Ready to Kickstart YOUR
Freelance Writing Biz?
Grab two of our most popular workSheets and get started TODAY!

Pitch Job Board AdsKevin Fleming is the founder and CEO of Contena, a service that helps freelancers find the best paid gigs. You can connect with Kevin on Twitter or Facebook. Remember that Contena is free to join, so go ahead and just create that account, already.

Have you ever subscribed to a paid job board? What was your experience?

This post contains affiliate links – if you have a problem with that, we might not be friends. Kidding of course, this is just my due diligence disclosure notes. Cheers!
Gina Horkey

Gina Horkey


Gina Horkey is a married, millennial mama from Minnesota. Additionally, she’s the founder of Horkey HandBook and loves helping others find or become a kickass virtual assistant. Gina’s background includes making a living as a professional writer, an online business marketing consultant and a decade of experience in the financial services industry.

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