How to Win Big on Job Boards


by Susan Finch

When I first decided to become a writer, I wrote a few bad novels and waited for instant fame and publication. This was in the late 90s, when Kindle publishing wasn’t mainstream and blogging was in its infancy. It’s probably no big surprise that nothing came from that strategy. So after getting over the shock of not being a “writer” I figured I needed to look at other avenues.

My next genius strategy was sending lots of cold pitches and emails to every magazine and newspaper on the planet. I amassed an endless sea of canned rejections and curt replies. Frustrated, I decided to sit down and figure out how to find people who actually needed writers. And that’s when I realized there were plenty of open positions on job boards.

By now my skin was a little thicker, and I knew it would take more than just saying, “I’m a writer! Pick me!” to make much headway in this industry. At the time, I was living in New York and some of my friends were featured writers in huge national magazines and novelists. I was intimidated to say the least, but determined to win big.

So I came up with a system that actually yields results. It’s how I regularly land work on highly competitive job boards like ProBlogger, UpWork and Craigslist to name a few. Here’s how it works:

Apply to Jobs Immediately

I won a copywriting job for a jewelry store in my Brooklyn neighborhood because I was the first to apply. It was one of my first big wins as a freelance writer, and they cited my great sample and speed at applying as a major factor in their decision to hire me. They simply didn’t want to weed through hundreds of applicants.

Applying within minutes is no easy feat when using a site like Craigslist, and is really just about luck. But if you’re competing for a choice work-at-home job, you can’t afford to waste much time. Apply the same day it’s posted by setting up Google alerts. For example, you can set-up an alert for “Freelance writer” or “remote copywriter” to open up a broad search for these terms. It also helps to keep copies of your cover letters so you can pick and choose the information you need quickly.

Find an Actual Email Address

Why only submit your application to a blind inbox where hundreds to thousands of other people are applying to? I still submit my application through whatever method the job board provides, but then I take it a step further and send it to an actual person’s email address.

If the hiring manager’s name or contact information isn’t listed, there are usually clues throughout the post. Does it tell you who you will report to? Does it tell you the company name? Do some Google searches based on the information you find it narrow it down. You can also copy and paste a paragraph from the job board you’re looking at into Google. Most of the time, that same job is posted elsewhere, including the company’s own website.

Add an Attention Grabbing Email Heading

Hiring managers receive hundreds of emails a day from hopeful applicants dutifully using the email heading, “Work-at-home project management job” or whatever the job title entails. But which do you think they would open? That same subject heading they see over and over again, or this one: “Seasoned project manager with 5 years of experience in online marketing!” Their eye will automatically spot that out of the generic pool of responses.

Here’s another tip. The majority of people fail to read the entire job posting. I would know, because I’ve hired freelancers many times for clients.  It’s not uncommon for companies to ask you to write a code word in the subject heading so they know you actually read through the listing. I once beat out hundreds of Blog Manager hopefuls because I was one of the few that followed directions down to the finest detail.

Create a Highly Relevant Sample

The work-at-home job landscape is a competitive one with more applicants than there are positions. But you can still win big and stand-out from the competition by creating a highly relevant sample. It takes time to do this, but can revolutionize your results. And once you’ve nailed down your samples, you can keep a library of them on hand in your Google Docs and borrow from them again and again.

So let’s say you’re a graphic designer and want to work with a new start-up in your city. If they’re looking for marketing materials, mock up a quick flyer showcasing your talent. Only send your best, polished samples to reputable companies. Unscrupulous companies could take your work and run with it without paying you. But in my experience, the pros to creating samples far outweigh the cons. Companies love seeing what you can do. Not just hearing you promise you can do it. But what if you’re skillset is something like customer service? Give them some incredible ideas of how you can help revolutionize the department or increase customer satisfaction.

Give Them a Reason to Say Yes Right Then

Don’t waste the opportunity to include a call to action in every cover letter. If you’re simply saying, “Please contact me at….”, you’re missing out on the chance to spark action. Instead, tell them what to do. Try this instead: “Thanks for letting me reach out and introduce myself! I would love to talk more about the position at your earliest convenience. I’m available most days at 3pm ET. Would that work for you?”

Keep your entire cover letter professional, but conversational. After all, who would you rather hire? Someone that just spent the last few paragraphs giving you an uninspired account of how great you are? Or someone who gave you actionable information, an amazing sample or ideas, and an invitation to connect?

What are some of your favorite ways to stand-out and win big on job boards? Let me know by leaving a comment below.

Want more? Get Susan’s free advanced job board training videos to find a work-at-home job with benefits at, where she writes about growing side businesses to do more of what you really want in life.

Win Big on Job Boards

  1. Cheri | WAH Inspiration says

    Hi Susan!

    This is almost exactly the advice I give my readers. I’ve been able to secure as much work as I want with a few simple tricks including these. Thanks for the great advice!

    1. LTruex says

      Thanks for visiting WAHS and commenting. I think Susan’s advice was spot on as well! Thanks again.

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