How To Win More Jobs On Upwork

blogphoto1Upwork can be extremely frustrating to new and veteran freelancers alike. Many of the jobs are low paying, there is a lot of competition, and the fees are high. Even with all that, it’s still one of my favorite places to pick up extra work. I generally get hired to one out of every five jobs I apply for. For most people that seems like an impossible feat, but there are some tricks I’ve discovered that put me ahead of the pack when it comes to pitching jobs on Upwork.


I’ve nearly got the application and bidding portion down to a science. Where I used to spend hours a day filling out applications only to get rejected, now I can apply for up to ten jobs in an hour. It’s a pretty easy set up if you follow a few easy rules to applying for jobs.

Fill Out Your Profile

Think of your Upwork profile as your portfolio, you want to fully flesh it out and keep it up to date. Make sure that you fill out every section because it is the first thing a potential client will look at if they are considering you for a job after reading your cover letter.

You’ew going to want to add all of your qualifications and relevant work experience to your bio. When you’re filling it out don’t get too personal, clients want to know what you can do for them not that you have had a love for writing since elementary school or that you’re looking to start building your portfolio. Focus on your strengths and what you have to offer them that other writers won’t.

Use a Quality Photo

There are thousands of people on Upwork and most of them aren’t too serious about freelancing. Maybe they read that it’s a good way to make some extra money and signed up on a whim, or put everything they had into it for a while before getting frustrated and giving up. Most of these profiles either don’t have a photo or have a picture that would be more at home on Facebook than as a professional reflection of themselves.

That’s not to say that you have to hire a photographer and get professional quality headshots, but you should put in some effort. A good photograph of you in some dress clothes in front of a solid background looking directly at the camera is perfectly fine. It shows clients that your treat freelancing as a business and will take their job seriously.

I had a pretty weak photo when I started on Upwork. It wasn’t a selfie or anything like that, but it had poor lighting, was shot at a weird angle, and was taken in front of my apartment doorway to my kitchen. I updated my profile picture and saw a huge rise in the jobs I won. If you aren’t sure if your photo is good enough to use for business purposes then enter it into and let other people vote on how professional it looks.

Set Up a Template, Then Adjust It

Most experts out there will tell you that a cookie cutter template is a bad idea, and then they will tell you that Upwork takes too much time and energy to find a job. What I’ve found is that writing a template to use for all of your bids is the fastest way to gain a lot of quality jobs on Upwork. However, the problem most people make when using a template is that they send the exact same cover letter to every potential client without ever making any changes.

What I do to send out more proposals in a shorter amount of time is to use a template but I leave a small area to personalize it for each individual client. The bulk of every pitch is just an overview of your work experience anyway, but by leaving a small space to customize the template you can pitch directly to the client. That paragraph lets you speak directly to them and focus your pitch for each individual job without starting from scratch each time.

This method has saved me time and landed me way more jobs. It used to take me a really long time to write proposals since I was starting over each time. With a template I can send out roughly five to ten proposals in an hour, leaving me more time to write and make more money.

Don’t Limit Yourself

The worst tip I have ever heard from anyone about Upwork is to use all the filters available to make your search super specific. They will tell you to search for keywords using your niche, then customize for the type of job you want by clicking on your experience level, hourly or per article, how many hours you available to work, and anything else you can narrow down to get your “perfect job.”

No offense to them, but that’s trash. One thing that I’ve found out on Upwork is that most people looking for a freelancer have no idea what they are looking for. Someone that says they want an expert freelancer may really only need an intermediate level writer. They might not put the exact title you search for in the description. Maybe they give the job an obscure title or a description that is the exact type of job you’re looking for but use a different terminology than what you searched for. Or maybe you find a job on there that peaks your interest that you would never have thought about until you see it listed.

Using ultra-specific searches is just handicapping yourself. If you truly want to win more jobs on Upwork that you need to see the jobs that are available.

Get Personal

There are a lot of people on Upwork looking for jobs, and that makes it hard to stand out. You have to do everything you can to really stand out and shine in such a large crowd. That’s why I always try and use the name of the person that I am messaging. If you look through the reviews of a client, many times the person reviewing them will use the client’s name. When they do that I start my proposal by greeting them personally.

Doing this will grab their attention right from the beginning. At first, they’ll think you’re someone they know. When they realize they don’t, they’ll still see that you put in more work than the average person applying right from the beginning. Until I started doing this I almost never got jobs, and the ones I did were pretty pathetic in terms of pay and quality. After I started using this trick I was able to get better-paying jobs that I actually enjoy doing, all because I used the person’s name.

Follow Up

If you follow any prominent freelance writing bloggers you have no doubt heard them tell you to get ahold of old clients if you are looking for new work. Somehow though I never see this advice applied to Upwork. I constantly send out follow-up messages to past clients or potential clients that went with another writer on a previous job. Most of the quality jobs, even the one and done jobs, come from actual businesses and websites. These people need quality content regularly and I want to be there before they even think to post it.

Just this past week I sent a simple message to two former clients that read;


  I really enjoyed working with you on our last project and I was just wondering if you had any other jobs coming up that require a writer. Please think of me if you do.


   Adam Leviness”

That landed me two jobs, one that paid $75 for one article and another that led to consistent work rewriting an entire website at $30 an article just to caption some list-based articles. Following up with a client is par for the course with freelancers, and yet most never use that practice on Upwork. Oh well, their loss is your gain.

Use All Your Connects

Ok, this should be a no-brainer but so many people never do it. You can’t get jobs if you don’t apply for them. If you don’t have the paid version than your connects won’t roll over each month, so why would you waste them? Even if I’m completely booked up for the month, I will message a potential client, let them know when I will be available, and try and win the job. Worst case scenario I won’t get it because I can’t start right away, but on the off chance that they are ok with waiting for me to start until the next month I won another job. Either way, I didn’t let any of my connects go to waste.

Upwork doesn’t have to be the headache it is for most people. While I wouldn’t have it as your only source of income as a freelance writer, or put all of your marketing energy into it, if done right Upwork can make you some decent cash.There are tons of bad writers on Upwork, that means with a little bit of time and work you can stand out over all of them. Follow these tips and you can start to win more jobs on Upwork.

What do you do that lands you a job on Upwork? Leave your favorite tips in the comments section below.

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