How to Make a Winning Bid on Upwork - Self-Made Web Designer
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How to Make a Winning Bid on Upwork

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It wasn’t long ago that Upwork didn’t charge for connects. You got a certain amount each month just for being on the platform and if you wanted to you could buy more.

Not any more.

Those days are long gone.

And, listen, there’s a lot that’s been said about how wrong Upwork is for doing something like that.

But, honestly, I think it actually helps freelancers.

Before you pick up the tomatoes to start throwing them at me, hear me out.

One of the things I see a lot of freelancers do is create a pitch and give the same one every single time and wonder why no one hires them.

Nothing motivates us quite like money. When somethings free I guarantee you’re not putting as much effort into thinking about it. But, when something costs you something IT’S A DIFFERENT STORY.

Now that we have to pay for bids it’s likely that everyone is thinking a lot more about the projects we are actually sending in proposals.

And, we’re probably all starting to put more effort into the actual bids themselves.

So, let’s talk about a few things that you can do as a freelancer to make sure you make winning bids on Upwork.

1. Look at Your Stats

First, let’s look at your stats.

You can find your stats fairly easily. After you log in to your account scroll over “Find Work” in the navbar and a few links down click the “My Stats” link.

Screenshot of Upwork Account

You’ll see three sections on this page: Client Satisfaction, Communication Effectiveness, and Marketing.

Marketing is what we’re after.

Here’s a screenshot of my latest marketing effectiveness stats. I will say that I’ve been focusing much more of my time on Self-Made Web Designer. So, this isn’t a great snapshot BUT I’ll use it to help you evaluate yours.

Screenshot of Marketing Effectiveness Stats

There are 3 stats that are really important to us here.

  1. How often your profile is viewed in comparison to others in your area of skill
  2. How many times you were interviewed in comparison
  3. How often you were hired in comparison

Each of those stats can tell you something about the effectiveness of your bids.

If you’re not getting a lot of views it might be time to spruce up your portfolio OR make sure that your bids are much more tailored to the skills and value you can offer to your client.

If you’re getting a lot of interviews but not hired as often IT MIGHT mean it is time to practice some verbal communication skills.

Or, maybe you need to level up a certain aspect of what you do so you are more appealing to a client.

It doesn’t really matter what the stats are. What matters is the conclusions that you can come to after looking at them.

Those conclusions can help you know how to change your pitch in the future.

For instance, from my stats, we can tell that I’m getting interviewed much more than people in my same skill category.

So, that means the jobs that I DO bid on are really good for me.

Which brings me to my next point.

2. Be Selective On the Projects You Bid

I’ve talked about this in another post of mine.

But, the general idea is that not every project is created equal. Some projects are worth your time and some aren’t.

The key is figuring out which ones are good for you and which ones you should pass up.

To do that we use something we call, “your ideal client.”

Your ideal client is a persona that you make up in order to know exactly the kind of person or company you’d be best suited to work with.

You can get as detailed as age, gender, years of experience and even give them a fake age.

My encouragement to you on this one is to get as specific as you can down to the industry.

As Amy Porterfield says, “The riches are in the niches.”

Why? Because if you know exactly who you’re suited for you can charge more and won’t waste time with clients that aren’t right for you.

So, take some time to think about exactly who you serve best.

Then filter the heck out of your job feed.

3. Filtering Jobs

There’s actually a lot of things you can do to filter out which jobs you’re seeing.

Let’s look at our job feed for a second. Right underneath the search bar is an option to do an advanced search.

Screenshot of Upwork

When you click that you get another screen that you can enter some specific details on the type of job you’re looking for.

Upwork Screenshot of Advanced Search

For the sake of this example let’s say we’re looking for jobs that have the words web designer in them and MAYBE have WordPress, Photoshop or Sketch in them.

That leads us to this page and the FILTERS button is where our bread and butter is.

Upwork Screen Shot Filtered Search

The filter button lets us really fine-tune the types of jobs we’re looking for.

For instance, when I was just getting started on Upwork, I knew I wouldn’t be able to land really high paying jobs at first. After all, I had no previous customer feedback.

So, I would filter out the Expert experience level jobs and those with a really high budget.

I also reasoned that I’d be more likely to get a project from someone that was new to Upwork since they were more likely to hire a newbie as well.

You can also change out the category of job and the keywords being used with the job posting.

All of this helps you really dial in the types of jobs you see.

Once you have you can save the search for quick access later on.

All of this helps you quickly find your Ideal Customer making it more likely to actually get a winning bid on Upwork.

4. Job Posting Age

The name of the game is being first in line.

Once a job posting has been up for a while it’s a sign that the client has either lost interest in the project or has already picked someone.

My general rule is that I want to be one of the first 5 freelancers to bid on a job. If the job has more than that I hardly ever bid.

To do this I scroll through the app on my phone whenever I’m taking a break.

A lot of times it’s a waiting game. The right job is hardly ever just THERE at the exact moment you need it.

You’ve got to be patient and wait for the right one to come along and as soon as it does APPLY QUICKLY.

5. How You Bid

How you bid is probably one of the single most important factors in making a winning bid on Upwork.

There are SO many things you can do to make sure your bid is the one that stands out.

  1. Do Some research

    A lot of times when a company puts a project on Upwork they’ll include some piece of information about themselves.

    That’s your chance to do a little digging and customize your bid specifically for them.

    If they’re a little bleak on the information they give you can scroll down and see their past projects. A previous freelancer might have given their first name in the feedback they left.

    Using the person’s first name in your proposal can help you to stand out.

    Even though that’s just a little detail it shows you’re making an effort and can leave an impression.

  2. Make an Impact With Your First Sentence

    The client will only see roughly the first 40 words of your cover letter as a first impression.

    So, if you’re not starting out strong the chances are they won’t click on you to find out more.

    Give them your best stuff right at the beginning. Don’t tell them about all the things you can do and how long you’ve been doing it.


    Tell them something specific to their project and then give them something you’ll do SPECIFICALLY ON THAT PROJECT to make it a success.

  3. Leave 2-3 Latest Projects in the Cover Letter

    You need to have proof of what you can do in the cover letter.

    After a client clicks on you, you don’t want to make them work to see what you’ve done by going to your profile.

    The more work they have to do to learn about you, the less likely you’ll get hired.

    I always put 3 of my latest and most impressive projects right at the end of the cover letter.

  4. Give Them Something

    As an icing on the cake, adding an attachment that somehow mocks up an approach you’d take with their project can be a deal winner.

    For instance, if someone is looking for a homepage redesign, you could mock up a navbar and hero image and attach that to your cover letter.

    I know this sounds like a lot of work BUT if you have a template handy you can always fill in the information you know about their project on that template quickly and send it on its way.

    Of course, you want to make sure that what you’re sending is in line with what they might have mentioned BUT it doesn’t need to be a work of art.

    Just something to give them that represents you.

  5. Be Yourself

    Every time I’ve hired someone on Upwork the amount of really bland bids from freelancers is always really surprising.

    It’s as if everyone is copying and pasting. Which they probably are.

    So, don’t be afraid to show some personality. Don’t fake it of course. But, don’t treat it like you’ve got a hazmat suit on.

  6. Tailor Your Bid to the Project Description

    Clients give clues as to what type of cover letter they’re looking for in their project description.

    If for instance, a client puts a lot of information in the project description they are most likely interested in getting a lot of information from a freelancer.

    Or if they use more relaxed language in their project description they probably appreciate a more conversational tone in a freelancer’s cover letter.

    The point is, try to look for clues about who the client might be in their project description and tailor how you interact with them based on that.

This may seem like a lot of work. And, it can be. But, the more you do it the better you’ll get and the quicker you’ll pick up on things.

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6. Communicate How You’ll Help with the Big Picture

At my job with Showit, we write a weekly report that’s due every Thursday night at midnight.

In it, we have to talk about what we did that week BUT more importantly, we have to connect the things we did with the money the company makes.

My encouragement to you as you bid on projects is not to just talk about what you’ll do BUT connect the dots for the client on the money they’ll make from it.

Don’t just say, “I’ll make you an awesome looking website.”

Say, “I’ll make you a website that doesn’t lose leads.”

That’s the connection between what you’re doing and the value you’re offering to the client THROUGH what you do.

7. Change How You Look at Rejection

A “No” is Feedback not Failure.

Every time a client passes on hiring you it’s not time to chalk it up to fate or give up altogether.

You should be analyzing and thinking critically about what you did and how the client responded.

Listen, I know it’s tough to hear, “No.”

As freelancers, we have to go through tons of rejection and it can get pretty taxing. BUT, if you look at that rejection as a chance to improve and not an attack on you as a person YOU WILL GROW as a freelancer.

So, with every rejection analyze what you did and how you might do it differently next time.

If you don’t, it was a wasted rejection and a waste of a few connections.

Wrapping Up

Like anything else, the more you do something the better you get at it.

So, when it’s all said and done just keep trying.

It was about 3 months before I got any interest from a potential client. So, if you’re new wondering whether or not you’ll be able to find work on Upwork trust me, you’re not alone.

Keep trying. Change your approach and eventually you’ll find success.

What about you? What kind of things do you do to make winning bids on Upwork?



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