How to Make a Winning Bid on UpWork

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Hi, I'm Chris and I'm super glad you're here. 7 years ago I taught my self-web design and freelancing. Now, I do my best to teach others what I've learned so they don't have to struggle as much as I did.

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Don’t want to read 1,000s of words on how to make a winning bid on UpWork? I got you. Listen to the podcast instead. Or you can watch the video.

If you haven’t figured it out yet, you can’t just create an account on Upwork and sit back as the jobs start rolling in. No! It takes effort and intentionality to make a winning bid on Upwork.

That’s not to say you have to lower your prices in order to compete. In fact, there are clients out there who are ONLY looking to pay top dollar for top-quality freelancers.

I’ve benefited from those types of clients as well as many of my friends.

But, in order to make a winning bid on Upwork and compete with all of the other freelancers who are just as motivated and talented as you are, you have to learn a few things about the platform itself AND you have to develop some soft skills that they don’t teach you in school.

I more or less cut my teeth as a freelance web designer working almost completely on projects I found on Upwork. I’ve made a lot of mistakes and learned A LOT from pitching to clients on what is now the number 1 freelancing platform in the world.

So, let’s take a second and look at some things that I’ve found help to make a winning bid on Upwork.

Honestly, some of them may surprise you.

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.

Looking at your stats to learn how to make a winning bid on Upwork

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.

Stats from my marketing effectiveness to learn how to make a winning bid on Upwork

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 what you can do to change and make it more likely to get a winning bid on Upwork in the future.

For instance, from my stats we can see that I’m getting interviewed and hired more often than other freelancers with my same skillset BUT the amount of profile views I’m getting isn’t all that great. So, I might need to make some changes to my profile and make it a bit more appealing to potential clients.

Upwork just released a new method for clients to hire freelancers called Project Catalog. It might be that since it’s a new initiative they’re pushing more clients to hire freelancers with this new service.

So, I might need to work on my Project Catalog a bit more and try to get more freelancers interested in my profile.

That’s the process of learning how to make a winning bid on Upwork.

  1. Look at your stats
  2. Make a hypothesis on how to improve
  3. Test out that hypothesis

Thankfully, Upwork has given you some tools to do more than just make random guesses.

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. And, as we’ve seen with the Marketing Statistics on your profile, Upwork is actually tracking how many projects you bid on verses how many you win.

I’ve heard of freelancers being kicked off of the platform because they bid on too many projects without winning anything. So, it’s not a good idea to bid on everything you can.

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 all of the projects EXCEPT those with Expert experience level jobs and 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.

Your job is to make an educated guess on what types of clients want to hire you the most. AND THEN, figure out how to filter down your search results so that you are seeing them more often than the other jobs that you are less likely to win.

This is how you make a winning bid on Upwork BEFORE YOU EVEN START TO BID.

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 Freshness

Job postings have a shelf-life.

Just like you don’t want to eat chocolate pudding that’s been in your cabinet for 4 years, you don’t want to bid on jobs that aren’t fresh any more.

The name of the game is being first in line as quickly as possible.

There are three things you want to look for here.

  1. How long ago the job was posted
  2. How many bids a posting has
  3. Whether or not someone is being interviewed already

Screenshot: How to make a winning bid on Upwork by looking at the job posting freshness

If a job was posted over a month ago, you have a very small chance of a client responding to you. It’s likely they’ve moved on and decided to go another route for hiring someone or getting the job done.

I even tend to stay away from jobs that were posted 4 to 5 days ago. That might change if the client has viewed the job posting recently. BUT, for the most part, I’m looking for jobs that are really fresh.

I also want to be one of the first ones to bid on a project. 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.

I’ve actually hired people on Upwork for random tasks. As a client, you get A TON of freelancers bidding on your project. It can be overwhelming. That’s why I try to be the first to the punch. It makes the decision much less pressured for the client and it’s more likely that I’ll get noticed.

Finally, if the job posting already has someone being interviewed I will hardly ever apply. Occasionally, if the job is a great fit I will throw my hat in the ring.

But, if a client is interviewing a freelancer that means they’ve already picked someone out who made a bid for the project. The likelihood that they’ll consider me is pretty slim.

Having these requirements for the jobs I bid on means I pass up a lot of opportunities and sometimes it takes a while before the right job pops up. So, when I’m searching for a new project I’ve got to make sure I’m looking pretty consistently at my job feed.

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.

    You have to be somewhat careful with this. Sometimes an account is used by multiple people from a company.

  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. Make it all about THEM
    So many freelancers make their bids all about themselves.

    “Here are all the things I’m great at.”

    “Here are all of MY accomplishments.”

    But, you’ve got to remember, you’re not the hero of the story. THE CLIENT IS.

    The client needs you to be their guide, not their savior. So, take the focus OFF OF YOURSELF and put it on them.

    Talk about how the project you’re going to help them with will help to advance THEIR vision. Use pronouns like You and Your way more than you use me and my.

  5. Give Them Something Special

    As icing on the cake, adding something that most freelancers won’t, can help you stand out.

    This could be a quick YouTube video introduction of yourself and how you’ll take them through the process of completing the project.

    It can’t be the same video you send everyone. It needs to be tailored and specific to that specific project.

    BUT, this has the added benefit of seeing if someone has viewed the video which let’s you know that your bid is being looked at.

  6. 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.

  7. 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.

  8. Leave a Call to Action

    As a web designer, I know of the importance of a call to action. A call to action is putting power in the clients hands to take the next step.

    You don’t want to leave the project without giving the client a next step. You’re trying to make it as easy for them as possible.

    So, tell them: “I’d love to chat more about the project! Just do x, y, and z and we can move forward.”

    Or something like that.

    Sometimes, I’ll add a link to set up an appointment on my calendar. Calendly allows you to make a free account where someone can sign up for a phone call within given time slots.

    This makes you that much more enticing to a potential client and makes it more likely for you to make a winning bid on Upwork.

    With the calendar link, it’s always important to remind them that if a time slot doesn’t work for them just let you know and you can work something out.

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.

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.

My friend, Anthony Garone, always says that you have to follow the money if you’re going to be heard.

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 on How to Make a Winning Bid on Upwork

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?

Man in desert celebrating


Hi, I'm Chris and I'm super glad you're here. 7 years ago I taught my self-web design and freelancing. Now, I do my best to teach others what I've learned so they don't have to struggle as much as I did.

Every week, I write an article and release a podcast episode. Sign up if you want to get notified when that happens.



  1. Thank you so much for this! You always manage to answer my current questions without fail! Can you read my mind or something? xD

  2. Zoe says:

    The filter options are different in my Upwork (outside the US): they come on the left-hand side of the screen. But they’re there, and you’ve made me think more about using them. Thank you!

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