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Freelance Guide: How to Bid & Win High Paying Freelance Jobs

It wasn’t that long ago that I had written off freelancing marketplaces completely. I had put in a good amount of time attempting to win clientele on various freelancing websites and had very little to show for it. It seemed to be that a large majority of workers on these websites were primarily Indian or Filipino – which is fine, but generally meant that I was being underbid on every job that interested me. I credited this as my reason for not being successful, but the truth was that I was just not doing a good job of marketing myself to my prospective clientele.

The barrier to entry on these sites is very low. Anyone from anywhere can sign up and begin bidding on projects inside of 10 minutes – although that doesn’t mean that they will be awarded any. Eventually, I came across a guide on one of my favorite forums that opened my eyes and really made me think about how valuable these websites could be to me if I was taking them more seriously. Make no mistake, you can find high quality, long term clientele that pay well on these websites. You just have to be willing to wade through pages and pages of one-off jobs for crappy pay to find the diamonds in the rough.

There are many different freelancing marketplaces online that can be valuable resources. Here is a list of the popular websites, separated into tiers based on my own experiences attempting to find work on these websites.

Popular Freelance Marketplaces

Freelance Websites for Bidding and Winning Jobs

The “Top Tier” (Best Jobs, Best Pay)

  • Upwork
  • Freelancer

The “Middle Tier” (Still worth your time, less quality jobs and gigs)

  • Guru
  • People Per Hour
  • Freelance
  • iFreelance

Anything below the middle-tier probably isn’t worth your time. Besides, these 7 websites should be more than enough to keep you busy on a daily basis. For all intents and purposes these websites are all the same, although there are differences in the intricacies. The way you bid on jobs, receive payment, or create a profile may differ, but the overall feel and workflow are fairly consistent between them. For the purpose of simplifying, I have left Fiverr and other low-dollar marketplaces off of my list. Yes, these can be a great way to earn additional income, but these websites operate very differently than normal freelancing marketplaces.

Understanding Freelancing Websites

freelance websites how they work

The good news is that most freelancing websites operate very similarly to one another. You bid on projects, your bid is selected by the job poster, and you are awarded the job. Most freelancing websites offer some sort of payment guarantee when you work hourly, and have protections in place for both the freelancer and the purchaser.

How Bidding Works

Bidding for these jobs is fairly straightforward. They post a listing for a particular job, along with a number of requirements. Freelancers bid (you can often choose to make your bid public or private depending on the website), and one or more freelancers are awarded the job after a set period of time.These websites take a percentage of each bid ie. if you bid $20 for a project, you will receive around $18, while the freelance marketplace of your choice will keep $2. It seems like a lot, but its the cost of doing business on these websites. If it bothers you enough, just raise your prices to account for the free.

Typically, freelancers are provided with a certain number of “Free bids” per month. Upwork, for example, allocates you about 30 applications per month for free. If you want to go over that number, you pay a monthly fee for more applications. Other websites have similar systems. They may give you a certain number of points which then can be spent applying for jobs, or simply count each job application as a single point. They all have similar systems in this regard.

How Jobs are Completed

Typically, there are two types of jobs on freelance marketplaces – hourly jobs, and fixed-price jobs. Usually the hourly jobs guarantee payment to the freelancer, who agrees to be monitored by software that takes screenshots of the screen throughout your workday to ensure that you are remaining on task – and that freelancers aren’t taking advantage of workers by clocking more hours than they actually worked. I personally have a bit of a strange workflow (also known as occasionally browsing Reddit while working), so I typically only bid on the highest paying hourly jobs.

Target Audiences and General User Base

In my experience, 90% of the user base on these websites will be international users that are willing to work for much less. They will underbid you every time, without fail. If you live in the US or in another first-world country, you definitely are not going to be able to compete with their bids. Don’t try. Limit the jobs that you bid on to those that are looking to find quality workers and pay quality prices for that work. It is not worth the headache to attempt to bid on every job that you could potentially complete.

Putting Together a Marketable Profile

freelancing portfolio profile

Let me make this clear – 100% of your success on freelancing marketplaces will be because of your profile and cover letter. These provide you with the best chance to market yourself and gain the attention of those that are posting jobs. In order to qualify for the high paying jobs, you need to have a profile that looks the part. Of few of the ways in which you can stand out include;

Profile Picture and Title

You must have a profile picture and solid user title to gain attention. Although there are many successful companies that operate as a brand name on these websites, I have had most of my success as an individual. A professional picture (try not to take one of those stuffy 1980s portfolio pics, get out in the sun and look like your having a good time) and a solid positional title can help you stand out. While the professional picture should speak for itself, I’ve noticed that not many people on these freelancing websites are able to put together a title that helps them stand out. The profile title is where you list your general overall profession, usually just above or just below your profile picture.

Good Positional Titles:

  • Viral Content Extraordinaire
  • Content Curation Specialist
  • Award Winning Blogger

Bad Positional Titles:

  • Article Writer
  • Content Creator
  • Freelance Writer

Take the time to really examine what you are able to bring to the table. What is it that you really do for companies? They see a hundred different “article writers” per day, but how often to they come across a “content curation specialist?” It might seem a little bit corny at first, but you shouldn’t be afraid to market yourself appropriately.


You should list any time of relevant experience that you can on your profile. This should include any education, long-term jobs, contracted jobs, or freelance jobs that you think would look good to a prospective employer. Remember – applying for a job on a freelance marketplace is not the same thing as turning a resume in to a potential employer. There is no reason to keep things “short and sweet,” or cut down on pages like you would when applying for a day-job.

Samples and Portfolio

Your portfolio can be a huge asset on these websites and I see far too many people under-utilizing this section of their profile. Take the best projects that you have ever been a part of and put your best foot forward. You want potential employers to see what you are capable of. If you haven’t started already, every freelancer should have started putting together a portfolio of the projects they have been involved in. There are plenty of good WordPress themes out there that make for great portfolios, such as the ones listed on this list here. These make it easy for yout o build out portfolios on other websites as well.


Most websites offer a number of “tests” that can be taken that test your skills in various ways. As a content writer, I usually take the basic spelling, grammar, and tone tests that these websites make available to build out that area of my profile, but don’t take them overly serious. You’re portfolio and cover letter will give you a lot more of a leg-up than a couple of completed tests.


Every time you complete a project, the client that hired you has a chance to rate your work. Your rating shows up every time that you bid on a project, and plays a key role in whether or not you receive the bid. Likewise, most sites will allow you to rate the client as well, to help freelancers avoid troublesome clients. When you receive a bad review from a client, you will have a chance to respond as well. I’d recommend never doing much more than a brief explanation of the disappointment, and an apology. No one wants to hire someone that publicly engages in arguments with former clients

Bidding on and Winning Jobs

bidding winning jobs freelance websites

Now for the tough stuff. On average, there will be 10-30 other applicants on any job that you apply for. While it might seem like this makes it impossible to find a steady stream of work, most applicants have already disqualified themselves from the process. If you sign up to these websites and post a job, you’ll find that most applicants are;

  • Copying and pasting the same exact cover letter to many jobs, without specifically referencing anything about a particular job posting.
  • Posting from accounts that have had numerous negative reviews about their work in the past.
  • Were not qualified for the position to begin with and therefore have no chance.
  • Are simply “trolling for jobs” by casting a wide net across the marketplace.
  • Have done nothing to make their profile stand out from the rest.

Even if a job has 30 applicants, there may be only 5 or so that have a legitimate shot at being awarded the position, particularly if it is an advanced position with some fairly in-depth requirements. Don’t be scared off by the competition –be willing to go the extra mile in your cover letter to win the job and you increase your chances exponentially.

Build Some Ratings 

No matter how you slice it, you’re going to have a tough time getting paid well when you have no previous work experience on a given website. Start by bidding on one-off jobs, and actively asking clients to rate you after the job is complete. Many of these websites have jobs that are posted specifically for this purpose, with the client stating that they leave feedback for completed work. Once you have build a solid foundation of ratings, then you have a much better chance to landing good, high-paying jobs on freelancing marketplaces.

Choosing Jobs to Bid On

Choosing which jobs to bid on is something that comes with experience. 95% of jobs that I come across on these websites are jobs that I would never, ever consider for the pay that is advertised. You have to pick and choose. Maybe 1 out of every 20 postings pays a legitimate amount – but on websites where thousands of jobs are posted each and every day, there should still be plenty of opportunities.

Avoid Bidding on Jobs That:

  • Are targeting low-skill, low-pay workers. You haven’t marketed yourself as that, and you are wasting your time applying for these positions.
  • Have very short job descriptions. If they aren’t willing to do their due diligence to find great candidates, they probably aren’t someone that you’d enjoy working for.
  • Seem fishy. Like anywhere online, there are plenty of scams being run on these websites. Don’t be afraid to ask for pay upfront, and never chase rainbows.

Bid On Jobs That:

  • Pay well. Clients that are willing to pay more demand a higher quality of work, but are usually much easier to work with in my experience.
  • Have an in-depth description of the job. If they’ve taken their time to entice the best candidates, it’s much more likely a position worth having.
  • Have clients that would like to communicate prior to beginning the work. Whether its over the phone or through Skype, agreeing to have a short chat with them will help you build trust and seem more legitimate.
  • Are long-term. Avoiding the daily bidding and applying grind is important. You want long term jobs that provide you with a consistent stream of work if possible.

By being picky when bidding on jobs, you’ll deal with many less headaches from clients, get paid more, and be able to really sit down and devote yourself to each project. This leads to satisfied clients and better ratings on your profile, which in turn leads to more work.

Building Job-Winning Cover Letters

cover letter for freelancing jobs

Your cover letter is the single most important part of the process. When I first built my profile, I took time to build an excellent general cover letter than I would use as a template for all job applications. While I never would recommend copying and pasting the same cover letter to multiple jobs – there are certain aspects of your cover letter that will be relevant to each position. Copying and pasting a paragraph that describes you, your hobbies, and your education isn’t a bad thing because it is relevant to the position. The basic Do’s and Don’ts for your cover letter include;


  • Tell them about yourself including your experience, hobbies, location and education.
  • Reference specific statements that were made in their job posting. Cater to each job.
  • Provide links to samples and portfolios directly in your cover letter. (Not your profile portfolio, a portfolio on your own website)
  • Invite them to contact you by phone or some other means.
  • Be straightforward. I’ve found that people on these websites like no-nonsense straight-talkers.


  • Copy and paste entire cover letters – they may be able to see your previous job postings.
  • Write a single paragraph. Go the extra mile for each and every job.
  • Be overly professional. People like to know that there is a real person on the other end.

Here is a general outline for one of the several different types of cover letters that I have put together.

Cover Letter Template:


Paragraph 1: Introduce yourself, state that you are interested in the position. Give a brief overview of your hobbies, career goals, qualifications, and education. State why you want the job.

Paragraph 2: I believe that I would be the perfect candidate for this position because… Give previous projects that were related in some way to the position. Give a more in depth overview of your qualifications and experience. This is where you tell them why they should hire you.

Paragraph 3: Sell your skills as a freelancer. Invite them to message you on Skype or give you a call. Give them your availability. Tell them what times you are available to chat, and which timezone you are in.

Paragraph 4: A short paragraph. Give them your price and the reason why you have bid the amount that you have bid. At the end of the paragraph, invite them to check out some items from your portfolio, and invite them to check out your profile.

Include 5-6 links to items from your portfolio. You want these to be out there on the web, credited to you, and easily accessible. Provide them with your contact details.


Your Name

This is the basic format that I have been using for my own bids and applications for the better part of two years. I am constantly tweaking it, and have put together several different cover letter templates for specific types of jobs.

Play to Strengths and Locale

Are you applying for a job to write articles for a sports websites? You should be changing your cover letter to include links to previous sports-related work you have done. Apply for jobs that are right up your alley, and focus your efforts on those. It will greatly improve your conversion rate.

Additionally, my own efforts have shown that targeting posts from individuals in your local area can greatly improve your chances of winning the position. People like knowing that they are working with someone that is close by, and it could potentially lead to much bigger things for you down the road if all goes well.

Ask Questions

Clients want to award the job to someone that is actively engaged. Even something as simple as asking a few questions can help you to stand out from the crowd and show that you are genuinely interested in the position. Ask questions that are specific to the job or company, and show interest in a broader range of roles with the company if applicable.

By | 2018-02-28T20:22:52+00:00 February 25th, 2016|Freelancing|0 Comments

About the Author:

Founder of Empowermented, software developer, and U.S. Marine, Dylan Bozeman is an avid learner with a diverse web development portfolio and an entrepreneurial drive.

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