How to submit proposals on Upwork strategically: The Complete Guide

Here’s the truth about hiring: the people who say the things you want to hear have never been on the other side of the table. That’s why you should never believe what they are saying.

I earned my first dollar from Upwork 10 years ago. This is for you if you’re just starting now or already using Upwork but struggling to get interviews and clients.

A lot has changed since then, and you can expect more changes as they adapt to the market. Some advise that you don’t use Upwork, while others say it’s a good place for beginners. My take is it’s a perfect place to get started. Businesses are actively looking for help, so there’s a market for your skills. But I recommend you only use Upwork as a channel for your freelancing business. Don’t rely on it solely.

Here’s what I’m not going to cover:

  • Optimising, your profile
  • Determining your niche
  • Creating an account
  • Setting up your portfolio
  • Determining your rate

There are tons of articles on those already. Feel free to check them out here.

What I’m going to cover is how you can get interviewed more often. The moment you get interviewed, you’re already one foot in. It’s easier to close a client when you’re already talking to the client.

Let’s get started.

Absolute Truths of the Hiring Process

I’ve worked on both sides of the hiring process when working in corporate and Upwork. So I know how it works. Here’s a quick overview of what really happens. Everything you think “should” happen, throw it away.

  1. Hiring managers are busy. Don’t expect them to read through everything in your resume or profile or application letter. Yes, it’s not fair. But that’s how life works.
  2. You have dozens or hundreds of competitors. Continuing from above, hiring managers are responsible for something else ASIDE from hiring. The entire interview process is a necessary evil. The easier you can make yourself stand out, the better chances you’d be interviewed.
  3. The interview process starts the moment you submit your application. Here are the stages of the interview process: application, initial message, exchange or calls, offer, acceptance.
  4. People get eliminated at each stage. If you didn’t get a message back from the client, you didn’t pass that stage. Don’t lament that this company didn’t give you a chance. They did, and you failed. Deal with it.
  5. You need to keep in mind a specific goal at every step: move to the next one. When you apply, your goal is not to get the job but to get the client to respond. When you hop on a phone interview, your goal is to get to an offer.

Re-read this entire section over and over so you understand what’s happening. When you hear yourself saying, “well, this company should…” — STOP. It’s nice if they should do those things, trust me. But like I said, that’s now how it works.

How to Get More Interviews in Upwork

The generic advice you read on Upwork is to do two things. First, they tell you to optimise your profile by adding a good summary and adding your portfolio. The other one is to apply for a lot of jobs.

While there is some truth behind it, I wouldn’t take them at face value. You’ll see more why below. Instead, follow these steps if you want to get more interviews and succeed in Upwork.

1. Advanced filters are your friend

When you apply for a job, don’t rely on what’s on your feed. Use advanced search features. First, type in any term you’re good at. It can be a skill or job title or a result of the work you do.

Job Search in Upwork • Screenshot by Author

The advanced search settings will show up. Here’s where you can filter those jobs you want to work on. The reason for this is twofold:

  1. Sending proposals in Upwork now comes at a price: Back then, it was free with no limits. Eventually, they introduced connections where free accounts are limited and renewed every month. Only if you want more will you have to pay.
  2. Your feed is a combination of a lot of job ads: It gets messy, and you can’t find the jobs you want. It also includes both shady clients and legitimate ones.

Save yourself the headache and do an advanced search.

Upwork Advanced Filters • Screenshot by Author

The filters will depend on your preferences and stage in your freelancing career, but here are some of the things I recommend starting with:

  • Job type — beginners, I suggest going for hourly. When you understand how to say “no” to clients, go for a fixed price and weekly retainer contracts.
  • Client history — I typically choose 10+ hires, so my risk of getting bad clients go lower.
  • Client info — I toggle between previous clients to see if there are projects I can help them with. If you did a good job with them before, there’s a high chance of getting hired again. But if you’re starting, I strongly recommend ticking the Payment Verified box. Combined with the hourly payment, you’ll be guaranteed you get paid for your work.
  • Number of proposals — The lower, the better, but I use this as prioritization only. Meaning, I apply to those first, then I increase it later. I don’t use it to disqualify opportunities.

The rest is self-explanatory and depends on your situation. Feel free to play around with these settings or change your search term to what you think is better.

For example, for my recent job applications, instead of using SEO or search engine optimization in the search term, I used “organic traffic” instead. I don’t want to work for clients who don’t know the result they want. The purpose of SEO is to grow your organic traffic and get new leads and business from it. If they only entered SEO or keywords in their job ad, I want to disqualify those immediately because there’s a high chance that they only want to add keywords to their pages and expect to grow.

Homework: think about the terms that describe the outcome of what you want to work on. Another way is to list down what you don’t want to work on. For writers, do you only want to do blog posts, or will you also work on website copy? What about sales pages? Scripts?

2. Focus on more recent job ads

From my experience, the longer time the job is posted, the less likely the client will hire anybody. That’s why you have to qualify for the recency of the post.

Check Date/Time of Job Post • Screenshot by Author.

For every job ad, you’ll see when it was last posted. As a general rule, if it’s within 48 hours, go for it. If it’s longer than that, add a few more criteria.

3. Check when the client last viewed it

If you’re applying for a job that’s more than 48 hours old, one thing you have to check is when the client last viewed it. You can find it under the job ad itself.

Upwork Job Post Details • Screenshot by Author

The example above is a job ad posted a month ago, but the last viewed by the client is one day ago. Meaning, the client is active, and the role might be something they need some help with.

4. Look for special instructions in the job ad

After picking the jobs you want, it’s time to apply. Read the job description and see if it matches what you want.

Some things to note are special instructions like these examples:

Upwork Job Post with Specific Instructions • Screenshot by Author

If you read the hiring process I mentioned earlier, there are dozens of applicants for a single job post. These are used as a filter to weed out applicants who can’t read or follow simple instructions.

Upwork Job Post with Specific Instructions • Screenshot by Author

5. Your first sentence matters

After reading the job post, it’s now time to apply. If they indicated some instructions to follow, please do so. Here’s why: that’s what the hiring manager sees. It’s what’s on the other side of the table.

What Hiring Companies See in Upwork Applications • Screenshot by Author

If they ask you to include the word “bananas” at the top, this is why.

That’s the first thing they see on every application. Hiring managers get to immediately disqualify who adds those and decline people who didn’t follow the instructions.

Is that fair? No. Necessary? Absolutely.

6. Focus on results and how you can help them

After your first sentence and introduction, focus on results and how you can help them. If you want to increase your chances of getting interviewed, you’ve got to make it easier for the hiring manager.

Here’s what every hiring manager thinks when they look at your application:

How can this person help me achieve XYZ?

  • For our content writer example, how can Ariel help me with writing blog posts? How can he help me grow my organic traffic and rank on search engines? How can he help me build my brand?
  • How can Stephanie help me increase engagement in my Facebook and Instagram channels for a social media marketer? Will I get new leads from this? Can I build a community?

Then, remember this principle in interviewing (or in life, for that matter)

It doesn’t matter how good you are. What matters is how they think how good you are.

That’s why your communication skills matter. Communicate your results, so they know and realise how good you are. Using the same examples above:

  • Content writer: I grew company XYZ’s organic traffic by 40% in 6 months by writing SEO-optimized articles. I did that by getting to know the company’s ideal buyer persona, their needs and then researching which topics they are interested in.
  • Social media marketer: I improved the engagement of the brand’s social channels from virtually zero to X% by mixing up social media posts. Before, the company was only posting links about its products. When I took over the social channels, I mixed this up with helpful content, curated posts, coming up with themes per day, and included surveys/asking questions. This brought together the community where every post now gets a lot of comments and shares.

Sidenote: This is where many applicants complain about the interview process, saying the interviewer didn’t ask the right questions or didn’t give them a chance. Nope. The burden falls on how you communicate how you can help the company.

7. Include an ideal time for an interview

Towards the end of your initial application, I always include a sentence that looks like this. Feel free to copy it and modify it to your situation:

I look forward to hearing from you. Your Upwork profile says you are from New York. I’m available for an interview daily on Skype or here from 8 AM to 1 PM your local time, but I’m flexible on that once we agree on a schedule.

Again, make it easier for the hiring manager to do their job. Let’s take a look at the same job post I shared above. At the right, you’d see the country/location of the client. This is often a good indicator of their current timezone. Upwork is a global marketplace, so it’s a good idea always to specify exact dates and timezones..

Check Location and Timezone of Client • Screenshot by Author

After checking, go to https://www.worldtimebuddy.com/, then enter your timezones there to see how the schedule lines up. If you’re from London and dedicate mornings to your writing and the afternoons for client work, that’s what you indicate in your application, just like the example I used above.

Time Zone Converter using worldtimebuddy.com

Over to You

Follow these steps if you want to increase your chances of getting an interview.

  • Don’t blindly apply for every job post
  • Prioritise more recent ones
  • Focus on results and communicate that
  • Make it easy for the hiring manager to do their jobs

Are you having trouble with getting companies to reply to your applications? Follow those principles and soon you’d get more replies. And if you’re really good, you’d realize that you don’t have to apply for jobs anymore. Companies will start inviting to directly to their job posts.

Blog Credits: Ariel Lim.

Author