How To Personalize Your Upwork Pitches To Show Value Upfront

My journey on Upwork for the past seven years has been a transformative one. It started with an uncomfortable unknown that eventually led to building a successful agency that did well over $1M in revenue in 2021.

I want you to find the same success that I did and have three tips to share to help you personalize your pitches to stand out from the crowd. This is my story, and my thoughts on how you can follow a path similar to mine.

• How my story began on Upwork
• 3 tips to help personalize your Upwork pitches
• Example of a message I send to clients

How my story began on Upwork

In 2016, an email arrived that would forever change the course of my life. As I sat in my 600 square foot apartment, I read those three sentences that notified me my consulting agreement had come to an end. A deep breath in, a cold sweat broke out. Freedom and anxiety struck simultaneously. With only $1500 in my bank account and no income, I felt the weight of the choices before me in the time it took to make a sandwich and return to my desk.

I gave myself 2 options.

1. Secure a traditional 9-5 office job
2. Embark on the journey of freelancing

My studio apartment had already served as my office for the past two years. The thought of stepping into a traditional office job felt archaic. So, on the same day my last consulting agreement ended, I joined Upwork. I decided to take my project management skills with me as a jump-off point to land my first client.

Starting from scratch, I had zero previous experience with Upwork and zero reviews.

Initially, I found myself doom-scrolling for jobs. Several jobs piqued my interest, some even seemed perfect for me. But each time, I was disheartened to see that 30+ people had already applied. In the first three days, I applied to over 80 jobs on Upwork and only received one response. I didn’t land that job.

It felt like stepping into a crowded arena, packed with freelancers all fighting for the same opportunities.

3 tips to help personalize your Upwork pitches

This experience forced me to rethink my approach. I began to explore ways to stand out, to find the middle ground between applying to as many jobs as possible and actually providing value to potential clients.

The epiphany was clear: I needed to focus on quality over quantity. Instead of attempting to apply to 80 jobs per day, I chose to focus on 15-20 high-quality applications. This required showcasing that I'd thoroughly read each job post, responded with unique insights that directly related to the job posting, and provided visuals of work I've done.

I employed three strategies to make my applications stand out.

1. Showcase attention to detail

Remember: Every single job post is unique. Approach each one individually.

Some posts are more detailed than others, while some include pre-application requirements or have attachments that contain additional project information. It’s vital to read each post thoroughly, twice even.

Then, directly address details like this from the job post in your application:

• Is the client requesting a specific answer to a specific question and are you answering it?
• Is there a part of the job that isn’t familiar to you that you’d like to know more about?
• Is there anything that you can challenge or advise the client on based on their request? For example, they want something “fully” custom but your advice would be to start with a template and build from there. Suggest smaller steps in the beginning and then evolve the project and relationship later.

Treat it like you’re in a conference room giving your client consulting advice. Offer any guidance you can to the client based on your experiences and what might work for them.

2. Show personality

Don’t be a faceless freelancer. Be you.

Bring your personality and your skills to the table in every application. Before you hit send on your next application or response to a potential client, assess if you are following this rule: Be hard to forget and easy to remember.

A positive attitude and unique personality can set the tone for a great working relationship. When engaging with a potential client, don't hesitate to share insights about your personal journey and passion. Discuss how you started in your field, what led you to freelancing, and what excites you about the work you do.

Giving clients a glimpse of your personal journey and showing your authentic self will make you more relatable and memorable.

Offering a video call can break down the digital barrier and further humanize the interaction, reassuring clients that there's a skilled and reliable person behind the pitch.

3. Offer instant (free) value

To stand out from the crowd, show, don't tell.

For instance, if you're applying for a marketing job, share a few campaign ideas you've thought about. Or, if you're a designer, send the client some initial thoughts about their brand.

Taking the time to provide unique insights and demonstrating your skills upfront can build the client's confidence in your capabilities. It communicates that you're already invested in the project, even before officially landing the job.

Over time, focusing on these strategies paid off in ways I couldn’t have anticipated.

I was no longer a faceless freelancer in the crowd, but instead, I reached the expert vetted level in three years. This showed I offered unique value from the outset. My success on Upwork serves as a testament to the power of personalization and upfront value. I hope sharing my journey can inspire others to find their own path to success in the world of freelancing.

Example of a message I send to clients

Check out this real example of how I’ve reached out to clients in a way that landed me the job. I often use this template as a starting point.

“Hey it looks like your job has been active for over [X] days on Upwork. Were you able to hire someone that can help you with [XYZ]? If not, I would love to throw my name in the hat. Because I was late to the party, I brought a few extra gifts with me.

First off, let me introduce myself. My name is Zlatko. I have over [X] years of experience as a project manager with businesses in your industry. Actually, I just finished a project for a client that required me to do some quick design work and I am not a designer. Our designer got sick and the deadline was creeping up on us. I got it done. It was a quick job. As a project manager I am ready to jump in and help my team in any way that I can. [Show sample design work].

After looking at your project and comparing it to what I’ve done in the past, I feel confident that I can help you with [XYZ]. Do you have a few minutes to jump on a video call and discuss [mention someone specific here about the project to show that you’ve understood and read everything]. I would love to share my experience and what I can do to help you with your project.”

Stand out in a crowded marketplace

All the early roadblocks and obstacles could have easily put me in a state of failure and I would have resorted to working a 9-5 job in an office somewhere. Instead, I pulled it together and figured out the path to success on Upwork, and you can too.

The three strategies that were instrumental in helping me stand out in a crowded marketplace:

• Showcasing attention to detail
• Showing personality
• Offering instant free value

These aren't merely tactics. They represented authenticity to the client. A level of value that was hard to come across when there are hundreds of applicants.

Every freelancer's journey is unique, but the lessons I've learned can serve as a guide for others embarking on their own path. If you find yourself lost in the sea of freelancers, remember to focus on quality over quantity, let your true personality shine through and, most importantly, show your prospective clients the value you can bring to their projects.

This approach not only increases your chances of landing jobs but also lays the foundation for meaningful and successful client relationships.

One of the main reasons I joined Upwork is because I didn’t want to work away from home. I had just rescued my dog, Buddy. I didn’t want him to be home alone.

I decided to prioritize him and our awesome life so that we could spend more time together and make money from home. Upwork was my only legitimate option, I didn’t consider anything else.

I specialize in entrepreneurship, product development agency building, and business coaching. Send an inquiry through my Upwork profile and we can discuss the best options for your needs.