My 5-Step Guide To A Killer Upwork Pitch

Pitching potential clients is an essential part of freelancing — so why does it feel so difficult and scary?

It’s no secret that cold pitching is a frightening undertaking. 

What should I say? How much do I share? Will they even open my message? Am I wasting my time?

This is a totally normal experience for any level of freelancer. But it doesn’t have to be this way.

Unlocking the secret to powerful pitching

What if, instead of hearing crickets after sending out countless cold pitches, you got a message like this:

Recently, on LinkedIn, I talked about the benefits of lukewarm pitching on Upwork.

(You should totally follow me on LI if you aren’t already, btw).

Basically, as a platform that hosts countless clients looking for talented work, Upwork is essentially offering training wheels for learning how to pitch — because everyone on the site is already in a solutions-oriented mindset and wants to hire a freelancer.

Talk about an advantage!

Claire’s 5-Steps to a killer Upwork pitch

Knowing this, you now need to capitalize on the opportunity to make your pitches land. Follow my simple yet effective guide to pitching high-quality clients on Upwork:

#1 - Personal introduction — Start with a short but simple introduction, ideally including the client’s name, if possible (we discussed how to find a new client’s name on Upwork in last week’s email).

#2 - Show interest in their project (with proof) — Next, I like to express my interest or expertise in their project, without just talking about me. This is a great opportunity to showcase your knowledge about a specific topic, validating the value you would bring to the project.

#3 - Share your relevant work — Whenever possible, the work samples you send should be in the specific niche of the project. If you don’t have samples that are a perfect match, you have two options (both of which I have done, and both of which are effective)

  • Send tangentially-related samples if available

  • Create a new, short sample specifically for this job pitch

#4 - Ask a thoughtful question — After sharing my work, I liked to ask a thoughtful question about the project. This helps to encourage a response while also showing your investment in their work.

#5 - Close with an invite to chat — Finally, close the pitch with an invite to continue chatting, either over Upwork messages or on a virtual call. Once you land an interview, the chances of getting hired for the job go up significantly, so always be sure to ask!

It’s time to get pitching

Using Upwork & my guide to your advantage, you now can craft a personalized and compelling pitch that makes you stand out for all the right reasons.

I hope you find this helpful — leave a comment and let me know how your first few pitches on Upwork go.

Happy pitching!

P.S. Want this system explored in greater detail, including examples of real pitches that got me clients? I’m working on some new resources to share exclusively with my newsletter followers, so stay tuned!

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1 Simple Trick You Need To Make Your Upwork Pitches Stand Out

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Riding The First Client Rollercoaster