5 Steps to Create a Successful Cold Pitch or Proposal

You can’t just keep flaunting your past experience, every time. And shouting out loud won’t work, either.

Anmol Ratan Sachdeva
The Startup
Published in
6 min readSep 23, 2020


Photo by Jason Rosewell on Unsplash

Waking up to an inbound lead is a bliss for every independent consultant or freelancer. You would agree, right?

But, attracting attention is just a battle half won. You still need to convince the prospect that this is ‘a match made in heaven’ before they shell out a contract to you.

Having worked as an independent consultant for almost three years, I realize that my biggest wins came when I was serious about the proposal.

I have always believed in the power of inbound and word-of-mouth, but one cannot deny that cold pitches and proposals are the biggest winners for the freelancing community.

In the last one year, I have written hundreds of pitches and proposals (mostly on Upwork where they are called cover letters) and I realize there is more to a proposal than just telling about yourself.

The other day, someone asked me about my approach to creating a winning proposal. So, I thought, why not share it with the world. Before I dig in deeper into the steps, let’s begin by setting the right premise.

General tips for writing a cold pitch or proposal

  1. Be Empathetic & Personal: Don’t talk fluff. Understand your prospect’s pain points, goals and aspirations and show that you care for their goal.
  2. Talk about ‘Them’ Not ‘You’: Never boast your past credentials. Instead, talk about their struggle and possible resolution along with showing them how you can solve their problem. A prospect always has a problem to solve, that’s why he/she is looking for external help.
  3. Never Copy/Paste or Use a Generic Template: The biggest mistake you can make is sending the same pitch to everyone. The world is already in the 21st century, my friend where ‘personalization’ is the winner. Spend some time to write custom proposals, meant just for the prospect.
  4. Offer Advice: This might sound absurd. Why would you offer a ‘free recommendation’ without even getting paid? But trust me, prospects love when they see…



Anmol Ratan Sachdeva
The Startup

Marketer. Writer. Branding Enthusiast. Someone who likes sharing knowledge backed by personal experience.