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How I reached a 57.5% win rate in 2023

In today’s newsletter, I’ll share exactly how I reached at 57.5% win rate in 2023, so you can get some inspiration and increase your win rate as 2023 is coming to an end. If you follow these steps, you’ll start more conversations, turn them into meetings, and create momentum to close your deals faster.

Let’s dive in:

Part 1: Refined my triggers

In 2023, you need 3 things to get replies from cold outreach: creativity, relevance, and timing. In the past, creativity and relevance were enough, but nowadays, you need to reach out to a prospect right when you find a trigger.

Here are two examples of triggers I used to start conversations:

Example 1: Product announcement

Back in October, I received a product announcement by email from Mixmax. The announcement was about an AI composer they had just released. Here’s the message I sent and the reply I got:

Image #1

Example 2: Webinar

In early December, I attended a webinar about influencer marketing in B2B. One of the speakers shared a breakdown of how they structured their deals, and the exact outcomes they were looking for.

On the day of the webinar I added this prospect to my new prospecting tracker (I’m now using Amplemarket), and the morning after, I reached out to them.

Image #2

And this is is what they replied:

Image #3

In both cases, a relevant and well-timed trigger allowed me to start conversations with a single touchpoint.

Part 2: Shortened my messages

As I’ve been prospecting mostly on LinkedIn, I focused on keeping my messages under 300 characters (the limit for a connection request). This forced me to stay within a strict limit and helped me convey my message in the shortest way possible.

I also doubled down on text only messages for people I had never met before, because I noticed that many prospects didn’t even watch my prospecting videos or LinkedIn voice notes.

But the most impactful change has been around the content of my messages. I started testing outbound message templates from B2B sales influencers, which I compiled in a Prospecting Template Swipe File. This made a major difference and took me from 38% reply rate to 46.31%.

Part 3: Made my offering crazy simple

The last point was also the most impactful on increasing my win rate. I define my wine rate as the number of closed won opportunities divided by all the opportunities I opened. In the past, I was selling two types of products:

I typically charge 5 figures for these engagements, without a trial period, or a smaller deal, which makes it challenging to close.

Now I’m focusing on selling sponsorship deals (I still offer training and consulting) but it’s incredibly easier to start with a small deal, close it, and expand when I can show results. I even close a majority of these deals by chatting on LinkedIn only.

Ideas to increase your win rate

For most people, increasing their win rate to 50%+ is not possible. They have limited flexibility on their offering and what they are selling. But here are some ideas:

And these are the 3 steps I followed to reach a 57.5% win rate in 2023.

Hope this helps.



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Write cold messages that get a 38% reply rate and 27% meeting rate here (90+ students)

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