#17 - AI Emails Don't Work

When a flood of AI copywriting tools came to market in 2023, I was excited by the potential but ultimately bummed by the results.

Over the course of a few years, and after failing to generate significant pipeline with high-volume, low-quality cold outreach campaigns, I was successfully able to build a process around personalized emails that effectively built pipeline in 2022.

Enter spring 2023:

I was excited because the high-quality, personalized email process I established (while effective) was pretty manual and very time-consuming. If personalized AI emails could increase my output from 50 to 500 emails/week, I could see a future of increasing my weekly meeting count by the same multiple.

However, I knew that every other rep would be leveraging these tools. These emails would quickly become white-noise, and performance would suffer because even my higher-quality manual emails would be lumped into the same heap. Double whammy.

The quality of these tools have proven to be garbage - doing nothing more than scraping generic stuff from a prospect’s LinkedIn that screams “AI wrote this.”

Some variation of “I am very impressed with your years of dedication at ABC company, it is clear you have a very strong skillset in XYZ.” Followed by an awkward transition into your company’s value prop.

After trialing a couple of tools and realizing the output is all the same because they use the same LLMs, I found my manual (but somewhat scalable) email process still cut through the noise by being human.

Below is the process I built in 2022 that has remained effective. Feel free to use it.

Subject Line/Part 1: This is the “hook” - show you’ve done research on them individually as well as their company. Even if it’s not a fit, the fact that you’ve put in effort will lead to many more opens and positive replies.

Part 2: This is the “thesis”- synthesize what you know about the company through research and your company’s value prop to create questions designed to elicit pains that you can solve. This is the most critical part.

Part 3: Concise value prop. This can be canned and should be framed to answer the leading questions asked in Part 2. For efficiency sake, copy/paste this in each email (make sure to include a call to action).

Each note takes roughly 15–30 minutes to research/write (maybe 35 mins once 6PM rolls around and you’ve already cranked out 20+ that day), so the outreach volume is much, much lower.

After this note is done, however, each subsequent step in the cadence should be automated on top of this.

2-3 follow ups should just focus on bringing the content of email 1 to the top of the email box. This is in case the prospect saw, was interested, but got distracted.

Layer on a couple calls and a few LinkedIn notes - all of which have the same messaging as email 1 - and you have easily built a 7-10 step cadence with extremely high-quality messaging.

In short, there are now many AI copywriting tools on the market. They don’t really work. Try them, but make sure you are using something that is free - either with ChatGPT, or a solution like LeadIQ which has the functionality built into their wider platform.

I’ve found that the process I’ve built, while not extremely scalable, is still far more effective in driving meeting conversion. Which is the ultimate goal.