Is Personalization Dead?


“Sales engagement” platforms are one of the most disruptive tools in the modern stack. I like to describe them as “Marketo for sales”. Tools like SalesLoft, Outreach, and (my favorite) Groove have enabled individual sales reps to build automated email, call, and text workflows with current and prospective prospects. However, with great power comes great responsibility.

Gone are the days of a sales rep finding creative ways to find a prospect’s phone/email, and more importantly, a reason to reach out. The sales engagement platforms like to call this “communicate at scale,” but I like to call it “spray and pray.” If tools like Marketo didn’t already ruin your inbox, these platforms are the final nail in the coffin. Outbound is commoditized; your inbox is f-ed.

So what’s the solution? Send more emails? Send better emails? Send personalized emails? The answer’s in there somewhere, but how can you tease it apart?

Enter Becc Holland. She certainly didn’t invent the concept of personalization, but she did leverage these sales engagement platforms and turned the process of “personalized” outbound into an art. This art is similar to core marketing principles; the right message, at the right time, to the right person. Becc has shared her learnings along the way via her (free) Flip the Script series. What once felt like my personal secret (buried in the is Chorus.ai blog) is now out there for anyone to watch, consume, and learn.

Now that the secrets out, the personalization playbook is available for anyone to use, everyone’s doing it. Wrong, literally nobody personalizes. Here’s how I know. Over the last several months, I updated my LinkedIn bio with a sentence that reads:

“*Cold Outreach Tip: Position your company/product/service in the context of an article from my blog (or simply mention an article you enjoyed) and I’ll gladly take the meeting and/or accept the random friend request.”



I’d like to think anyone who sends me a cold LinkedIn InMail or connection request would at least read my bio, right? Wrong! Over three months, 150 connection requests, only two personalized messages 🤯. Shout-out to Rees Bayba of Spekit and Taylor Aubry of Seismic, who read my bio and wrote thoughtful messages. Both Rees and Taylor got the meeting, and both were very clearly excellent sales reps.





Pro Tip: Don’t personalize the first email of a sequence/cadence; this takes too much time at scale. Instead, send something generic, wait for some level of engagement (email open/click), then personalize the following message.

– Rob