Piloting a new Email "BigDripper" sales tool

As CEO of my startup, I sometimes have to be in sales mode. (Well, every owner of a company is always in some sort of sales mode, but in this case I mean prospecting for customers of new product offerings).

I recently wrote about what it takes to create an effective sales team. But here I just want to share one pro-tip, and see if I can find a few other interested people to beta-test a new tool with me.

We have a new product that we're piloting, and so I'm in sales mode for a bit testing the waters. I always like to do the initial sales myself, so I can tweak it and figure out what's working and what's not, before I pass it over to a sales team. Plus, hearing the inevitable "no's" from prospects is a great way to get honest feedback about the product so we can iterate on it quickly.

As part of this, I'm sending targeted emails out to CMOs of large brands. I have a very specific methodology I follow to find the CMOs I believe will be most likely to have interest in our product. And I always start at the top of an organization -- even if the CMO isn't the one making the direct buying decision, they almost always control the P&L, and if the CMO sends an email to a direct report to check something out, then it's much more likely to be followed up on (and quickly) than if I targeted that person directly. To learn more about this sales philosophy, read this blog post I wrote many years ago about selling effectively.

One thing I've always wanted, and have never been able to find satisfactorily, is a way to follow up on emails I send in an automated manner that won't feel spammy. There are great tools like Boomerang (which I mention here and here) which can remind you if nobody has responded, but then it's up to you to send the followup manually.

I wanted a tool that would automate that part of the following up according to rules I set: If the target doesn't respond in 4 days, then ping them. Six days after that, ping them again with a variation of the text. And 10 days after that, ping them one last time with a quick line saying you won't email them again, and requesting that they reach out if they're interested.

So I approached a good developer friend of mine to build something like this, and he did. I call it the "Email BigDripper" (cheesy name, I know, but fun too), and I've been using it for the past several weeks. And the results are as amazing as I thought they might be. See the screenshot above, which is the CMO of a Fortune 500 company responding to my email after one of the automated pings.

A system like this can be abused easily, so before we open it up for anyone to use, we're going to put more safeguards in place. But I'd be willing to talk to specific people about piloting it with me, so we can work on making it even better and more effective. If you're interested, please leave a comment below, and I'll private message you directly to continue the conversation.