Automation Frustration and Email Marketing

One of my goals for this year is to automate as many things as possible at Manage 2 Win. In the past we have been bogged down with so many manual tasks it has been difficult to actually focus on work that matters most.

Emailing emailing each newsletter and podcast episode. Changing customer credit card information over the phone. Manually requesting information for talent assessments. What a waste of time!

Every blog post and podcast episode should be emailed automatically to anyone who wants to receive them. If a credit card needs updating, our customers should be able to log into their account and change it themselves. Upon purchasing a talent assessment, each customer should immediately be able to tell us which assessments they want and who should take them.

But automation isn’t all that easy.

For instance, take email marketing. In the past we would send an email newsletter 1-3 times a month to our whole list, and I then posted it to our blog and shared it on social media. It consisted of one, full-length article. The whole process of reviewing & editing the article, sending it through Constant Contact, posting it to our blog, and then posting it to social media could take up to 4 hours. I would send emails about podcast episodes too, individually, in about 30 minutes.

That’s a lot of valuable time, so I decided to spend the better part of last week automating our email marketing.

First I looked at our current provider Constant Contact. They couldn’t help me. Next!

Then I checked out Squarespace, the hosting provider for our site. They have a new email marketing feature that is currently free for early adopters. It’s not the best design, but I can pull content right from our site and add it to an email, then send the email. I can even grab multiple posts from multiple locations, like our blog and podcast.

But I would still have to send each email individually. Deal-breaker.

Then I found out it’s possible to create RSS campaigns through MailChimp and automatically send each post to a list. Hooray! But wait… I can’t figure out how to change the title of each email, the images don’t resize properly for Outlook, and I don’t think everyone on our list wants to receive every, single, piece, of, content, we, produce.


I tried to be patient, researched RSS campaigns, tested multiple solutions, and troubleshooted email formatting problems (damn you Outlook!). I must have sent over a hundred test emails. It was exhausting.

At one point I was ready to give up and thought:

People don’t need to hear from us every time we post something new! They get so many emails, texts, pop-ups, and posts every day it’s enough to make their heads explode. I hate this crap. Why would we want to contribute to this mess of information spam?

That was the theme of my pity party. It sounds logical. Unfortunately, it’s only partially true.

While we do receive a lot of distracting spam these days, a lot of it is useful, and a lot of people appreciate our content. Furthermore, email marketing is a really important part of our business. It’s how we connect with our friends and fans, share our expertise, and advertise our products and services.

People want to hear from us, and they should be able to.

Eventually, with much patience, I was able to set up MailChimp’s RSS campaigns properly. They are very robust, and I am mostly happy.

We now have a big contact list separated into 4 groups:

  1. Monthly newsletter

  2. Blog posts

  3. Podcast episodes

  4. Announcements, Special Offers, Free Stuff

We can target any of these groups in our campaigns, including the automated campaigns for blog posts and podcast episodes. Additionally, our subscribers can edit their preferences and decide which types of emails they want to receive. It’s a win-win.

This saves me a ton of time, time that can be used to improve our client experience.

Automated Assessment Ordering

We have also changed the Talent Assessment ordering process. Previously, when a customer ordered an assessment they would communicate with Sinal in multiple emails to figure out who should receive which type of assessment. Also, Sinal didn’t even receive the order confirmation emails. She was delivering assessments simply based on David’s instruction or the track record of the client.

So we made a few changes.

Since a few of us need or want to receive order confirmation emails, I was able to create a catch-all address and forward incoming orders to the right people. Now Sinal receives confirmation of an order prior to delivering the assessment (clients can also request an invoice if they prefer). This saves David time, he no longer has to forward orders to Sinal.

Also, we created a new Thank You page for assessment orders. Every person who orders an assessment is redirected to this page:

This immediately let’s the client request specific assessments for specific people, eliminating one step of work for Sinal. If Sinal doesn’t receive info from a client, she will reach out to them.

As for other automations, we are going to continue working on them. Our Dave’s Charm School subscribers can update their billing information in their account, but it could be designed better. Software users still often contact us to update their billing information, but that’s just a necessary evil at this point as it reaches old age.

What are you automating at your business?

I’m curious, what are you doing in 2019 to automate processes in your business? Many things require a human touch, it’s true, and as we say in our new Hire the Best e-book, your customers buy from you because of your people.

But you can improve the customer experience AND save yourself extra work at the same time. That kind of efficiency and attention to detail is exactly the type of ingenuity your clients will appreciate.