Email Marketing Automation For Small Business Owners

In August, I did the unthinkable: I unplugged for an entire week! 

While I was out, my business could have fallen off a cliff, and I wouldn’t have know!

And to top it off, my sole employee, Rene, had no way to get in touch with me!

He was alone, adrift – everything was at risk!

Or was it?

Business Automation

The reality is that when I went off the grid, Rene felt more empowered, not less.

My planned disappearance forced Rene to stretch his skills a bit, make some executive decisions, spend some company money supporting our customers, etc.

Empowering stuff!

In fact, my customers were happier when I was gone!

That’s business automation: The sausage is getting made & the checks are being deposited without me being anywhere near the factory!

And ya know what?  Later this month, I’m going to take another 2 weeks off, unplugged, for paternity leave. 

And my business will be stronger for it.

[RELATED: Here’s how to prepare to take a vacation.]

Goal of Business Automation: Enable You to Do the Work of Your Dreams

Business Automation will help your biz become calmer, more sustainable, & more profitable by:

  1. Increasing your close rate.
  2. Increasing your customer lifetime value.
  3. Running while you sleep.

And this isn’t some b.s. I’m pitching you: My high-end WordPress development business makes me money while I sleep!  

My biz is very hands-on, very customer-service-oriented, very in-depth-understanding-required, etc.  The stuff that you’d think the owner needs to be involved with. 

But one thing separates my biz from others of its kind: I automate.  Therefore, I work very reasonable hours (and never at night).

I am able to disappear and take vacations, because I automate all sorts of tasks in my business.  (Not the least of which is automating the actual deliverable work of the business, customer communication, etc.)

Business Automation Has Two Parts:

  1. Human Automation (employees doing the work)
  2. Digital/Machine Automation (computers/machines doing the work)

If you deliver a digital product like me, the solution to your lack of human automation problem is simple:

Human Automation is the only sustainable way for small business owners to make money while sleeping (or vacationing, gardening, racing, whatever).

Related Note: To see failed human automation in action, watch any episode of Hotel Hell.

Digital Automation

Digital Automation is when computers do the work while you sleep.  

I’ve increased my business profit & decreased headaches through these digital automations:

Email Marketing Automation

One of the ways I increase my profits is by giving my customers a better experience both pre-sale, while they are customers, and after they leave.

Email Marketing Automation pre-sale Workflow:

My sales workflow is built to have my leads start automations, which frees me up to…get more leads! 

Here’s my basic pre-sales workflow:

  1. They email me via my website contact form.  They are automatically-added to my Contactually “7 day” bucket (via Gravity Forms + Zapier).  An automatic email is sent to them asking them to select a date from my calendar for our initial call.
  2. They schedule a meeting via Calendly.  It gets added to my calendar automatically.  
  3. At the end of our call, if they are ready to buy, I sign them up using a simple WordPress payment page that has a number of automations attached (detailed below).
  4. Otherwise, if they aren’t ready to buy, I just email them the link to our payment page via an auto-generated Gmail Canned Response.
  5. When they fill out the payment form, they are automatically-sent a receipt and are automatically-added to my onboarding email automation for whichever product they purchased.  The onboarding emails are super short and come in a series of about 7 emails.  They include: “Welcome”, “Meet the Team”, “Send us your passwords”, “SEO Basic Research”, “How to Best Get Support”.  Depending on the product you buy, they might also include “Advanced SEO Research” & recommend our free Beginner WordPress by Email Class (which is a separate marketing automation), an off-boarding email, etc.

New Customer Email Automation Workflow

  1. After they purchase a product I get notified to fill out a Gravity Form checklist I created that asks me do a number of business-related things like: add to relevant spreadsheets, confirm payment went through, mail them a card (via Handwrytten), add note & tag in Contactually, and more.  Also, when I submit this form, it automatically sends a direct message to Rene in Slack, creates a record of the work I just did, subscribes the user to relevant Mailchimp automations, and sends me an email summary.
  2. As noted above, they will start to receive my daily email onboarding series related to their specific product.  

Ongoing Customer Marketing Email Automation

“We’ve hired someone to redesign our website,” a long-time customer told me via email.

“That’s what I do!  Why didn’t they contact me first?” I thought.

Because I wasn’t first in their mind.  In fact, it had been a year since we last chatted about the weather!

Ever since then, I’ve vowed to stay in touch with all customers quarterly.  (Contactually is the perfect tool for this.)

For example, I might send:

  • Mailed cards (sometimes with Starbucks or Target gift cards included)
  • Check-in Emails
  • “Review me on Google” emails
  • “Let’s grab coffee!” requests
  • “Here’s something else we can do for you” emails
  • Email newsletter
  • Customer Joy Survey (see below)
  • etc.

When I worked in politics, we’d get our candidate in front of people at least 7 times (post-card, coffee, mailing, door-knocking, etc).

We wanted to be first in their mind when they went to vote.  Smart marketing!

Customer Joy Survey

One way we stay in touch is through our “Customer Joy Survey”. 

At the end of every week, we send this 10-second survey to everyone we worked with during that week.

Our goal with this 1-question email-to-web survey is 3-fold:

  1. To learn how we are doing
  2. To nip problems early
  3. Another positive customer touch-point.

The Most-Important Thing We Do For Marketing

I learned a few years back that people might hire me for my WordPress expertise, but they stay with me, because we listen & respond quickly.

Even when we get fired, we are listening!

The best marketing is a product well-delivered!

Referrals make the best customers, are quickest to close, and are the most-important signal of business success.

Effective Business Automation Requires:

  1. Curiosity / Mindset of Innovation / Constant challenging of our own assumptions
  2. Effective work (i.e. different than efficient)
  3. Letting bad things happen

Most business problems are human-centric. If you don’t solve your human problems, they’ll only be accentuated by automation. 

Fwiw, Automation always helps me discover my very real human blind spots!  So, my advice is usually to get started automating today!

As you automate your small business, if you just practice the 3 things above, the rest will take care of itself!

Toby Cryns

Toby Cryns is a freelance CTO and WordPress Guru. He also writes for