Shout out to @lincolnmurphy for the inspiration to write this one (and for contributing to it).

Thanks for sharing Jimmy

Cool post @jimmydaly! Love all the different ways you can engage with customers.

I love the idea of automating personal things, I think coupons by mail was the first automated personal thing in the world.

Really well written with lots of useful advice. My favorite quote "When it gets to the point that you can’t keep up with the volume, considering automation. " - I think if marketers put every email through this very simple test, their communication will become outright awesome. At Riddle.com we have been very successful with sending personal emails to small user segments (using Intercom) - it is not 100% personal but it gets close enough.

Loved this point:

"Resist the urge to include links and buttons. Those diminish the personal feel and will water down your results."

One thing I've learned is that people love emails that look like they came from their friend rather than a robot. As soon as links and buttons are thrown in, the email becomes more corporate and less of a human to human experience.

Great article - Really loving the work coming out of the GetVero blog as of late. Awesome insights for any marketer looking to take their email marketing skills to the next level.

Disclosure: I hadnt even finished reading the whole thing when I started making some changes to our triggered emails... thanks, Jimmy!

Nice one Jimmy. Thanx for sharing various ways that we can use to engage with customers. Wish to hear more from you.

Thanks for sharing Jimmy

Great heuristics, Jimmy, especially this one: "Would I send this email to every customer manually if I had the time?"

I think most business emails today do nothing but TRAIN their customers to ignore messages from them.

Something *clicks* when you realize that the person reading your messages is an actual human being ... deep into her problems and frustrations.

This quote is what made it click for me:

“ … keep in mind that direct marketing is a reading experience and a reading experience is a very private experience.

"You can propose benefits or talk about problems that people wouldn’t necessarily talk about if you were in conversation with them. You can talk about things such as personal deficits or address competitive instincts like making your lawn the best lawn in the neighborhood. You can talk about things that people would never admit … you can talk very intimately and address these deep needs in a direct mail letter in a way you can’t do probably in any other sales medium.”

anyway, great guide and examples of behavioral emails to send. I'd just add very short follow up emails for non repliers (most people).

I'm crazy about follow up, it's one of the most important lessons in our concierge onboarding email course (http://us7.campaign-archive2.com/?u=e7889016118078dfdf0ab1cbc&id=a013db5846)

Something like:

subj line: Re: checking in

body: Hey Jimmy, everything ok?

The subject line "Re:" and the fact that it's very short makes people think, "Oh shit, someone's actually typing this stuff. It's personal"

Some very interesting questions to ask subscribers. Good read!

As a general rule, I am not the biggest fan of automation. It has to be done, no doubt about it, but there are so many traps. My favorite line is "Would I send this email to every customer manually if I had the time?" With automation, there is much less of a cost or barrier to doing things, so there is the temptation to do it anyway and see what sticks.

Although there are many digital marketing tools can automate a lot of our work, the best user engagement you can never automate, and should never..

“premature-automation can lead to blindness.” I am sure it is a true quote but it is not about automated email with FROM and REPLY_TO being your genuine email and, if you read and respond them quickly - it is fine.

I have just sent 260K emails from my personal email with 20% opened rate in 24 hours. The only problem here is a good GMail filter to send auto responders to Trash which I am still polishing but happy to share when done. Currently I have 1600 responses in Newsletter folder in GMail with 95% being 'out of the office' in about 20 languages and 40 styles. So it is extremely hard to get real responses and we prompt people to reply to any email we sent out explicitly saying 'hit reply and share your experience or ask us a question'.

We also send automated Welcome email but again from a real email from CEO and we have a great response and we always reply back in 24 hours and obviously read what people say.

Regarding cases when people used and stopped using - still can be automated and get personal. I do not think you can do it with any SaaS like Intercom until you are integrated with them very deeply (for our userbase Intercom will be 4K monthly - can not simply afford it) and can add variables to bring your personal knowledge and mention real scenario and ask why. We do all such automations in-house for this reason and we have all data in either DB or ElasticSearch. So you are not just saying 'we haven't seen you lately' but something which tells your client - you really spent time looking as to what could cause them to slip away. Hopefully they appreaciate it and reply back ... and you recover them. I wish all to be able to do that :)

Remember: even quick reply to exit survey sometimes let's you to save a customer or two a day

Loved your points. In fact it's gonna save my time. :) Thank you.

Excellent post, Jimmy! I just bookmarked your excellent guide to perform the email automation in a perfect manner.

I'm going to start an email marketing campaign and thus searching for some effective guide to implementing it. I found the helpful post here, thanks for your great contribution.

Great advice, I especially agree with the fact that OVER automation can lead to some really inauthentic relationships with customers. But I do appreciate it when it seems that the sender is actually typing the email (even if I know that it's probably automated).