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July 25, 2017

A Complete Walkthrough of 5 Vital Email Drip Campaigns (With Examples)

When I moved from traditional marketing to digital marketing at Wishpond, I couldn’t have imagined the complexity of what I was diving into.

Sometimes it feels like all us marketers do is try to fix what’s lacking. Once everything is set up, all we do is plug the holes.

In our product pages, our sales/checkout pages, pricing pages, free trial dropoff emails… The list goes on and on. And yet so many prospective customers (and free trialers) keeps slipping through the gaps.

The solution is marketing automation a strategy which allows you to make your sales funnel as solid as you can, without constant attention and late nights trying to do it all manually.

But it’s intimidating.

This article breaks it all down into bite-sized pieces. I’ll outline five of the most dangerous “holes” in your sales funnel, and show you how to plug them with optimized email drip campaigns:

  1. Winback Drip Campaign: Recapturing those customers who bought from you once and left. Or, in the case of software, people who used your service but left.
  2. Upselling Drip Campaign: Turning those free-plan users or single buyers into premium plan holders or purchasers of something more valuable.
  3. Subscriber Drip Campaign: Turning your blog subscribers into customers through intelligent email nurturing.
  4. Billing Dropoff Drip Campaign: Emailing bounced leads (who visited your billing page but left) and encouraging them to convert.
  5. Free Trial Onboarding Drip Campaign: Boosting the percentage of free trialers that become paid customers.

I’ll show you diagrams which outline the flow and triggers of these marketing automation campaigns, as well as break down exactly what content to include in the emails.

Winback Drip Campaign Example


Drip Campaign Trigger:

This campaign is sent to people who cancelled their plan or last purchased from your business more than six months ago. If they haven’t yet unsubscribed from receiving emails you have an opportunity to recapture them as customers. The goal of this campaign is to get them on a call.

drip campaign examples

Email #1:

Subject: Updates to the [Business Name] Platform/Service

What to Include: Introduce yourself, personally, and break down the biggest change that has been made since they left (you can do this by segmenting people who left before you updated your platform or service). Invite them for a call.

Email #1a:

Subject: Get 30% off your first [biggest change]

What to Include: This is the email which is sent/triggered only if your recipient clicked through on the previous email. You send it because you know they’re interested in whatever update you made. Include a discount for that specific addition or change to your service or platform.

Email #2:

Subject: Top Tips for [Strategy Related to your Business]

What to Include: This is an educational email designed to provide value beyond your service or platform. Relate it directly to something you do, however.

Email #2a:

Subject: Get 30% off [Product Related to the Strategy in Email #2]

What to Include: This is a promotional email only sent if recipients opened Email #2, sent because you know they’re interested in the subject of your promotion. They wouldn’t have opened email #2 otherwise.

Email #3 (Sales Email):

Subject: Do you have time to talk about changes to [Business Name’s] Platform/Service?

What to Include: Make this one super personal and short, but to the point. You’re trying to get this person on a one-on-one call in order to better understand why they left and to address their specific pain points.

Top Tips for This Drip Campaign Example

Send this drip campaign to people who last visited your site or last-bought more than 60 days ago. This way you’ll be able to ensure there’s enough time for significant changes to have occurred to your service or platform. If you hit them with an immediate winback campaign a day after they left, they won’t believe anything will have improved.

Upselling Drip Campaign Example


Drip Campaign Trigger:

This is a campaign sent to your free plan holders (WordPress, perhaps), as well as people who have been on your Basic plan for more than 60 days. It’s often easier to upsell existing, happy customers than it is to get new ones. The goal of this campaign is a more expensive plan upgrade or more valuable purchase.

drip campaign examples

Email #1:

Subject: [Until July 31st]: Get 6 Months of Our Pro Plan for the Price of Basic

What to Include: This email is all about communicating the difference between the plan they’re currently on and what they could get with the more expensive plan, and then giving them an economic reason to move

Email #2:

Subject: How [Business Like Theirs] Achieved [Positive Result] with [Business Name Advanced Plan]

What to Include: This is a case study email with an embedded video (or sending people to a video via a link) from a company like the recipient’s. It shows people that they can get better results if they upgrade to a better plan.

Email #2a:

Subject: [Business Name] Found Success with our Pro Plan. Want to Talk about You?

What to Include: Only sent if the recipient clicked through on the case study video email above, this email is a demo prompt, which ties that previous case study to possible success the recipient could have.

Email #3:

Subject: 24-Hours Left to Upgrade your Plan (Save $588!)

What to Include: Very simply, this email is a final attempt to upsell people. Prompt an email reply or VIP demo to better communicate the difference between what they have and what they could.

Top Tips for This Drip Campaign Example

Where possible, use peer pressure and case studies when upselling. People respond far more to the success of others than they do to promised success from you.

Subscriber Drip Campaign Example


Drip Campaign Trigger:

This drip campaign example triggers as soon as someone subscribes to your blog.This is an optional drip campaign, because (of course) you can simply send your blog subscribers your newsletter whenever you publish a new article.

However, we’ve started to drip our subscribers because it gives us a better chance of turning subscribers into customers in the early stages of the relationship. Also, dripping enables us to segment more effectively, as we can see what article they were reading when they chose to subscribe. This means we can send more content and frame our messaging around that subject.

What it looks like:

drip campaign examples

Email #1 & 2:

What to Include: The first two emails in this drip campaign are educational – related to what they were reading when they subscribed. Before we can get anywhere near a sales email, we need to send (at least) two educational, value-oriented emails.

Email #3 (Sales Email):

What to Include: This is your first sales email, so keep it chill. We’ve found success with framing this email as a “consultation” rather than a demo, as it feels like less commitment. Ask if your recipients want to jump on a call to discuss a strategy which relates to their interest.

Email #4, 5, 6 & 7:

What to Include: More educational emails,. You need to be providing overwhelming value to your subscribers so that when you do prompt a sales ask they feel that A) you know what you’re talking about and B) you have their best interests at heart and, also C) they’ve received enough context for the value of what you’re selling.

Email #8 (Sales Email):

What to Include: This is your second sales email, and you can go full-on with this one. Ask if they have time this week (test giving a specific day and time) to jump on a cal. If you like, add a follow-up email to be automatically sent the next day (if they haven’t responded) making sure they received the previous email.

Email #9 & 10:

What to Include: Again, educational emails. Keep them focused on your subscriber’s interest, but be sure you’re also communicating the value of your service. Consider sending case studies or including examples of a strategy which show screenshots of your platform/service.

Email #11 (Sales Email):

What to Include: Final sales email before this subscriber gets dropped into the general subscriber list and starts receiving non-automatic newsletters. My recommendation would be a discount or limited-time promotion alongside the demo prompt.

Billing Dropoff Drip Campaign Example


Drip Campaign Trigger:
This short set of emails is sent as soon as your prospective customers leave from your billing page without purchasing (this would also be the “abandoned cart” drip for ecommerce businesses). It’s a pageview trigger where they’ve seen your sales page and seen your billing page but not seeing your “Thank You for Purchasing” page.

drip campaign examples

Email #1:

Subject: “Forget Something?” (Ecommerce) or “Oops! Was there an error at our end?” (SaaS/B2B)

What to Include: A reason to return. As you can tell from the subject lines, these emails don’t assume that the person who dropped off your billing page did so intentionally, though of course 90% of the time it was completely intentional. This is so we don’t assume the reason (plus these lay the blame on someone other than the person who left). This email, though, should address the most likely reason they left (usually price) and either explain it or reduce it.

Email #2:

Subject: How [Business Like Theirs] Achieved [Positive Result] with [Your Business Plan/Product]

What to Include: This is a case study email with embedded video. It uses the success story of another business or customer to sell a reason to finish a purchase.

Email #3:

Subject: How [Your Business] Stacks Up Against the Competition

What to Include: This is the third and final email (though you could add a demo prompt if you wanted) and addresses the second-most-likely reason someone bounced from your billing page: they were shopping around and believe someone else may be better than you. So this email (and the whitepaper or “competitor comparison” page you send them to) needs to address why you’re the best.

Top Tips for This Drip Campaign Example

You should definitely retarget those people who dropped from your billing page while this drip campaign is sending. Retargeting (also called remarketing) ads only send to a specific segment of your website visitors – those who viewed specific pages. They allow you to target people with very specific copy (like “Return to [Your Company] and Finish Your Purchase!” and know with confidence that you’re addressing their experience.

Free Trial Onboarding Drip Campaign Example


Drip Campaign Trigger:

This drip campaign is your onboarding strategy, designed to improve the chance of your free trialers completing their trial and purchasing. It’s triggered as soon as someone signs up for your free trial.

drip campaign examples

Email #1:

Subject: Welcome to [Your Business] Free Trial!

What to Include: This email is very much about introducing yourself and your brand. Focus on tone, here, and deliver value. We always prompt a demo in our welcome emails, links to our help content and any videos we might have to make using our platform as simple as possible.

Email #2:

Subject: How [Business Like Theirs] Achieved [Positive Result] With [Specific Part of your Platform or Service]

What to Include: This is a video case study, showing free trialers the success they can have if they choose a paid plan. Focus on a specific element of your platform the customer took advantage of.

Email #2a:

Subject: Want to talk about how your business can find the same success as [Case Study Business]?

What to Include: Only sent if they opened the previous email, this follow-up (prompting a call) is sent very soon after the second email, and includes something like “I’ve just seen that you checked out our case study from [business]. Would you want to schedule a time to talk about how it relates to your business specifically?”

Email #3:

Subject: How’s your free trial going?

What to Include: Prompt a conversation, whether over the phone or via email. If you start building a personal relationship with your free trialers they’ll be less likely to leave after their trial has completed.

Email #3a:

Subject: Did you want to talk?

What to Include: Only sent if the previous email was opened but not clicked-through on (or replied to), this short email prompts the call referenced in the previous email.

Top Tips for This Drip Campaign Example

Free trial onboarding is a bit of a challenge for me to recommend, as every business is different and every business has different resources. If you have enough staff to get every free trialer on a call, do so. If not, create awesome help content (particularly video) which shows the personal side of your business and drives a relationship.

Wrapping it Up


This article only scratches the surface (though it is a bit of a gouge, I admit) of what’s possible with drip campaigns.

Get creative with what you put together, and be sure to test your email subject lines and formatting to determine what your recipients respond to best.

And if you have any comments or questions, don’t hesitate to reach out in the comment section!

If you want to try out email automation and drip campaigns for your business,


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