7 Emails that Keep Customers Coming Back for More


You’re lucky and you don’t even know it. With a SaaS business, you already know that your customers want to hear from you. They’ve signed up for your service, which means they’re interested.

Pity then our poor sales brethren, who are picking up the phone each day or shooting out yet more emails to people who mostly aren’t listening. An “ocean of rejection,” as one poor soul put it.

But there’s one upside to the salesperson’s eternal struggle. They’ve come up with the perfect techniques for turning cold leads into hot prospects.

These techniques work for customer engagement at all levels, including in lifecycle and retention email campaigns after you have that initial lead. In fact, this is where some of these techniques come into their prime, warming customers up and turning them into your most passionate fans.

Let’s look at 6 techniques of sales teams that you can apply to your lifecycle emails today.

1. The Power of Now

One of the greatest sales techniques you can adopt for email marketing is the power of now. Salespeople want to get customers engaged right away. For them, this means the phone call they are on right now. For you, that’s the very first email you send out.

Don’t wait for users to find everything wonderful in your product. Your engagement effort starts immediately — and the welcome email is one of the best opportunities you’ll have, with as high as 4x the open rate and 5x the click rate of other types of emails. You have attention and interest at this point — after all, they just signed up to your service.

Instead of pestering and pushing them to upgrade to a paid or higher plan at this early stage, you can start working together. One suggestion for immediate engagement is to ask them a single question, just as Groove does:

Groove welcome triggered email

This is immediate engagement. It plants the idea in the customer’s mind that you’re embarking on a relationship — and that you’re interested to hear what they have to say.

By getting the conversation going and making decisions together, you can help your customers get more out of their product and increase the chance of them staying and paying.

2. The Ultimate Follow-Up Schedule

The timing of follow-up emails will, of course, depend on your business, content, and customers. Midmorning, midweek is what you’ve been told. But in reality, that works every time except for all the times it doesn’t.

That’s why salespeople should vary their follow-ups by the time of day they are sent, according to Steli Efti, CEO and co-founder of Close.io, a sales platform for following up sales calls. He sends out his first cold email to a prospect, then follows that up one day later with a modified version of the same message, but at a different time of day.

The prospect might have missed the first email. By closely following up with a new email, with a different structure, at a different time of day, Steli increases the chance that this information gets across.

This fits with the timing research out there. Sending out an email in the midmorning might be a great way to get it seen…

best time to send email
(Source: Experian)

But not to get a response. People may read emails in the morning, but tend to respond later in the day:

best time to send email for replies
(Source: Experian)

If you follow Steli’s advice and send your first email in the morning of Day 1, and then another follow-up in the evening of Day 2, you’ll get the best of both worlds: people can read your email on day one, and then the follow-up reminds them to act on it and re-engage with your service.

3. Include the Negative

If you’re sending emails out to users as part of your retention process, you’re probably including a list of your awesome features.

Sure, they’re awesome, but compared to what? Information on its own doesn’t tell us much. In fact, without a direct comparison, you may be losing out on customers who don’t see your features as all that.

The best thing to include in your list of awesome features is a few of your shortcomings.

It may sound ridiculous, but this works. Research from Stanford, has found that by adding a few negatives to product descriptions, the positives stand out more. In their 2012 paper “When Blemishing Leads to Blossoming”, the authors note that “adding a minor negative detail in an otherwise positive description of a target can give that description a more positive impact.”

These small, honest blemishes on an otherwise strong offering can increase attractiveness. Note: we’re talking about minor negative detail here. You don’t need to go to town on how bad you are, just enough to paint the positives in a better light and add a bit of transparency to the conversation.

With a feature upgrade, for example, pointing out the negatives of the old feature in your email can make the new one seem even better. Here’s how iDoneThis does this:

idonethis feature announcement email

4. Become Their Curator

The most powerful sales technique available today is to stop selling completely.

Information is ubiquitous. From your pocket, you can produce a device that can find the answer to almost anything. You can find out whether the salesperson on the other end of the phone is telling the truth or not. The information asymmetry that used to pervade sales is now closer to information parity.

In order to stand out then, the old ways of selling and marketing are obsolete. Dan Pink in his book To Sell is Human: The Surprising Truth About Moving Others suggests that the old ABC of sales Always Be Closing should be replaced by a newer, albeit less catchy ABC: Attunement, Buoyancy, Clarity.

This means businesses should understand their customers, understand themselves, and understand the world. It’s this understanding that really drives sales in the information revolution — particularly, providing your customers with a clear view of the world. Salespeople should no longer be the people who can talk the loudest, but instead the people that know the most.

This is excellent advice for SaaS business owners — you are already experts. Offering your knowledge to your customers is of far greater value to them than any sales spiel you might have. Buffer has been following this strategy with their weekly emails. Once you sign up, they’ll send you a weekly curated article that they know you’ll be interested in, even if you haven’t posted any updates yourself.

Buffer weekly email campaign

There is no sell there. No information about how to use Buffer or how to upgrade. Just an interesting article that will help you do your job. But when it does come time to use a social sharing tool, Buffer is now the name that springs to mind.

5. Reduce Choices

You have an ultimate aim with your retention campaign. It might be to get people to continue after a free trial expires, upgrade accounts within your pricing structure, or just to keep them from churning. Whichever it is, make sure that is the only option available.

Too much choice is the enemy of the right choice.

It’s in our nature to want to offer people more, but with more choice comes more information, more chance of overload, and more decision paralysis. Reducing choice can increase acceptance and steer people towards the ultimate decision you want them to make.

Take this example from Wistia. They send their customers instructional videos on how to make better video.

Buffer weekly email campaign

I’m sure you’ve received emails where they’ll tell you about 10 blog posts that you should read. Or when it comes time for a new feature announcement, they’ll cram 5 announcements into one email.

Not Wistia. They give me a single thing to do, and in doing that, they make it more likely that I’ll do it.

6. The Breakup Email

Sometimes leads are just eternally cold. There is no chance of warming them up.

If you get to this point, the breakup email is the nuclear option of sales emails. The breakup email is set out like this:

  • I’ve repeatedly tried to do something good for you.
  • You’ve never replied (maybe you’re too busy, not interested, or have moved on).
  • This is the last email you will be getting from me.
  • If at any time you ever want to [insert desired outcome], I’d be more than happy to speak to you.
  • Here’s my contact details.

These emails are all about loss aversion. It’s easy to avoid cold emails or trash them each and every time they come in. But if you get one that suddenly says “This is it — your last chance ever,” your brain goes into loss aversion mode if the offering was of any initial interest.

You can use this type of persuasion to win back customers after a period of inactivity. It might go something like this:

  • We’ve did some great things together
  • We’d love you to come back
  • Your account is still active, and we’ll even give you some more free time.
  • Here’s why we think you should

Trunk Club, a personalized styling service, unleashes this strategy if you haven’t responded to your stylist. If, after 3 emails in their activation campaign you don’t reply, you’ll receive a breakup email. Here’s what Steli from Close.io received:

Trunk Club break-up email campaign

What Sales Teams Avoid: Emails Going Nowhere

Salespeople don’t waste their energy sending out random emails with no intention. The point of every single sales email is to eventually get a sale. That should be the ultimate point of each and every one of your lifecycle emails as well. You are looking for a sign up, an upgrade, or to make users happy — understanding that this is made possible by delivering value, not an empty sales pitch.

A common issue with retention campaigns is to send out emails just because. You or some higher-up has a schedule set up that makes it seem like you have to churn out something to fill in that slot. Email is valuable real estate. “Just because” is a wasted opportunity, increasing the odds that your emails end up marked as spam without any opens.

Use the advice above to make sure your emails mean something to your customers, not just to you.

  • Use them to engage
  • Show off your best features
  • Give your users the right choices
  • Give them great information

From a sales perspective, every communication with a lead is a chance to nudge them towards hot. You can use your lifecycle and retention emails the same way, re-engaging customers and continuing to deliver value, to keep your customers nice and toasty.

Your turn! How have you applied sales techniques to your lifecycle email marketing?

Andrew Tate is a UK-born, US-based writer. He spent 10 years working as a scientist in labs around the world and now specializes in using data to tell stories. Say hi on Twitter at @ajtatey.

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