November 19, 2019

Keeping Users Engaged After The Conversion

One of the earliest stories I remember about sales is from my Dad. He knew a sales rep who always hit his numbers, consistently hitting revenue targets year after year.

His model was very simple… He built a list of clients and spent the entire year taking care of them. He never deviated from that unless the company launched new products that he felt his clients would benefit from. Every time contract renewal came up, he got the signature because he spent all of his effort on that list of clients. They trusted him.

His sales director was fine with this because he consistently hit his numbers. And the sales rep was fine with it because he knew how much he was making every year. He wasn’t concerned about growing his list of accounts and making more money.

One day, the sales director was replaced by a new one. That sales director started mandating quarterly results and a specific amount of new business. The sales rep pushed back, saying that he would hit his numbers, but that he wasn’t interested in the daily grind of building additional business.

Ultimately, the sales rep was fired. He wasn’t hitting the new, quarterly goals. Over the next few years, the company lost many of his clients, who were no longer receiving the same care as they had been. I don’t think they ever got those clients back.

Say what you will about pushing your sales people to grow and yes, it’s weird that there exists a sales person that doesn’t want to make more money, but this sales rep understood a core thing about business that his new sales director forgot.

The way to build a healthy business is to have your current customers stay with you and, if possible, spend more over time.

For a media company, the same is true, but with subscribers instead of software buyers. While it is important to continue growing the number of new subscribers, I believe it is even more important to keep your current subscribers renewed.

Take the story of The L.A. Times, which was looking to reclaim the subscription business it once had when print was dominant. In a memo that Poynter published, the first half of 2019 wasn’t going so well:

Our future depends on rapid and substantial subscription revenue growth. We had hoped to double digital subscriptions this year, to 300,000. (Doubling them again would get us close to covering editorial costs.)  Performance for the first half of the year, however, has been disappointing. While we added 52,000 digital subscriptions, significant cancellations during the same stretch left us with a net increase of only 13,000.

The bold is my emphasis, but it’s so important to call it out. While 52,000 people agreed to subscribe, 39,000 unsubscribed, leaving them with only 13,000 additional paying customers.

What a bad business.

Ultimately, The L.A. Times was focused more on getting users to subscribe than it was on keeping them interested. The result are evident.

The question is, what can a publisher do to engage audience? I break this down into two categories: analytics and communication.

Analytics to track

To have any sort of effective communication, it’s important to first understand how the audience is actually engaging with the platform. But it can be overwhelming trying to track everything, which leaves many publishers feeling paralyzed.

At minimum, there are two numbers I would look to track:

Number of visits per subscriber

The easiest way to know if someone is interested is if they are actually coming back to the site. The number can be different from publisher to publisher, so it’s hard to say what’s right. However, if you find that they’re barely hitting the site once or twice per subscription-period, you’ve probably got someone that’s going to bounce.

Type of content they read

There are two parts to this. The first is the piece of content that got them to convert. That tells you something about what they find most interesting.

Then you want to track what kind of content they continue to consume. If you find a lot of your subscribers read a specific type of story, that can give you insight into what they care about. If you’re light on that and enough users have shown interest in that content, it might mean it’s time to make an investment.

This metric also shows how well a piece of content is doing.

The Athletic does a good job of this with their “pick a team” model. Assume a hypothetical Knicks fan; theoretically, they should be reading a decent amount of that content because they’ve explicitly said they’re interested in that topic. If they’re no longer reading that content, there’s a sign that either they no longer care about that team or that the content is no longer engaging them.

The sports publisher gets specific here. The metric it is tracking is what percentage of users of a “picked team” have come and read a piece of content from that picked team. If it’s high, that’s a good sign. If it’s not, it’s time to reevaluate. The Athletic told Bloomberg that 40% is a good number.

Start here. Build these dashboards out and then you can expand from there. At the very least, if you know how often your subscribers are coming back and what content they gravitate to, you’re well on your way to then being able to communicate with them.


This is where you want to get creative and specific because it’s how you’re going to remind the subscriber that you exist.

Welcome email series

Once a user actually converts, you should automatically add them into a welcome series of emails that walks them through the various content offerings that you’ve got. Here’s a basic flow that could work:

  • Day 0: Thanks for subscribing. Let them know that there are a few more emails coming in the next couple of days.
  • Day 2: Want to stay up to date on our reporting? Here are a few newsletters that you might find interesting. What newsletters should you show? At minimum, one that is related to the piece of content that finally got them to subscribe.
  • Day 7: Here are a few subscriber-only benefits that you may not have known about. The Athletic offers subscriber-only podcasts. The Information does sporadic conference calls. Let people know that these exist.

The number of days between each email is something to test. Perhaps two days between subscription and the first engagement email is too fast. Or, on the other hand, you may find that this email should go immediately.

The point here is to immediately build a rapport with the subscriber by communicating with them.


The easiest way to remind users that you have content worth reading is to send it to their inboxes with newsletters. And yet, there are publishers that don’t even do this!

The reason is pretty simple. If a user sees a story that they find interesting in the newsletter and they click it, you’ve succeeded in bringing that user back to the site. Then, while on site, you can attempt to get them recirculating through other pieces of content, which makes them stickier.

You can even take it a step farther and build a subscriber-only newsletter. This gives a semblance of exclusivity that the subscriber will probably appreciate.

I spend a lot of time thinking about newsletter strategy, so will likely write a piece about it at some point in the future.


I’m a subscriber to The New York Times and, from time to time, I see ads on Facebook or Twitter promoting a specific piece of content. At first, this was weird to me. Why was The Times spending money promoting content to a paying customer?

Once I made the connection, the rational made perfect sense.

The New York Times is trying to show me content that they believe I will find interesting. And since I don’t subscribe to many of their newsletters, this is a great way to get me back to the website.

You should consider doing the same thing. If a user has not looked at a piece of content in a while, go where they are spending time—typically on social media—and share a piece of content that is doing particularly well with other subscribers of a similar profile.

This is where you need to do a little bit of math. How much can you comfortably spend on engaging with possible unsubscribes? There’s an easy way to do this and a more advanced way. The first is to simply spend less than the subscription cost.

The more advanced method requires more steps.

First, calculate the LTV of the subscriber. Let’s say it’s $100. Next, you want to understand where the user is on the lifecycle. Are they 50% of the way through? Okay, that means you’ve got another $50 of expected value to accrue. Therefore, if you were to spend $25, would that be enough to get that $50 in value, thus earning $25 in profit from a user that might otherwise unsubscribe?

You can also use the advertising to try and get the subscriber to engage with another form of communication, such as a newsletter, which gives you a longer lifetime of communication.

I will caution that this can be a very difficult exercise to do correctly. You want to pay very close attention to how much money you’re spending because it can quickly go from a profitable enterprise to one that’s costing you more than the value of the subscriber.

Focus on retention

Ultimately, the name of the game is retention. The difference between a successful and unsuccessful subscription business is the retention rate. If you’ve got a high churn, I will wager that you’re ultimately going to fail.

However, if you’re spending a lot of your effort on keeping your current subscribers happy, they’ll return the favor by staying subscribed. The easiest way to do that is to communicate efficiently to them about the content that made them subscribe in the first place.