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Why You Should Apply User Roadmaps to Improve Customer Retention (and How To Do It)

Learning to improve customer retention can be overwhelming for a fledgling business, but it’s also a vital aspect of building and scaling over time. Retention depends on more than just offering a valuable, dependable service. Rather, it’s a proactive process where you need to continually be a step ahead of potential issues. It can be helpful to think of customer retention as essentially a new, retention-based funnel that takes over once a sale has been made.

From the initial trial period through the lifetime subscription value of the user, there are a handful of moments where customers tend to actively decide to stick with you. It can be overwhelming trying to anticipate issues, but improving customer retention doesn’t have to be a guessing game. It’s possible to proactively map out the customer journey and pinpoint the moments where customers tend to make these critical decisions. From here, you can create systems to counteract potential churn at each of those junctions.

Get a sense of when and why user churn occurs

You can't improve customer retention unless you know where your churn stands. The easiest way to get started here is exit surveys. You should see certain trends coming out of the responses.

Tracking how long users stayed with you, and what concerns they had that convinced them to leave is a great way to start mapping out the user experience and learn what specific roadblocks are impacting your customers. Visualizing this data with a cohort table can give you a broader sense of when customers entered your “retention funnel” and at what point they exited.

This is an image on the Churn Buster blog on a post on how to improve customer retention. The first step to improve customer retention is to understand your churn. We suggest using cohort tables, which is what this image is. It's an example of a cohort table you can use to improve customer retention.

Getting a sense of your user churn and where it occurs can take time, but it’s worth investing in the data. You’ll have a mix of quantitative and qualitative information to help you improve customer retention- i.e. both the “when” and the “why”. From here, you’ll be able to get a sense of the decision points where you lose users.

Map out the “crossroad” points where users churn

While businesses and services vary, there are predictable points in the lifecycle of a SaaS customer where they are forced to stop and reevaluate their need for your particular solution. It’s vital to be proactive in these periods.

Think about this process in terms of a series of decisions. At what points in their journey are customers pausing to reevaluate?

The free trial is over- should I invest in a paid subscription? I’ve used the service for a month- is it worth my money to continue?It’s important to be proactive in connecting with your customers at these specific points. Helpful content, email campaigns, and even a personal text or call can be valuable ways to impact customer decision making at these important points.

Remind customers of the value that you provide to them and the value they could be getting. This can be a great point to inspire them to use your product in new ways and build it more deeply into their workflow.

So what are these common decision points, and how can you use them to (re)invest the user in your product and improve customer retention?


Whether it’s the first time you actually make a photograph look better on Photoshop or the first time you listen back to a loop you’ve made using Logic, you’ve probably experienced an “aha moment”. This is the point where you have your first meaningful success with a product, and it’s absolutely vital to getting past the first churn hurdle.

When you’re onboarding new users, you have a finite amount of time to get them here- an “aha moment” needs to happen as quickly as possible. Ideally, you’d like it to occur the first time a customer uses your product. Consistently offer helpful tips and tricks during your onboarding to move customers towards this point.

Build training sessions and tools specifically around creating an “aha moment” and consider offering different onboarding experiences depending on the user’s previous experience within your niche. It will take a broad focus across your team, but this is the first step toward properly churn-proofing your product and starting to improve customer retention.


The Second Activation Point

Once a customer has had a meaningful success with a product, it’s time to shift from novelty status into becoming an integral part of their workflow. Essentially, you want to move from being a shiny new toy into an indispensable, well-worn aspect of the user’s life. Timing-wise there should be a shift at this junction into more and more consistent use.

The biggest difference between an “aha moment” and a second activation point is in the relationship developing between the user and the product. Ideally, you are creating a point of no return- think in terms of the phrase “I could never go back to _____.” What does this look like? On an eCommerce site, for example, this is likely a user’s first sale. For a communication software like Skype or Slack, it’s the point where email starts to feel like a clumsy alternative.

Not sure how to create this experience? Think about the tools you use everyday. Which features sealed the deal for you?


End of the First Month

After a month of use, most customers will take a moment to analyze data, and evaluate the success or failure of your tool. Most likely, this is also where the first bill will be due, meaning that customers are feeling the effect of your product on their wallet. Essentially, this is a point where they are making important value judgements.

On your end, you need to make sure to be engaging both before and after this milestone. A summary of the progress they’ve made in their first month can be a great way to feature their work and show the different ways that your solution has made an impact.


At any Failed Payment

Strategies to improve customer retention are all about proactivity. But, a billing issue is probably the only crossroad point on this list where you don’t want to be proactive. We’ve talked about this pretty extensively in the past, but we’ll summarize briefly here.

With any impending payment issues, your goal should be a seamless transition- no pre-dunning emails, no reminders to update information before payment fails, nothing. Why? In a nutshell, involuntary churn is the simplest issue to solve, and you don’t want to create an unnecessary opportunity for the user to re-think their subscription. Pre-dunning messages, in particular, can also come across as demanding and spammy, more of an irritation than a helpful reminder.

Instead, have systems in place to deal with these changes. Set up campaigns for failed payments, and build processes specific to the needs of different customers. A whopping 70% of failed charges can be fixed with automatic retries, so make sure you have custom retry schedules in place. Mobile-optimized card update pages provide the quickest, simplest way for customers to update their information. Make sure these pages are clean, clear, error-free, and secure.

This is an image on the Churn Buster blog on a post on how to improve customer retention. We suggest highly optimized card update pages to make involuntary churn a non-ssie. This image shows a great card-update form provided by Churn Buster that would help to improve customer retention.

This can seem like a tricky crosspoint at first, but it's actually quite simple. Check out our in-depth guide on dunning.


Following a CS Complaint or Feature Request

When a customer complains or asks for something new, they're usually on high alert looking for issues or reasons to leave. Your goal when this happens is to get on top of it ASAP. Don't let one issue poison the rest of their experience.

Your first concern should be that the customer feels listened to. Consider automating reminders to reach out and respond specifically, possibly offering workarounds or helpful content to give them the closest experience possible to their request. Whether or not you can give them exactly what they need, it’s important that they feel you are concerned and that their input can have an effect.

Moving forward you can add these users to different lists based on their concerns, essentially making sure that they are the first to know when their issue is fixed or their suggestion becomes part of the product. You may even choose to tailor specific content to these users.


New Feature Releases/Product Updates

Big changes to a product or service often make users (understandably) uncomfortable. Think, for example, of the backlash every time Facebook or Instagram has gone through a redesign. In many cases, users may be concerned that the product is moving in a direction that doesn’t service their needs, or that they will need to work harder to continue to use the same features that brought them to the product initially.

Get ahead of the curve by creating ample amounts of content in the lead-up to new releases, and continuing the flow after the changes go live. You want users to understand why the change is happening, how they can harness the new version for their needs, and what steps (if any) they need to take to use the updated features. Videos, webinars, and other visual communications are huge for helping users to navigate a new interface or implement a new feature. Here's a great example from Ghost.

improve customer retention

The process of communicating a large product update should mirror the process of communication when onboarding a new user. You want the same “aha moment” and secondary activation point, only this time it needs to happen for your existing user base.


After an Upgrade or Downgrade

Don’t freak out: a customer choosing to downgrade their subscription is not always a bad sign. Sometimes a more limited feature set is better suited to their needs. This can make them a more valuable customer in the long-term- the more comfortable they are using a product, the more likely they are to stick with it through thick and thin.

If a downgrade is what they need, help them find the right plan and leverage it to maximum capacity.

In the case of an upgrade, users need to understand the new features that are now available and how these features relate to their specific needs. What-if’s are the killer here. It’s easy to become overwhelmed when the floodgates open and too many options appear.

Think of it this way: have you ever gotten less value out of a product or experience because you’re stuck worrying if you are really getting enough from it?

Regardless of whether it’s an upgrade or a downgrade, the key is clear communication tailored to the needs of those users. Automating chat reminders to check in on how the process is going can open up conversation and give your team a chance to clarify with customers before problems develop.


After Their First Referral

Referrals are proof that customers find value in your product- enough to share it with others and attempt to bring them on-board. This is an exciting junction point because it’s essentially all positive. You have a high-value customer, the kind that all companies covet. Reward them. A free or vastly discounted month of subscription can be a powerful way to show your appreciation and encourage more referrals. Companies like Winc offer financial rewards for both the initial user and the new customer they bring on-board, essentially sweetening the deal for both parties.

improve customer retention

You have a chance to go above and beyond here. If you make your users feel awesome for utilizing referrals, they are bound to do it again. Shout them out. Make them the hero. It’s an issue of culture. Users are far more likely to stay with you if they feel actively engaged with and valued by your company. Let them know that they matter.


New Competition Arrives

At some point, there’s going to be a shiny new tool with similar features to yours. This new competitor is going to target your audience by advertising a lower price-point, a broader feature-set, or some other form of industry disruption.

You can prepare ahead of time by consistently reminding users why you are the best at what you do. Content that compares newcomers point-by-point with your existing service can be a great opportunity to improve customer retention by showing off the important elements of your toolset that they may not instantly associate with your brand. You can also use a new competitor entering the market as an opportunity to take a good look at your own product.

Which features are most tempting to your user base? Are they worth developing for your own product? Learn from your competition and you’ll be much more likely to improve customer retention in your own business.

Improve Customer Retention Beyond these Checkpoints

Obviously, retaining customers and fighting churn is a process that lasts through the entire lifecycle of the user. How do you continually retain a customer who’s passed all of these milestones?

Invest in your customers in the long-run. As they grow and scale, make sure that you are able to grow and scale with them.

Communicate consistently so you can anticipate and meet their needs. Remember that some of these checkpoints are recurring- you will make updates to your product, and every time this happens you need to be actively ensuring that the experience is positive and tailored to your user base.

While these points are consistent for many SaaS businesses, they aren’t the end-all, be-all moments to improve customer retention. Where do you see crossroads moments in your own user journey? How do you respond? Let us know in the comments!