Critical Moments: Getting the Most out of Your Customer’s Journey

6 minute read

November 24, 2017

Critical Moments: Getting the Most out of Your Customer’s Journey

The job of customer success (CS) is to accompany customers along this journey. The value of CS is at its highest during these critical moments; each represents a potential decision for or against your product.

  • Will the customer drop out and try one of your competitors (churn)?
  • Will the customer press forward to success (retention)?
  • Will the customer invite others to join them on the journey (advocacy)?

These challenging moments provide you with an incredible opportunity to grab on to a customer and convince them of your value, so they share it with the world.

In this post, I want to show you how to maximize 5 critical moments along a customer’s journey.

But first, a quick word about automation.

For each of the following critical moments, there’s going to be ample room for automation. I think you should fully embrace automation and put as much of this advice on “auto-pilot” as you can.


Don’t lose the human touch. Use automation to free up time spent on menial tasks (such as sending out welcome emails) and funnel back into high-level work (like consulting with clients and working on product development).

With the right balance, automation will amplify the amount of human touch in your organization without tapping out your human resources. If you overuse automation, however, then your customers will feel like they’re interacting with a team of robots.

And nobody wants to do business with a team of robots.

1. Onboarding

Depending on whom you ask, onboarding can either refer to what happens after a user plunks their money down for your service, or the entire sequence from their first encounter with your brand to when they decide to become a paying customer.

For our purposes, we’re going to assume it’s the latter.

Recently, I wrote a guide on how to optimize your onboarding process. I won’t rehash all of that now. Instead, here’s a summary of the most relevant points.

The key to maximizing the value of your onboarding process is to keep friction to an absolute minimum. Don’t ask for everything up front. Give customers time to build a profile, import contacts, transfer data, and so on. The more you can particularize the process, the more momentum customers will build on their way to realizing first value.

Speaking of first value, this is probably the most important point in the onboarding process. First value describes the moment when your customer first realizes tangible value with your product—whether this means they generated an invoice, successfully designed and exported a graphic, or uploaded a file into the cloud.

From the moment the onboarding process begins, you’re locked into a race against the clock. The time between initial acquisition and first value is the riskiest time for churn. The majority of your customers will drop at this point. Cutting down friction and developing early success milestones will shrink that gap.

To keep your customer engaged along the way, send a welcome email honoring their decision to start the journey with you. When they hit their first value milestone reach out either via an in-app congratulatory notice or through email.

2. Product Milestones

A product milestone refers to the moment when the customer gets tangible value out of your product. First value is technically your first product milestone. Additional product milestones indicate that the customer is progressing along their journey successfully, i.e., that they’re actually getting their money’s worth.

This sounds obvious, but to maximize these moments, you have to make sure they’re happening! This means training your customers to use the product to its full potential. You can do this by way of in-app tutorials, tool-tips and automated guides. You can also distribute content specifically designed to show them how others have succeeded with your product.

When each of these product milestones are reached, make sure to celebrate it with your customer as much as possible. Congratulatory reminders (in-app or via email) aren’t just cheesy ways of letting customers know they finished a task. They’re concrete reminders that say, “Hey, our product is doing exactly what you expect it to do. Aren’t you glad you paid for this?”

To squeeze a little extra out of the congratulatory message, couple it with a valuable offer—whether that’s a usage report, a discount or a custom product/service offer. This communicates value to your customer.

It also sets up the next critical moment…

3. Up-/Cross-Sell Milestones

Some product milestones represent both an ending and a beginning.

Take MailChimp’s forever free plan, for example. Once a customer hits the 2,000 email subscribe barrier, it’s time to graduate to a paid plan. In coming to the end of the plan, the customer has a reason to rejoice—they’ve built up a substantial email list!

But obviously, MailChimp doesn’t want that to be a true ending. Instead, they want the customer to upgrade to a paid plan. In that sense, this is only the beginning of a paid relationship that will likely lead to more revenue in the future (renewals, upgrades, etc.).

To maximize moments like these, you need to know your customers and their usage better than they do. This is where targeted feedback surveys and data analysis come in. You need to know precisely how your customer got to this point, what they need in order to justify the expense of moving forward, and whether they’re willing to pay to stay on the journey with you.

Content marketing plays a vital role here. Part of the CS department’s job is to work with the marketing team to collect and tell compelling stories about customer success with the product.

But interesting use cases aren’t just about telling the world how great your product is. They also offer a valuable opportunity for up- and cross-selling. Using case studies, you can demonstrate for your entry-level and mid-tier customers how much value your premium customers get from the product.

This becomes an important apologetic tool for convincing lower-tiered customers to fork over a few extra bucks for the premium package. Pieces of content like these may not make your whole case, but they soften the ground; so that when a customer reaches a critical milestone, they’re more willing to take the next step.

4. Invitations to Advocacy

If we want to maximize a customer’s lifetime value, we have to talk about advocacy.

What is an advocate? Advocates are super-users who’ve gotten so much value out of your product that they’re willing to support you in any way they can. This includes generating content, helping with community moderation and telling your brand’s story.

As far as repeat business goes, advocates are worth about 5 times as much as one-time customers. In addition, an advocate is 2-3 times more likely to convince someone to buy than a regular customer. That’s why a 12% increase in advocacy can double revenue growth.

A product milestone is  a critical moment to invite someone to become an advocate, but you must be strategic in your execution.

Start with patience. Relatively new customers aren’t ready to put their reputation on the line for your product. You need to develop a relationship with the customer first.

Concentrate on providing them with so much value that sharing your product with their friends will effectively become a no-brainer. Once you’ve suffused your entire customer journey with that mentality, then you can focus on the critical moments you’ll use to recruit advocates. When those critical moments hit, there are two ways to spur initial advocacy.

The first—customer testimonials—is almost self-explanatory. Once your customer wins enough with your product, ask them for some kind words which you can then plaster all over your website, social media and email marketing.

Testimonials are important, but you can take it to the next level by asking for referrals. A referral is more potent than a testimonial because it requires the referrer to take a real risk with their social capital. If their friend or associate loves the product, they’re safe. If not, their reputation takes a hit.

There are a number of ways to ask for referrals. The best way to reduce friction and increase the likelihood of an accepted referral is to attach a valuable offer on both sides. Lyft, for example, doesn’t just reward current drivers and riders for referrals; they reward the new user as well. This creates an incentive for current drivers to reach out to their friends, and for their networks to respond when they do.

5. Renewal

The final critical moment in your customer’s journey is renewal. This is when the customer decides whether or not to continue with you.

This may seem a touch dialectical, but the way to maximize this moment is to minimize it. In other words, make it so a customer who chooses to renew—or better yet, auto-renew—doesn’t really notice the moment at all.

If they do perceive the moment in anything more than a passing way, then it means they’ve decided to leave you, or are perhaps begrudging their renewal decision. In either case, somewhere along the way you failed to adequately sell the value of your product.

The best way to maximize this moment is to handle the previous 4 so well, that the renewal hardly feels like a decision at all. Instead, prepare the customer in such a way that renewal feels almost like a foregone conclusion.

Speaking of conclusions, our journey in this article has come to an end. Your new customers’ journey, however, is just getting started.

If you haven’t already, take the time today to plot out that journey. Then, you’ll be ready to develop a plan for how you’ll deploy your CS resources to make the most of each critical moment along the way.


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Kenny S.

Written by Kenny S.

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