Triggered Outreach: Delivering High-Touch Customer Success At High Volume

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Do you have customers coming out your ears? Congratulations! Welcome to “high volume” customer management. That’s fantastic news for your business, and a wonderful problem to have.

Now it’s time to start knocking it out of the park on the scaling front. You and your team can’t possibly have a personal relationship with every one of those customers. Or can you? It might sound like pie in the sky, but it’s not out of reach. As long as your customer data house is in order and you leverage it well, you can cook up some systematized triggers to kick off highly automated customer outreach that’s also very personalized. In other words, even as each individual customer represents an ever shrinking proportion of your base, there’s no need for them to feel any less like individuals.

It’s not just the number of customers you are managing, but also what they are paying you that might impact your strategy and execution in this area. If you have customers paying you $99 per month, you will likely need to rely fairly heavily on automation and scale to success. If, on the other hand, you have customers paying you $25,000 per year, you can afford to be more one-on-one oriented. But still, as you grow, automation for certain tasks will enable your team to prioritize their time and spend it on the highest value activities.

customer success Considerations

  1. Don’t over-engineer. You don’t have to go from fully manual to fully automated overnight. This kind of shift lends itself to a phased, iterative approach, and it’s really an ongoing process. Take things one step at a time, have an experimental mindset, and learn as you go. Also, keep in mind that the goal should probably not be to automate absolutely everything. There might be certain customers (ex. top tier), timing (ex. during onboarding), or other circumstances (ex. when follow-up communication is needed) where you want to keep the kid gloves on and maintain fully person-to-person outreach.
  2. Don’t over-message. You should never use automation as an excuse to intentionally or unintentionally inundate your customers with emails or message pop-ups in your application. Remember that, even though you are enlisting the super-human powers of automated outreach, your customers are still human and will get bored or annoyed by incessant communications from you, no matter how timely or relevant they may be.
  3. Don’t under-apply. The examples below are primarily focused on Customer Success initiatives. But there are other realms where a similar approach can be equally useful. For example, does your sales team want to get more systematic and scale-oriented around trial conversion? Or would your product team love to reach out to the users adopting that newly released functionality for feedback?

triggered outreach

Read the below basic examples of triggered outreach through the lens of your customers, your company and your application.


The logical place to start – reach out to re-engage a customer who might be a churn risk because they simply have not been active in your application.

Trigger: Last login date by any user at the customer account is greater than 30 days ago. (Define how long is too long for your application and customers.)

Channel: Templated email that’s automatically triggered and sent to all users at customer account. Phone follow-up to primary user(s) if no response or activity.

Message: ‘We miss you! Is something wrong? Here’s how to pick back up…” Consider including a single-question survey (ex. “What’s been holding you back?“) with pickIist options (ex. “Too Busy”, “Hard to Use”, “Stuck in implementation”, etc.) powered by a survey engine that automatically tracks responses and enables updates in your CRM.


Renewal time for annual or multi-year contracts is inherently risky. Make sure you get out ahead and do an excellent job demonstrating value to your customer as it approaches. And if contracts are set to auto-renew, don’t be tempted to stay quiet and just hope that event passes unnoticed. Take advantage of the opportunity to engage with your customer.

Trigger: End of current contract term is in 60 days (or whatever period makes sense for your terms, customers, application).

Channel: Templated email that’s automatically triggered and sent to decision-maker, including option to request a call or otherwise connect directly with CSM on any questions.

Message: “Here’s what you’ve accomplished so far, here’s the vast potential. Looking forward to our ongoing partnership!” Consider multiple versions for “successful” vs. “unsuccessful”



It’s crucial to guide customers who are not effectively using what they’re paying for, or at least on a solid path to be doing so soon. And in SaaS, there are as many utilization measures as there are pricing models. Pick and track such a metric for your app.

Trigger: Ratio of paid to used licenses, features, records, etc. is below that of similar customers and/or is trending downward for that specific customer.

Channel: Templated email that’s automatically triggered and sent to primary user(s), and in-app messages. Individual email or phone follow-up if downward trend continues or increases.

Message: Clear case for how and why increased utilization will translate to enhanced value for the customer. (Remember, they are concemed about their ROI, not yours.)


Ever get antsy when you can tell that a customer started but didn‘t finish something with a subscription implication? (Wait, did you even know it happened?) Those partially-completed events should definitely be considered signs of things to come, and acted on accordingly.

Trigger: Explored functionality or information about functionality in a higher plan, level, or add-on module, but did not purchase. Or visited cancellation page, but did not cancel.

Channel: Templated email auto-sent to the user who initiated the action. Prompt phone follow-up to that user and primary user if no response or follow-through activity.

Message: ”Noticed you were checking out other plans/ how to cancel your account. Did you find the information you needed? Can we help?” Be prompt and persistent on this front- the window of opportunity to meet a need or preempt chum can be very narrow.

Advanced use cases - automated customer success outreach

If the examples above seemed like old hat to you, then you’re ready to take on more advanced use cases of triggered, automated Customer Success outreach. The following examples utilize more layers and types of customer data and/or more complex customer insights.


ls your customer not quite grasping the most effective way to utilize your application? Are they logging in plenty, doing lots of stuff, but not really the “right” things that you know would generate the most value for them? Time to intervene!

Trigger: Once past onboarding, sessions and/or particular usage activities in the application are high, but one or more specific, important actions are low frequency or absent.

Channel: In-app messaging during usage.

Message: “You’re rocking at this! But did you know you could do that? Here’s why it’ll pay off and the resources to help you figure out how.” Having those high quality resources available, easily accessible, and up-to-date is critical. And bonus points if you can track whether message recipients take you up on visiting them.


We all know this is the crux of Customer Success, right? Understanding whether and how your customers are gaining value by utilizing your application, and guiding them toward always achieving more. So make sure you are actually monitoring the attainment of that value – which might not always align with usage – and jumping in to course correct if its not on track.

Trigger: New leads per week (for a marketing app), new job applicants per month (for an HR app), (or whatever value metric serves for your customers and application) are low compared to other similar customers.

Channel: Possible templated email or automated alert to initiate personal outreach.

Message: “You’re off to a good start, but there’s a ton more potential I can help you achieve.

Let’s talk!” Automation can help to flag and initiate, but this one is usually best served by a person-to-person conversation.


First make sure you are capturing trends for important value metrics, then tune your systems to watch for unusually high levels compared to past performance. Everyone loves to be called out for doing well!

Trigger: Dollars raised per week, applicants hired per month, records created per day (or whatever value metric serves for your customers and application) are many times better than the previous norm for that customer.

Channel: Templated email to primary user(s) of account.

Message: ”Congratulations on your recent stellar day/week/month when you accomplished XYZ!! You are achieving great things using this application!” This is a moment of pride – make it a message they’ll want to forward to their boss.


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There are likely specific steps that you need to check off during a customer’s initial implementation or onboarding lifecycle phase, and also certain “first value” milestones that you expect they’ll accomplish. But what if they aren‘t getting it done? Time to reach out and offer a hand.

Trigger: Has not done X (ex. made first hire) within 60 days (or appropriate period) of purchase/provisioning.

Channel: ln-app messages if usage activity is strong otherwise templated email to primary user(s).

Message: “Let’s start using this to its fullest! Here are some useful resources to help you understand why and how.” Again, make sure the resources are indeed useful, and highly usable.


Think you might have untapped potential customer references, testimonials, or case studies? You’re probably right! And you don‘t have to take a shot in the dark to find them anymore. Just follow the signs to your greatest growth asset, and unleash automation to sign them up.

Trigger: User has trifecta of Power User persona (strong, consistent application usage activity); out-of-this-world, beyond expectations results; and promoter-level survey responses. And is not already signed on to serve as a reference!

Channel: Automated email or alert for personal outreach, depending on level of commitment.

Message: “You’re doing things right, and have fantastic results to show for it! Up for sharing your experiences with a prospective customer from time to time?” Make sure to promise you’ll respect their time, and to honor that promise.


Application usage aside, can you help steer your customers toward better utilization of the resources you provide (ex. knowledge base, support tickets, etc.)?

Trigger: Submitted X number of support tickets in the past 90 days, but have not viewed any recorded trainings or searched the knowledge base even once.

Channel: Series of templated emails.

Message: “Hot off the press – a new knowledge base article on this topic. And here are some helpful tips from our trainer. By the way, did you know you could also find this and that in our resources? Some guidelines for searching.. etc”

The moral of the story: You don’t have to be personally, manually recognizing the need for and generating all of the communications to your customers to do outreach well. Enabling automation to shoulder some of that burden can, in fact, result in more personalized, more timely, more useful messages reaching your customers.

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