Customer Success: Let machines do the hard work

By Jeremy Gillespie

It's easy to let your busy schedule get in the way of providing exceptional customer success. Many success teams spend a lot of time designing the optimal customer journey and defining best practices: The hard part comes when they need to put those processes into practice. When managing a large portfolio of customers, it becomes difficult to stay proactive and stick to the playbook.

When your team is facing this challenge, having a smart system that automates common procedures is invaluable. Here’s a blueprint for how to build one.

The Frame

Your machine will be an internal "smart system" designed to keep the important activities at the top of your list. These are activities that should happen for every customer. 

The system is a series of notifications built around the long-term goals of your customer success organization. Each notification should tie to a particular goal. Common goals include metrics related to onboarding, product adoption, engagement, expansion, or renewal. The important thing here is to proactively monitor and manage your customer portfolio at key milestones in their lifecycle.

The Nuts and Bolts

Before you get started you’ll need to have some tools in place. A list of customers and the ability to trigger reminders based on timelines will form the core of your machine.  This means at a minimum you’ll need a CRM (i.e. Salesforce, Sugar) to manage rules and notifications for your team.

Next, you’ll need a way to automate messages that go out to clients. This can be a very simple tool (i.e. Mailchimp) or a more complex marketing automation solution (i.e. Marketo, SendGrid). Check with your marketing team to see what they are using, and try to leverage what you already have in place.

If you want to step it up, you can use a customer success platform (i.e. Gainsight, Totango). Adding a CSM system will allow you to tailor your communications to particular actions customers have taken, while providing your team with important customer health data.

The Engine

Build with the end in mind.  It is often easiest to design backward from a goal through earlier stages in the client’s lifecycle.

For example, if retention is a goal, start by automating the creation of renewal opportunities. From here, work backward and build a series of tasks that should occur throughout the contract period.  It's important to customize these tasks by segment if your customer base is broken out into groups. Finally, build a notification system to remind CSMs when it's time to engage with customers. 

Here are some commonly automated tasks you can use as a springboard in designing your own smart system:


  • Hand off account from sales to success, and transfer client info
  • Verify account is active and has the proper plan, package or service
  • Schedule a kick-off call and trainings


  • Provide a scorecard on product adoption and usage
  • Deliver targeted messages to users with low scores


  • Identify active users to turn into advocates
  • Seek new potential users on adjacent teams
  • Request warm introductions to relevant groups


  • Send thank you messages for purchasing and renewing
  • Schedule an engagement checkup meeting 3-4 months in
  • Provide tips and resources to users with low engagement scores
  • Document and share customer feedback internally

Business Reviews

  • Remind CSMs to cover topics like business outcomes and ROI
  • Request a quote or participation in a case study
  • Schedule meetings to discuss new features and product roadmap
  • Offer training sessions to clients who meet specific criteria


  • Create a renewal opportunity
  • Build account renewal plan
  • Identify strategic initiatives, up-sell or expansion opportunities
  • Communicate pricing increases and other changes
  • Execute the renewal agreement

The Finish Line

This is a system that will take time to implement, but will pay off in the long run. You don’t have to build the entire machine overnight, so don’t be intimidated by a long list of things you want to automate.  Start with a few pieces of your process, perhaps the ones that cause the most frustration, and expand your machine from there.

As with all machines, they need a tune up from time to time. Revisit your automation bi-annually to make sure it is still meeting the needs of your team, and adjust as necessary.

Do you need help designing your own customer success smart system?  The Success League is a customer success consulting firm that works with executives who are ready to build and develop a top performing team.

Jeremy Gillespie - Jeremy is a growth-oriented marketing geek, technology enthusiast and customer evangelist. He loves using complex data to build creative retention solutions. By leveraging technology, Jeremy excels at creating scalable retention marketing programs. He serves as the Director of User Growth at Mixmax, holds a BA from the University of Pittsburgh and MBA from Point Park University.  Jeremy is a proud former Pittsburgher, but currently lives in San Francisco, CA.