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A summary of The Customer Success Leadership Network Virtual Meetup Feb. 27th by Lauren Costella, VP Customer Success at GoodTime.io

As CS Leaders, you can’t go on LinkedIn or to virtual conferences without hearing about the importance of developing a digital CS strategy and successfully implementing it.

The Customer Success Leadership Network recently held a MeetUp to discuss this very topic. Hosted by Mark Peccorero, Principal Consultant at CSLeadership, this dynamic discussion included both Keri Keeling (Global Head of CS Innovation and Intelligence for VMWare) and Carlos Quezada (Head of Digital Strategy and Customer Service for Aruba, an HP Company), who shared their experiences with building a digital strategy and let me tell you, the stories were amazing.

Capitalizing on the trend toward Artificial Intelligence, Carlos and the Aruba team have actually built out a “virtual” CSM named Steve! 

This blog alone couldn’t possibly capture the stories and success built by these CS veterans, but thankfully, you can find the recording on the Customer Success Leadership Network website. For now, I’ll summarize the key highlights.

  1. Start with your Data & Build your Story
  2. Buy-in and Alignment is Key: Stakeholders Don’t Destroy what they help Build
  3. Agile Development: Not Waterfall
  4. Meet Your Customers Where They Are
  5. Don’t Let the Tail Wag the Dog for your Tech Stack

Start with the Data & Build Your Story

Keri and Carlos can’t emphasize it enough. You have to start with data. Whether you’re a startup or a Fortune 500 company, you need to understand what’s happening with your customers. And the challenges of acquiring that data are very real. For many, where to start is the question. 

When Carlos began his journey at Aruba, he quickly came to see there was no renewal process with their customers, and there was no concept of continuous service. It was very much: “Here’s your hardware; here’s your services, and move on.”

He suspected there was churn, and his first strategy was exploring the idea of getting a small team together to reach out about renewals. But in order to really execute that strategy, he needed data to support that case. That’s when Carlos hired Matt Harmon and together they dug into the data.

Very quickly, they found that they had a churn problem. And an even bigger one than they thought. Armed with this data, they began to build their story of the issue. And, by meeting with other CS organizations, they started to map out a solution and a charter for the CS team to solve it.

Buy in is Key: Stakeholders Don’t Destroy what they help Build

Carlos and Matt wouldn’t have been able to solve this issue of churn alone, especially as they scaled. They needed help from IT and Engineering to build out systems and processes to support their long-tail customers. They would need help from Marketing and Sales to have messaging to the right customers at the right time, so they needed to get buy-in across organizations.

Armed with that data, and thoughtfully showcasing how they could fix it with additional resources, Carlos and Matt did a 30-day roadshow with other departments. As they went to other departments, they asked for feedback. This feedback built the CS charter for the Aruba organization. And as Carlos says, “People aren’t going to destroy what they help build.”

Once all of the feedback had been heard and taken into consideration, they finalized the CS charter and asked each organization for resources to support it, and the “tiger team” to address their churn problem was born!

At this point, all teams had a stake in CS Success AND Matt had full license to get the data he needed to inform the building of their CS journey.

Agile Development; Not Waterfall

Now that Matt had the data and the roadshow was complete, the Core Team needed to understand the install base more intimately. For example, they needed to answer questions like: what do customers look like and how do they act? They did an analysis and found that 96% of customers were long-tail customers and needed more long-tail strategies; 4% were Tier 1. However, revenue make up was almost half and half. 

Carlos couldn’t ignore the long-tail customers, given they were half the revenue. And given the Sales team had some relationships with the Tier 1 customers already, and their team was bootstrapped: they needed to focus on a tech touch strategy first, then work the high touch.

Carlos and the team jumped into Journey mapping and spent months putting sticky notes and ideas on their “wall” of how the journey should go. But, like many of us have experienced, they were spinning. They were talking but not executing! 

This is the classic waterfall mentality: perfecting everything before executing. And yet, if they continued that process, they would never start. So, they broke apart the journey into smaller and smaller chunks landing on things they could do in the next 3 months at a time. For Aruba, they landed on onboarding, and breaking it down further to a simple quick win execution tactic: a welcome email. As they put these pieces into place, a pattern of agile development emerged:

Discover, Design, Build process, Deliver, Iterate down the line.

As ideas surfaced, they put them into their backlog for future iteration, but the important thing to do first was to get an MVP in most journey areas (onboarding, adoption, renewal) and iterate on the ideas that come up throughout the process.

Meet Your Customers Where They Are

Carlos and Keri both discussed heavily the need to consider your audience and the form of communication you’re using to reach them. As you map out the touchpoints, you must think about how that audience will receive information.

For example, Keri shared that CEOs and VPs are going to be hard-pressed to have a QBR meeting anymore; there’s simply not enough time. In fact, Carlos and Keri both believe the traditional QBR (heavy slide deck and PowerPoint slides) is dead. We need to think about QBR delivery and touchpoint delivery in new ways.

If C-Suite and budget holders aren’t going to take meetings, and if they aren’t likely to answer email, we must explore new ways to reach them. Can we make things mobile? For instance, cast.app delivers QBRs in a virtual, mobile way and on-demand. This could be the future of delivery to the executive level with a call to action to meet with a CSM, Sales rep, or renewals manager in the future.

Keri referred to this process as “Meeting your Customers Where They Are” and this is exactly the execution practices the Aruba team followed. They started with a welcome email, but eventually, they iterated and iterated and now they have a virtual CSM. This virtual CSM named “Steve” actually serves as the touchpoint for all of their longtail customers. He walks customers through the steps of onboarding, adoption, and (you guessed it) QBRs. Steve offers uptime with a “live” CSM, but this is rarely abused. And when that time is used, they have classified these meetings into categories to understand where they need better training, documentation, or other clarification. 

Developing your strategy to meet customers where they are in the best medium for them will be key to success, especially in the Digital CS Strategy development.

Don’t Let the Tail Wag the Dog when Choosing Your Tech Stack

Keri pointed out that “meeting customers where they are” remains critical for success, and equally as important: selecting the technology to support that effort. Many CS Leaders and teams get trapped in what they know, and there’s no exception when it comes to tools. They love certain tools and want to keep them. Her biggest advice: “Don’t let the tail wag the dog!” 

As a leader, you need to look at your organization, your customers, and the needs of delivery, and choose tools based on needs, not what you like.

For digital delivery, you will need a different set of tools. For example, you may need more marketing/campaign delivery types of software. You may also need monitoring and visualization platforms to see when drop-off is happening within the product to understand the types of communication campaigns to send. The point here: don’t let comfort and past choices dictate the future of your digital strategy. 

As the Aruba team found, when developing their communication strategy, they needed mass communication campaigns and then they needed a focus on digital communication. They do a lot of AB testing on the types of messaging used and look at open and engagement rates to see what’s working for customers and what isn’t. They invest in technologies that help them to achieve these goals, and if the technology doesn’t exist, they combine technologies together.


One really great example is their process of guiding customers through various stages of onboarding with digital CSM Steve. Using a combination of email and in-app campaigns, and then integrating with tools like Calendly, they allow the customer to choose to schedule time with the CSM, if they run into trouble. To make this work, they need to invest in vendors that can integrate and vendors that do mass communications. 

The takeaway here is to think about the needs of your customers and the digital journey you’re providing. Don’t just myopically choose technology because of its brand or because that’s what you’ve used before.

These are just a few of the key takeaways from the incredibly fun and dynamic conversation about developing your Digital Customer Success Strategy. I encourage you to check out the recording as well! 

For more information on the latest meetups, follow The Customer Success Leadership Network on LinkedIn. And also check out our Slack Channel. With over 3K followers, you can engage on all things CS! And finally, don’t forget to sign up for our next meet up!