July 2020 CxO Roundtable Recap

Transform by Simon held a CxO roundtable yesterday led by Nick Drake, VP of Global Marketing at Google, Doina Harris, CPO at Simon, and Richard Demato, Head of Transformation at Simon. 

The event brought our speakers together with ten marketing and experience leaders from across verticals, including finance, education, retail, insurance, and entertainment.

While most business conversations since March 2020 have been around digital transformation concerning COVID-19, the lens of these changes is only getting longer. Many experts don’t expect to see the light at the end of this particular tunnel until summer 2021. This ends the era of  “digital transformation” as a buzzword. Now it’s all anyone — at least in marketing — is thinking about. 

One attendee brought up their research into successful digital transformations. With the acknowledgment that there are as many ways to transform as there are people attempting transformation, the attendee pointed out two extreme cases.

  1. The Hardcore Version: In which a global enterprise pressed pause on all front-end development for two years while a task force ripped and replaced all systems, a process that would’ve taken 5–7 years if done iteratively. 
  2. The “Lighthouse” Version: In which the Experience Team at a different global enterprise transformed a handful of customer journeys and slowly gained momentum until the entire organization had joined the cause.

It’s likely that, at this point, you — like the attendee recounting this research — will find yourself somewhere between the two extremes. We hope our recap from this event will play a small part in your digital transformation, and that partnering with Simon Data will play a much, much more significant role in that process. 

Some of the top concerns voiced by those in attendance revolved around the intersection of accelerating digital transformation with a real concern for staying employee- and customer-centric. Such topics included:

  • Focusing on employee well-being and company culture during COVID-19
  • Fully integrating your human capital with new technologies to drive real transformation instead of just acquiring a high-cost investment no one uses
  • Maintaining the momentum of digital acceleration without losing the customer experience as the center of your world
  • Keeping a human touch in an increasingly digital organization

One of the attendees made the salient point about the four fundamentals of digital transformation, which are:

  1. People
  2. Process
  3. Culture
  4. Technology

Align your marketing organization on transformation

From the perspective of a marketing or customer experience executive, technology will move at a pace that is almost entirely out of your control. If you are going to manage real digital transformation, the “softer elements” (people, process, and culture) must align on a grand vision that is simply enabled by the technology. Without this alignment, any new technology would be rejected, like a mismatched organ donation. 


People & Culture

Adapting to an indefinitely distributed, isolated workforce was a big topic, with different leaders contributing their experiences and initiatives toward balancing employee productivity, mental health, motivation, inspiration, and camaraderie. Some of these initiatives include: 

  • Rewards and recognition
  • Surprise-&-delight mailed boxes
  • Group learning events (like wine tastings and cooking classes)
  • Special speaker series
  • Encouraging connection through the Slack plugin, Donut



The discussion then pivoted to how the group is prioritizing the specific changes in the customer experience that each executive is building or anticipating over the next year.

The hottest topic to come up in that discussion was around reinventing the funnel with more in-depth, more dynamic segmentation to get at a better diagnostic on signals of intent.

The pandemic has accelerated the volume and diversity of digital signals, with so many customers facing abrupt changes in lifestyle and needs. The question now is how to find the absolute best way to respond to a signal of intent.



The issue uncovered with the above concern is the difficulty of bridging the gap between data and interactions, which is less a process issue than a technology issue. 

Another executive recounted their revelation that the acquisition funnel model is fundamentally broken because it doesn’t account for intent. When this executive’s program switched to a segmented approach, they found a small high-intent group of users and two larger groups comprising medium-intent and low-intent users. 

By focusing on segments, this executive’s company was able to zoom in on actions or activities that correlate with low customer acquisition cost (CAC) or high lifetime value (LTV). Each activity is then put under the microscope to determine if it’s correlated or causal. Using app downloads as an example, the team found it to be causal in relation to high LTV. They then leaned significant effort into promoting app downloads and saw LTV climb in parallel. 

This segued into dynamic segments. With the world in flux as it is, you can only serve customers as well as you can read them. Thus, another executive focused on adopting dynamic microsegmenting abilities. This refers to being able to pick up on behavioral signals and automatically shifting customers from one highly targeted segment to another to serve the customers better. 

Customer retention after COVID

A big fear expressed across those in attendance is that, even in verticals with a fortunate influx of customers, no one knows who these customers will be in 12–18 months when conditions return to (basically) normal. Will the tide ebb back to something resembling January 2020, or are we living in a new normal that will persist beyond the pandemic? 

Which came around to the parting thought of paying down “technical debt” and “process debt,” i.e., replacing legacy systems that are expensive to operate and maintain in favor of flexible, adaptable models that can just as comfortably accommodate an international pandemic as it can a world of perfect health and peace.


Curious about our Transform events and community? Transform is a private, invite-only community where executives come together to network, learn, and collaborate with their peers. 

Next up, Simon is hosting a public fireside-chat-style webinar with Nick Drake again on Digital Transformation Wednesday, August 12th at 1 pm ET. Register here.

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