How to sell a technology strategy to senior executives

I've started writing about my time as a CTO when I was responsible for turning around and transforming an online video platform to scale 10X as the business doubled down on its growth strategy by investing more heavily into marketing, acquisition and retention drives. As a result, the impact on the engineering team was very high, much higher than when the team built the first version of its platform "Delta 1.0" - and now, under new leadership, I was tasked to take this platform that was lacking in several areas and transform the stack to a future 2.0 vision. It all became more complicated and ambiguous a year later, when another business was merged and we ended up with having two video platforms, offering different product experiences, for different segments of customers.

Despite the technology ambiguity and business uncertainty, the ask from the top was for the Delta product & engineering teams to come up with a plan for a unified stack, showcasing the 2.0 experience. 

I previously shared the technical narratives to help communicate my technology plan. Alas, the docs were too lengthy and detailed for high-level business executives. I needed a way to sell my vision and at the same time secure funding to be allowed to multiple tracks of work running.

How do I show to non-technical business executives, the current state and our future desired state?

What words do I use to show we need to leap from A to B?

How do I convey a story that creates excitement?

How do I gain credibility that my planning is sound?

How do I show complex technology stack layers incl. infra to reset mental model of a "simple app"?

If you've been reading my other posts, you'll learn that I like visualisations, a lot. I also like story-telling - and even way back then, in 2017 - I was familiar with Amazon's future press release concept - and decided to use the future press release headline summaries as a way for me to communicate the release plan. Who knew, that five years later, I myself would end up working for Amazon!?

Here's the anonymised deck that shares concepts you could use, if you find yourself owning a technology platform modernisation challenge, moving your platform from V1.0 to a Nextgen 2.0 state, and sell the strategy to non-technical business executives. By the way, I put this strategy together during my first 100 days into my assignment, in the midst of many other operational responsibilities: