Simple is hard

Some of the most chaotic (remember: this isn’t necessarily bad!) environments I have worked in all had one of two things in common:

  1. We were live in a market(s) but there was massive friction between what the Sales team was out selling and the speed at which the Product team was delivering the roadmap

  2. We were making a strategic pivot and had to paint a future that didn’t yet exist

In both instances, we had more questions than answers and because we were running so fast, nobody had the time to step back to see the forest through the trees.

When you are in hyper-growth mode and running 1 million miles per minute, it’s not uncommon to reach a point where teams realize they either haven’t answered foundational questions or taken stock of new questions that have come up in the journey.

You’d be shocked to know the number of times I’ve heard, “What are we selling and to whom?” at companies with a household brand name or seeming product-market fit.

Again, this isn’t uncommon. But it requires the leadership team to take a beat amid the chaos to 1) define a clear strategy, 2) remove complexity and extrapolate key messaging and priorities and 3) explain those answers, in layman’s terms, to customers, employees or investors.

This is a very hard thing to do.

Why? Because simple is hard.

Let’s take a real-life example: my company is in the throws of a strategic pivot, transitioning from a horizontal foreign exchange currency provider into a vertical SaaS (‘software-as-a-service’) business.

“Pivot from horizontal FX to vertical SaaS.” I come from an industry where buzzwords like this are thrown around all the time and even I think that sentence is a bit of a vaporware statement.

So let’s simplify:

  • “Horizontal FX”: we sell a payment solution to any type of company in any sector; we go wide & horizontal

  • “Vertical SaaS”: we will combine our payments solution with software that is built specifically for the painpoints and challenges of a specific industry; we will only sell into companies in that specific industry; we will go niche & vertical

But why would we make that change? Why is making a pivot into something more niche a better strategy than selling to a broader set of industries and companies? How do you explain to employees how we will go from here to there? What will happen to our legacy, non-strategic client accounts during this pivot?

And, remember the question I mentioned earlier? “What are we selling and to whom?” It all comes full circle…

Let’s go back to our earlier real-life example: we kicked off this strategic pivot 1 year ago, rebranded our holding company 8 months ago, hired a new Chief Product Officer 5 months ago, hired a new Chief Revenue Office 2 months and only just 4 weeks ago did we publish our first ever global Product strategy & roadmap.

To our (relatively) new leadership team, it has finally begun to feel like our mission, vision and go-forward plan is crystalizing. However, what also became apparent in prepping for our latest global Town Hall was that we are still quite far from giving our employees the clarity they need to reach the same level of conviction that we have built over the past year.

So what did we do? We went back to first principles. We created a visual representation of the future we were building. We showed a diagram of how different acquisition channels yield vastly different customer lifetime values. We explained why investors will give our business a higher valuation multiple if we are a vertical SaaS business than a direct-to-consumer one.

We had to bring everyone on a journey that we, as leadership team, had already gone on ourselves. In doing so, we realized that you also have to tell that story assuming that your listeners have no context for the topic at hand.

Not only was it a test of our own understanding of the vision we were selling - it was a great reminder that if you can’t explain it to a 5 year old, you don’t really understand it yourself.

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