The Core Message
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The Core Message

How to Tell “Strategic” Stories About Your Company: Part 2

In Part 1 of this mini-series, we looked at two types of storytelling by two very different kinds of founders — “heroes” who charge into battle, and “generals” who stand back and strategize first.

I argued that even for hero-type founders, the general’s craft of strategic storytelling can be very useful.

So today, let’s look at a prime example of strategic storytelling: the Rippling Memo. It’s one of the best pieces of writing I’ve seen from startup (or public company for that matter), I’d strongly recommend reading the whole thing.

For context, Rippling’s software to helps enterprises manage their employee information. Its co-founder is definitely a general — Parker Conrad who previously founded HR and insurance unicorn Zenefits. So yeah, he’s done some stuff and knows a bit about the industry.

So how does Conrad tell a strategic story?

What’s So “Strategic” About it?

The memo’s opening is typical of most startup pitches— with the problem:

This, Conrad believes, is the cause of most admin headaches. So far so good, but nothing unique right? Everyone knows you should start with the problem.

But then things got interesting.

Usually this is where “hero” founders go: “and we have the perfect product to solve this problem!” They’ll then go crazy on the features, technical details, and benefits, etc.

But that’s not what Conrad does.

Instead, he devotes TWO full pages to Rippling’s strategy, NOT product. And he does it in three logical steps.

1. Lay out what competitors are doing

Conrad begins with the basic premise:

But then Conrad throws a curve ball — he reveals that all of his competitors, from ADP and Microsoft to Gusto and Zenefits, already know this and are going after the same thing:

Like any good general, Conrad doesn’t just go straight into the product. Instead, he surveys the whole competitive field to see what everyone is doing, before he picks an angle that could be the key to victory.

And this is exactly what he does in step 2:

2. Identify Key to Victory

If everyone else from ADP to Microsoft is already trying to be the employee system of record, how could Rippling beat them?

Conrad reveals the answer:

And there it is — he pinpoints “onboarding” as the key to victory, because if every company uses Rippling to hire employees, Rippling automatically becomes the birthplace of all employee data.

And then every other system would have to get its data from Rippling!

All I gotta say is…

But the next paragraph is notable as well:

Do you see how he uses the strategy to explain the product focus?

Most other entrepreneurs we’ve seen would present their product focus in isolation, without laying out why that focus made sense and fit into a larger strategy.

But wait, the next paragraph gets even better:

He isn’t just thinking about success. He’s thinking about what comes success — what if competitors finally saw what they were doing, and came after the same prize? He’s thinking two moves ahead.

He’s not an entrepreneur, he’s a chess player!

That leads us to step 3…

3. Stave Off Competitive Response

If competitors came after them, what would Rippling do? He wastes little time getting to the answer:

His thesis, essentially, is that whoever builds a solution to satisfy ALL enterprise departments will win. And that’s why Rippling is actually three systems, not one:

  1. Payroll, benefits, and HRIS
  2. Identity and access management
  3. Endpoint device management

This would seem strange on its face — diluting the company’s focus by going after so many systems. But predicated on his strategy, it makes total sense.

Even better: he believes that his much larger competitors don’t think this way, as a later paragraph in the Competition section makes clear:

Our competitors won’t be able to do this because it’s not in their nature.


The way Conrad tells the story in this memo is quite unlike 90% of the pitches and writing we’ve seen from entrepreneurs.

It’s not even about the he uses — rather, it’s the order and logic of his narrative, and the way he builds on fundamental assumptions to move the reader towards a conclusion.

The rest of the memo is full of potential learning for startup founders who’d like to think and write more strategically — from the way he answers the Why Now question to his deft positioning of Rippling as a new category.

Go read it, seriously.

But for the next and final part of this series on strategic storytelling, we’ll dive into some of the “how” of building a strategic story.

Stay tuned.



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Andrew Yang

Former presidential speechwriter. Now helping CEOs and founders tell better stories. Co-founder of Presentality