What I Learned Positioning 40 Companies

Andy Raskin
Feb 23, 2016 · 5 min read

Two and a half years ago, I accepted an interim role as VP of Marketing at 500friends, a startup that had been incubated by Y Combinator. Nine months later, as we were being acquired, I asked 500friends CEO Justin Yoshimura if he felt the money he paid me had been worth it. He immediately said yes, so I asked him why.

“You got our story straight,” Justin said.

Justin’s answer pleased me because I had been thinking about starting a consulting business to help leadership teams get their strategic stories straight, but I wasn’t sure entrepreneurs would see the value. So I asked Justin, “If nine months ago I had told you that I would charge you what you’ve paid me to get your story straight, would you have hired me?”

Justin again said yes. But I didn’t believe him until a week later, when he sent an note to the Y Combinator founders’ email list about our work together. The response from entrepreneurs was overwhelming, and led to my first full-time strategic messaging and positioning engagements.

I’ve now been privileged to work with more than 40 leadership teams — spanning seed stage through acquisition/IPO prep — in defining the strategic stories they’re using to power fundraising, sales pitches, marketing campaigns, employer branding assets, and product development. So I thought this would be a good time to reflect on what I’ve learned over the past couple of years, and what I’m doing differently now as a result.

Whether you’re building your own company story or positioning companies for a living (like me), I hope you’ll find these 5 points valuable.

#1. Story should dictate product — not the other way around

Leaders often think about their strategic story as a kind of packaging for their product— a collection of catchy phrases for making the product they’ve built more attractive:

Many leaders think about their story as a kind of packaging

But if your product team isn’t first aligned around a well-defined story—that is, if the people who prioritize your feature backlog don’t have a crystal clear understanding about whose lives they’re trying to transform, how, and why— how can they build a great product?

Again and again, I’ve noticed that successful teams come to view their customer’s transformation story as the primary thing they’re building. Their product? While they see it as critical, of course, to them it functions a medium for telling their story (and making it come true).

Successful teams, in other words, embrace a wholly opposite view of the relationship between product and story:

Successful teams view their customer’s transformation story as the main thing they’re building.

#2. Positioning is the CEO’s job

As a corollary to #1, CEOs must actively drive strategic messaging and positioning. Marketing teams can facilitate, but unless the CEO leads the creation and dissemination of a clear high-level story, subordinates around the company (in product, HR, customer service, and everywhere else) will create and disseminate their own stories. The result will be muddled market presence.

Former Vine GM Jason Toff (now at Google) puts it best:

#3. Differentiation works best when it’s framed by an effective Promised Land

Everyone knows that good positioning answers, “How are you different?” But if your answer starts and ends with your product and its capabilities, your audience has zero context for why those things matter.

Instead, effective differentiation begins by aligning your team around a strategic Promised Land—a future that your customer wants, that you can uniquely deliver, and that your customer will find difficult to attain without you. If your Promised Land is compelling and credible, differentiating versus competitors is easy:

To be sure, you’ll have to back that up with credible, relevant product capabilities. But by first setting the stage with a differentiated Promised Land, you give your audience a framework for understanding how those capabilities will (uniquely) improve their lives. (Steve Jobs was a master of Promised Land differentiation: I wrote about his 2007 keynote for the first iPhone from this perspective.)

#4. You can get better at telling strategic stories by constantly asking 2 questions

Writers improve by studying other writers. Same for filmmakers, visual artists, and musicians. Likewise, I’ve found that I can boost a team’s skill at telling a compelling strategic story by having them examine the strategic stories of other companies.

Every time you visit a company’s website, consider the following two questions:

  • Who is the main character whose life the company is saying it can transform?
  • What Promised Land is the company conveying through its words and images?

It’s especially enlightening to consider these questions while looking at your competitors’ websites. In my experience, by the time you return to your own website, pitch decks, and sales collateral, you’ll have a clearer sense about the story you’re telling, and how it should best evolve.

#5. The hardest thing about messaging is (still) leaving things out.

Last summer, I wrote about the lessons I had learned in my first 15 strategic messaging and positioning engagements. One was how hard it is to get teams to leave things out of their high-level messaging. As I said back then, frequently the toughest part of my job is helping leaders come to terms with de-prioritizing parts of their story — sometimes parts that they love — in service of becoming more effective.

That continues to hold true. For a venture-backed startup in New York City, I recently proposed a Promised Land around higher revenue for their customers. (Not exactly: I’ve disguised the Promised Land to protect client confidentiality, but you’ll get the point). In contrast, their competitors talked mostly about operational efficiency.

But the company’s CTO objected. “Our product also promotes operational efficiency,” he said. “Shouldn’t we get credit for that?”

My response to him, and to you: Your product does many things. The question is, Which do you most want to be known for?

Firm Narrative

How to tell strategic stories

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