What I Learned About Strategic Messaging From 5 Millennial CEOs

Lessons in crafting—and rolling out—the company story from younger leaders

Andy Raskin


Millennials are popularly defined by their tech-savviness, but in that sense I’ve never felt I had much to learn from them. By the time they reached their 2000 coming-of-age, I had been coding for 21 years and editing digital video for six. Texting? My friends and I started doing that back in 1983—on IBM 370 mainframes over BITNET via the VM/CMS “tell” command, but still.

Yet when it comes to strategic narratives for positioning your company, some of my most valuable lessons have come from millennial leaders. In some cases they outright schooled me. In others, they posed new challenges that we worked through together.

Here are the top 5 things I’ve learned about aligning your team around a strategic narrative — the story that powers sales, marketing, fundraising, recruiting, and everything — in my engagements with millennial CEOs:

#1. DEEPA SUBRAMANIAN, CEO, WOOTRIC: Craft a narrative for what your company is—and what it will become

Wootric CEO Deepa Subramanian

HQ: San Francisco, CA; Investors: Cloud Apps Capital Partners, Array Ventures

When I first met Deepa Subramanian, back in 2015, Wootric’s platform was in its infancy. Business customers could use it to run Net Promoter Score surveys — those “how likely would you be to recommend this to a friend?” questionnaires — but Deepa’s vision was grander. Her challenge to me: Can we craft a story that expresses not only what Wootric actually is, but also what it could become?

Particularly challenging was nailing down what I call the Promised Land message — the future state you commit to making real for customers.¹ We considered lines like “make customers love you” or “boost retention,” but none were bold or inspiring enough. Then, one day, we noticed what a Wootric customer had written on his Linkedin profile: “My mission is to win customers for life.” That message still works today, even though Wootric has since added not only only surveys for customer effort score (to gauge onboarding) and customer satisfaction (to evaluate support support), but also AI-driven sentiment analysis for understanding large volumes of customer feedback data:

Wootric home page (2018)

Working with Deepa and her team, I learned not only how a story could bridge both the current state of a product and the future vision, but also how often great messaging comes from customers’ mouths.

#2: YAN-DAVID ERLICH, FORMER CEO, PARSABLE: To align your team on the story, aim for “that’s right”

Parsable former CEO Yan-David Erlich

HQ: San Francisco, CA; Investors: Andreessen Horowitz, Lightspeed Venture Partners, GV, Kleiner Perkins, First Round Capital, Saudi Aramco, Schlumberger

If I’ve gotten better at aligning leadership teams around a new strategic narrative, it’s in no small part thanks to Yan-David “Yanda” Erlich.

After Yanda and his team at Parsable had settled on the bones of their strategic narrative, one of his salespeople caught wind of it—then sent out a mass email about why he hated it. At Yanda’s request, I met with the man to see if we could make changes that would bring him in line, but he only dug in further. Just as I was losing hope, Yanda stepped into the room and began asking the man a series of questions. And in a shift that seemed almost magical, the man came around. He agreed to fully support the new messaging, and I could tell he meant it.

Beyond impressed—more in awe—I asked Yanda what he had just done. He told me it was a technique he had learned about in a negotiation book called “Never Split the Difference” (by former FBI hostage negotiator Chris Voss). The idea was to try and summarize the other side’s position until they said some version of “That’s right.” That signaled the other side felt understood, and would be more open to working with you.²

Today I use variations that approach whenever I encounter resistance to a new way of telling the company story (what I call “story backlash”). Working with Yanda also taught me how important it was to involve key sales leaders in the story’s development and initial rollout, rather than having the CEO —or, god forbid, marketing—foist it on them fully formed.

#3: MATT TALBOT, CEO, GOSPOTCHECK: Get customers to help you roll out the new story

GoSpotCheck CEO Matt Talbot

HQ: Denver, CO; Investors: Insight Venture Partners, Hinge Capital, Techstars

Speaking of rolling out the story, GoSpotCheck CEO Matt Talbot came up with an idea for doing that that worked so well, I’ve been advising every team I work with to copy him.

After Matt and his senior team aligned on a new strategic narrative for GoSpotCheck’s real-time field operations platform, he first trained his sales and marketing teams on it. Then, to convey it to all of his 150 employees, we sketched out an agenda for an all-hands session. As in similar sessions I’d supported other CEOs to lead, we would have salespeople talk about how the new story was helping them in deals, and we would have marketing people unveil new content—web pages and other collateral—that told the new story.

Matt had another idea: What if we invited a customer to speak at the all-hands?

The customer Matt invited was a man we had interviewed while building GoSpotCheck’s story, a field support engineer at one of the world’s biggest healthcare companies. In our interview, he told us that a single naysaying doctor could scuttle a multi-million-dollar contract at a hospital, so it was crucial for his field reps to have real-time intelligence about which doctors had been briefed on new offerings, as well as which might harbor less-than-favorable views (i.e., who might be targets for follow-up briefings). At the all-hands, the customer said he had data to prove that his company saw larger revenue gains at hospitals where his field reps used GoSpotCheck to manage their doctor briefings than at those where they didn’t.

Matt didn’t coach the customer at all on what to say, but because we had crafted the GoSpotCheck narrative based on his and other customers’ input (all about how “the field” has become a real-time battleground), his talk was brilliantly on the mark. In a survey afterwards, GoSpotCheck employees rated the event a huge success, singling out the customer’s talk as the highlight.

Now, every CEO I work with gets an earful from me about why they should invite customers to help roll out the new story.

#4: TYLER SMITH, CEO, SKYSLOPE: Position inside your parent company

SkySlope CEO Tyler Smith

HQ: Sacramento, CA; Parent company: Fidelity National Financial

Tyler Smith first contacted me two years ago about crafting a strategic narrative for SkySlope, a SaaS platform he founded for real estate brokers and agents. Scheduling prevented us from working together back then, but Tyler obviously knew how to tell a great story: last October he sold a majority stake in SkySlope to Fidelity National Financial, the country’s largest title processing company.

Last month, Tyler reached out again. Now that SkySlope was part of a larger organization, he said, it was even more critical to get the story right. As he told me:

“We have to make the case for why we matter in this bigger company and why they should invest in growing our part of the business. If we’re successful, our story could become a big part of the story our parent tells to customers and to the world.”

I had never thought about Tyler’s application of strategic narrative before —positioning a subsidiary to its owners. While Tyler and I are just getting started, I’m learning a lot about how to craft a story that plays to them, as well as to his customers and his 150 employees.

#5: JUSTIN YOSHIMURA, FORMER CEO, 500FRIENDS: Helping CEOs get the strategic story straight could be a thing

500friends former CEO Justin Yoshimura

HQ: San Francisco, CA; Investors: Intel Capital, Crosslink Capital, Fung Capital, Y Combinator

Justin Yoshimura once told me he had dropped out of every educational institution he ever attended—including preschool. Which made it all the more fun to watch him wow gray-haired leaders of global retail giants by schooling them on the finer points of customer acquisition and retention.

I met Justin five years ago, when he hired me as interim VP of marketing at 500friends, the retail loyalty platform he founded through Y Combinator. Nine months later, as 500friends was being acquired by Merkle (which was in turn bought by Dentsu Aegis), I asked if he felt the combination of money and stock he paid me had been worth it. He 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 CEOs and their leadership teams get the strategic story straight. Still, I doubted whether leaders would allocate a line item in their budget for that. 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?”

“Yes,” he said.

“I don’t believe you,” I said.

A week later, Justin sent an note to the Y Combinator founders’ email list about our work together. The overwhelming response from CEOs led to my first full-time strategic narrative engagements—and the dawning realization that, well, maybe this could be a thing.


¹For more on the “Promised Land message” and how it fits into my strategic messaging framework, check out “The Greatest Sales Deck I’ve Ever Seen” and “Founders: Pitch the Promised Land.

² I wrote in detail about Yanda Erlich and how he introduced me to Chris Voss’s negotiation techniques in “To Be a Better Leader, Learn This FBI Hostage Negotiation Tactic.” In that post I concealed Yanda’s identity, but he granted me permission to reveal it here.

About Andy Raskin: I help CEOs align their leadership teams around a strategic story — to power success in sales, marketing, fundraising, product, and recruiting. Clients include teams backed by Andreessen Horowitz, KPCB, GV, and other top venture firms. I’ve also led strategic storytelling training at Salesforce, Square, Uber, Yelp, VMware and General Assembly. To learn more or get in touch, visit http://andyraskin.com.



Andy Raskin

Helping leaders tell strategic stories. Ex @skype @mashery @timeinc http://andyraskin.com