The Best Pitches I Heard at SaaStr Annual 2019

Andy Raskin by

Editor’s Note: This article was first featured on LinkedIn here

Two weeks ago, I found myself with a ticket to SaaStr Annual, so I roamed the sponsor area, listening to pitches from SaaS startups large and small.

Conference booths are a great place to gauge how deeply a company’s pitch (a.k.a. strategic narrative) has permeated its ranks because they’re usually staffed by a mix of sales, marketing and product people. Or haven’t permeated those ranks: One sales rep told me if I wanted to hear a really good version of the pitch, it was too bad because his CEO, who would be back shortly, was really good at that.

As you might expect, I mostly heard product-centered descriptions that started and ended with: “We’re a __ platform that does x, y and z.” But as Drift’s David Cancel is fond of saying, markets are so crowded now that you can no longer differentiate on product and features. Instead, differentiation is about building a connection to customers. And it’s certainly easier to do that if everything everyone does at your company is in service of a strategic narrative—that is, a story about getting customers to a desirable, difficult-to-reach Promised Land.

While I didn’t make it to every SaaStr sponsor’s booth, these are the folks from whom I heard solid strategic stories:

#1. Geoff White, CRE Lead, Blameless

As I’ve often said, a great pitch starts not with your company, your product, or anything about you. Rather, it starts with a change in the customer’s world that is creating opportunity and risk.

Geoff followed that recipe by kicking off his pitch with a question:

Do you know about the blameless post mortem?

I didn’t, so Geoff elaborated:

It’s an approach to site-reliability engineering that Google has championed over the last few years and more teams are adopting. Basically, when something goes wrong, they recover and learn more effectively if they do the post mortem without pointing fingers, without assigning blame.

By starting with the change—and connecting it to stakes—Geoff divided the world into winning site-reliability engineers (who, like Google, don’t assign blame during a post mortem) and losing ones (who do).

Having accomplished that, Geoff is no longer pitching a product. Instead, he’s pitching belonging to a club of winners. Likewise, Blameless’ features are no longer disembodied capabilities, but weapons for slaying monsters standing in the way of any site-reliability engineer who wants to join that club. (I wrote more about the benefits of starting pitches with change here.)

#2. Mallory Surpless, Director of Customer Success, DataGrail

Mallory (left, with DataGrail CEO Daniel Barber) similarly started with a question about a change in the customer’s world:

Are you dealing with GDPR?

Mallory delivered the question with exactly the right amount of pained anguish— just enough to convey empathy for anyone dealing with the unwieldy new privacy regulations.

I liked Mallory’s opener (and her way of asking it) for two reasons. It’s a qualification screen for leads, of course, but it also invites prospects to open up about the challenges they’re facing. That’s really what we’re aiming for when we start with a change in the customer’s world—having them interrupt us and start talking about how that change is playing out for them.

#3. Tarmo Van der Goot, Sr. Business Developer, Cleverbridge

How do you pitch against a competitor who has already nailed the category story? That’s a challenge for Cleverbridge and others that play in the subscription billing space alongside Zuora, which went public last year thanks, in no small way, to a simple, powerful story. (I broke down why Zuora’s story works in The Greatest Sales Deck I’ve Ever Seen).

When Tarmo pitched me, I told him his story sounded similar to Zuora’s, and he agreed. So I asked him point blank: How do you differentiate from them?

“I like to say that if the two of us are pitching to the same client, one of us doesn’t belong,” Tarmo replied. “We’re going to be much lighter weight, with a faster implementation that’s better suited to e-commerce customers.”

I’m not in a position to evaluate whether that’s true, but I like that Cleverbridge has identified a target audience for whom it believes it shines at making good on the subscription economy Promised Land.

(I wonder if Cleverbridge might do even better by starting with a newer change that uniquely impacts its target — for example, “now, the subscription economy has come to e-commerce”).

#4. Kasey Byrne, VP Marketing, Postman

Having once run product marketing at Mashery, the API management platform now owned by TIBCO, I appreciate how hard it is to build a story in this category. (At least now people know what an API is — in Mashery’s early days, when I explained what I did at cocktail parties, most just walked away).

Kasey started with the story of Postman’s founder, who got tired of executing curl commands to retrieve web pages, and who then added more functionality for developers building APIs. The founder’s story isn’t always effective in a pitch, but I thought Kasey used it nicely to gain trust and build empathy.

#5. Brian Chan, Account Executive, Boast.ai

Brian’s pitch started out with pure product description — how Boast.ai helps companies reap tax credits for research and development, which often requires complex documentation.

It got more interesting, though, once Brian mentioned a change in his customers’ world.

“The IRS recently added R&D tax deductions to its ‘dirty dozen’ list of audit triggers,” Brian said.

Now I get why Boast.ai is suddenly relevant. By the way, starting with change works for fundraising pitches, too. Investors will be thinking, “How come no one’s done this before?” When you start with change, they’re more likely to smell an opportunity.

HONORABLE MENTION: Tom Scopazzi, Sales Director, Lohika

Tom garners honorable mention here for an approach to pitching that, while following none of my advice, nevertheless helped Lohika stand out from others in its category, who typically try to sound like something they’re not.

“I’m not going to dress it up,” Tom said. “We’re a dev shop.”

Still, Tom, I bet we could do better with change, stakes and Promised Land.

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, IBM, Uber, Yelp, VMware and General Assembly. To learn more or get in touch, visit http://andyraskin.com.

Strategic Messaging & Positioning Leader