Photo by Olu Eletu

It’s Zuora’s, and it’s brilliant. Here’s why.

A few months ago, my friend Tim took a new sales job at a Series C tech company that had raised over $60 million from A-list investors. He’s one of the best salespeople I know, but soon after starting, he emailed me to say he was struggling.

“I’ve landed a few small accounts,” Tim said. “But my pitch falls flat at big enterprises.”

As I’ve written before, I love helping teams craft the high-level strategic story that powers sales, marketing, fundraising — everything. …


Brilliant category narratives evangelize a new discipline for winning—while positioning the old one as obsolete.

In the 1990s, I ran the New York City Marathon three times.

Each year, the night before the race, I would attend a carbo-load party at a popular running club. Joining hundreds of other runners, I would stuff my face with pasta in the hopes of not “hitting the wall” — running out of carbs to power my muscles across the finish line.

The final year I ran the race, the club invited a celebrity running coach to be the dinner’s guest speaker. I don’t remember his name, but I’ll never forget his message:

“Not to ruin your meal,” he…

Because billions of dollars in valuation are at stake.

The weapons are words.

The stakes? Billions of dollars in valuation.

The combatants? and, two companies that have raised over $50M to build and dominate a category known as — well, that depends on how this plays out.

Both companies were founded in 2015. Both promised to make your sales team more successful through AI. Both do that by analyzing recordings of your sales calls to answer big questions: How can my worst reps be more like my best ones? Which of our messages are resonating? Why are we winning or losing deals?

Until recently, both companies described…

5 that went beyond “We’re a ___ platform that does x, y, z.”

One of the many startup pitches at SaaStr Annual 2019

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.


5 lessons from helping CEOs align their teams around a story

Photo by Kristen Sturdivant via Unsplash

The most Japanese of Japanese proverbs, to my mind, is “Three years, even on a rock” (石の上にも三年). The literal meaning is that even a stone is worth sitting on for a long time because it will eventually heat up. In other words, persistence begets rewards.

A little over three years ago, I perched myself atop a rock called “Helping CEOs align their teams around a strategic story,” and there are still plenty of chilly moments. …

The greatest sales deck isn’t—until your sales team buys in.

Bellies full of beignets, my parents and I were exiting San Francisco’s Just for You Cafe when when a middle-aged man called my name.

“Andy, it’s Christoph!” he shouted. “Do you have time for a quick question about messaging?”

(Later, my mom asked, “People stalk you for messaging advice?”)

It was fun having my parents think I was some kind of messaging celebrity, but I recognized Christoph as the CEO of an early-stage tech company who had recently attended one of my workshops. He was waiting for a table, but didn’t wait to tell me what was going on.


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

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. …

I thought she was too touristy. I was an idiot.

Original photo by John Jason on Unsplash

We’d been dating for nearly a year. Everything was going great, when Emily said, “I have always wanted to ride in a gondola in Venice.”

I winced. “What?”

“It would be romantic,” she said.

Some people refrain from touristy activities because they look down on them. In my case, it’s fear. Fear that people who don’t do clichéd, touristy things will judge me.

“What kind of loser rides the horse-drawn carriages?” they’d whisper in Central Park, so I’ve never ridden one. I’ve never hopped on a cable car in San Francisco, never toured Buckingham Palace during visits to London. …

How to structure your story to resonate with different personas

Photo by Helena Lopes via Unsplash

In helping CEOs align their teams around a strategic story, there’s one question I hear more than any other. Recently, I heard it from a marketing leader at a public tech company valued at over $1 billion:

“We’re in an unusually complex situation in that we have to speak to multiple target audiences —multiple industries, multiple buyer roles (CEOs on down to field reps). Can we do that with one story, or should we be telling many stories?

When answering, I always reassure the questioner that his or her “situation” is totally normal. …

Drift thrives by acting less like a software company and more like a reality TV show. Here’s how to follow their lead.

Drift CEO David Cancel (left) and VP of Marketing Dave Gerhardt

Embarrassing, but true: I know more about the daily lives, hopes and dreams of some employees at Drift—the Boston-based sales and marketing software company that’s raised over $107 million in VC cash—than those of some of my closest family members.

Of course, I’ve barely spent time with anyone at Drift. (I was a speaker at one of their events last year, and have no stake in the company.) Yet I know, for example, that Madelyn Ligtenberg, a Drift salesperson, loves chatting with prospects through Linkedin Messenger, and that she goes by “Mads.” I know that product lead Maggie Crowley built…

Andy Raskin

Helping leaders tell strategic stories. Ex @skype @mashery @timeinc

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