From songwriter to CMO: An interview with messaging master Jeffrey Pease

Jeffrey Pease interview find a way media message mechanics

By Chris Gillespie, Co-Founder, Find A Way Media


Just a bit of poetry

Those who crave clarity ask for Jeffrey Pease by name. He has a way of listening that helps talkers untangle their thoughts—professional, personal, or otherwise. It’s a lifelong skill and he has become so well known for it in the B2B software community that slowly and reluctantly he is coming to acknowledge that the name of his consulting practice might as well be his own.

“I’ve sort of succumbed to the idea that I’m the brand,” he says, patting his golden retriever on the head. “Don’t print that.”

It’s late on a Friday. People are drawing cold beer from a tap in the WeWork commissary and many are trickling out. Jeffrey has graciously agreed to stay and share the story of how he parlayed a brief foray into songwriting into a lifetime of marketing success.

This interview has been edited for clarity and brevity, but not much. Jeffrey has the unusual skill of speaking in entirely publishable prose.

The Beat: How’d you get your start?

Jeffrey Pease: Which one? There was a great deal of trial and error. I did a lot of exploration between quitting high school and getting an MBA, and it didn’t stop there. I’m the son of a newspaper man who decided very early not to try to make my living as a pure author or creative, so it took a long time to find the combination of creativity and consistency that would deliver a value somebody would pay for.

My first actual product marketing job was working for Business Objects. I was launching a new product line for them and was given a message structure by the CMO Dave Kellogg. I can’t remember if he called it a message matrix or something else, but the bones were there. The idea was to boil the story down to one short existential statement, three key messages, three proof points for each, and that’s it. That becomes the basis for all marketing. I thought, wow, that’s fantastic. But I struggled with how to get to that level of compression and punch. Then I took time off to write songs.

You went from Business Objects to songwriting?

Yeah. I studied with Bonnie Hayes, who wrote some of Bonnie Raitt's bigger hits, like “Have a Heart” and “Love Letters.” If you want to get schooled in brevity, punch, and clarity of message, learn to write pop songs. I got the crap very politely beaten out of me the first time I submitted a song to an A&R guy at a conference. He didn't even let it play to the chorus. It wasn’t clear enough, sharp enough, or structured enough. You've got 10 seconds to get somebody's attention on the radio and there are no switching costs.

Why songwriting?

I was following a long-held desire. I'd actually wanted to learn to write songs for a long time, but it didn't seem like a viable career path. Even when I was working at it intensely, I wasn't necessarily thinking that’s what I would always do. But I had some financial leeway, so I explored it fully.

There was a period when I was writing a song a week, which is a lot. Just studying, learning, and pounding them out. I didn't have a background as a musician, which gave me very specific weaknesses and strengths different from my peers. I spent long, agonizing hours at the computer doing shitty demos until I finally started to collaborate with other musicians.

What were those weaknesses and strengths?

Not being trained as a musician, I focused a lot on lyrics, which was unsurprising, given my background. But I also would tend to write melodies that were strong enough to be remembered even without all the music and instrumentation around them. It’s different from a musician playing chords they like and then deriving the melody from them. 

Spending almost two years writing songs did something for me as a marketer that B-school and previous jobs hadn’t. It honed a feel for brevity and clarity and the lightning that can occur when you take wild creativity and channel it into a sharp structure. 

The message matrix was amplified and strengthened by this fusion of creativity and discipline from music. When I discovered that, and when it was time to go and get a real job again, it became the core of what I brought to my role—a messaging structure and a bit of poetry to inhabit it.

What brought you back to marketing? 

Money, and the desire to have more of it. I made a few dollars as a songwriter, but it wasn’t a living. I had a song used as the title track in an independent movie and some small successes. I had 10 seconds of one of the songs that I co-wrote used in the Winter Olympics coverage. There were very cool little moments. But making a living as a songwriter is so, so competitive—and even then it had become really the era of the producer, not the traditional songwriter. I also realized what I enjoyed most about it would be diminished if I had to do it as a job. I decided it was time to get a tech marketing job again. So that's when I went to Oracle.

And you took the message matrix with you?

I did. And it's actually what got me in. Because here I was, I mean I had a decent pedigree, a good MBA from Cornell, and my experience at Business Objects. But relative to my competition for this product marketing job, I was hardly the obvious choice.

I had spent the last two years learning to write music versus the guy with the Stanford or Harvard MBA coming straight off another relevant job. But the hiring manager was smart and gave us actual work to do as a test. He asked us to rewrite a draft piece of collateral for a product line. All finalists did the rewrite. I redid the messaging more coherently as a message matrix, rewrote the piece based on that matrix, and provided the matrix and explanation of the methodology as part of my delivery. 

So how did you get to your current consulting practice?

I developed a reputation within Oracle for being the messaging guy. There was a real hunger for this kind of help. The product marketing department was full of smart, confident people who knew a great deal about their area, but the combination of brevity and punch that a songwriter or a messaging expert brings wasn't necessarily their chief gift. After working on several different product lines and teaching messaging on the side, I got to create the Oracle messaging team as an internal consulting organization within Oracle marketing.

After that, I got an opportunity to be head of marketing at a startup, ran my own consulting practice with the messaging matrix for a while, and was drawn back to Oracle. Then I moved from San Francisco to New York City to take what became my first CMO role with Medidata Solutions and then another startup. But after the last one, I was thinking, “Well, that's the last job I ever want to have.”


Because even interesting companies and great jobs have boring parts. And ultimately, the messaging part always comes out for me—the songwriter piece. I always find that interesting.

I decided to return to messaging as a consulting practice and it worked out well. I’ve been lucky enough to have clients on both coasts and as far away as Delhi, Puna, and Amsterdam—essentially all by referral. And it’s been fun to watch clear messaging contribute to more sales, better press, or even fundraising for those clients. My favorite result is having clients come back to me early because they’ve become so successful with their messaging that they’ve outgrown it.

(Read some of Jeffrey’s writing: Has success broken your brand message?)

Advice for B2B writers?

Don't just start writing. Get familiar with the messaging for the company or the initiative you are writing in service of first. If no matrix exists, help create at least a rough one. First, create a positioning statement. What are your three key messages? And there aren't four, by the way. Four shall not be the number. Five is right out. People can't remember that. Our brains like three.

If you don't have a message matrix, it’s worth drafting one before you start writing because that will give you far more clarity when you do start writing. It will save you time, it will save you effort, it will give you more punch than if you just start laying down words.

Like in the movie business, it’s always cheaper and easier to alter the film when it’s just a script than after you’ve already produced the whole thing. So, messaging first. 

Do you still write songs?

I will write when provoked. I have a couple of songwriting partners who provoke me. I had songs on the last five albums by Jeffry-Wynne Prince’s bands The Kimberly Trip and The Bitter Elegance. My long-time collaborator essence and I did a children's album as well as her album Black Wings. My two worlds collided when I helped her develop a workshop called Finding Your Voice where she teaches people how to use the singer-songwriter's toolkit to become better presenters and more creative collaborators. She’s even done it for Google and YouTube, so the tech-songwriter connection is now very meta.

Final thought?

When I talk to people earlier in their careers, I usually try to at least impart the idea that mastering something you love and making it into a job is possible. I want them to find that out sooner. If you don't think it's possible, you won't even look for it. I ask them questions like, "What do people come to you for? Not just in your work, but in your life?" 

People come to me for clarity. Sometimes they talk to me, I'll ask a few questions, and somehow, it clarifies things. What do people come to you for?

Check out Jeffrey’s practice, Message Mechanics. Plus, examples of the message matrix.

Black and White

Chris Gillespie, Co-founder, Find A Way Media

Chris helps brands ditch the jargon and grow by telling stories. Chat with him on Twitter.