here’s the short of it
I’m a former teacher, lifelong weirdo, and community organizer with a big heart.
My kids challenge me to think smarter and play harder every day.
My chosen family reminds me that connection is what we’re all really after.
here’s the rest of it
CHAPTER 1: THE TEACHER
I grew up inside books the way some kids grow up inside sports or music. Obsessively. Gratefully.
As I neared the end of undergrad, I started looking for rooms where stories were the designated vehicles for transformation.
I found those rooms as a high school English teacher.
Every lesson I designed was an argument for why this moment mattered to a fifteen-year-old who had a hundred reasons not to care.
I ran stakeholder interviews in the form of one-on-one check-ins.
I designed campaigns in the form of units.
I measured outcomes in the form of noticing how kids changed from the first to the last day of school.
I loved it.
I loved the students. I loved the craft of it. I loved the days when something bloomed open in a room full of people who had been closed off all morning.
But I was also growing a family. And I was hungry.
There was more to my story, and the classroom was my first chapter.
So in 2016, I did the thing that felt both obvious and terrifying: I went out on my own.
CHAPTER 2: THE MAVERICK
From 2016 to 2022, I freelance wrote for startups and established brands across industries I had no business knowing as well as I came to know them.
Cannabis. Cybersecurity. Cryptocurrency. DEI. Food delivery. Ed tech.
I ghostwrote web copy, email campaigns, blog series, press materials.
I launched a 20-episode podcast featuring cannabis entrepreneurs and advocates, all sharing their stories to expand public perception.
Every client was a new audience.
Every project was a new challenge.
Every industry was a new language.
Six years of that built something real: range across industries and a quiet confidence that I could find the thread in anything.
It was exhilarating. And it was lonely.
The pivot to agency work was a chance to discover what I could do with a team of storytellers wielding their own wild power.
CHAPTER 3: THE TEAM LEAD
As senior strategist and lead copywriter, I’ve spent the past four years becoming the one who shapes—not just executes—the brief.
Leading cross-functional teams of designers, strategists, and developers, I’ve seen great ideas get stronger when divergent minds collide.
I’ve led brand strategy engagements from kickoff to completion.
Facilitated stakeholder research.
Co-written insights briefs.
Run brand workshops with credit union founders, nonprofit CEOs, and tech executives.
Co-facilitated strategy sessions with entire organizational staffs.
Developed brand architectures for national movements.
Written the headlines that weave together a website, a campaign, an organization’s new understanding of itself.
THE NEXT CHAPTER
I’ve spent over a decade making hard things softer.
For students, clients, brands, organizations trying to say the true thing in a world that rewards the safe thing.
I know what it takes to build something excellent from the inside out.
I know how to lead a room.
I know how to hold a creative vision steady while the work catches up.
I’ve spent my whole career finding the right rooms. The next one is where I get to hold the door open for everyone else.
Want to work together? Reach out.
Shoot me an email at dianna.k.benjamin@gmail.com, and I’ll get back to you within one business day.
Dianna K Benjamin | Senior Creative Strategist 