Dart Strickland

Enablement Leader · Storyteller · Occasional Chaos Agent

“You are not work D’Art
and personal D’Art.
You are just D’Art.”

I make complex things feel human.
At work. On stage. In writing. In life.

Sometimes all at once. I have spent a career sitting in the gap between what a product does and what people actually understand about it. That gap is where deals stall, teams lose confidence, and good ideas go quiet. Turns out, the right story at the right moment changes everything.

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D'Art to Heart

The stuff that doesn't fit in a LinkedIn post.

That quote up there? A leader said it to me on a work trip when I was falling apart and trying to hide it. I told her I was worried my personal life would affect my work. She told me that if it didn't, she'd be concerned.

That moment is why I write. Because I think most of us are carrying more than we let on at work. And I think the people who are honest about that tend to be better at their jobs. Not despite it. Because of it.

D'Art to Heart is where I put the rest of it. The stolen car. The train ride I took because my soul needed it. The 4-year-old who scooped out my heart with a wooden spoon and gave me a new one. The stuff that doesn't belong on a resume but somehow explains everything on it.

Read on Substack

"Twenty days between 'I am going to own this fucking year' and 'I hope I survive this fucking year.' Sometimes leadership changes your life in a single sentence."

Twenty Days — D'Art to Heart

"Sparkle is rarely, if ever, found in the most convenient thing. It's hiding in the depths of our souls, and the mundane convenience dulls it."

Train Thoughts — D'Art to Heart

"All you have to do is just keep showing up."

Just Keep Showing Up — D'Art to Heart
Storytelling That Works Making Things Click Revenue Enablement Team Transformation Hosting & Facilitation Narrative Architecture Making the Complex Simple Storytelling That Works Making Things Click Revenue Enablement Team Transformation Hosting & Facilitation Narrative Architecture Making the Complex Simple

A lot of teams aren't struggling because the product is weak.

They're struggling because nobody can explain it.

What that usually looks like:

The gap between what a product does and how it is understood? That is where things stall. That is the gap I tend to focus on.

20+
Years as a Practitioner, Enablement Leader, & General Chaos Agent
Moments Where a Story Changed the Room

How I Think

Six things I keep coming back to. All of them true.

01
Enablement isn't training. It's translation.

Training tells people what to do. Translation helps them understand why it matters, and how to carry it into any room they walk into.

02
If sales can't explain it, it doesn't exist.

It doesn't matter how good the product is if the person selling it can't make it land. Clarity isn't a nice-to-have. It's the whole game.

03
Features don't lose deals. Confusion does.

Most lost deals aren't lost on specs. They're lost when buyers couldn't connect the product to their actual problem. That's a story problem, not a product problem.

04
Story isn't a layer on top of the product.

It's how the product is understood. The narrative isn't something you add at the end of the roadmap. It's what makes everything else make sense.

05
Simplicity isn't dumbed down. It's earned.

The clearest explanations come from the deepest understanding. If you can't say it simply, you probably haven't figured it out yet.

06
You are not work you and personal you. You are just you.

A leader said this to me when my world fell apart. It's the most grounding thing I've heard about what it means to bring yourself to work. The whole person is the point.

Currently

What I'm actually working on right now.

This isn't a highlight reel. It's the actual work: the things I'm building, hosting, and thinking through at the moment.

Internal Talk Show · BigID

D'Art & The Deal

A recurring internal show where I sit down with AEs right after they close a deal. We break down what actually happened: the conversation that shifted things, the moment the story landed. Real wins, in their own words.

Event Host · BigID

2026 CKO & SKO

Hosting BigID's Customer Kickoff and Sales Kickoff for 2026. The job isn't just to keep things moving. It's to hold the narrative thread across two days so the whole event lands as one coherent story.

Ongoing Work

Enablement Programs & Storytelling Frameworks

Building the infrastructure that helps teams carry the story without needing a slide deck to do it. Frameworks that travel. Programs that actually change how people talk about what they do.

Out in the World

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Podcast
Being Human in Enablement
On shifting from transactional to relational, and what that actually means in practice, not just as a talking point.
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Webinar · Speaker
BigID On-Demand Session
Live session now available on demand. Product positioning in practice, for real audiences.
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Webinar · Speaker
Cloud Chaos to Control
A deep dive into Cloud DLP & DDR, making a technical subject land for a mixed audience.
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LinkedIn
Thinking Out Loud
Where the day-to-day thinking lives, on storytelling, enablement, and the gap between what products do and how they're explained.

Get in Touch

If any of this resonates, feel free to reach out.

No pitch. No deck. No carefully managed personal brand. Just a real conversation about storytelling, enablement, speaking, or whatever problem you are actually trying to solve.