About.

My bio.

I use stories and systems to help people create clarity, trust, and competence.

Basically, I help people make sense of stuff… untangling, revealing, translating, recalibrating—those kinds of things.

That’s the short version.

My longer, more official-sounding bio below basically says the same thing, but with more detail:

Derek MacDonald has spent 15+ years building resilient communication strategies and enablement teams. He’s the founder of Unobstructed, a narrative nonfiction publication committed to elevating emotional clarity and personal agency. Derek credits his formative years as a wilderness guide and snowboard instructor with showing him that authentic storytelling is what best helps people navigate fear and uncertainty. This eventually led him to compete in The Moth’s StorySLAM competitions and to be featured on GBH’s Stories From The Stage.

Throughout his career, Derek’s been passionate about working with both students and organizations alike to help them better understand the crossover between systems thinking, outdoor education, and proactive mental health. In 2026, he was recognized as Massachusetts HOBY’s Volunteer of The Year, for his help facilitating annual workshops on leadership development, which he’s been doing with them since 2010.

Derek lives in Burlington, Vermont, where he likes building websites, running, and getting lost in a good book with a strong cup of coffee. You can learn more about Derek, his writing, and his podcast at derekmacdonald.com.

My work.

I shape intuitive, value-driven environments that elevate capable people.

I’m a director-level enablement and change-management leader with 15+ years experience driving technology adoption, communication strategy, and organizational effectiveness.

I went from wilderness guide and hospitality GM to writer, marketer, enablement director, and keynote speaker.

Eventually, technical work with RevOps and CRM configuration led to managing sales enablement teams and building out full training programs with marketing, learning & development, and internal comms partners. My sweet spot is designing the systems themselves, though, and then overseeing their implementation across teams and throughout a tech stack. Doing that well comes from developing repeatable frameworks to protect strategy, decision-making, and processes as things change (because they always do). That’s why I like to find and prioritize the most effective puzzle pieces in a given situation to create leverage.

I’ve found it makes things more efficient along the way, too.

About DMDC Systems, LLC.

I founded DMDC Systems, LLC to help people and brands design more intuitive user experiences for the folks using sales and marketing software. As an independent consulting practice, DMDC Systems, LLC focuses on closing the gap between “good in theory” and “good in practice.”

Said simply: I specialize in technology adoption, communication, and operational systems design.

See for yourself.

The Unobstructed platform itself actually showcases the type of user experience I build through DMDC Systems, LLC. In terms of the content development, categorization, distribution, and governance systems used across the Unobstructed ecosystem, those are the kinds of workflows and automations that help users know where to go, what to do, and how to find all they need to succeed along the way.

For a better idea of the kind of work I do, check out my more detailed, personal background (also pronounced ré·su·mé).

Thanks for being here.

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onward.