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 literary 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’m a director-level enablement, change management, and operations 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 the tech stack.

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

Doing that well comes from developing repeatable frameworks to protect strategy, decision-making, and processes as things change (because they always do). So I like to find and prioritize the most effective puzzle pieces in a given situation to create leverage. I’ve found it also makes things more efficient along the way.

To get a better idea of what that looks like, check out my detailed background (also pronounced ré·su·mé).

Thanks for being here.

The best way to stay connected is to subscribe to my newsletter.

Or, contact me here to get in touch.

onward.