Managing Director, iConnect Douglas Massiah

Infinite IT Team Member Since: March 14, 2016

If there is one thing everyone at Infinite IT can agree on, it’s this: Douglas Massiah has stories. Remarkable ones. Whether he’s recalling life back home in Barbados, explaining the finer points of island culture, or describing a legendary hot sauce that should probably require a waiver, Doug has a way of turning everyday conversation into something vivid, memorable, and often hilariously insightful. It’s never loud, never over‑the‑top—but somehow everyone ends up listening when he speaks.  He often shares stories about his experiences running telecom setup using coconuts for people to connect, but we all know this is just part of his funny humour.

And behind that easygoing charm is one extremely capable and disciplined Managing Directors at Infinite IT.

Overseeing iConnect, Doug is responsible for the commercial and operational performance of Infinite’s connectivity services—everything from carrier relationships to data centre excellence. He takes those responsibilities seriously, holding carriers accountable, safeguarding uptime, and ensuring that every circuit, network path, and infrastructure component is delivering exactly what it should. If something isn’t right, Doug knows before anyone else does—and he has already started fixing it.

He keeps data centres immaculate, optimized, and relentlessly secure. No cable out of place, no rack unmanaged, no vendor unchallenged. Doug has an almost uncanny ability to spot inefficiencies, foresee problems, and bring order to complex technical environments. It’s part engineering discipline, part instinct, and part the unique perspective you get from someone who grew up on an island where resourcefulness was a way of life.

Professionally, Doug’s experience runs deep: network engineering, systems administration, telecom operations, infrastructure design, and real‑world technical problem solving across both Canadian and Barbadian environments. He has led major connectivity turn‑ups, coordinated multi‑site carrier deployments, negotiated SLAs, and built reliable, high‑performance network solutions for hundreds of business environments.

But technical mastery alone isn’t what makes him invaluable.  (See previous note about how he ran telecom services using coconuts!)

Doug has a rare gift for translating complex problems into relatable narratives, connecting people through shared experience, and reminding teams that leadership can be both serious and human. His humour is subtle but constant, his timing precise, and his ability to lighten a room effortless.

Whether he’s dialing in from a frozen highway, unpacking a carrier issue with razor‑sharp clarity, or sharing an island anecdote that somehow becomes a perfect analogy for a customer situation, Doug brings people together while elevating their work.

Doug keeps the networks running, the partners honest, the data centres flawless, the fires under control, and the culture richer. iConnect wouldn’t be the award-winning solution without him.  And Infinite IT is lucky to have someone that cares so much about our clients by keeping the lights blinking green.

Be sure to connect with Doug on LinkedIn!