About Jason Reid:

Meet Jason Reid

Jason Reid is a leadership keynote speaker and former Head of Content at The Weather Network who developed the concept of Awkward Leadership—the idea that the leadership moments managers most want to avoid are often the ones that build the deepest trust inside teams. 

As Head of Content at The Weather Network, one of North America’s most trusted broadcast brands, Jason led diverse teams through rapid change and high-pressure environments — doubling productivity, sparking innovation, and helping his team win national and international journalism awards for the first time in the network’s history. 

Under his leadership, The Weather Network became a respected news and information brand. Jason’s clear communication and people-first leadership also led to successful leadership roles on multi-million-dollar media projects.

His leadership philosophy is simple but powerful:

Connection beats perfection.

Drawing on his own experience managing teams while navigating invisible disabilities, Jason developed the leadership concept “Awkward Leadership.”

He shows organizations how authenticity, trust, and a willingness to embrace uncomfortable conversations can unlock engagement, collaboration, and unexpected performance inside teams.

In addition to his leadership background, Jason has roots in journalism, screenwriting, and comedy. This storytelling foundation allows him to bring a rare blend of humor, insight, and emotional honesty to every keynote.

Audiences leave his talks laughing, reflecting, and—most importantly—ready to lead with greater courage, clarity, and connection.

As a leadership keynote speaker, Jason helps organizations build trust, communication, and resilience inside teams.

Jason is also a storytelling mentor who helps experts craft powerful keynote talks.

Jason is the author of Embracing Invisible Disabilities in the Workplace. The book explores how leaders can support neurodivergent and chronically ill employees while building stronger teams.

The Awkward Leadership Moment that Changed Everything

The story below shows how Jason’s leadership approach—Awkward Leadership—transformed the culture and performance of a national newsroom. When Jason took over as Head of Content at a national television network, the newsroom was struggling. Productivity was declining and morale was low.
At his first national staff meeting, Jason made a decision many leaders would avoid: he shared his invisible disability.
What happened next surprised him.
One by one, team members began sharing their own invisible challenges — from mental health struggles to neurodivergence and chronic illness.
That moment of honesty transformed the culture of the newsroom.
Within a year, productivity had doubled, and the department won national and international journalism awards for the first time in the network’s history.
Jason calls this kind of leadership Awkward Leadership — the idea that the leadership moments we most want to avoid are often the ones that build the deepest trust.

The feedback we received on Jason was entirely and overwhelmingly positive. Our people loved the balance of anecdotes and concrete actions that they can immediately take away and use.

Melanie Bodi Ontario Teacher’s Pension Plan

More than 80 percent of our members gave Jason’s keynote the highest rating possible.

Ryan Strang, Executive Director, Canadian Association of Communicators in Education

Jason has a lot of testimonials. This PDF includes six pages subdivided by industry. Simply click here.