About Terrence Cummings

How it Started

I didn’t grow up around executives, boardrooms, or startups. My first jobs were bagging groceries at A&P, folding shirts at the Gap, and serving tables at Red Robin. Those early experiences taught me humility, hard work, and how much grit it takes just to keep moving forward.

One day at Red Robin, in a moment of serendipity, I served Jim Collins, author of Good to Great and Built to Last. That chance meeting turned into a two-year conversation about what makes great organizations great. Why do some teams thrive while others stall? What separates good leaders from great ones? Eventually, Jim asked me to join his research team, where I studied the foundations of enduring business success.

From there, I joined McKinsey, helping executives navigate complex challenges. But I didn’t just want to study or advise, I wanted to build. So I stepped into operating roles, working in companies from just a handful of people to over a thousand. I’ve led across marketing, partnerships, product, operations, and people, helping to scale businesses from zero to nine figures and profitability.

Most recently, I served as Chief Opportunity Officer at Guild, where I helped design and scale education, coaching, and career mobility programs. Over eight years, I led multiple functions at Guild, including partnerships that reshaped how leading companies invest in talent.

Terrence brings a calm, credible, courageous and consistent influence to every interaction. His ability to listen deeply, give constructive, specific advice, and chart a practical path forward make him an invaluable partner.

Ellie Bertani

CEO

How It's Going

Through all of it, one truth has stood out: strategy and operations matter, but people are the multiplier. The way a leader shows up, the way a team communicates, the way an organization stacks the deck in its favor — that’s what turns potential into performance.

That’s why I coach. My approach blends powerful questions that unlock what’s already inside you with practical insights from years in the trenches. I don’t coach people because they’re struggling; I coach them because they’re already good, and ready to become great.

Get In Touch

I also bring lived human experience. As a Black man who rose from humble beginnings into executive leadership, I’ve often been the only one in the room with my perspective. That journey gives me empathy, resilience, and a different lens on what leadership can look like.

Today, I work with executives, founders, and teams facing moments of change, challenge, or opportunity — people who want to think bigger, communicate better, and build the clarity and cohesion that unlock extraordinary results.

Terrence provides powerful and practical transformative guidance. He doesn’t hide behind polish. What you see is who he really is. Smart, humble, unfiltered in the best way. When he speaks, you listen. Not because he’s loud, but because he’s real.

Sandy Gould

Chief People Officer

About Me

How it Started

Terrence brings a calm, credible, courageous and consistent influence to every interaction. His ability to listen deeply, give constructive, specific advice, and chart a practical path forward make him an invaluable partner.

How It's Going

Terrence provides powerful and practical transformative guidance. He doesn’t hide behind polish. What you see is who he really is. Smart, humble, unfiltered in the best way. When he speaks, you listen. Not because he’s loud, but because he’s real.

Let's Work Together