Terrence Cummings - Executive Coaching for Teams and Individuals

Terrence Cummings, wearing a black blazer and gray shirt, gesturing with his right hand against a multicolored gradient background.

My Story

I've Been Where You're Headed

I’ve studied what makes great companies great — and built them myself. From working with Jim Collins and McKinsey to scaling startups to nine figures, I’ve led across every function from product to people.

My coaching combines the powerful questions that unlock potential with the practical tools leaders need to win. Grounded, pragmatic, and human — that’s how I help good become great.

I also bring lived experience: rising from humble beginnings to the executive level, and navigating leadership as a Black man in spaces where perspectives like mine were rare. That journey makes me both deeply practical and deeply human in how I coach.

Learn more about Terrence

When everyone is going left, Terrence goes right, and challenges the status quo. He doesn’t hesitate to ask the questions that no one else will ask, and makes people better."

Bijal S.

CEO

I work with high-performing leaders and teams who face something big: a daunting project, a critical transformation, a new level of responsibility, or a moment of growth that demands more than business-as-usual.

My clients are strong performers — founders, executives, and teams who want to sharpen their edge, break through barriers, and accelerate what’s next.

Individual Coaching

Unlock clarity, overcome limiting beliefs, and expand your leadership potential through powerful questions and actionable strategies.

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Team Coaching

Build trust, alignment, and momentum so your team can communicate better, move faster, and deliver when it matters most.

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Speaking

Inspiring, story-driven talks on leadership, change, trust, and decision-making that move audiences to think and act differently.

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Clarity and confidence in their leadership and decisions

Greater self-awareness and presence that inspires others

Teams that communicate clearly and move faster together

Energy, focus, and momentum toward what matters most

Get in touch

Terrence sees patterns quickly and helps teams move. With our team, he turned messy topics into a clear path forward—who’s doing what, by when, and why it matters. I trust him, and I’d work with him again in a heartbeat.

Kristie G.

Head of Talent

Stack the Deck in Your Favor

I've Been Where You're Headed

When everyone is going left, Terrence goes right, and challenges the status quo. He doesn’t hesitate to ask the questions that no one else will ask, and makes people better."

Lead with Strength. Transform with Purpose.

Individual Coaching

Team Coaching

Speaking

Turn Insight into Action. Turn Action into Impact.

Terrence sees patterns quickly and helps teams move. With our team, he turned messy topics into a clear path forward—who’s doing what, by when, and why it matters. I trust him, and I’d work with him again in a heartbeat.

Let's Work Together