City skyline

COO & Operations Leader

Brett
Chereskin

Turning complexity into clarity. Building the systems and teams that scale ambitious companies.

12+

Military Leadership

COO

at dub

West Point

2006 Grad

NYC

Based

Expertise

What I Do

I help ambitious companies build the operational foundation for sustainable growth.

Scale Operations

Transform scrappy processes into scalable systems. Build the infrastructure that lets teams move fast without breaking things.

Build Teams

Hire, develop, and lead high-performing teams. Create cultures where people do their best work and grow their careers.

Drive Strategy

Turn vision into execution. Bridge the gap between ambitious goals and the daily work that makes them happen.

Experience

Where I've Led

Current

COO at dub

Leading operations at a NYC fintech. Building scalable systems, driving cross-functional execution, and scaling the team through rapid growth.

Visit dub
Digital payments
Previous

Affirm

Business Operations

King Air aircraft
12 Years

U.S. Army

Aviator • Manned & Unmanned • Leadership

Advisory meeting

Startup Advisor

Early Ops • GTM • Fintech

Collaboration

Let's Build Something

Whether you're scaling a startup, navigating a transition, or just want to connect—I'd love to hear from you.

Get in Touch