About Me
Brett Chereskin
12-year Army veteran turned tech operator. I bring military precision to startup chaos—scaling operations, building teams, and turning ambitious visions into reality.
Experience
Career Journey
COO at dub
New York City
Leading operations at a NYC-based fintech company. I drive growth by building scalable systems, leading cross-functional teams, and turning strategic vision into execution.
Business Operations at Affirm
San Francisco Bay Area
Drove operational initiatives at one of the leading buy-now-pay-later fintech companies. Streamlined processes and helped scale the business through a period of rapid growth.
U.S. Army Officer
Aviator • Manned & Unmanned • Leadership
Served 12 years as an Army officer with assignments across the globe. Led teams in high-stakes environments, managed complex operations, and developed the leadership skills that now drive my approach to business.
Fort Huachuca, AZ • Hohenfels, Germany • Wiesbaden, Germany • Fort Rucker, AL
Background
Education & Credentials
West Point
United States Military Academy • Class of 2006
Four-year undergraduate program combining rigorous academics with military leadership training.
Licenses & Certifications
- Commercial Pilot — Fixed Wing & Rotary (FAA)
- Series 99 — Operations Professional (FINRA)
- Securities Industry Essentials (FINRA)
Services
Advisory Work
I advise early-stage startups on operations, scaling, and go-to-market strategy. My sweet spot is helping founders navigate the transition from scrappy startup to structured scale-up.
Early Ops & GTM
Startup to scale-up
Fintech
Regulated at scale
AI + Enterprise
Leaders harnessing AI
Beyond Work
Life in NYC
Based in New York City. When I'm not building operations or advising startups, you'll find me exploring the city's incredible diversity through its food, art, and theatre—or writing about how non-technical leaders can leverage AI tools to amplify their impact.