
Meet the Executive Team

Founder & CEO
Charlie Drury
Charlie founded Win-Win in 2023 after recognizing a major opportunity: US companies were underutilizing the vast pool of talented Sales Developers working remotely in Latin America.
With nearly ten years of experience in both B2B and B2C Sales Development, Charlie has built a strong track record of success. Before founding Win-Win, he served as the Sales Development Director for a New York City-based company generating $28M in ARR, where he played a key role in driving growth.

Director of Recruitment
Emily Frank
Emily is our dedicated Head of Recruitment, responsible for sourcing, recruiting, and onboarding top-tier SDRs at Win-Win.
With over 7 years of experience in Human Resources for early-stage SaaS companies, Emily brings a wealth of knowledge to her role.
She is the architect behind our comprehensive onboarding program, designed to prepare new recruits with best-in-class practices for seamless placement and success in their roles.