Greg Leos is a seasoned revenue executive with more than 20 years of senior leadership experience driving growth for SaaS, FinTech, and Cybersecurity companies. Over the course of his career, he has served in President, Chief Revenue Officer, and Head of Sales roles, building and leading global revenue organizations and transforming go-to-market strategies for high-growth technology businesses.

Greg has extensive experience partnering with Private Equity-backed companies navigating rapid scale, operational complexity, and market expansion. He has played a leadership role in two successful company exits with a combined enterprise value of more than $2.1B. Known for building disciplined revenue engines and high-performance cultures, Greg specializes in aligning strategy, talent, and execution to produce sustainable revenue growth.

Today, Greg serves as General Manager of Payments for Weave (NYSE: WEAV), a publicly traded SaaS platform serving the healthcare industry. In this executive role, he leads all aspects of the company’s payments business, including strategy, revenue performance, and operational execution.

Previously, Greg served as Chief Revenue Officer for VikingCloud, a global leader in cybersecurity and payments compliance. There, he led all revenue functions for the Private Equity-backed organization, including direct sales, channel and partner sales, inside sales, SMB, and enterprise segments. His organization included more than 125 team members operating across five continents.

In addition to his corporate leadership roles, Greg advises growth-stage companies on revenue strategy, organizational design, and go-to-market execution. Through his work as a fractional CRO and strategic advisor, he helps companies accelerate growth, improve sales productivity, and build scalable revenue organizations.

Greg is also an Executive and Career Coach, working with founders, senior leaders, and professionals navigating leadership transitions, career growth, and complex organizational challenges. His coaching approach combines real-world operating experience with practical frameworks for leadership development and performance.

Greg is an active participant in the Chicago technology startup ecosystem, serving as both an investor and advisor to early-stage companies. He is a General Partner and member of the investment committee at Propellant Ventures, a venture capital firm investing in pre-seed and seed-stage technology companies across the Midwest.

Outside of his professional work, Greg is committed to community engagement and philanthropy. He serves on the Board of Trustees for Lincoln Park Zoo and supports several nonprofit organizations focused on community development and education.