Tought Leadership
A big thank you to Sherry Winn for including me in her new book, “Winning Wisdom: 247 Powerful Business Secrets to Bring Out the Champion in You.”
Sherry delivers to the reader an incredible collection of insights from an impressive array of leaders. I’m sure it will soon become a go-to resource for anyone looking to level up their leadership game.
Gregory Leos
General Manager and Head of Payments | Weave
Online Course
Hosted by Brandon Wan and Greg Leos
Overwhelmed to In Control: Mastering the 2026 Job Market
February 24—March 20, 2026
Interviews in 2026 test judgment, composure, and self-leadership as much as skills. Learning to manage emotions before, during, and after interviews helps you show up clearly, think under pressure, and recover faster from setbacks. Over time, this builds confidence, consistency, and the resilience needed to turn strong conversations into offers.
Podcast
Revenue Operations Alliance
Most Revenue Problems Aren't Sales Problems – They're Orchestration Problems
February 3, 2026
The conversation covers three primary themes: Evolution of the Revenue Leader, Winning the Talent War, and Building Cultures that Multiply Revenue. Each theme is explored in depth, highlighting the changing role of revenue leaders, the importance of winning the talent war, and the impact of culture on revenue multiplication.
The Revenue Insights
Why 69% of Workers Don't Engage & How Revenue Leaders Can Fix It
August 14, 2025
Speaking
Revenue Operations Alliance
Greg Leos | Speaker
November 18, 2025
Previously, Gregory was Chief Revenue Officer at VikingCloud, overseeing global revenue operations across five continents for this private equity–backed cybersecurity and payments compliance leader. Before that, he spent over six years at Fiserv (NYSE: FI), leading enterprise sales, the Franchise Solutions unit, and the joint venture with Bank of America.
A big thank you to Sherry Winn for including me in her new book, “Winning Wisdom: 247 Powerful Business Secrets to Bring Out the Champion in You.”
Sherry delivers to the reader an incredible collection of insights from an impressive array of leaders. I’m sure it will soon become a go-to resource for anyone looking to level up their leadership game.
Gregory Leos
General Manager and Head of Payments | Weave
- 100 South State Street Chicago, IL 60603
- 2023 by GKA & Associates