In 1990, former General Electric CEO Jack Welch wrote a prophetic passage in the company’s annual report. “Our dream for the 1990’s is a boundaryless company…where we knock down the walls that separate us from each other on the inside.” However, large enterprises who have attempted to live by Welch’s dream remain hampered by set hierarchies: development teams and product owners exist on one level, business management and system engineers on another, while enterprise architects and portfolio managers reside atop the organizational food chain. Employing a top-down estimation approach to project management can help organizations overcome boundaries and satisfy the three V’s of corporate success – vision, value, and velocity. This article, originally published in ISV Insights, takes a closer look at how this approach can work for software companies, particularly larger organizations, to help them improve project management, team collaboration, and development practices.