Eric Olson

About Eric Olson

I’ve spent 40 years working across commercial telecom, enterprise-scale systems, Federal law enforcement, national-security–adjacent missions, and cabinet-level technology leadership. That path has given me a distinct, practitioner’s view of how complex, high-risk digital enterprises actually behave—and why modernization so often stalls despite best intentions.My Federal career included a decade in senior IT leadership at the Department of Justice, supporting nationwide law enforcement, sensitive-but-unclassified environments, and interagency information-sharing initiatives that routinely intersected with national-security and intelligence partners. I later served as Chief Information Officer for the U.S. Department of the Treasury, responsible for a $5B technology portfolio tied to economic stability, sanctions enforcement, financial intelligence, and critical-infrastructure protection. These roles offered a front-row view into the structural dynamics—mission, governance, risk, appropriations, and oversight—that shape outcomes across civilian and national-security domains.After leaving government, I joined Gartner as an analyst advising agencies and technology firms operating at the boundary of defense, intelligence, homeland security, and critical infrastructure. That perspective confirmed something central to my work today: meaningful insight in these environments requires firsthand operational experience, not abstract frameworks.I founded Six Point Perspectives to provide independent, practitioner-led analysis of the structural forces governing Federal and national-security technology. My work focuses on the underlying “physics” of complex enterprises—how incentives, constraints, and mission pressures interact to shape real modernization outcomes.ConnectionsI welcome engagement with leaders across Federal, defense, national security, intelligence-adjacent missions, and dual-use technology sectors.ProcessI use modern AI tools the same way I used staff analysts—accelerating drafting and sharpening distinctions. The judgment is mine; the tools help express it more clearly.

Experience

1. Chief Analyst & Principal

   Six Point Perspectives

   Jan 2023 — Present · Reston, VA, US

   Six Point Perspectives is a practitioner-led research and advisory firm analyzing the structural forces that govern Federal and enterprise-scale IT. Our work focuses on the underlying “physics” of complex digital enterprises—how mission, governance, budget mechanics, oversight, and systemic risk interact to shape modernization outcomes.We bring a unique, experience-grounded perspective shaped by four decades across commercial telecom, enterprise systems, Federal law enforcement, national security–adjacent missions, cabinet-level CIO leadership, and analytical roles.We provide independent, practitioner-based insight for Federal civilian agencies, defense and national-security organizations, dual-use technology companies, and investors operating in complex, regulated, or mission-critical environments.

Education

• William & Mary – Raymond A. Mason School of Business

  Master of Business Administration (MBA), Finance, General

  1987 — 1989

• University of Pittsburgh

  Mathematics

  1982 — 1984

• Penn State University

  BS, Mathematics

  1984 — 1986