About Fifth Season Advisors

Experienced judgment.
Personally engaged.

Fifth Season Advisors is a principal-led advisory practice for leaders making decisions at the intersection of defense, cybersecurity and technology.

Your advisor

John Bergin

Principal, Fifth Season Advisors

View John's LinkedIn profile

A perspective that connects institutional requirements with the realities of operating technology.

John's background includes senior government leadership and commercial technology work. His experience spans enterprise business modernization, government cloud and the relationship between security, governance and operations.

He previously served as Deputy Assistant Secretary of the Army for Financial Information Management and as Business Technology Officer in the DoD CIO organization. His Microsoft experience includes government cloud and security work documented in a 2024 MITRE publication.

At Fifth Season Advisors, John works directly with leadership to frame decisions, examine tradeoffs and establish an actionable path forward.

Selected experience / public record

Context behind
the perspective.

These sources document prior responsibilities and published contributions. They provide a factual foundation for the practice.

Enterprise modernization

Army business systems

As Deputy Assistant Secretary of the Army for Financial Information Management, John was identified by the Army News Service as a leader of enterprise business-system modernization.

Army News Service · July 2020
Defense technology

DoD CIO perspective

A Microsoft secure-cloud event announcement identified John as the DoD CIO's Business Technology Officer and a featured speaker on defense technology.

Microsoft event announcement · May 2017
Cloud security & governance

Published contribution

John is a credited coauthor of the Cloud Safe Task Force's National Cloud Cyber Feed Initiative paper. Its biography also documents his Microsoft government cloud and cybersecurity work.

MITRE publication · June 2024 (PDF)

References to prior organizations describe experience. They do not imply endorsement, affiliation or representation by Fifth Season Advisors.

The practice

Clear scope.
A useful work product.

We support commercial technology businesses entering defense, established Defense Industrial Base organizations and selected regulated businesses facing comparable decisions.

Engagements take the form of a focused decision review, a scoped advisory project or ongoing executive counsel. We agree the question, the boundaries and the output before the work begins.

Our role is advisory. We do not imply assessment authority, procurement influence, legal expertise or a managed-service capability.

Your next decision

Start with the question
in front of you.

A short description of the decision, its context and your timing is enough to begin.

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