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Breaking the Sabotage Cycle

By Jenn Spykerman

A Practical Guide to the Software Acquisition Pathway

Contributors: Bryon Kroger, Ryan Moore, Sheetal Patel, Captain Brian Phillips, and Lieutenant Colonel Melissa Sayers

This paper exposes how the Department of Defense has inadvertently adopted the tactics from a 1944 CIA sabotage manual—referring decisions to committees, insisting on perfect documentation, and applying rigid regulations—that now undermine modern software delivery. Author Jenn Spykerman demonstrates how these well-intentioned processes have become the greatest obstacle to delivering mission-critical capabilities to warfighters who need them.

This comprehensive guide provides DOD acquisition professionals with a practical roadmap for implementing the Software Acquisition Pathway (SWP), featuring real-world case studies from successful programs like Navy Forge and Kessel Run. The paper systematically addresses four critical transformation areas: developing transformative leadership, shifting from milestone-driven to momentum-driven processes, implementing DevSecOps as infrastructure rather than theater, and providing a concrete 90-day adoption framework. Through detailed analysis and field-tested strategies, it shows how to reverse decades of self-sabotage and deliver software that accelerates mission success rather than bureaucratic compliance.

  • Format PDF
  • Pages 50
  • Publication Date September 16, 2025

Features

  • Process Revolution

    Replace rigid milestones with continuous user feedback and iterative capability releases.

  • Leadership Framework

    Build leaders who create psychological safety and operate across vision, systems, and action.

  • Practical Implementation

    Apply a field-tested 90-day adoption guide with concrete steps and proven strategies.

  • Mission Focus

    Prioritize working software in warfighters' hands over documentation completeness.

About the Resource

This paper exposes how the Department of Defense has inadvertently adopted the tactics from a 1944 CIA sabotage manual—referring decisions to committees, insisting on perfect documentation, and applying rigid regulations—that now undermine modern software delivery. Author Jenn Spykerman demonstrates how these well-intentioned processes have become the greatest obstacle to delivering mission-critical capabilities to warfighters who need them.

This comprehensive guide provides DOD acquisition professionals with a practical roadmap for implementing the Software Acquisition Pathway (SWP), featuring real-world case studies from successful programs like Navy Forge and Kessel Run. The paper systematically addresses four critical transformation areas: developing transformative leadership, shifting from milestone-driven to momentum-driven processes, implementing DevSecOps as infrastructure rather than theater, and providing a concrete 90-day adoption framework. Through detailed analysis and field-tested strategies, it shows how to reverse decades of self-sabotage and deliver software that accelerates mission success rather than bureaucratic compliance.

Jenn Spykerman
Jenn Spykerman

Jenn Spykerman

Jenn Spykerman is a strategic technology leader with over twenty years of experience driving digital transformation across aerospace, defense, and mission-critical systems. Jenn has led cross-functional teams delivering production-scale transformations for major aerospace contractors and Space Force engineering teams. During her seventeen-year tenure at a major defense contractor, Jenn managed complex software integration challenges in aerospace and defense. She directed the integration of human-critical software systems for NASA’s Orion Crew Module Program and led a major software transformation for DoD heritage space ground systems, achieving $100M in cost savings through innovative process optimization. Jenn has a Master of Science in Computer Systems Engineering with an emphasis in Aerospace from the University of Denver.

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