WOOLPERT / SENIOR PROJECT MANAGER, BUSINESS TRANSFORMATION
I turn ambiguous, cross-functional work into clear plans, disciplined execution, decision structures, and measurable readiness.
My background combines 19 years of high-consequence Air Force technical and operational leadership with current founder-led systems, operating-model, research, and decision-support work through Moonroot. The recurring pattern is the same: understand the environment, define what must be true, align stakeholders, establish controls and milestones, execute, measure, and improve.
85 / 57
Proficiency tasks executed / deficiencies identified during Department of Energy-linked nuclear technical-order validation.
3 agencies
ATAK command-and-control implementation improved Emergency Operations Center interoperability across three wing agencies.
>45%
Reported readiness-rating improvement after rebuilding a struggling training/readiness system.
Formal validation, defect capture, and approval
Problem: High-consequence nuclear technical procedures required representative validation against real proficiency tasks.
Known / uncertain: The procedures existed, but representative execution had to expose defects before acceptance.
Approach: Validate the procedures against representative proficiency tasks and capture deficiencies during execution.
Action: Worked directly with the U.S. Department of Energy to review two nuclear technical orders; executed 85 proficiency tasks, identified 57 deficiencies, and authenticated Broken Arrow procedures.
Outcome: The Air Force Commendation Medal citation credits the work with the first Broken Arrow response-procedure update in 20 years.
Control / learning: Clear expected behavior, representative testing, defect capture, corrective action, and verification are stronger than assumption-based acceptance.
Applied technology across three agencies
Problem: Emergency-response organizations needed better shared command-and-control interoperability.
Known / uncertain: The operational need crossed organizational boundaries; the implementation had to connect technical build work with real users and requirements.
Approach: Coordinate the ATAK platform build with operational users, cross-agency requirements, wing server development, and Air Force Research Laboratory support.
Action: Led wing server development and coordinated with the Air Force Research Laboratory to build an ATAK command-and-control platform; coordinated users and requirements across emergency-response stakeholders.
Outcome: Emergency Operations Center interoperability improved across three wing agencies.
Control / learning: Technology adoption depends on requirements, interfaces, stakeholder alignment, and usable operating integration—not the technology alone.
Readiness system redesign
Problem: A struggling training/readiness system was producing weak readiness outcomes and slow qualification cycles.
Known / uncertain: Readiness problems were visible; the operating mechanisms behind tracking, scheduling, practical exercises, and qualification needed redesign.
Approach: Rebuild training tracking, scheduling, practical exercises, and qualification controls across the affected readiness programs.
Action: Reworked training tracking, scheduling, practical exercises, and qualification controls across separate programs.
Outcome: Records document more than 45% improvement in the unit’s reported readiness rating; separate programs reduced qualification and upgrade-training cycles 33% and 40%.
Control / learning: Process improvement works when ownership, cadence, criteria, and performance signals are explicit. The three metrics remain separate program outcomes.
Cross-enterprise procedure development and standardization
Problem: A Pacific Air Forces Rapid Airfield Damage Repair exercise focused on developing and testing UXO mitigation methods and synchronizing procedures across commands and services.
Known / uncertain: The source documents five Major Commands and three Department of Defense services in the synchronization effort; it does not establish broader enterprise deployment or adoption.
Approach: Develop and test mitigation methods during the exercise and synchronize tactics, techniques, and procedures across the participating organizations.
Action: Developed and tested 13 UXO mitigation methods and synchronized tactics, techniques, and procedures across five Major Commands and three Department of Defense services.
Outcome: The documented exercise produced 13 tested mitigation methods and aligned procedures across the participating commands and services.
Moonroot: externalized project state and decision governance
Problem: Multidisciplinary founder-led work spanning research, financing, conservation, stakeholder outreach, operating design, and AI-assisted workflows created continuity and decision risk.
Known / uncertain: Different workstreams changed at different speeds, and assumptions could become stale or conflict.
Approach: Externalize project state, decisions, handoffs, source identity, review gates, go/no-go criteria, and human approval boundaries through standardized artifacts and workflow controls.
Action: Built and used standardized briefs, state files, decision/activity logs, source controls, role routing, verification gates, and explicit human approval boundaries; designed capacity-aware role and continuity structures.
Outcome: The work became a repeatable operating environment for research, comparison, decision support, revision, and multidisciplinary coordination.
Control / learning: Strong delivery systems make dependencies, decisions, assumptions, and authority visible enough to inspect and update.
Supporting evidence
- 88 pages — six flight operating instructions revised to correct outdated references and clarify terminology against major-command requirements.
- 18 / 19 / $6.9M / $300K / 128 — Airmen / Unit Type Codes / contingency equipment / annual O&M budget / purchase orders at documented Superintendent scope.
- 37% — separate reduction in internal-control discrepancies in equipment/readiness work tied to a $313K budget.
- 64 → 57 → 24 / 34 — intelligence reports translated into realistic training devices used across 24 operations for 34 personnel.
- Bilateral partnership — nine U.S./Republic of Korea engagements and 16 training events; separately, bilateral technical instruction included five practical exercises for 61 allied personnel.
Approach
Understand → Define outcomes and requirements → Map stakeholders and dependencies → Establish governance and milestones → Execute → Surface risks and decisions → Validate readiness → Measure → Improve.
Scope & boundaries
This portfolio translates documented military and founder-led work into business-transformation and project-delivery language. It does not present the record as conventional corporate ERP implementation, prior civilian Senior Project Manager tenure, PMP certification, or Smartsheet proficiency. Moonroot evidence is described according to whether work was executed, analyzed, built, or designed; modeled outcomes are not presented as realized business performance.
Contact
Kentucky | U.S. Remote