Summary
Overview
Work History
Education
Skills
Accomplishments
Certification
Timeline
KEY WORDS
LINKEDIN
ACTIVE TOP SECRET CLEARANCE
Generic

Charlie Eastwood

Round Hill

Summary

Professional with robust background in directing and managing large-scale operations, consistently driving success through strategic planning and execution. Adept at implementing innovative solutions that enhance productivity and operational effectiveness. Known for fostering teamwork and adapting to evolving business needs, ensuring alignment with organizational goals.

Overview

20
20
years of professional experience
1
1
Certification

Work History

Director of Managed Services / Program Management Lead

Visioneering
10.2019 - Current
  • Direct and manage a multi-program portfolio valued at over $24 million annually, delivering mission-critical IT and infrastructure services for major federal clients including JSP/DISA, the Department of Transportation (DOT), and the Navy NSWC.
  • Provide comprehensive program oversight encompassing budgeting (P&L), resource allocation, scheduling, risk mitigation, and performance tracking across multiple high-visibility contracts:
  • Joint Services Pentagon (JSP) – $18M program; 24 direct reports.
  • DOT Infrastructure & Operations – $4M program; 200+ remote sites, 5 indirect reports.
  • Navy NSWC – $2M program; 13 locations, 2 direct reports.
  • Act as primary interface with government stakeholders, ensuring program alignment with strategic objectives, compliance with federal standards, and on-time, within-budget delivery.
  • Lead development and execution of project plans, performance metrics, and reporting tools to ensure operational excellence and contract compliance.
  • Manage the full program lifecycle for major IT initiatives, including system modernization, cyber accreditation, and contingency planning.
  • Led the JSP/DISA cyber accreditation process—developed all artifacts and documentation in accordance with RMF and NIST standards.
  • Standardized program documentation across teams by creating templates and reporting formats used by senior management and client leadership.
  • Drive continuous improvement across all programs through lessons learned, stakeholder feedback, and strategic planning.
  • Contribute to Visioneering’s growth by supporting proposal development, teaming strategies, and talent acquisition aligned with program needs.
  • Serve as Senior Technical Advisor to DOT’s Infrastructure & Operations group—developed and implemented a roadmap for voice communications modernization across 200+ sites, transitioning to a virtualized core system.
  • Maintain comprehensive program documentation including operational procedures, cybersecurity accreditation artifacts, and continuity plans.

Director, Managed Services

Black Box Network Services / Tyto Athene
06.2019 - 10.2019
  • Directed nationwide managed services programs supporting multiple federal agencies, overseeing 3 Senior Program Managers, 202 indirect personnel, and a portfolio valued at $100M+ annually.
  • Held full P&L accountability, providing leadership across personnel management, contract execution, proposal development, and program performance.
  • Oversaw high-impact federal programs across key agencies, including:
  • U.S. Air Force (Global 911 Systems): $3M contract; 300+ sites, 20 indirect reports.
  • Department of Transportation (DOT): $5M contract; 200 sites, 5 direct reports.
  • Veterans Affairs (Multiple Programs): $9M across 20+ locations, including VISN 17 (8 medical centers); 13 direct reports.
  • Ft. Belvoir: $4M contract; 10 direct reports.
  • Social Security Administration (SSA): $4M contract; 12 direct reports.
  • Department of Health & Human Services (HHS): $1M contract; 4 direct reports.
  • Provided strategic direction and operational leadership to evolve the Managed Services division’s culture, shifting focus from purely metrics-driven outcomes to employee development and customer satisfaction, ensuring sustainable program success.
  • Empowered Program Managers to drive decision-making, accountability, and proactive engagement with customers—strengthening trust and contract performance.
  • Maintained daily involvement with customer operations to remain aligned with evolving mission requirements and to offer responsive, expert-level support.
  • Advised customers through critical infrastructure modernization efforts, leveraging deep technical and operational knowledge to support informed decision-making and long-term planning.
  • Championed continuous improvement and innovation across the service delivery model to enhance operational efficiency, service quality, and stakeholder value.

Voice Modernization Project Manager (Detail Assignment – Pentagon)

Black Box Network Services / Tyto Athene
01.2017 - 07.2018
  • Led a critical modernization effort for the Joint Services Pentagon’s voice infrastructure, overseeing the planning and execution of a multi-phase project to transition legacy systems to a secure, virtualized SIP-based voice platform.
  • Coordinated cross-functional contributions from nine industry-leading partners including AudioCodes, Avaya, Dell, Ribbon, Oracle, Ventraq, and Visioneering LLC, in collaboration with prime contractor Verizon, five internal government entities, and six DoD organizations.
  • Successfully delivered the first three spirals of the Pentagon’s long-term voice modernization roadmap—achieving significant milestones in infrastructure transformation and operational capability.
  • Designed, deployed, and tested secure virtualized Ribbon AS SIP voice solutions across two geographically redundant core sites, ensuring mission resilience and cybersecurity compliance.
  • Directed the “white glove” migration of 2,500+ executive user users from legacy CS2100 platforms to Ribbon SIP infrastructure with minimal disruption, maintaining service continuity and high user satisfaction.
  • Authored all required project documentation, including system maintenance procedures, operational guides, and cybersecurity accreditation artifacts, in compliance with DoD RMF and NIST frameworks.
  • Developed strategic rollout plans for continued modernization, including the consolidation of a legacy 5ESS switch and expansion of the solution to additional DoD installations across the National Capital Region (NCR).
  • Served as a trusted liaison between government stakeholders and industry partners, ensuring clear communication, alignment on objectives, and smooth execution of complex modernization efforts.

Senior Program Manager

Black Box Network Services / Tyto Athene
08.2009 - 01.2017
  • Directed 10 concurrent federal programs totaling more than $20M in annual value, managing a team of 95 direct reports across diverse agency contracts while ensuring full P&L accountability, strategic oversight, and compliance with contract performance metrics.
  • Delivered enterprise-scale program leadership and customer-focused solutions for key federal clients, including:
  • Walter Reed National Military Medical Center: $2M; 5 direct reports
  • U.S. Air Force (Global 911 Systems): $3M; 300+ sites, 20 indirect reports
  • Department of Transportation (DOT): $5M; 200 sites, 5 direct reports
  • Veterans Administration (Multiple Contracts): $9M; 20+ locations, 13 direct reports
  • Ft. Belvoir: $4M; 1 site, 10 direct reports
  • Department of Health & Human Services (HHS): $1M; 4 direct reports
  • Social Security Administration (SSA): $4M; 12 direct reports
  • Developed and executed long-term technology modernization roadmaps, including:
  • Centralized voice infrastructure deployment for the VA Southeast Region.
  • Evolutionary communications modernization for DOT voice architecture.
  • Led full contract lifecycle management, including system design, implementation, and transition to sustainment, while ensuring compliance with agency requirements and IT governance standards.

Site Program Manager for USPTO

Black Box Network Services / Tyto Athene
02.2005 - 07.2009
  • Built and nurtured a high-performing workforce, driving team retention and effectiveness through structured performance evaluations, employee coaching, and career development initiatives.
  • Authored and implemented mission-critical documentation including:
  • Corporate Accident Prevention Plan compliant with Army Corps of Engineers EM 385-1-1
  • Organization-wide SOPs, Quality Assurance, Implementation Plans, Root Cause Analysis, and Training Frameworks to drive consistent, high-quality service delivery
  • Cultivated a reliable and responsive subcontractor network, ensuring optimal performance and scalability to meet fluctuating contract demands and customer expectations.
  • Regularly engaged stakeholders and agency customers to provide end-to-end operational and technical guidance, maintaining strong client relationships and deepening awareness of evolving mission needs.
  • Supported proposal development, white papers, and ad-hoc executive-level briefings to inform future business growth and contract acquisition strategies.
  • Conducted proactive trend analysis and industry consultation, guiding clients through modernization, sustainment planning, and transformation initiatives aligned with federal IT priorities.

Education

Coursework Completed - Business Administration

University of Maryland University College

Certificate of Achievement - Executive Leadership Development

Sprint University of Excellence
Overland Park, KS

Skills

  • Executive Leadership & Vision
  • Emotional Intelligence
  • Program & Portfolio Execution
  • Strategic Operations Management
  • Resource & Talent Management
  • Enterprise Project Management
  • Process Improvement & Engineering
  • Executive & Stakeholder Communications
  • Training, Coaching & Team Development
  • Technical & Policy Documentation
  • Information technology management
  • Process improvement

Accomplishments

  • Designed, executed and maintained the Department of Transportation, agency wide infrastructure modernization roadmap resulting in improved operations and reduced operational costs.
  • Program Manager responsible for successfully executing a "first of it's kind" infrastructure modernization for the Department of Defense Headquarters.
  • Received Admiral's Challenge Coin for streamlining the infrastructure accreditation process and documentation packages reducing turn-around time by two-thirds.

Certification

  • Information Technology Infrastructure Library (ITIL)
  • A+ Certification
  • National Management Practices Certification
  • Project Management Professional (PMP) – Expected 2025-08
  • Network+ Certification
  • Microsoft Certified Professional
  • Sprint Project Management Certification

Timeline

Director of Managed Services / Program Management Lead

Visioneering
10.2019 - Current

Director, Managed Services

Black Box Network Services / Tyto Athene
06.2019 - 10.2019

Voice Modernization Project Manager (Detail Assignment – Pentagon)

Black Box Network Services / Tyto Athene
01.2017 - 07.2018

Senior Program Manager

Black Box Network Services / Tyto Athene
08.2009 - 01.2017

Site Program Manager for USPTO

Black Box Network Services / Tyto Athene
02.2005 - 07.2009

Coursework Completed - Business Administration

University of Maryland University College

Certificate of Achievement - Executive Leadership Development

Sprint University of Excellence

KEY WORDS

  • Technical & Operational Keywords
  • IT Infrastructure, Cloud Strategy, Cybersecurity, Disaster Recovery Planning, Data Center Management, Network Operations, System Integration, DevOps Practices, Virtualization, Enterprise Architecture, Agile, Scrum, Waterfall, Kanban, Lean, Six Sigma, Problem Solving, Budgeting, PMP, PMBOK
  • Strategic & Business Alignment
  • IT Strategy Development, Digital Transformation, Business Continuity, IT Roadmap, Technology Alignment, Change Management, Process Optimization, Technology Lifecycle Management, Innovation Leadership, Business Process Improvement
  • Leadership & Management
  • Cross-functional Team Leadership, Executive Stakeholder Communication, Organizational Leadership, Talent Development, Succession Planning, Staff Mentorship & Coaching, Performance Metrics, Strategic Planning, IT Team Scaling, Culture Transformation
  • Financial & Service Management
  • IT Budgeting & Forecasting, Cost Optimization, Vendor Contract Negotiation, Service Level Agreements (SLA), ITIL/Service Management, Capital & Operational Expenditures (CapEx/OpEx), Outsourcing & Managed Services, Governance, Risk & Compliance (GRC), KPI Development & Reporting, Procurement Strategy

LINKEDIN

http://www.linkedin.com/in/charlie-eastwood-b753692

ACTIVE TOP SECRET CLEARANCE

Top-Secret