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Washington, DC, USA

Greg C.

Building Technology Strategy, AI Readiness, and Modernization Programs for Growing Companies

I deliver and build the things most consultants only recommend. Over 20 years, I've built architecture teams from zero, modernized 3M-line legacy platforms, and shipped production AI products.

Companies bring me in when they need a technology leader who can define the AI and modernization strategy, build the roadmap, stand up the team, and stay through execution. I've done this across VMware, Civil/Defense USG agencies, and a travel technology company, and now run an AI-native consulting practice building agents, workflows, and LLM integrations.

Sectors: Federal, travel, energy, healthcare, financial services

Certifications: Google AI, Claude AI, JHU Applied AI, BerkleyHaas Digitial Transformation, PMP, TOGAF, ITIL v4, VCP, Security+

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Greg C.

Work

SkyeStaq AI Practice

SkyeStaq AI Practice

Built an AI-native consulting practice from the ground up, shipping production AI products and internal automation across the business. Delivered a multi-tenant SaaS marketing agent, an AI-powered receipt processing demo used for client prospecting, and a real-time research briefing tool for pre-meeting intelligence. Automated daily operations through Claude-powered job analysis pipelines and agentic proposal generation. Full stack: Claude API, Azure AI, Vercel, GitHub Actions, Notion.

Mission-Critical Multi-Site Infrastructure Migration

Mission-Critical Multi-Site Infrastructure Migration

Directed the rescue of a behind-schedule cloud migration at two of DOE's most highly secured facilities (Y-12 and Pantex), serving 15,000+ employees across multiple sites. Brought in sixteen months into a struggling program with an aggressive six-month deadline to migrate 90% of Exchange and Skype data, the team deployed a structured migration strategy, custom automation across Teams, Exchange, Skype, and Azure Sentinel, and rebuilt change management discipline while completing missing prerequisites in parallel with the migration itself. Surfaced schedule risks early with quantified options so leadership could make real decisions under a fixed timeline. Delivered the Teams migration 2.5 months ahead of schedule and the overall data migration 1.5 months early, with minimal disruption to mission-critical communications.

Enterprise Architecture Practice Build & Vertical Market Launch

Enterprise Architecture Practice Build & Vertical Market Launch

Built an enterprise architecture consulting practice from scratch, creating methodology enabling 15+ consultants to deliver $150K+ engagements independently. Developed 92+ reusable IP components and personally delivered 26+ customer engagements (1,117 artifacts) across federal, state, and commercial sectors. Then launched 4 vertical market solutions in ~6 months with complete go-to-market strategies, building a $1B strategic partnership and national delivery network.

Legacy Modernization Roadmap

Legacy Modernization Roadmap

Led technology transformation for a major travel technology company, building and directing the architecture team from 0 to 10+ in 14 months. Defined the modernization strategy, established the first enterprise-wide Architecture Design Review governance, and equipped the team with frameworks to assess a 3M line-of-code portfolio. Delivered a 3-year cloud transformation roadmap with cost reductions across three licensing categories. Orchestrated 5 concurrent vendor partnerships.

Experience

Jun 2025 — Present
SkyeStaq

SkyeStaq

Managing Partner, Strategy & Technology

Fractional CTO and AI strategy practice serving organizations navigating AI adoption, digital transformation, and technology capability building.

  • Advise executive leadership on AI readiness, technology investment strategy, and responsible AI governance; translating technical complexity into business-aligned roadmaps
  • Design and build AI-powered workflows, agents, and enterprise LLM integrations with emphasis on practical adoption and measurable outcomes
  • Develop reusable delivery frameworks across AI strategy, governance, operationalization, and change management; drawing on 20+ years of practice-building experience
Mar 2023 — May 2025
Agiletek Solutions

Agiletek Solutions

Vice President, Solution & Enterprise Architecture

Agiletek Solutions is a leading provider of cloud services and DevOps solutions, dedicated to transforming businesses with innovative technologies.

  • Directed AgileTek’s architecture practice, leading 140+ consultants through full lifecycle projects from requirements through operations.
  • Spearheaded the development of turnkey service offerings like Vision & Strategy, aligning technology outcomes with business objectives.
  • Fostered strategic partnerships with vendors and analysts to stay ahead in industry trends and technological advancements.
Jun 2021 — Aug 2022
Airlines Reporting Corporation (ARC)

Airlines Reporting Corporation (ARC)

Director, Solutions Architecture

ARC is a leading business solutions provider that specializes in air travel intelligence and commerce.

  • Built and led a team of 10+ architects to drive modernization and strategic planning for ARC's $110M travel data portfolio.
  • Pioneered organizational change strategies for the enterprise, including the creation of architecture governance processes.
  • Led ARC's digital transformation initiatives, including strategic business-to-technology mapping and innovative technology evaluation.
May 2016 — Jun 2021
VMware

VMware

Solutions Development & Partnerships Lead

Rally Software is a part of Broadcom, a global leader in semiconductor and infrastructure software solutions.

  • Led the VMware Solutions & Innovations team in designing customer-centric solutions for Government, Education, and Healthcare verticals.
  • Orchestrated cross-functional collaboration across software vendors, service providers, and internal teams to enhance solution offerings.
  • Managed the go-to-market strategy for VMware’s S&I team, aligning with executive sales leadership to refine and execute solution launches.
  • Successfully led a DevOps assessment for a large-scale data center migration at a DoD client, developing a comprehensive roadmap for transformation.
  • Designed and packaged the Enterprise Architect service offering, establishing the foundation for VMware PSO's consultant engagements.
  • Crafted professional service delivery kits and marketing materials to promote VMware’s enterprise architecture initiatives.
Oct 2004 — May 2016
Booz Allen Hamilton

Booz Allen Hamilton

IT Program Manager

Booz Allen Hamilton advances the nation’s most critical missions with innovative solutions in civil, defense, and national security sectors.

  • Spearheaded the development of Booz Allen's Strategic Alliances Operating Model, managing partnerships with major tech firms like Docker and Red Hat.
  • Directed a critical data center build for the National Children’s Study, coordinating across teams to meet tight deadlines with zero disruption.
  • Led an infrastructure security assessment for SPAWAR, ensuring compliance with DoD security standards in cloud environments.
  • Led the successful transition and migration of FDA’s eLEXNET systems to a new hosting facility with zero user disruption.
  • Managed a team of 24 professionals in executing the migration and infrastructure security project for SPAWAR's DCAO program.
  • Oversaw virtualization architecture for FDA, managing 18 hosts and 500 VMs across various environments.
  • Executed major upgrades and migrations, including transitioning 40 TB of storage and VMware environments.
Jan 2001 — Jun 2004
EDGAR Online, a division of OTC Markets Group

EDGAR Online, a division of OTC Markets Group

Technical Support Analyst

EDGAR Online aggregates real-time SEC regulatory data and financial analytics for extensive financial disclosures.

  • Provided critical user and technical support for NASDAQ's private site, enhancing user experience and resolving technical issues swiftly.
  • Managed user account activities including creation, activation, and troubleshooting to ensure seamless operations.