Greg C.

Washington, DC, USA

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…

Greg C.

Work

  • 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, Sk…

  • 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

    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

  • SkyeStaq

    SkyeStaq

    Managing Partner, Strategy & Technology

    Jun 2025 - Present

    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
  • Agiletek Solutions

    Agiletek Solutions

    Vice President, Solution & Enterprise Architecture

    Mar 2023 - May 2025

    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.
  • Airlines Reporting Corporation (ARC)

    Airlines Reporting Corporation (ARC)

    Director, Solutions Architecture

    Jun 2021 - Aug 2022

    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.
  • VMware

    VMware

    Solutions Development & Partnerships Lead

    May 2016 - Jun 2021

    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.
  • Booz Allen Hamilton

    Booz Allen Hamilton

    IT Program Manager

    Oct 2004 - May 2016

    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.
  • EDGAR Online, a division of OTC Markets Group

    EDGAR Online, a division of OTC Markets Group

    Technical Support Analyst

    Jan 2001 - Jun 2004

    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.

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