James Gibson

CIO | Transforming Transportation through Technology | Technology Strategist | Innovation Leader

Kansas City, Missouri, United States

About

Technology and business executive with a proven record of leading transformations, operational turnarounds, and large-scale modernization initiatives. Experienced in aligning technology investments with strategic priorities to improve profitability, accelerate growth, and strengthen competitive advantage. Recognized for building strong teams, simplifying complexity, and delivering measurable business outcomes through disciplined execution and practical innovation.

Experience

  • Strategic Technology Advisor at Self-employed
    Dec 2025 - Present · 8 mos

    Advising organizations on technology strategy, digital transformation, and AI-enabled business improvement. Drawing on experience leading large-scale modernization initiatives and operational turnarounds across transportation and logistics environments, including LTL, brokerage, and enterprise operations. Helping leadership teams align technology investments with business priorities to improve profitability, efficiency, and long-term growth. Areas of focus include: - Technology strategy and enterprise architecture - Digital transformation - AI and business process automation - Operational efficiency and cost optimization - SaaS, Cloud and infrastructure modernization - Transportation and logistics platforms - Executive advisory and growth initiatives

  • Chief Information Officer at Standard Forwarding Freight / Jack Cooper Transport
    Apr 2024 - Nov 2025 · 1 yr 8 mos

    Recruited to build and launch new LTL carrier; strategically pivoted to lead assessment and acquisition of distressed carrier facing closure, directing technology and back-office transition and rebrand to Standard Forwarding Freight across 14 terminals while maintaining zero operational disruption. - Structured and negotiated Transition Services Agreement with prior owner spanning 50+ systems, ensuring immediate operational continuity while simultaneously standing up new enterprise infrastructure including managed services, email/collaboration platforms, and security architecture. - Deployed enhanced freight weight and dimension capture, increasing revenue by more than 350% through accurate billing and elimination of revenue leakage. - Implemented end-to-end technology architecture integrating TMS, telematics, infrastructure, web platforms, back-office systems, and enterprise integrations to support scalable regional operations. - Built and led cross-functional technology team, establishing project delivery capabilities and maintaining 99.95% system uptime throughout acquisition integration and ongoing operations. - Led systematic transition from TSA services to modernized technology stack including migration of on-premise TMS to cloud-based platform, achieving operational independence within 10 months. - Introduced AI strategy and training to position the organization for future optimization, automation, and data-driven decision-making.

  • Yellow (24 yrs 1 mo)
    • Director - Technology, Digital Solutions
      2020 - 2023 · 3 yrs

      Drove enterprise digital transformation through the launch of MyYellow.com, establishing a unified customer platform for self-service and engagement across a multi-brand LTL network. - Delivered modern web, mobile, and API platforms using Salesforce, Adobe, AWS, and cloud architectures. - Built and scaled global digital product teams of 100+ and established agile, product-centric delivery models that improved speed and stakeholder alignment. - Leveraged modern CX/UX principles and stakeholder involvement to deliver engaging experiences. - Implemented specialized transportation management solution (TMS) for truckload brokerage services. - Drove accelerated deployment of pool distribution to secure multiple profitable large retailers.

    • Director - Product Development
      2015 - 2020 · 5 yrs

      Directed product development for multiple divisions including Sales, Customer Service, Marketing, and Brokerage/Logistics. - Unified multiple CRM platforms into Salesforce, enabling a single enterprise view of customers. - Drove accelerated migration of complex case management solution to Salesforce saving $1.5M annually. - Skillfully negotiated large SaaS/cloud agreements with Microsoft, Oracle, and Salesforce achieving favorable long-term protections, while driving significant savings of more than $10MM. - Supported rapid technology stand-up for a new logistics business, enabling 300%+ revenue growth. - Led development of modern shipment pickup solution providing accurate status and order visibility. - Deployed enhanced self-service and workforce management solutions to customer care centers. - Implemented new accelerated shipping service from concept to launch in under 4 months.

    • Director – Architecture & Governance | Enterprise Architect | Director – Service Delivery
      1999 - 2015 · 16 yrs

      Directed strategic oversight across multiple technology domains, including Architecture, Finance, PMO, Security, Service Delivery, Data Center, and End User Services. - Enhanced cybersecurity through robust perimeter defenses, training and adherence to key controls. - Provided strategic guidance for the selection and adoption of technology solutions across all lanes. - Delivered large-scale cost-reduction initiatives exceeding $20M annually. - Led technology finance and capital budgeting processes, ensuring alignment with corporate goals. - Enhanced IT service delivery by implementing ServiceNow platform and leveraging ITIL best practices. - Developed technology capital planning and portfolio allocation process balancing investment across risk reduction, asset modernization and new business capabilities. - Recipient of the Yellow Chairman’s Award for leadership and service excellence.