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Lisa WebbLW

Lisa Webb

Fractional CIO / CTO

€862/day
Washington D.C., US
15+ years

Average response time: 1 hour

About Lisa

Executive technology advisor specializing in AI strategy, digital transformation, and revitalizing product and engineering teams.


I work with organizations that need experienced technology leadership to solve complex challenges, modernize platforms, or stabilize underperforming teams. With experience leading global engineering, product, and IT organizations, I help companies align technology strategy with business goals while improving delivery, governance, and operational efficiency.
  • English

    Native or bilingual

Remote only
Primarily works remotely

Experience

  • BANK FUND
    VICE PRESIDENT, INFORMATION TECHNOLOGY – PRODUCT MANAGEMENT & ENGINEERING
    DIGITAL AND IT
    January 2021 - Today (5 years and 5 months)
    Washington, DC, USA

    Technology and product executive specializing in digital transformation, AI strategy, and enterprise technology leadership. I help organizations modernize technology ecosystems, scale engineering teams, and align IT investments with business strategy.

    Led enterprise technology initiatives overseeing $5M operating budgets, $4M in capital programs, and teams of up to 50 engineers, product leaders, and technology professionals. Known for transforming IT from a cost center into a strategic business enabler by implementing scalable architecture, modern delivery frameworks, and strong governance.
    AI Strategy & Implementation: Designed and launched an enterprise AI adoption program for leadership seeking to operationalize emerging technologies. Developed the AI strategy, governance model, intake process, and training framework while aligning stakeholders across business, security, and risk teams. Delivered two internal AI-powered solutions within seven months with full cybersecurity and data risk assessments.
    Digital Transformation & Technology Governance: Established enterprise governance frameworks including an Architecture Review Board to improve decision-making, reduce redundant infrastructure, and increase transparency into technology investments. Reduced operational inefficiencies by 30% and improved executive visibility into technology roadmaps.
    Technology Investment & Portfolio Strategy: Rebuilt IT budgeting, resource forecasting, and portfolio management to align technology delivery with business priorities. Implemented structured planning models that improved project execution by 35%, reduced unplanned expenditures, and strengthened collaboration between engineering and business leadership. Available to support organizations with technology strategy, AI adoption and governance frameworks, product and engineering organizational design, technology portfolio planning, and executive advisory or fractional CIO/CTO leadership.
    artificial intelligence Digital Transformation Change and Transformation Management Leadership Development IT Strategy
  • FREIGHTHUB (ACQUIRED BY HUDSON CAPITAL)
    CHIEF INFORMATION OFFICER
    E-COMMERCE
    August 2017 - January 2020 (2 years and 5 months)
    New York, NY, USA
    Technology leader specializing in digital marketplace platforms, product innovation, and technology strategy for growth-stage companies. I help organizations modernize platforms, implement scalable engineering practices, and align technology investments with revenue growth, operational efficiency, and investor readiness.

    Served as the technology lead for a global eCommerce company, guiding platform modernization and operational transformation during a critical growth stage. Partnered directly with executive leadership to align technology strategy with fundraising goals, product expansion, and acquisition positioning. Revitalized infrastructure, introduced Agile development practices, and established a customer experience capability to support marketplace growth.

    Sales Technology & Operational Automation: Replaced manual spreadsheet-based sales processes with an integrated CRM and workflow platform that automated pipeline management and forecasting. Delivered the solution in six weeks on a constrained budget, improving deal visibility, accelerating sales cycles, and strengthening the company’s investment narrative.

    Product & Platform Strategy: Led competitive analysis and customer research to identify gaps in the initial eCommerce platform. Developed proof-of-concept prototypes with projected ROI and secured leadership approval for a rapid product redesign. Directed engineering execution of a beta platform release in 90 days, improving customer adoption, expanding market positioning, and establishing the foundation for future product expansion that supported the company’s acquisition.

    I work with organizations that need help with digital marketplace strategy, product and platform modernization, sales technology transformation, and scaling engineering organizations during periods of rapid growth or investor readiness.
    Product Development Leadership Development Start-up E-commerce Mobile first
  • ADP
    DIRECTOR, PROGRAM MANAGEMENT & ENGINEERING OPERATIONS – TECHNICAL PROGRAM MANAGEMENT
    January 2016 - January 2017 (1 year)
    New York, NY, USA
    Reported to the CEO of ADP R&D, managing $10M in annual technology investments and overseeing a 30-person team driving engineering and operational transformation across ADP's $18B human capital management (HCM) business. Modernized program management methodologies and optimized technology investment strategies to increase IT efficiency and business alignment.
    • • Agile & DevOps Leadership / Change Management & Cultural Transformation: ADP's 30 development teams operated with inconsistent engineering methodologies, leading to misaligned product launches and operational bottlenecks. Assessed inefficiencies, identifying Agile transformation opportunities. Designed a standardized Scrum framework, trained teams on Agile methodologies, and introduced real-time performance tracking. The initiative accelerated product delivery timelines, improved cross-team collaboration, and optimized development workflows, reducing time-to-market by 30% while enhancing cost efficiency.
    • • Enterprise Digital Transformation: ADP's lack of a centralized portfolio management system made it difficult for executives to prioritize IT investments and track financial returns on technology projects. Designed/implemented an enterprise-wide portfolio management framework, integrating real-time dashboards for project health, budget utilization, and ROI performance. The initiative standardized executive decision-making, optimized IT resource allocation, and improved alignment across multiple product lines.
    Agile method IT Project Management Leadership Development Change and Transformation Management PMO

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Education

  • MBA
    DeVry University, Keller School of
    MBA
  • MA
    University of Kentucky
    MA

Skill set

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