Dataprise Executive and Leadership Team

September, 2026

Leadership Overview

Dataprise has 5 executives leading key functions including strategy, revenue growth, financial management, operational excellence, and human capital development.

Focused on delivering comprehensive IT solutions, Dataprise empowers small to medium-sized businesses through expert consulting, robust network support, and scalable cloud services to drive digital transformation.

Leadership Roles at Dataprise

  • Chief Executive Officer - William Flannery
  • Chief Financial Officer - Siobhan de Leeuw
  • Chief Operating Officer - Howard Malloy
  • Chief Revenue Officer - Walt Strubbe
  • Chief People Officer - Amanda Gill
  • William Flannery - Chief Executive Officer

    William Flannery, the Chief Executive Officer at Dataprise, directs the overarching corporate strategy and long-term vision for the organization. Flannery architects the expansion of IT service offerings to ensure small and medium-sized enterprises receive top-tier consulting and cloud support. By aligning internal resources with market demands, the Chief Executive Officer maintains a competitive edge across North American technology sectors. This leadership role involves constant collaboration with the Board to refine service delivery models and enhance client value propositions. William Flannery monitors key performance indicators to ensure sustainable growth and operational efficiency. Through rigorous oversight of organizational health, the Chief Executive Officer secures the firm's position as a leader in managed IT services. Flannery drives innovation by prioritizing investments in emerging cloud technologies, ensuring the company remains at the forefront of the digital consulting landscape while fostering a culture of excellence and client-centric service delivery.

    Siobhan de Leeuw - Chief Financial Officer

    Siobhan de Leeuw, the Chief Financial Officer at Dataprise, directs all fiscal planning, budgeting, and financial reporting activities. Overseeing the financial health of the organization, the Chief Financial Officer ensures capital allocation supports the company's mission of providing high-quality IT services and cloud consulting. This leadership role involves managing complex financial risks and ensuring compliance with industry standards across all regional operations. By optimizing cost structures and improving operational margins, Siobhan de Leeuw directly impacts the firm's ability to invest in new technology infrastructure. Ultimately, de Leeuw secures the financial foundation necessary for sustained growth in the competitive IT services market. The Chief Financial Officer collaborates with other executive leaders to evaluate the profitability of new service lines and market opportunities. Through rigorous financial analysis, de Leeuw provides the insights required to make informed decisions regarding resource distribution, ensuring the company maintains a strong balance sheet while delivering exceptional value to clients.

    Howard Malloy - Chief Operating Officer

    Howard Malloy, the Chief Operating Officer at Dataprise, directs the daily execution of IT service delivery and network support operations. Overseeing the technical teams, the Chief Operating Officer ensures that all cloud services and consulting projects meet rigorous quality standards for small to medium-sized business clients. This leadership role involves streamlining internal processes to enhance service efficiency and response times across all operational regions. By implementing scalable infrastructure solutions, Howard Malloy directly impacts the reliability and performance of the company's service offerings. Ultimately, Malloy secures operational excellence by fostering a culture of technical proficiency and continuous improvement. The Chief Operating Officer manages the integration of new technologies into the existing service portfolio, ensuring seamless transitions for clients. Through proactive management of service delivery workflows, Malloy drives the operational success required to maintain high client satisfaction levels and support the company's broader strategic objectives in the managed services industry.
    Howard Malloy

    Walt Strubbe - Chief Revenue Officer

    Walt Strubbe, the Chief Revenue Officer at Dataprise, directs all global sales initiatives and market expansion efforts. Overseeing the enterprise sales teams, the Chief Revenue Officer ensures alignment with corporate revenue targets and client acquisition goals. This leadership role involves expanding market share through targeted digital campaigns and strategic partnerships within the IT consulting space. By optimizing the sales funnel and refining pricing models for cloud services, Walt Strubbe directly impacts the company's financial growth. Ultimately, Strubbe secures long-term stability by cultivating deep relationships with small to medium-sized business clients. The Chief Revenue Officer manages the entire sales lifecycle, from initial lead generation to contract negotiation, ensuring consistent pipeline health. Strubbe drives revenue performance by implementing data-driven sales methodologies that address the specific network support needs of diverse clients, thereby solidifying the firm's reputation as a premier provider of managed technology solutions.
    Walt Strubbe

    Amanda Gill - Chief People Officer

    Amanda Gill, the Chief People Officer at Dataprise, directs all human capital strategies, talent acquisition, and organizational development initiatives. Overseeing the workforce, the Chief People Officer ensures the company attracts and retains top-tier technical talent capable of delivering superior IT consulting and network support. This leadership role involves designing comprehensive training programs that keep staff updated on the latest cloud technologies and service methodologies. By fostering an inclusive and high-performance culture, Amanda Gill directly impacts employee engagement and overall productivity. Ultimately, Gill secures the human resources necessary to support the company's growth and service delivery goals. The Chief People Officer collaborates with other executives to align talent management with the firm's long-term business strategy. Through the implementation of robust performance management systems, Gill drives professional growth across the organization, ensuring the team remains equipped to solve complex IT challenges for small to medium-sized businesses in a rapidly evolving market.

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    Frequently Asked Questions Regarding Dataprise Top Executives and Leadership Team

    Who leads Dataprise?
    Dataprise is led by William Flannery (Chief Executive Officer), along with executives such as Siobhan de Leeuw (Chief Financial Officer) and Howard Malloy (Chief Operating Officer).
    Who is part of Dataprise’s executive team?
    The executive team of Dataprise includes leaders such as William Flannery (Chief Executive Officer), Siobhan de Leeuw (Chief Financial Officer), Howard Malloy (Chief Operating Officer) and other senior executives.
    How many executives does Dataprise have?
    Dataprise has 5 executives leading key business areas.
    What roles are included in Dataprise’s leadership team?
    The leadership team of Dataprise includes roles such as Chief Executive Officer, Chief Financial Officer, Chief Operating Officer, Chief Revenue Officer, Chief People Officer.