Dataprise Executive and Leadership Team

August, 2026

Leadership Overview

Dataprise has 5 executives leading key functions including strategy, operations, finance, revenue, and human resources.

Focused on delivering comprehensive IT solutions, Dataprise empowers small to medium-sized businesses through expert consulting, network support, and cloud services to drive operational excellence and digital transformation across the North American market.

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 consulting services, ensuring the company maintains a competitive edge in the managed services sector. By aligning internal resources with the evolving needs of small to medium-sized enterprises, the Chief Executive Officer fosters sustainable growth and market stability. William Flannery maintains direct oversight of high-level partnerships and board relations, securing the necessary capital and infrastructure to support nationwide service delivery. Through rigorous analysis of industry trends, the Chief Executive Officer identifies emerging opportunities in cloud computing and network security. This leadership approach guarantees that Dataprise remains a premier provider of technical support. Ultimately, Flannery drives the organizational culture toward innovation, efficiency, and client-centric service delivery, ensuring that every department contributes to the broader mission of simplifying complex technology for diverse business clients.

    Siobhan de Leeuw - Chief Financial Officer

    Siobhan de Leeuw, the Chief Financial Officer at Dataprise, governs the financial health and fiscal planning of the organization. de Leeuw architects the budgetary framework that supports the company's investment in cloud infrastructure and technical talent. By managing capital allocation, the Chief Financial Officer ensures that Dataprise maintains the liquidity required for strategic acquisitions and market expansion. Siobhan de Leeuw oversees financial reporting, audit compliance, and risk management, providing the transparency necessary for informed executive decision-making. This financial leadership role involves analyzing revenue streams from IT consulting and network support to optimize profitability. de Leeuw collaborates with the executive team to forecast market demand, adjusting financial models to reflect the shifting needs of small to medium-sized business clients. Through rigorous cost control and strategic investment, the Chief Financial Officer secures the long-term financial viability of the firm. de Leeuw drives fiscal discipline, ensuring that every dollar spent directly supports the company's core mission of delivering superior IT services.

    Howard Malloy - Chief Operating Officer

    Howard Malloy, the Chief Operating Officer at Dataprise, manages the daily execution of IT service delivery and internal operational workflows. Malloy optimizes the deployment of network support teams, ensuring that service level agreements remain consistent across all client engagements. By streamlining internal processes, the Chief Operating Officer enhances the efficiency of cloud service provisioning for small to medium-sized businesses. Howard Malloy coordinates with department heads to refine resource allocation, reducing overhead while maximizing technical output. This operational focus supports the company's commitment to reliable, high-quality IT consulting. Malloy monitors performance metrics to identify bottlenecks in service delivery, implementing scalable solutions that accommodate rapid client growth. Through the oversight of technical infrastructure, the Chief Operating Officer ensures that Dataprise maintains robust, secure, and high-performing systems. Malloy drives operational excellence by standardizing best practices across all regional service centers, ultimately securing the company's reputation for technical reliability and consistent service quality.
    Howard Malloy

    Walt Strubbe - Chief Revenue Officer

    Walt Strubbe, the Chief Revenue Officer at Dataprise, directs all sales initiatives and market acquisition strategies. Strubbe architects the go-to-market approach for IT services, focusing on expanding the client base among small to medium-sized enterprises. By aligning marketing efforts with sales targets, the Chief Revenue Officer accelerates the adoption of cloud and network support solutions. Walt Strubbe manages the sales pipeline, ensuring that the company captures significant market share through targeted outreach and consultative selling. This leadership role involves building strong relationships with key stakeholders and identifying new revenue opportunities within the technology consulting sector. Strubbe monitors conversion rates and customer acquisition costs, refining sales tactics to improve overall profitability. Through the implementation of data-driven sales strategies, the Chief Revenue Officer ensures that Dataprise meets its aggressive growth objectives. Strubbe drives revenue performance by fostering a high-performing sales culture, ultimately securing the company's position as a leader in the managed IT services industry.
    Walt Strubbe

    Amanda Gill - Chief People Officer

    Amanda Gill, the Chief People Officer at Dataprise, oversees human capital strategy and organizational development. Gill architects the recruitment, retention, and training programs necessary to maintain a highly skilled workforce of IT consultants and network engineers. By fostering a culture of continuous learning, the Chief People Officer ensures that the company remains at the forefront of technical expertise. Amanda Gill manages performance evaluation systems and employee engagement initiatives, aligning individual career growth with the broader objectives of the firm. This leadership role involves designing compensation structures that attract top talent in the competitive technology sector. Gill collaborates with the executive team to cultivate an inclusive environment that supports the diverse needs of the workforce. Through the implementation of robust talent management strategies, the Chief People Officer drives organizational productivity and employee satisfaction. Gill ensures that Dataprise retains the human capital required to deliver exceptional IT services, ultimately strengthening the company's internal foundation for long-term success.

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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.