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Goodwill Central Florida seeks a transformational technology executive to serve as its next Vice President of Information Services. As a member of the Executive Leadership team, reporting to the President and CEO, the VP of IS will lead the organization's technology strategy and oversee enterprise applications, infrastructure, cybersecurity, data and analytics, vendor partnerships, and technology-enabled business transformation.
This role represents a unique opportunity to elevate technology from a primarily operational function to a strategic business enabler. As Goodwill continues its growth trajectory, the organization requires a leader who can align technology investments with business priorities, strengthen enterprise capabilities, and build a scalable foundation for future expansion. Working closely with executive leadership, the VP of IS will modernize core systems, advance project and portfolio management disciplines, enhance enterprise data and analytics capabilities, and develop a technology roadmap that supports both retail operations and mission delivery. The successful candidate will serve as a trusted business partner, ensuring technology investments
improve decision-making, operational effectiveness, and organizational performance.
Strategic Priorities:
During the first 24-36 months, key priorities will include:
• Develop and execute a multi-year enterprise technology strategy and roadmap aligned with organizational growth, operational excellence, and mission objectives.
• Lead the modernization of core business systems, including evaluation and replacement of the General Ledger platform and assessment of the broader enterprise application portfolio.
• Define a future-state technology architecture that improves scalability, integration, data accessibility, and organizational effectiveness.
• Establish formal projects, portfolio, and technology governance disciplines to improve prioritization, execution, accountability, and investment outcomes.
• Build a scalable enterprise data, analytics, and business intelligence capability that strengthens decision-making across retail operations, mission services, finance, human resources, and real estate.
• Enhance data-driven planning and investment decision support, including real estate analytics and organizational performance measurement.
• Evaluate and implement technology solutions that improve program management, CRM capabilities, workflow automation, service delivery, and outcome tracking.
• Strengthen integration across enterprise applications and data platforms to improve operational efficiency, reporting, and user experience.
• Assess, develop, and align the technology organization, capabilities, and talent needed to support future growth and transformation.
• Foster stronger cross-functional partnerships and position technology as a strategic business enabler across the enterprise.
Key Responsibilities:
Strategic Leadership & Business Partnership
• Serve as a trusted technology advisor to the CEO and Executive Leadership Team.
• Develop and execute an enterprise technology strategy aligned with organizational goals.
• Translate business priorities into technology solutions that improve performance and decision-making.
• Build strong partnerships across Finance, Human Resources, Operations, Retail, Real Estate, and Mission Services.
• Evaluate emerging technologies and identify opportunities for innovation and efficiency.
Enterprise Systems & Transformation
• Lead enterprise application strategy, selection, implementation, integration, and optimization.
• Drive modernization of financial, HR, retail, CRM, and operational systems.
• Establish governance frameworks for technology investments and project prioritization.
• Lead technology-enabled business process improvement initiatives.
• Develop scalable enterprise architecture supporting long-term growth.
Data, Analytics & Decision Support
• Establish a vision and roadmap for enterprise data and analytics.
• Implement data governance standards and accountability.
• Enhance reporting, business intelligence, and executive decision-support capabilities.
• Deliver actionable insights across retail operations, workforce programs, real estate, and organizational performance.
IT Operations & Cybersecurity
• Oversee infrastructure, networks, applications, and technology operations.
• Ensure a secure, reliable, and scalable technology environment.
• Lead cybersecurity, risk management, disaster recovery, and business continuity efforts.
• Manage technology vendors, contracts, and service-level performance.
Project & Portfolio Management
• Implement formal project management methodologies and governance.
• Lead multiple concurrent initiatives while balancing organizational priorities.
• Ensure projects are delivered on time, within budget, and aligned with strategic objectives.
Leadership & Team Development
• Lead and develop a team of seven IT professionals.
• Assess future organizational needs and evolve team structure accordingly.
• Foster a culture of accountability, collaboration, innovation, and customer service.
• Build organizational confidence in technology through effective communication and stakeholder engagement.
Professional Experience & Qualifications
The ideal candidate is a strategic, business-minded technology executive who combines enterprise IT leadership, digital transformation expertise, and strong operational execution. This individual will possess the ability to align technology investments with organizational priorities, leverage data to improve decision-making, and build scalable capabilities that support growth, operational excellence, and mission impact.
Required Experience
• 15+ years of progressive technology leadership experience, including responsibility for enterprise technology strategy, digital transformation, and organizational change.
• Demonstrated success serving as a senior technology leader and trusted business partner to executive leadership teams.
• Proven experience leading enterprise systems modernization initiatives, including ERP, financial, HR, CRM, and other core business applications.
• Strong track record assessing current-state technology environments, defining future state architecture, and executing complex transformation programs.
• Experience building enterprise data, analytics, business intelligence, and reporting capabilities that enhance decision-making and organizational performance.
• Experience leading technology organizations within multi-site, distributed operating environments.
• Strong understanding of the technologies, processes, and operational demands required to support multiple locations, frontline employees, and customer-facing operations at scale.
• Demonstrated expertise overseeing cybersecurity, infrastructure, technology operations, risk management, business continuity, and technology governance.
• Proven success establishing project and portfolio management disciplines that improve prioritization, execution, accountability, and return on technology
investments.
• Experience managing technology vendors, consultants, and strategic partners.
• Strong financial and budget management skills, including capital planning, vendor management, and investment prioritization.
Preferred Experience
• Experience within retail, consumer-facing, hospitality, restaurant, healthcare, nonprofit, or other complex, distributed operating environments.
• Experience supporting organizations undergoing significant growth, expansion, or business transformation.
• Expertise in ERP, CRM, enterprise data management, business intelligence, workflow automation, and systems integration.
• Experience leading data governance and enterprise analytics initiatives.
• Formal project management training or certification (PMP or equivalent).
• Bachelor's degree in Information Technology, Computer Science, Engineering, Business, or a related field; advanced degree preferred.
Leadership Characteristics
The successful candidate will demonstrate:
• Executive presence and the ability to establish credibility and influence with senior leadership, boards, and key stakeholders.
• Strong business acumen with the ability to translate organizational priorities into technology strategies and measurable outcomes.
• Strategic thinking balanced with a pragmatic, hands-on approach to execution.
• Exceptional relationship-building, communication, and cross-functional collaboration skills.
• A data-driven mindset with a passion for leveraging information and analytics to improve decision-making and organizational performance.
• Intellectual curiosity and a continuous-improvement mindset, with the confidence to challenge the status quo constructively.
• High emotional intelligence, humility, and a collaborative leadership style.
• A results-oriented approach with a demonstrated ability to lead change and deliver complex initiatives successfully.
• A commitment to developing talent, building organizational capability, and fostering a culture of accountability, innovation, and service excellence.
• Passion for advancing Goodwill's mission and improving lives through the power of work