Executive Technology Leader: AI, Data & Security Strategy

OwnersEdge; City of Pewaukee (WI); On-site; USD 180,000 - 240,000; Full time

Job summary

OwnersEdge, a 100% employee-owned holding company, seeks a Director of Technology to chart enterprise technology strategy and govern MSP relationships while guiding major digital transformation initiatives.

The role combines executive partnership with hands-on depth to evaluate architectures, lead complex projects, and manage significant incidents or escalations across multiple operating companies.

Qualifications

• Bachelor’s degree in information technology, computer science, information systems, business, engineering, or a related field; advanced degree preferred.
• 10+ years of progressive technology experience, including meaningful leadership responsibility.
• Experience managing an MSP or major outsourced technology relationship.
• Demonstrated success developing technology roadmaps, budgets, capital plans, and executive-level business cases.
• Experience leading data, analytics, AI, automation, cybersecurity governance, and digital transformation initiatives.
• Working knowledge of cloud platforms, Microsoft 365, enterprise infrastructure, cybersecurity, applications, integrations, and incident management.
• Experience in a multi-company, decentralized, acquisition-oriented, or holding-company environment preferred.

Responsibilities

• Develop and maintain an enterprise technology strategy and multi-year roadmap aligned with OwnersEdge and operating company priorities.
• Establish technology governance, policies, standards, decision rights, and portfolio prioritization.
• Translate business needs into scalable technology solutions and present recommendations and business cases to executive leadership.
• Monitor emerging technologies and recommend practical investments that improve growth, productivity, risk management, or customer value.
• Lead technology due diligence, integration planning, and execution for acquisitions.
• Serve as the primary owner and executive contact for the MSP relationship.
• Define service expectations, performance measures, service-level requirements, escalation protocols, and accountability.
• Lead operating reviews and resolve significant service, security, capacity, or relationship issues.
• Ensure clear ownership and communication between OwnersEdge, its operating companies, the MSP, and other technology vendors.
• Evaluate vendors, negotiate commercial terms, and manage contract performance and renewal decisions.
• Set the enterprise data, reporting and analytics strategy.
• Serve on AI Executive Leadership Council to establish the enterprise AI strategy.
• Partner with operating company leaders to improve decision-making through trusted data and actionable insights.
• Identify and prioritize generative AI, automation, and digital workflow opportunities with measurable business value.
• Establish appropriate data governance, quality, access, stewardship, and responsible AI practices.
• Provide executive oversight of cybersecurity strategy, risk, policy, compliance, insurance requirements, and remediation priorities.
• Challenge and validate MSP security recommendations, reporting, vulnerability management, employee awareness and incident response activities.
• Coordinate executive decision-making and communications during significant cybersecurity or technology incidents.
• Promote security awareness and ensure risks are communicated clearly to leadership.
• Own the strategic direction and lifecycle of corporate applications and integrations.
• Partner with business leaders to modernize processes, improve adoption, and reduce manual work.
• Provide technical leadership for complex initiatives involving Microsoft 365, cloud platforms, systems integration, enterprise applications, and cybersecurity.
• Step into architecture decisions, vendor escalations, and critical projects when internal leadership is required.
• Develop and manage technology operating budgets, capital plans, forecasts, and investment analyses.
• Balance service, security, scalability, and cost when recommending investments.
• Lead, coach, and develop the Data Analyst and entry-level technology staff member.
• Build a service-oriented, accountable, and collaborative culture across the internal team and MSP.

Skills

Executive leadership

Strategic thinking

Cross-functional collaboration

Communication with executives

Education

Bachelor’s degree in IT/CS/IS/Engineering

Advanced degree preferred

10+ years technology leadership

Tools

Microsoft 365

Job description

OwnersEdge, a 100% employee-owned holding company, seeks a Director of Technology to chart enterprise technology strategy and govern MSP relationships while guiding major digital transformation initiatives.

The role combines executive partnership with hands-on depth to evaluate architectures, lead complex projects, and manage significant incidents or escalations across multiple operating companies.