Director of Technology in Waukesha, Wisconsin at OwnersEdge

OwnersEdge is a diversified, 100% employee-owned holding company with six operating companies. The Director of Technology is the senior-most internal technology leader and is accountable for enterprise technology strategy, managed service provider governance, digital transformation, data strategy, cybersecurity oversight and technology investment planning and leadership of internal technical staff. This leader will partner with other company leadership to establish artificial intelligence strategy. A third-party managed service provider and an internal technical staff member perform most day-to-day technology operations, while this leader retains strategic ownership, business prioritization, vendor accountability, risk oversight, and leadership of complex initiatives. The successful candidate will combine executive-level business partnership with hands-on technical depth to evaluate architecture, guide major projects, and lead through significant incidents or escalations.

• 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.

• 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.

• Pragmatic, hands-on when necessary, and comfortable leading through ambiguity and change.
• Strategic and commercially minded.
• Credible with executives, operating company leaders, technical teams, and external partners.
• Able to challenge technical recommendations constructively without becoming the routine operational owner.
• Clear communicator who converts technology complexity into business decisions.
• Committed to employee ownership, collaboration, accountability, and continuous improvement.

• A disciplined MSP governance model with transparent performance, accountability, and escalation.
• A technology roadmap that supports business strategy and acquisition growth.
• Improved service consistency, cybersecurity posture, application effectiveness, and user experience.
• Data, automation, and AI initiatives that produce measurable operating value.