Director of Technology & Digital Transformation

The Director of Technology & Digital Transformation leads Willamette View's technology services, business systems, cybersecurity, vendor partnerships, and digital transformation roadmap. The role ensures reliable, responsive technology support for staff and residents while building the organizational capabilities needed for integrated systems, data-informed decisions, automation, and responsible use of AI and chatbots.

In a small, service-oriented IT environment, the Director balances strategic leadership with hands-on execution. This position leads the internal IT team, manages Portland Internetworks and other technology partners, and helps reduce long-term dependence on external transformation partners by building internal ownership, documentation, governance, and adoption practices., Technology Strategy and Governance

• Develop and maintain a multi-year technology and digital transformation roadmap aligned with organizational strategy, resident experience, workforce priorities, security, and affordability
• Translate business needs into practical priorities for systems, data, automation, AI, infrastructure, and service delivery
• Establish governance for technology requests, project prioritization, implementation readiness, resource planning, and post-launch support
• Advise senior leadership on technology risks, investments, trends, tradeoffs, and opportunities to improve organizational effectiveness.

IT Operations and Service Experience

• Lead daily technology support for staff and residents, including help desk, resident technology support, endpoint support, applications support, and operational troubleshooting
• Establish service standards, documentation, escalation practices, and performance metrics that support reliable, respectful, and responsive service
• Provide hands-on leadership and escalation support when needed while ensuring the Director role remains focused on service quality, team leadership, and organizational outcomes
• Identify recurring issues and lead improvements that reduce rework, clarify communication, and strengthen user experience.

Vendor and Managed Services Leadership

• Manage vendors to ensure strong service, security, responsiveness, documentation, value, and roadmap alignment
• Define clear accountabilities between internal IT, managed service partners, application vendors, consultants, and department system owners
• Monitor vendor performance, contracts, service levels, escalation paths, risks, costs, and support expectations
• Ensure vendor work is documented, secure, supportable, and designed to reduce over-reliance on any single consultant or partner.

Business Systems, Data, Automation, and AI

• Partner with departments to strengthen business systems, workflows, reporting, data quality, integration, and system ownership practices
• Identify opportunities to reduce duplicate entry, manual workarounds, fragmented reporting, spreadsheet dependency, and disconnected workflows
• Lead or coordinate data governance, reporting standards, dashboard priorities, data definitions, role-based access, and integration planning
• Guide the planning and governance of automation, RPA, dashboard, workflow, and AI/chatbot initiatives; engage external specialists when advanced build capacity is required
• Ensure automation and AI efforts are secure, ethical, compliant, documented, human-centered, and aligned with measurable business value.

Internal Capability Building and Digital Adoption

• Build repeatable standards for intake, requirements gathering, process mapping, solution design, testing, documentation, training, and support
• Develop internal system/product owners, department super users, and cross-functional partners who can define needs, test solutions, support adoption, and sustain improvements
• Require documentation, administrative handoff, training, and knowledge transfer from external partners before final acceptance of deliverables
• Partner with People & Culture, Communications, Compliance, Finance, Operations, and department leaders to support change management, digital literacy, and adoption

Cybersecurity, Privacy, and Resilience

• Oversee cybersecurity strategy in partnership with managed service providers, leadership, and relevant stakeholders
• Ensure appropriate safeguards for resident, employee, financial, operational, and health-related information
• Lead disaster recovery, business continuity technology planning, access controls, incident response expectations, and security awareness
• Support compliance with applicable laws, contracts, insurance requirements, privacy expectations, and internal policies

Team and Fiscal Leadership

• Lead, coach, develop, and evaluate the IT team within established corporate policies and practices
• Clarify team roles, responsibilities, escalation paths, development needs, and staffing recommendations as technology needs evolve
• Develop and manage operating budgets, project budgets, vendor costs, contracts, services, and technology investments within approved guidelines
• Build business cases and progress reports that communicate cost, risk, value, adoption requirements, support implications, and measurable outcomes

Do you have experience in Vendor relationship management?, Do you have a Bachelor's degree?, * Bachelor's degree preferred; equivalent combination of education, certification, and relevant experience may be considered.

• 8-10 years of progressive technology leadership experience, including IT operations, business systems, vendor management, project leadership, and service management.
• Minimum of 3 years of experience managing staff and overseeing external service providers, managed service partners, consultants, or application vendors.
• Demonstrated experience leading technology projects or digital transformation efforts across business and technical stakeholders.
• Working knowledge of cybersecurity, privacy, disaster recovery, data governance, reporting/analytics, integrations, automation, and emerging AI concepts.
• Experience developing or executing a technology roadmap and translating business needs into actionable technology priorities.
• Experience with enterprise software in healthcare, senior living, hospitality, nonprofit, or complex service environments preferred.
• Experience with Microsoft 365, Power BI, Power Platform, Azure, Microsoft Fabric, or similar data and automation platforms preferred.

Willamette View participates in E-Verify. We will use E-Verify to confirm your eligibility to work in the United States.

Willamette View is a resident-centered continuing care community grounded in connection, purpose, and a commitment to creating a vibrant place to live and work. Guided by our vision to transform the experience of aging, we build systems, processes, and capabilities that help staff and residents feel supported, engaged, and empowered.