Location: Hybrid – Sarasota, FL (Local candidates preferred. Candidates outside the area must be willing to relocate for a hybrid work schedule.)
Employment Type: Contract
Experience Required: 19+ Years
Job Summary
We are seeking an experienced Program Director to lead a large-scale Enterprise Data Modernization Program for a leading Property & Casualty (P&C) Insurance organization. This executive leadership role will drive the transformation of legacy data platforms and siloed data environments into a modern, cloud-native, scalable data ecosystem built on Medallion Architecture principles.
The ideal candidate will have a proven track record of leading enterprise-wide data transformation initiatives in regulated financial services or insurance environments. This role requires strategic leadership, executive stakeholder management, architectural guidance, vendor governance, and deep knowledge of enterprise data modernization.
Key Responsibilities
Program Leadership & Strategy
Lead end-to-end delivery of enterprise data modernization initiatives, including scope, schedule, budget, risk, quality, and resource management.
Define and execute the strategic roadmap for enterprise data transformation.
Establish governance frameworks, steering committees, operating models, and decision‑making processes.
Serve as the executive escalation point for complex program risks and cross‑functional dependencies.
Drive successful execution across multiple business and technology workstreams.
Lead the migration from legacy data platforms to a modern cloud‑native data ecosystem.
Drive implementation of Medallion Architecture (Bronze, Silver, Gold) and enterprise data management best practices.
Collaborate with Data Engineering and Enterprise Architecture teams to establish standards for:
Data Contracts
Metadata Management
Data Quality
Promote scalable, secure, and governed enterprise data platforms.
Executive Leadership & Thought Partnership
Act as a trusted advisor to executive leadership on enterprise data strategy and modernization initiatives.
Provide guidance on platform selection, modernization sequencing, and enterprise architecture decisions.
Share industry best practices and lessons learned to accelerate delivery and reduce program risk.
Drive alignment between business objectives and technology strategy.
Lead vendor evaluations, RFP processes, contract negotiations, and technology partner selection.
Manage system integrators, cloud providers, and third‑party delivery teams.
Evaluate technology roadmaps and recommend build vs. buy vs. partner strategies.
Ensure vendor performance aligns with organizational goals and governance standards.
Cross‑Functional Collaboration
Partner with Data Engineering, Enterprise Architecture, Security, Infrastructure, PMO, Business Leaders, and Change Management teams.
Support organizational readiness, user adoption, communication, and training initiatives.
Foster collaboration across business, technology, and executive leadership teams.
Required Qualifications
19+ years of overall IT experience.
Minimum 5+ years of experience leading large‑scale enterprise data modernization programs as a Program Director.
Proven experience delivering enterprise‑wide data transformation initiatives within Property & Casualty (P&C) Insurance or Financial Services organizations.
Strong expertise in enterprise program governance, executive stakeholder management, and strategic planning.
Experience with enterprise data architecture, cloud‑native data platforms, and modern data engineering practices.
Strong understanding of Medallion Architecture, enterprise data governance, metadata management, and data quality frameworks.
Experience managing large cross‑functional teams, vendors, and system integrators.
Excellent leadership, communication, negotiation, and decision‑making skills.
Preferred Qualifications
Experience with Databricks Lakehouse Platform.
Strong background in enterprise Data Architecture and Data Engineering.
Experience with cloud platforms such as Azure, AWS, or Google Cloud Platform (GCP).
Experience leading enterprise transformation programs in regulated industries.
PMP, PgMP, SAFe, or equivalent Program Management certification.
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