Randy Ledbetter
Metamora
Summary
Dynamic Technology Manager with a proven track record at Pekin Insurance, driving enterprise data strategy and analytics. Spearheaded cloud migration and automation initiatives, enhancing operational efficiency and executive decision-making. Expert in financial systems management and data governance, complemented by strong executive communication skills.
Overview
9
9
years of professional experience
1
1
Certification
Work History
Technology Manager – Data Platform & Financial Systems
Pekin Insurance
08.2025 - Current
- Lead enterprise data platforms and financial systems, ensuring technology investments deliver measurable business value, scalability, and operational efficiency.
- Established a centralized data foundation as a single source of truth, enabling consistent, trusted enterprise reporting and paving the way for a semantic layer.
- Automated commissions and accounts receivable processing within Workday, reducing manual effort, improving accuracy, and strengthening financial controls.
- Advancing financial data controls and audit readiness across enterprise platforms and financial processes through automation, standardization, and governance.
- Drive cloud migration, automation, and analytics enablement to improve executive decision-making while managing multidisciplinary teams and enterprise budgets.
Technology Manager – Data Reporting
Pekin Insurance
04.2022 - 08.2025
- Built and led a high-performing analytics organization delivering enterprise insights to senior and executive leadership, supporting the business in achieving $65M in commercial lines growth (2024).
- Drove enterprise data governance and regulatory reporting, improving data quality, consistency, and compliance while reducing legal and audit risk.
- Developed and executed enterprise data and analytics roadmaps, aligning IT and business leadership on strategic priorities and investment decisions.
- Delivered IT performance management analytics supporting merit-based budgeting and improved executive visibility.
- Led data platform modernization, including Guidewire Cloud migration and conversion of legacy SQL reporting to Snowflake, improving scalability and analytics enablement.
Data Analyst
Ascot Group
10.2021 - 04.2022
- Designed and delivered SQL-based dashboards and automated reporting, improving visibility into operational and regulatory metrics.
- Supported regulatory reporting and compliance initiatives through accurate, timely data analysis and validation.
- Partnered with business and technology stakeholders to streamline reporting processes and improve data reliability.
- Contributed to data standardization and quality improvement efforts, strengthening confidence in enterprise reporting.
Data Analyst I
Pekin Insurance
04.2021 - 10.2021
- Delivered analytics and reporting solutions supporting underwriting, finance, and operational decision-making.
- Developed SQL-based reports and data extracts, improving accuracy, timeliness, and usability of business information.
- Partnered with stakeholders to translate reporting needs into actionable insights.
- Supported data validation and reconciliation activities, improving trust in reported results.
Statistical Reporting Analyst
Pekin Insurance
01.2017 - 04.2021
- Led enterprise statistical and regulatory reporting, ensuring data accuracy, consistency, and audit readiness.
- Supported pricing, underwriting, and actuarial analytics, including loss ratio analysis and rate review preparation.
- Contributed to Guidewire data migration and modernization efforts, improving data accessibility and reporting efficiency.
- Collaborated with actuarial and finance teams to resolve data issues and reporting discrepancies.
Education
Bachelor of Science - Business / Managerial Economics
Illinois State University
Normal, IL12-2016
Associate of Science - Business Administration
Illinois Central College
East Peoria, IL08-2014
Skills
- Enterprise data strategy and analytics
- Financial systems management
- Technology modernization
- Data governance and reporting
- Executive communication skills
- Budget leadership and cost management
- AI and advanced analytics
Certification
• CPCU - The Institutes
• CIDM - The Institutes
• AIDA - The Institutes
• AINS - The Institutes
• API - The Institutes
• AU - The Institutes
• IBM – Introduction to DevOps
• Coursera – Machine Learning Foundations, Python Data Structures
• CIDM - The Institutes
• AIDA - The Institutes
• AINS - The Institutes
• API - The Institutes
• AU - The Institutes
• IBM – Introduction to DevOps
• Coursera – Machine Learning Foundations, Python Data Structures
Timeline
Technology Manager – Data Platform & Financial Systems
Pekin Insurance
08.2025 - Current
Technology Manager – Data Reporting
Pekin Insurance
04.2022 - 08.2025
Data Analyst
Ascot Group
10.2021 - 04.2022
Data Analyst I
Pekin Insurance
04.2021 - 10.2021
Statistical Reporting Analyst
Pekin Insurance
01.2017 - 04.2021
Bachelor of Science - Business / Managerial Economics
Illinois State University
Associate of Science - Business Administration
Illinois Central College