As Director, IT PMO, you will lead the IT Project Management Office (PMO) and oversee the successful delivery of strategic technology initiatives supporting Property & Casualty (P&C) insurance operations. This role drives portfolio governance, program execution, resource management, budgeting, and alignment of IT investments with business objectives across underwriting, claims, policy administration, billing, data, and customer experience platforms. This role is critical in ensuring that all projects are aligned with budgetary constraints, financial goals, and organizational strategies. The ideal candidate will have a strong background in project management, portfolio management, financial management, project accounting, vendor management, negotiation, and contract administration, stakeholder engagement, and reporting.
Principle Duties / Responsibilities
- Lead and manage the IT PMO, improving project governance standards, methodologies, tools, and reporting frameworks.
- Oversee a portfolio of complex technology programs and projects supporting P&C insurance operations.
- Partner with executive leadership, business stakeholders, and technology teams to define strategic roadmaps and investment priorities.
- Ensure successful delivery of large-scale initiatives including:
- Core systems modernization and improvements
- Digital customer experience initiatives
- Data and analytics programs
- Drive portfolio planning, prioritization, resource allocation, skill inventory, and demand/capacity management.
- Provide oversight of project budgets, forecasts, vendor financials, and financial performance.
- Provide oversight of vendor management, contract negotiations, and contract performance.
- Establish and monitor IT Portfolio KPIs, project health metrics, and executive dashboards.
- Identify and mitigate portfolio-level risks, issues, and dependencies.
- Promote Agile, Waterfall, and hybrid delivery methodologies across the organization.
- Ensure compliance with regulatory requirements, security standards, enterprise risk management practices, and audit controls.
- Develop and mentor PMO staff, project managers, and program managers.
- Demonstrate commitment to Company's Code of Business Conduct and Ethics, and apply knowledge of compliance policies and procedures, standards and laws applicable to job responsibilities in the performance of work.
- Bachelor's degree in Information Technology, Business Administration, Computer Science, or related field.
- 15+ years of progressive IT project/program/portfolio management experience.
- 7+ years of PMO leadership experience managing enterprise portfolios.
- Exceptional executive communication and stakeholder management skills.
- Strong experience within Property & Casualty insurance organizations.
- Proven success delivering large-scale enterprise transformation programs.
- Experience managing budgets exceeding $10M+.
- Experience with Agile, Scrum, SAFe, and traditional project methodologies.
Preferred Qualifications
- PMP/PgMP/PMI-ACP Certification
- SAFe Program Consultant (SPC) or SAFe Agilist
- MBA or advanced degree
- Experience with platforms such as Guidewire InsuranceSuite, Duck Creek Technologies, Majesco, Origami Risk
- Proficiency with PM tools such as Microsoft Project, Jira, Smartsheet, Power BI
Key Competencies
- Strategic Leadership
- Portfolio & Program Management
- P&C Insurance Domain Expertise
- Financial Management
- Change Management
- Vendor Management
- Risk Management
- Executive Presence
- Team Development
- Digital Transformation Leadership
Work Environment:
- Hybrid (3 days on site per week in Blue Bell, PA Headquarters)
Skills Required
- Strong background in project management, portfolio management, financial management, project accounting, vendor management, negotiation, contract administration, stakeholder engagement, and reporting
- Commitment to Company Code of Business Conduct and Ethics and compliance policies
- Bachelor's degree in Information Technology, Business Administration, Computer Science, or related field
- 15+ years of progressive IT project/program/portfolio management experience
- 7+ years of PMO leadership experience managing enterprise portfolios
- Exceptional executive communication and stakeholder management skills
- Experience within Property & Casualty insurance organizations
- Proven success delivering large-scale enterprise transformation programs
- Experience managing budgets exceeding $10M
- Experience with Agile, Scrum, SAFe and hybrid delivery methodologies
- PMP, PgMP, or PMI-ACP certification
- SAFe Program Consultant (SPC) or SAFe Agilist
- MBA or advanced degree
- Experience with Guidewire InsuranceSuite, Duck Creek Technologies, Majesco, or Origami Risk
- Proficiency with Microsoft Project, Jira, Smartsheet, Power BI
PMA Companies Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about PMA Companies and has not been reviewed or approved by PMA Companies.
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Leave & Time Off Breadth — Time off is described as generous, with a sizable PTO bank and a broad paid-holiday schedule. Feedback suggests the ability to accrue and use substantial leave is a standout element of the package.
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Retirement Support — Retirement support includes a 401(k) with company contributions and immediate vesting on certain employer dollars. Profit-sharing and automatic eligibility are positioned as meaningful additions to total rewards.
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Flexible Benefits — Benefits are organized in a cafeteria-style format with multiple medical plan choices, HSA options, FSAs, and a broad set of voluntary coverages. Feedback suggests this flexibility enables tailoring coverage to individual needs.
PMA Companies Insights
What We Do
PMA Companies provides risk management solutions and services, specializing in workers’ compensation and offering property & casualty insurance, in the United States. Headquartered in Blue Bell, PA, PMA Companies is a member of Old Republic Companies. Old Republic International Corporation (NYSE: ORI) is one of the nation’s 50 largest publicly held insurance organizations. PMA Companies includes: PMA Insurance Group, specializing in workers’ compensation, and providing other commercial property & casualty insurance products; and PMA Management Corp. and PMA Management Corp. of New England, providing results-driven TPA and Risk Services specializing in workers’ compensation and liability. We maintain a large client retention rate of 90% or higher and a client satisfaction rate of 96% per an independent survey. At PMA, we still build relationships the "old-fashioned way." Our clients know we care. They know we say what we do and do what we say. And they know that they can count on us to deliver tangible value to their business and to work passionately on their behalf.
