Manager, Program Management Office (PMO)

Dellwood Insurance Group LLC

$100K — $130K *
Finance & Insurance
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 10+ years of experience in insurance and/or program management, including 5+ years in a managerial role
  • Strong understanding of commercial insurance operations and technology ecosystems
  • Excellent skills in project planning, executive communication, risk management, and stakeholder management
  • Experience with enterprise project and portfolio management tools such as MS Project, Jira, and Power BI
  • Bachelor's degree required; PMP, Agile, Scrum, or related certifications preferred

Responsibilities

  • Establish standardized PMO toolkits, methodologies, and governance models
  • Partner with Business Sponsors, Product Owners, and Technology leaders to ensure successful delivery of initiatives
  • Develop and maintain detailed project plans and integrated schedules
  • Manage multiple concurrent initiatives across various operational platforms
  • Facilitate project governance forums and executive status reviews
  • Report on project health, risks, issues, and key milestones transparently
  • Identify and manage project risks, issues, and resource capacity

Benefits

  • Medical, dental, and vision insurance
  • Retirement savings plan
  • Paid time off
  • Flexible/remote work options available
Full Job Description
What's the Role?

Overview

We are seeking an experienced and highly organized Manager, Program Management Office (PMO) to join our growing Insurance Operations organization. Reporting to the Chief Operating Officer (COO), this role serves as a key delivery and governance leader responsible for ensuring the successful execution of strategic business and technology initiatives across the enterprise.

As a key member of the Operations organization, the Project Management Office Manager, Insurance Technology Delivery will help strengthen governance processes, standardize delivery practices, and foster a culture of accountability, transparency, and operational excellence while supporting the company's continued growth and transformation objectives.

Core Responsibilities
  • Working closely with COO, continue to establish standardized PMO toolkits, methodologies, and governance models across the enterprise to ensure projects stay on track and within budget.
  • Partner closely with Business Sponsors, Product Owners, Technology leaders and their teams, Underwriting, Functional support units such as Claims, Finance, Actuarial and Operations, and External Vendors to ensure successful delivery of strategic initiatives from business case development through implementation and production launch.
  • Develop and maintain detailed project plans, integrated schedules, milestones, dependencies, resource plans, and delivery roadmaps.
  • Manage multiple concurrent initiatives across underwriting, policy administration, claims, finance, distribution, forms management, data, and reporting platforms.
  • Establish and facilitate project governance forums, steering committees, and executive status reviews.
  • Provide transparent reporting of project health, risks, issues, decisions, dependencies, and key milestones.
  • Proactively identify, assess, and manage project risks, assumptions, issues, dependencies as well as resource capacity.
  • Escalate critical issues and delivery risks in a timely manner to prevent project delays.
  • Promote consistent project management standards, methodologies, templates, and controls.
  • Ensure strategic initiatives deliver intended value, tracking OKRs and conducting health checks and independent reviews where applicable.

Operational Governance Philosophy
  • Drive transparency through timely and accurate project reporting.
  • Surface risks, issues, and dependencies early before they become delivery obstacles.
  • Facilitate informed decision-making through clear options and recommendations.
  • Foster accountability across business and technology teams.
  • Focus on business value realization, not simply project completion.
  • Occasional travel may be required.


Qualifications
  • 10 + years in insurance and/or program management; 5+ years in managerial capacity.
  • Strong understanding of commercial insurance operations (UW, Claims, Finance, Reinsurance, Regulatory Compliance) and technology ecosystems.
  • Excellent project planning, executive communication, risk management, and stakeholder management skills.
  • Working knowledge of enterprise project and portfolio management (PPM) tools such as MS Project, Jira, Power BI
  • Bachelor's degree required; PMP, Agile, Scrum, or related certifications preferred.


Location: Flexible/Remote Option available within the United States

We offer a competitive benefits package, including medical, dental, vision, retirement savings, and paid time off.

Applicant must be currently authorized to work in the United States on a full-time basis.

Dellwood

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