Remote Chief Operating Officer Insurance Jobs in New York

When we talk E&S, We Mean Expertise & Speed

Are you ready to make a real impact in the world of insurance? At Dellwood, we're not just another insurance company we're a team of passionate professionals who are modernizing the way business insurance gets done. Dellwood is built to deliver outstanding service and support for our partners with a balanced approach of technology and personal service, honoring the human nature of the business. Dellwood is purpose-built to bring speed, efficiency, and know-how to the E&S market.

Our Mission:To create a collaborative community of professionals focused on providing exceptional service and delivering innovative insurance solutions.

Why Dellwood?

Industry-Leading Expertise

Our team has extensive relationships throughout the insurance industry and decades of experience in E&S solutions. Our team of experienced underwriters craft solutions specifically for hard-to-place small and middle-market commercial risks.

Financial Stability

Backed by leaders in the industry, Dellwood has the strength and resources to make a significant impact.

A Culture of Innovation

We thrive on collaboration, creativity, and communication to address dynamic market needs.

Whats 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 companys 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