Director of Strategic Operations

Job Description

Posted Tuesday, August 11, 2026 at 4:00 AM

Chesapeake Employers’ Insurance Company is a purpose-driven organization dedicated to improving the lives and livelihoods of our policyholders, injured workers, team members, and the community. As a leading workers' compensation specialty insurer in the mid-Atlantic region, we take pride in being a force for good. Our 350 team members are committed to making a positive impact every day in the lives of all our stakeholders.

Join our motivated, professional team as we foster a culture of values, teamwork, innovation, and collaboration. Established in 1914, Chesapeake Employers Insurance, headquartered in Towson, Maryland, has over a century of experience, a strong financial foundation, and an "A" rating from AM Best.

This is a unique opportunity to join an organization as the leader responsible for shaping Chesapeake's operating model. This role sits at the center of how Chesapeake sustainably translates strategic and operational intent into focused action and impact.

A successful

Director of Strategic Operationswill help Chesapeake mature a disciplined, sustainable operating system for execution. Over time, success in this role will look like:

• Maintaining Growth System Standard Operating Procedures: playbooks, templates, tools, processes and communication materials.
• Ensuring the Growth System is understood, consistently applied, and continuously improved across the enterprise.
• Supporting leaders’ understanding of how the elements of the Growth System work together within Chesapeake’s operating model.
• Guiding the senior leadership team to prioritize Strategic Execution Wildly Important Goals (WIGs) aligned to enterprise strategy and scope WIGs into executable programs and projects within the 4DX model.
• Orchestrating delivery across the Strategic Execution WIG portfolio.
• Coaching leaders on 4DX operating model disciplines, including WIG design, scoreboard development, team kickoffs and syncs, and celebration rituals.
• Supporting team leaders in identifying, creating a backlog, prioritizing, and launching Focused Improvement WIGs that deliver targeted, measurable growth and improvement outcomes.
• Designing, maturing and running Chesapeake’s Enterprise Project Portfolio Council (EPPC) and overarching governance model that supports Growth System WIG capacity assessment, prioritization decisioning and execution coordination.
• Helping leaders assess team capacity, authority, resources, and focus needed to execute WIGs successfully.
• Providing executive leaders with clear visibility into progress, blockers, and capacity concerns.
• Helping teams see how their work connects to Chesapeake’s purpose and strategy.
• The Growth System becomes a trusted way of working.

Connects goals, priorities, and execution to a larger mission and helps others understand the impact of their work.

Builds trust, listens with curiosity, and helps teams navigate change with empathy and clarity.

Breaks down silos, fosters collaboration, and creates environments where teams succeed together.

Fosters curiosity, encourages experimentation and guides the organization to turn bold ideas into meaningful progress.

Join us and shape how Chesapeake sustainably translates strategic and operational intent into focused action and impact.

The Director of Strategic Operations is an enterprise-wide systems design and execution leader responsible for owning, sustaining and maturing the company’s operating model. Chesapeake Employers’ Growth System is the company’s Four Disciplines of Execution (4DX)-based operating model enabling Strategic and Focused Improvement (operational-level) execution to continuously and sustainably grow stakeholder value.

This role sits at the center of how Chesapeake sustainably translates strategic and operational intent into focused action and impact. The Director of Strategic Operations ensures that Wildly Important Goals (WIGs) are well-formed, appropriately prioritized…