Director of Strategic Operations

Job Description Posted Tuesday, August 11, 2026 at 4:00 AM Who We Are 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. Why This Role Matters 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. What Success Looks Like A successfulDirector 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. Be a Part of Inspiring Chesapeake’s Values-Based Leadership Mindset: Purpose Driven Connects goals, priorities, and execution to a larger mission and helps others understand the impact of their work. People First Builds trust, listens with curiosity, and helps teams navigate change with empathy and clarity. Committed to Winning Together Breaks down silos, fosters collaboration, and creates environments where teams succeed together. A Risk Taker at Heart 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. Position Summary 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 and resourced, actively managed, and connected to the company’s strategic direction, Key Performance Indicators (KPIs) and annual business plan. They ensure the Growth System is not treated as an additional layer of work but becomes The Chesapeake Way of working to focus capacity, surface and address blockers, and achieve desired outcomes to continuously elevate tangible delivery of Chesapeake’s purpose to stakeholders. The Director of Strategic Operations does not primarily lead through formal authority. Instead, this person must lead through influence, clarity, structure, trust, and disciplined follow-through. They can constructively challenge thinking, influence senior leaders, facilitate challenging prioritization discussions, and establish alignment across varying priorities. They must be able to inspire and motivate others, help leaders understand the “why” and “how” behind the Growth System, and create the conditions for teams to sustainably improve the business solving important, challenging problems together. Duties and Responsibilities Serve as the enterprise owner and steward of Chesapeake’s Growth System. Maintain fidelity to the 4DX operating model, including WIG selection, lead and lag measures, scoreboards, team syncs, accountability rhythms, and celebrations. Ensure the Growth System is understood, consistently applied, and continuously improved across the enterprise Support leaders in understanding how the elements of the Growth System work together within Chesapeake’s operating model. Coordinate periodic refreshes of corporate-level KPIs and facilitate team-level KPIs development enterprise-wide via process management. Ensure that team-level KPIs and Focused Improvement WIGs are aligned with corporate-level KPIs. Monitor and ensure consistent reporting of KPIs and WIGs within Growth System channels. Maintain and update Growth System Standard Operating Procedures: playbooks, templates, tools, processes and communication materials. Strategic Execution Manage the Strategic Execution practices of the Growth System. Facilitate executive level decisioning to align priorities, resources, capacity and planning with enterprise strategy and operational targets. Manage the Strategic Execution portfolio and backlog scope and structure WIGs into executable programs and projects within the 4Dx model. Orchestrate delivery across the Strategic Execution WIG portfolio. Surface and guide resolution of risks, blockers, capacity constraints, and decision-making through the company’s governance framework. Operational Excellence & Focused Improvement Ensure leaders’ consistent adoption of Standard Operating Procedures. Coach leaders on 4DX operating model disciplines, including WIG design, scoreboard development, team kickoff, team syncs, and celebration rituals. Support team leaders in identifying, creating a backlog, prioritizing, and launching WIGs that deliver targeted, measurable growth and improvement outcomes. Guide leaders on identifying and moving appropriate Focused Improvement WIGs to and through the governance model. Maintain visibility of Focused Improvement WIGs, priority and capacity decisioning across the enterprise. Monitor the health of Focused Improvement WIGs without over-centralizing ownership of team-level work. Governance & Enterprise Alignment Design, mature, and run Chesapeake’s Enterprise Project Portfolio Council (EPPC) and overarching governance model that supports Growth System WIG capacity assessment, prioritization decisioning and execution coordination. Manage the enterprise-wide backlog of prioritized Strategic Execution and Focused Improvement WIG opportunities, ensuring they are aligned with and responsive to existing backlogs across governance bodies. Clarify enterprise-wide priority and capacity decision ownership and create feedback loops. Prepare materials for Enterprise Project and Portfolio Council (EPPC) meetings, including WIG prioritization decisions, in-flight WIG status, risks, blockers, capacity considerations, recommended decisions and measurement of return-on-investment. Ensure the right leaders have the right level of visibility into the right work at the right time. Create practices to minimize duplication, overcommitment, and misalignment across enterprise priorities. Assess Organizational Capacity Support leaders in distinguishing between availability and true capacity. Help leaders assess whether teams have the capacity, authority, resources, and focus needed to execute WIGs successfully. Identify where the organization may be overcommitted or where WIGs need to be narrowed, sequenced, paused, or escalated. Encourage disciplined prioritization so the Growth System strengthens focus rather than adding unmanageable work on top of the whirlwind. Serve as a champion and translator of the Growth System across the organization. Help leaders and teams understand why the Growth System matters and how it enables the organization to continuously and sustainably grow stakeholder value. Own, sustain, and mature enterprise-wide change management practices. Communicate in ways that are credible with executives, useful to team leaders, and accessible to team members. Facilitate conversations that surface resistance, clarify concerns, and move teams toward action. Surface learnings, recognize progress, and help teams celebrate wins. #J-18808-Ljbffr Chesapeake-Employers