Director of Strategic Operations

Chesapeake Employers' Insurance Company • Towson, MD

2d • $142,685 - $228,300 • Hybrid

About The Position

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. At Chesapeake Employers, we believe great strategy only creates value when it is consistently translated into focused execution. We are seeking a Director of Strategic Operations to serve as the enterprise steward of Chesapeake's Growth System; our Four Disciplines of Execution-based (4DX) operating model. Reporting directly to the President & CEO, this highly visible leadership role is responsible for owning, sustaining, and maturing Chesapeake’s operating model (The Growth System) enabling focused, enterprise-side strategic and operational execution. The Director of Strategic Operations will work closely with executive leaders and teams across the company to ensure priorities are clear, resources are aligned, and the organization's most important work moves forward. This is an opportunity for a systems designer, disciplined operator, and influential leader who thrives on creating clarity, building alignment, and driving execution in a collaborative environment. This leader will influence not only what Chesapeake achieves, but how it achieves it; helping make the Growth System the Chesapeake Way of working.

Requirements

• Bachelor’s degree in business, management, organizational leadership or related field required
• 5 to 8 years of hands-on experience in leading complex management systems design and execution
• Experience supporting management operating systems such as 4DX, Objectives & Key Results (OKRs), Hoshin Kanri, Lean, Agile, or similar strategy execution frameworks
• Experience creating repeatable management system SOPs, operating rhythms, playbooks, templates, and communications
• Experience program and project managing enterprise-wide strategic initiatives with executive engagement
• Experience facilitating governance bodies, meetings, and operating rhythms
• Experience coaching leaders and teams through change
• Experience building dashboards, scoreboards, status reports, or executive visibility tools
• Experience managing backlogs, prioritization processes, and cross-functional dependencies
• Familiarity with Microsoft tools and enterprise collaboration platforms

Nice To Haves

• Deep knowledge of the 4 Disciplines of Execution is a plus
• Certification in Agile, Lean, Six Sigma, change management, project management or related disciplines is a plus

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.
• 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.
• 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.
• 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.
• 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.
• Build confidence and consistency in the Growth System over time.

Benefits

• health, vision, and dental coverage
• a robust PTO plan
• an 8% employer contribution to retirement regardless of team member contribution
• educational assistance
• opportunities to participate in team member appreciation events
• STD, LTD and group life insurance 1X a team members salary
• free tickets to community attractions
• flexibility to thrive in a hybrid work environment
• opportunity to participate in development and volunteer programs

What This Job Offers

• Job Type: Full-time
• Career Level: Director