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Chief of Staff

Hawaii Medical Service Association

Executive Strategy And Operations Lead

Support the President & COO in setting enterprise strategy, shaping organizational focus, and coordinating across business functions. Provide leadership and direction ensuring high priority corporate strategy initiatives are clearly scoped, well resourced, and executed with accountability and enterprise impact. Serve as a central orchestrator between strategy development and execution, partnering closely with the Enterprise Acceleration Office (EAO) to ensure alignment and integration. Translate strategic priorities into actionable plans with clear milestones, decision paths, interdependencies, and follow through mechanisms. Provide executives with decision ready insights, including financial, operational, strategic, and risk related perspectives. Identify and resolve misalignments, competing priorities, and execution bottlenecks across the enterprise.

Lead planning, agenda design, decision framing, and follow through for enterprise leadership forums. Ensure executives receive clear, concise, and integrated materials that synthesize cross functional perspectives. Facilitate intentional and meaningful connection points between the CEO, President & COO, CAO, and leaders across the organization. Maintain ongoing visibility into enterprise operations to proactively surface issues requiring executive attention.

Provide leadership and oversight ensuring the executive office operates with consistency, rigor, and enterprise first prioritization. Establish expectations and performance standards for executive office operations, workflows, and communication rhythms. Provide functional oversight of Executive Assistants (via the Manager, Executive Office), ensuring they operate as a coordinated, high trust team aligned to executive intent and strategic priorities. Ensure executive calendars, workflows, and administrative processes enable focus on the highest value enterprise priorities.

Coordinate development of enterprise incentive goals. Prepare high quality Board and committee materials integrating financial, operational, and strategic insights. Oversee board compensation policy and practices. Maintain governance discipline, accuracy, and timeliness across all board related workflows.

Partner with Enterprise Risk Management (ERM) to surface operational, financial, compliance, and strategic risks. Ensure executives have the data, context, and scenario analysis needed to evaluate risks and mitigation options. Integrate risk insights into enterprise strategy, operating plans, and leadership team discussions. Serve as an early detection point for organizational issues that may impede execution, alignment, or performance.

Reinforce leadership expectations, shared norms, and a culture of accountability and transparency. Ensure consistent and coordinated messaging from top executives. Facilitate intentional engagement between senior leaders and key stakeholders to strengthen cohesion and reduce silos. Foster trust and alignment across senior officers through structured communication routines and cross functional integration.

Lead high impact, cross enterprise initiatives requiring executive sponsorship and coordination. Represent the CEO, President & COO, and CAO as a delegate when appropriate to maintain momentum and continuity. Manage and negotiate sensitive contracts and executive level agreements on behalf of the President & COO and CAO, ensuring financial rigor, confidentiality, and alignment with enterprise goals. Navigate sensitive organizational, strategic, or personnel matters with discretion, sound judgment, and executive maturity.

Bachelor's degree and six years of related experience; or equivalent combination of education and experience. Three years of leadership experience.

Vacancy posted 4 days ago
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