Manager, Executive Office & Operations

Hawaii Medical Service Association; Honolulu (HI); Hybrid; USD 68,000 - 133,000; Full time

Job summary

Hawaii Medical Service Association in Honolulu seeks a Manager, Executive Office and Executive Operations to provide high-touch support to the President, coordinate governance, and lead the Executive Office team.

This role requires strategic calendar management, complex project oversight, budget awareness, and the use of AI tools to boost productivity while maintaining confidentiality and security. Reporting to the Chief of Staff, you will interface with board members and executives.

Qualifications

• Bachelor's degree or equivalent with eight years' executive support/operations experience.
• Eight years progressively responsible executive support and staff leadership experience.
• Excellent written and verbal communication, including board materials.
• Ability to design operating rhythms, governance, and metrics.
• Advanced project coordination, risk management, and issue escalation.
• Knowledge of budget planning, procurement, and vendor coordination.
• Understanding of health plan operations and regulatory context.
• Ability to create polished executive and board presentations and manage meetings.
• Experience applying automation and AI tools to improve productivity.

Responsibilities

• Provide high-touch executive support to the President and Chief of Staff.
• Strategically manage complex calendars and travel.
• Prepare briefing materials, agendas, and presentations.
• Coordinate executive travel and meetings, including logistics.
• Lead executive office staff and establish service standards.
• Develop and administer the Executive Office operating budget.
• Oversee governance processes and board materials.

Skills

Executive communication

Strategic writing

Calendar management

Board governance

Project management

Budget and expenses

Microsoft 365

Presentation development

AI productivity tools

Education

Bachelor's degree in business administration, communications, health care administration, project management, or related field

Tools

PowerPoint

Outlook

SharePoint

Teams

Excel

Job description

Pay Range: $68,000 - $133,000, position is eligible for an incentive bonus

Note: Individuals typically begin between the minimum to middle of the pay range

The Manager, Executive Office and Executive Operations serves as the lead executive operations partner for the Office of the President and provides direct, high-touch, anticipatory support to the President. Reporting to the Chief of Staff, this role integrates support the the executive office including; personal executive support, collaboration to implement enterprise planning, staffing of board and governance operations, implementation of project management, leadership communications, travel and event execution, and day-to-day business management of the Executive Office.

The position leads and develops the Executive Assistant team, manages Executive Office resources and operating practices, and ensures the President is consistently prepared with the time, information, materials, logistics, and follow-through needed to advance organizational priorities. The role exercises substantial independent judgment, handles highly confidential matters, anticipates needs and risks, and acts as an extension of the President and Chief of Staff with internal and external stakeholders.

This role acts as the primary operational liaison between the Executive Office, Chief of Staff, senior leaders, Board members, and key internal and external stakeholders and handles complex, sensitive, and time-critical projects and responsibilities as directed by the Chief of Staff or President.

Minimum Qualifications

• Bachelor's degree in business administration, communications, health care administration, project management, or a related field; or an equivalent combination of education and directly related work experience.
• Eight years of progressively responsible executive support, executive operations, business management, project management, or related experience, including at least three years leading administrative or support staff.
• Exceptional executive-level written and verbal communication skills, including strategic writing, editing, synthesis, presentation development, and adaptation of complex content for board, executive, employee, and external audiences.
• Demonstrated ability to design and implement executive operating rhythms, project plans, governance processes, service standards, metrics, controls, and efficient administrative systems.
• Advanced project and program coordination skills, including scope definition, work planning, milestone and dependency management, risk and issue escalation, decision tracking, and executive reporting.
• Working knowledge of budget planning, forecasting, expense management, purchasing, vendor and contract coordination, and workforce administration.
• Knowledge of board and committee operations, executive protocols, records and information management, and handling of highly sensitive and confidential information.
• Understanding of health insurance or medical operations and the regulatory, member, provider, and community context in which a health plan operates.
• Advanced proficiency with Microsoft 365 applications, including Outlook, Word, Excel, PowerPoint, Teams, SharePoint, OneDrive, and collaborative file-sharing and document-management practices.
• Demonstrated ability to create polished executive and board-level PowerPoint presentations and to administer virtual and hybrid meeting technologies.
• Practical experience applying automation and generative AI tools to improve executive office productivity, content development, meeting preparation, knowledge management, and workflow efficiency, with appropriate attention to accuracy, confidentiality, security, and human review.

Duties and Responsibilities

• Executive Partnership and Anticipatory Support
  • Provide comprehensive, high-touch executive support to the President, serving as a trusted partner who anticipates needs, independently resolves issues, protects executive focus, and ensures readiness for each commitment.
  • Strategically manage a complex and rapidly changing calendar by evaluating business priority, urgency, stakeholder impact, preparation requirements, travel time, and adequate transition and break time.
  • Prepare complete briefing materials for meetings and engagements, including agendas, biographies or background information, decision points, talking points, presentations, directions, transportation details, and required follow-up.
  • Manage complex executive travel and itineraries, including air and ground transportation, lodging, meeting coordination, contingency planning, and real-time support when schedules change.
  • Provide responsive support outside standard business hours when required by executive, board, travel, event, or urgent business needs.
  • Draft, edit, and coordinate sensitive executive correspondence, presentations, talking points, reports, briefing documents, and strategic communications for internal and external audiences.
• Board and Governance Operations
  • Provide administrative and operational support for the Board of Directors and its committees and subcommittees in partnership with the Chief of Staff, executive leadership, Legal, and other accountable functions.
  • Coordinate annual calendars, agendas, board and committee materials, secure portal submissions, meeting logistics, executive preparation, action tracking, and post-meeting follow-through.
  • Maintain governance records, deadlines, and decision or action-item tracking with a high degree of accuracy, confidentiality, and judgment.
  • Plan and execute board, executive, and leadership meetings or offsites, including venue selection, budgets, contracts, participant communications, materials, technology, transportation, meals, and on-site support.
• Executive Office Leadership, Human Resources, and Financial Management
  • Lead, supervise, coach, and develop Executive Office staff, including Executive Assistants supporting senior officers; establish service standards, performance expectations, development plans, workload allocation, and backup coverage.
  • Manage Executive Office workforce activities in partnership with Human Resources, including selection, onboarding, goal setting, performance management, development, compensation recommendations, succession and coverage planning, and employee relations support within assigned authority.
  • Develop and administer the Executive Office operating budget; forecast expenses, monitor actuals, process and approve invoices within delegated authority, manage vendors and contracts, and identify resource and cost-management opportunities.
  • Oversee business office operations, facilities coordination, supplies, records, access, visitor protocols, and service standards to ensure a professional, secure, and highly responsive Executive Office.
  • Create a consistent operating model, standard work, metrics, and quality controls for executive support across the senior leadership team.
• Enterprise Project Management and Executive Planning
  • Lead and coordinate cross-functional projects and special initiatives sponsored by the President, Chief of Staff, or other Senior Leaders, establishing scope, work plans, milestones, dependencies, risks, decision points, and accountability for deliverables.
  • Maintain integrated action, decision, risk, and deadline tracking; proactively identify issues, escalation barriers, and drive timely follow-through across senior leaders and project teams.
  • Coordinate the forward-looking executive planning calendar for the organization, anticipating annual governance cycles, strategic planning, operating reviews, major communications, community engagements, and other enterprise milestones.
  • Prepare concise executive status reports, decision briefs, dashboards, and meeting materials that synthesize complex information and enable timely decisions.
  • Assist in planning and execution of executive, board, and leadership offsites and other high-profile events, from objectives and agenda design through logistics, budget, vendor management, and after-action follow-up.
• Digital Transformation and Operational Excellence
  • Lead modernization of Executive Office workflows through responsible adoption of HMSA approved AI-enabled productivity and generative AI tools, automation, shared workspaces, templates, and standardized practices.
  • Establish and sustain effective use of Microsoft 365, including Outlook, Word, Excel, PowerPoint, Teams, SharePoint, OneDrive, and collaborative file-sharing practices to improve access, version control, communication, and continuity.
  • Develop high-quality executive and board presentations in PowerPoint, translating strategic concepts, operating information, and recommendations into clear, audience-appropriate narratives and visuals.
  • Assess administrative processes and service delivery, identify opportunities for simplification and automation, and lead change management, training, adoption, and continuous improvement.
  • Establish appropriate protocols for security, confidentiality, records management, and human review when using collaboration, automation, and AI-enabled tools.
• Performs all other miscellaneous responsibilities and duties as assigned or directed.

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