The Role
Leads executive office operations and provides high-touch support to the President and Board. Oversees calendars, travel, governance, meetings, staff, budgets, vendors, facilities, and confidential communications. Coordinates enterprise projects and executive planning while establishing operating rhythms, metrics, and quality controls. Modernizes workflows through Microsoft 365, automation, and generative AI, ensuring secure and effective adoption.
Summary Generated by Built In
Job Summary & ResponsibilitiesPreferred Qualifications
- 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, escalate 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.
- 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.
Skills Required
- Bachelor’s degree in business administration, communications, health care administration, project management, or a related field, or equivalent education and directly related experience.
- Eight years of progressively responsible executive support, executive operations, business management, project management, or related experience.
- At least three years leading administrative or support staff.
- Exceptional executive-level written and verbal communication, strategic writing, editing, synthesis, presentation development, and audience adaptation skills.
- Ability to design and implement executive operating rhythms, project plans, governance processes, service standards, metrics, controls, and administrative systems.
- Advanced project and program coordination skills, including scope definition, work planning, milestone and dependency management, risk 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 confidential information handling.
- Understanding of health insurance or medical operations and the regulatory, member, provider, and community context of a health plan.
- Advanced proficiency with Microsoft 365, including Outlook, Word, Excel, PowerPoint, Teams, SharePoint, OneDrive, and collaborative document management.
- Ability to create polished executive and board-level PowerPoint presentations and administer virtual and hybrid meeting technologies.
- Experience applying automation and generative AI tools to improve productivity, content development, meeting preparation, knowledge management, and workflow efficiency while maintaining confidentiality, security, accuracy, and human review.
HMSA Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about HMSA and has not been reviewed or approved by HMSA.
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Healthcare Strength — Medical and dental coverage are described as solid, with preventive services and select zero‑cost features adding value in recent plan years. Employer-sponsored plans can have affordable premiums in certain groups and broad access options.
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Retirement Support — A 401(k) with company match and potential discretionary contributions forms a strong component of total rewards. Retirement support complements the core medical and dental package.
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Leave & Time Off Breadth — Paid holidays and PTO that increases with tenure provide meaningful time‑off flexibility. Time‑away benefits scale with service length.
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The Company
What We Do
The Hawaii Medical Service Association (HMSA), an independent licensee of the Blue Cross and Blue Shield Association, is a reliable name in Hawaii health care. Established in 1938, we are the largest and most experienced provider of health care coverage in the state. Over half of Hawaii’s population have chosen HMSA for their health care coverage. We are dedicated to providing quality, affordable health plans; employee benefit services; and worksite wellness programs. HMSA also offers a variety of programs, services and support to help improve the health and well-being of our members and community.
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