Executive Assistant (HR & Legal)

Advantage Insurance; San Juan (PR); On-site; USD 42,000 - 64,000; Full time

Job summary

Advantage Insurance seeks an experienced Administrative Assistant to support executives and optimize daily operations in San Juan, Puerto Rico. You will manage calendars, coordinate meetings and travel, and oversee cross-functional initiatives with discretion.

The ideal candidate is bilingual in English and Spanish, highly organized, capable of independent work, and a collaborative team player who maintains audit-ready records and efficient processes.

Qualifications

• Bachelor’s or associate’s degree in Business Administration, Office Management, or related field (or equivalent experience).
• 3–5 years of administrative or office support experience in corporate or fast-paced environments.
• Proficiency in Microsoft Office (Outlook, Word, Excel).
• Proven calendar management, scheduling, and meeting coordination skills.

Responsibilities

• Manage and prioritize executive calendars and align schedules with priorities.
• Coordinate meeting logistics, prepare materials, and track action items with follow-up.
• Provide advanced administrative support to leadership and cross-functional initiatives.
• Liaise with internal and external stakeholders, handling communications discreetly.
• Prepare, analyze, and maintain reports and tracking tools for decision-making.

Skills

Bilingual English/Spanish

Strong organizational skills

Prioritization

Independent work

Team player

Relationship building

Adaptability

Accountability

Judgement & discretion

Education

Bachelor’s or Associate degree in Business Administration/Office Management

Tools

Microsoft Office

Job description

Job Overview

Provides administrative and operational support to leaders and teams by coordinating schedules and meetings, preparing and organizing information, supporting communications and logistics, maintaining records, and helping ensure efficient day‑to‑day operations.

Job Responsibilities

• Manage and prioritize executive calendars, exercising independent judgment to align schedules with strategic priorities.
• Coordinate and oversee meeting logistics, including preparation of materials and follow‑up, ensuring alignment with leadership objectives. Independently track, assess, and follow up on key action items, escalating risks or delays and recommending solutions as appropriate.
• Provide advanced administrative and operational support to leadership, including coordination of cross‑functional initiatives.
• Serve as a key liaison for internal and external stakeholders, exercising discretion in managing communications and resolving issues on behalf of leadership.
• Prepare, analyze, and maintain reports and tracking tools used to support operational, compliance, or management decision‑making.
• Develop and maintain document management systems and processes to support audit readiness, compliance, and operational efficiency.
• Plan and manage complex domestic and international travel, assessing cost, timing, and business impact. Review, prepare, and monitor expense reporting, ensuring compliance with company policies and flagging discrepancies as needed.
• Coordinate visitor and stakeholder engagements, exercising discretion and professionalism in representing the company.
• Oversee office operations activities, including vendor coordination and process improvements, within established guidelines.
• Manage and curate shared resources and administrative tools to improve efficiency and consistency across teams.
• Lead or support special projects with minimal supervision, independently managing timelines, priorities, and stakeholder communication.

Skills And Qualifications

• Fluency in English and Spanish, both written and spoken
• Strong organizational skills with high attention to detail
• Ability to prioritize tasks and manage multiple deadlines simultaneously
• Ability to work independently and follow through on assignments with minimal supervision
• Team player who collaborates well across departments
• Build and maintain strong working relationships across internal and external stakeholders
• Adapt to changing priorities, processes and organizational needs with flexibility and professionalism
• Proactively anticipate needs and identify issues early to support efficient office and executive operations
• Exhibit strong sense of accountability, ownership, and follow‑through on assigned responsibilities
• Exercise sound judgement and discretion when handling confidential and sensitive information

Job Requirements

• Bachelor’s or associate’s degree in Business Administration, Office Management, a related field or equivalent work experience will be considered in lieu of a formal degree
• 3–5 years of administrative or office support experience, preferably in a professional, corporate, or fast‑paced environment
• Proficiency in Microsoft Office (Outlook, Word, Excel required)
• Proven experience with calendar management, scheduling, and meeting coordination