Full Time Insurance Executive Assistant Jobs (NOW HIRING)

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+ Benefits include Medical, Dental, Vision, Tuition Reimbursement, Pet, and Legal Insurance

+ 401k
+ Community Service Day

+ Spotlight Awards

+ National Sales Excellence Awards

+ CFSP Prep Certification Program

POSITION SUMMARY:

• The Executive Assistant reports to the Executive Assistant to the CEO

• This position is based in Mansfield, Massachusetts
• Regular in-office presence is expected, with the specific schedule determined by business needs and the executives supported.
• Travel may be required to support leadership meetings, conferences, and company events.
• Flexibility outside standard business hours may occasionally be necessary based on executive travel, event schedules, and time-sensitive business needs.
• Full-Time

The Executive Assistant provides high-level administrative and operational support to multiple executive-level leaders across the organization. Reporting to the Executive Assistant to the CEO, this position will help ensure consistent, coordinated, and high-quality executive support while assisting with complex travel arrangements, leadership meetings, and company events.

The ideal candidate is highly organized, resourceful, discreet, and comfortable balancing the needs of multiple executives whose schedules and priorities may change frequently. Success requires strong judgment, attention to detail, professionalism, and the ability to anticipate needs in a fast-paced, evolving environment.

ESSENTIAL FUNCTIONS & RESPONSIBILITIES: 

Executive Support

• Provide comprehensive administrative support to multiple executive-level leaders.
• Manage complex and frequently changing calendars, including meetings, appointments, travel, and competing priorities.
• Proactively identify scheduling conflicts, recommend solutions, and ensure executives are prepared for upcoming commitments.
• Draft, review, and format correspondence, presentations, meeting materials, reports, and executive communications.
• Prepare and submit timely and accurate expense reports in accordance with company policies.
• Track executive priorities, commitments, deadlines, and follow-up items to support accountability and timely execution.
• Handle confidential and sensitive information with the highest degree of discretion and professionalism.

Travel Planning and Coordination

• Coordinate complex domestic and international travel arrangements for executives, including air and ground transportation, accommodations, dining reservations, and other logistics.
• Develop detailed travel itineraries and proactively address scheduling, timing, and destination-specific requirements.
• Monitor travel plans and provide timely support when disruptions, cancellations, or last-minute changes occur.
• Coordinate group travel for leadership meetings, conferences, and company events.
• Ensure travel arrangements align with company policies, budgets, and executive preferences.
• Reconcile travel expenses and maintain appropriate documentation.

Meeting and Event Planning

• Plan and coordinate executive meetings, leadership conferences, town halls, off-site meetings, and company events.
• Manage event logistics, including venue selection, contracts, accommodations, transportation, catering, audiovisual needs, room setup, agendas, and attendee communications.
• Partner with internal teams and external vendors to ensure events are delivered professionally, on time, and within budget.
• Prepare agendas, presentations, pre-read materials, attendee lists, and other meeting resources.
• Attend or support events as needed to oversee logistics, troubleshoot issues, and ensure a positive attendee experience.
• Capture key decisions and action items and coordinate follow-up after meetings and events.
• Track event budgets, invoices, contracts, and vendor commitments.

Communication and Relationship Management

• Serve as a professional point of contact between executives and employees, customers, vendors.
• Manage incoming requests and communications, using sound judgment to prioritize, respond, redirect, or escalate matters appropriately.
• Build strong working relationships across functions, business units, and levels of the organization.
• Partner closely with the Executive Assistant to the CEO and other administrative professionals to coordinate executive calendars, travel, meetings, and events.
• Provide backup support to other administrative professionals as needed.

Operational and Project Support

• Assist with special projects, research, data gathering, presentations, and other business initiatives.
• Develop and maintain administrative processes, files, contact lists, organizational materials, and shared resources.
• Identify opportunities to improve efficiency, communication, and coordination across the executives and teams supported.
• Help establish and maintain consistent executive support practices across the organization.

COMPETENCIES:

• Executive presence and professional judgment
• Confidentiality and discretion
• Travel and event coordination
• Organization and attention to detail
• Prioritization and time management
• Proactive problem-solving
• Adaptability and composure
• Relationship building and collaboration
• Communication and follow-through
• Service-oriented mindset

QUALIFICATIONS & EXPERIENCE:

• Associate’s or bachelor’s degree preferred, or an equivalent combination of education and relevant experience.
• Minimum of five years of progressively responsible administrative experience, including direct support of senior executives.
• Demonstrated experience supporting multiple executives with competing priorities.
• Experience coordinating complex domestic and international travel.
• Demonstrated experience planning executive meetings, conferences, off-site sessions, or company events.
• Advanced proficiency in Microsoft Outlook, Word, PowerPoint, Excel, and Teams.
• Strong written and verbal communication skills.
• Exceptional organization, time management, and attention to detail.
• Demonstrated ability to exercise independent judgment, solve problems, and maintain confidentiality.
• Ability to work effectively with limited supervision and adapt quickly to changing business needs. 

Success Measures

Success in this position will be demonstrated through:

• Effective management of multiple executives’ schedules, priorities, and commitments.
• Seamless execution of executive travel, meetings, and company events.
• Consistently accurate, timely, and high-quality work.
• Strong executive and stakeholder confidence in the support provided.
• Proactive identification and resolution of scheduling, communication, and operational needs.
• Professional handling of confidential and sensitive information.
• Strong coordination with the Executive Assistant to the CEO and broader administrative team.

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