Executive Assistant

Administrative Assistant

Boston, Massachusetts and Newburyport, Massachusetts

The Administrative Assistant is primarily responsible for providing administrative support to management and other staff members of Cross Insurance for the region’s largest, high-profile accounts. In addition, this position supports the Sales and Service departments of Commercial Lines, Personal Lines and Benefits with business analytics and special projects. The position demands a high level of organization, customer service, excellent communication skills and strong working ability with Microsoft Office applications.

Duties of an Administrative Assistant include, but are not limited to:

Executive & Administrative Support

• Provide high-level administrative support, including complex calendar management, meeting coordination, and preparation of agendas and materials.
• Anticipate leadership needs by proactively preparing documentation, summaries, and follow-up actions.
• Track action items, deadlines, and operational priorities to ensure timely execution.
• Draft and manage internal communications on behalf of regional leadership.
• Serve as a primary point of contact for administrative matters directed to the Regional VP – Operations.

 Regional Operations Coordination

• Coordinate day-to-day operational initiatives across offices and departments.
• Identify workflow gaps, risks, and follow-up needs before escalation.
• Support office logistics, vendor coordination, and facilities-related matters as needed.
• Maintain organized shared document repositories and operational resources.

Data & Financial Oversight Support

• Maintain and enhance Excel-based tracking tools for expenses, revenue, new business, lost business, and net growth.
• Validate and reconcile data from multiple internal systems to ensure accuracy and consistency.
• Prepare performance summaries and dashboards for leadership review.
• Track regional budget performance and analyze variances between projected and actual results.
• Monitor pipeline activity and revenue trends, identifying risks and growth opportunities.
• Support development and tracking of operational action plans tied to margin and growth goals.

Project & Initiative Management

• Provide coordination support for regional projects, including acquisitions, integrations, training initiatives, and planning efforts.
• Track milestones, dependencies, and accountability to ensure forward progress.
• Support execution of regional performance and growth initiatives.

Performance Indicators

• Anticipation and responsiveness to leadership needs;
• Accuracy and reliability of financial and operational tracking;
• Quality of both written and oral communication;
• Timely execution of initiatives and action plans;
• Early identification of operational or financial risks; and
• Strength and usability of reporting tools.

Required Qualifications

• Bachelor’s degree in Business Administration or related field preferred
• 2+ years of experience in operations, office management, or senior-level administrative support
• Advanced proficiency in Microsoft Excel and other Microsoft platforms