Flexible Virtual Assistant Jobs in Springfield, MA

The Administrative Assistant provides high-level administrative and operational support to the EVP, Head of the Transformation & Delivery Office (TDO) and the broader leadership team. This role is responsible for helping the team operate efficiently by managing calendars, coordinating meetings and travel, preparing materials, organizing leadership routines, and supporting day-to-day administrative needs.

This individual will play an important role in helping to establish strong operating discipline for the TDO as the organization is built and scaled. The ideal candidate is highly organized, proactive, detail-oriented, and comfortable supporting senior leaders in a fast-paced, complex environment.

*The title and career band/level for this position are flexible based on the candidate's experience.

Key Responsibilities

Administrative Support

• Provide direct administrative support to the EVP, Head of the TDO, including calendar management, meeting scheduling, travel coordination, and day-to-day support.
• Anticipate scheduling conflicts and help prioritize meeting requests, leadership commitments, and time-sensitive issues.
• Prepare and coordinate materials for meetings, leadership discussions, and business reviews.
• Support follow-up actions, reminders, and tracking of key deliverables and commitments.
• Handle sensitive and confidential information with professionalism and discretion.

Leadership Team Support

• Provide administrative support for the broader TDO leadership team, including calendars, meetings, and operating routines.
• Organize leadership meetings, offsites, and working sessions, including agendas, logistics, materials, and follow-up items.
• Help ensure meetings are well prepared, efficient, and supported with the right documentation.
• Assist with cross-leadership scheduling and coordination across multiple stakeholders and functions.

Meeting & Event Coordination

• Coordinate internal and external meetings, including room reservations, virtual meeting logistics, catering, visitor coordination, and related support.
• Support planning and execution of team events, leadership offsites, and other organizational gatherings.
• Prepare meeting materials, distribute agendas and pre-reads, and capture follow-up items as needed.
• Help maintain smooth execution of recurring leadership routines and key organizational events.

Travel, Expenses & Administrative Operations

• Manage travel arrangements and related logistics for the EVP and as needed, members of the TDO leadership team.
• Prepare and submit expense reports in a timely and accurate manner.
• Support invoices, purchase requests, and other administrative items as needed.
• Maintain organized records, files, and administrative documentation.

Communications & Coordination

• Support internal communications and coordination on behalf of the EVP and leadership team.
• Help draft, format, and distribute communications, presentations, and other leadership materials.
• Serve as a reliable coordination point across leaders, teams, and partner functions.
• Help ensure requests, decisions, and follow-up actions are communicated and tracked appropriately.

Team & Organizational Support

• Support onboarding logistics for new team members, including scheduling, coordination, and administrative setup.
• Assist with organizational charts, distribution lists, team contact information, and other team administration needs.
• Help create a well-organized and professional operating environment for the TDO leadership team.
• Take on additional administrative and coordination responsibilities as the TDO evolves.

• Bachelor's degree preferred; equivalent experience acceptable.
• Minimum of 5 years of experience providing administrative support to senior executives and leadership teams.
• Experience in insurance, financial services, or another complex corporate environment is preferred.
• Demonstrated ability to manage complex calendars, competing priorities, and logistics in a fast-paced environment.
• Strong organizational skills, exceptional attention to detail, and proficiency in Microsoft Office and other business productivity tools.
• Excellent written and verbal communication skills.
• Professional, dependable, proactive, and able to work independently with sound judgment and discretion.
• Calm under pressure, collaborative, service and team oriented, and committed to strong follow-through.