Executive Assistant to the CEO

Executive Assistant to the CEO

About Working at the Eastern States Exposition

The Eastern States Exposition—home of the iconic The Big E—is more than a fairground. It is a year-round organization dedicated to celebrating New England’s culture, agriculture, business, and community. Located in West Springfield, the Exposition brings together millions of visitors annually through events, educational programs, and one of the largest fairs in North America.

Working at the Eastern States Exposition means being part of a mission-driven organization that preserves regional traditions while creating experiences that bring people together. Team members play a role in producing world-class events, supporting agricultural heritage, and delivering memorable experiences for guests from across the country.

Job Description

Position Summary

The Executive Assistant to the Chief Executive Officer provides high-level administrative, operational, and strategic support to the CEO and Executive Office. This role serves as a trusted partner to the CEO, ensuring seamless daily operations, proactive coordination, and clear communication across the organization.

The ideal candidate is highly organized, adaptable, calm under pressure, and acts as a safeguard for the CEO’s time, energy, and priorities. This person can operate independently, anticipate needs, and work collaboratively as part of a leadership team. Absolute discretion, sound judgment, and strong interpersonal skills are essential.

Key Responsibilities

Executive Support & CEO Partnership

• Serve as a trusted, strategic gatekeeper for the CEO, managing access, priorities, and sensitive information.
• Manage complex calendars, schedules, travel, and communications with foresight and precision.
• Anticipate CEO needs, proactively identify issues, and take initiative to resolve problems before they escalate.
• Act as a strategic thought partner to the CEO, keeping him informed of key organizational concerns, developments and deadlines.
• Handle a wide variety of ad hoc, time-sensitive requests with professionalism and flexibility.

Executive Office Operations & Administration

• Oversee day-to-day operations of the Executive Office, serving as ambassador of the Brooks Building and ensuring efficiency and organization.
• Maintain comprehensive and well-organized filing systems, trustee records, and executive documentation.
• Screen mail, calls, emails, and requests, prioritizing appropriately and responding on behalf of the CEO when needed.
• Review and sign weekly accounts payable checks and verify accuracy prior to approval.

Board, Trustee & Committee Support

• Serve as primary liaison to the Board of Trustees across six New England states.
• Coordinate quarterly Board meetings, including agendas, board packets, logistics, minutes, and follow-up action tracking.
• Manage scheduling of all Committee meetings, take minutes, distribute and follow-up on action items.
• Organize and support six regional trustee meetings annually, including communications, attendance tracking, and documentation.
• Maintain professionalism and confidentiality in all Board-related interactions.

Meetings, Communication & Follow-Through

• Prepare agendas, attend key meetings, take detailed minutes, and distribute follow-up documentation promptly.
• Track commitments, deadlines, and action items to ensure accountability and follow-through.
• Serve as a central communication hub between the CEO, Board members, senior leadership, internal teams, and external stakeholders including elected officials.

Events, Travel & Special Projects

• Coordinate executive travel and oversee the organization’s travel program.
• During the 17-day Big E Fair, manage guest passes, social receptions, accommodations, and the CEO’s itinerary.
• Support special projects and organizational initiatives as assigned.

Professionalism, Adaptability & Teamwork

• Remain calm, resourceful, and solutions-oriented in high-pressure or rapidly changing situations.
• Balance independent decision-making with strong collaboration across departments.
• Demonstrate a strong work ethic, flexibility in hours and responsibilities, and a “no task too small” mindset.
• Contribute to a positive, respectful, and high-performing leadership culture.

Qualifications & Traits

Experience & Skills

• Proven experience supporting a CEO or senior executive in a fast-paced, complex environment
• Exceptional organizational, communication, and prioritization skills
• Strong attention to detail with the ability to manage multiple priorities simultaneously
• High level of discretion, integrity, and emotional intelligence
• Advanced proficiency with office technology and productivity tools

Personal Attributes

• Highly protective of the CEO’s time, priorities, and confidentiality
• Calm under pressure; thrives in unpredictable, high-demand environments
• Self-directed, proactive, and comfortable making independent decisions
• Strong team player who builds trust and credibility across all levels of the organization
• Flexible, adaptable, and willing to handle ad hoc responsibilities

Job Type: Full-time

Pay: $60,000.00 - $100,000.00 per year

Work Location: In person