Senior Executive Assistant, Executive Operations

Job Category: Associate

Requisition Number: SENIO
004502

• Posted :
  October 9, 2026
• Full-Time
• Hybrid

Showing 1 location

Boston, MA 02210, USA

Senior Executive Assistant, Executive Operations

Reporting to: Chief Operating Officer & Chief of Staff

Department: Executive Office

Position Summary

Grand Circle Corporation is the leader in international travel, adventure and discovery for Americans aged 50+. Headquartered in Boston MA, and with more than 35 offices globally, more than two million Americans have traveled with our award-winning travel brands:
Grand Circle Cruise Line, Overseas Adventure Travel and Grand Circle Travel.

We’re looking for an exceptional, technology-forward Senior Executive Assistant, Executive Operations to support our COO and Chief of Staff as part of a highly collaborative Executive Office.
This is not a traditional Executive Assistant role.

The ideal candidate combines outstanding executive support and organization with strong business judgment, program and project management capability, executive communication, presentation development, and fluency with modern technology and AI. This person will move comfortably between complex executive logistics and higher-leverage operating work: turning conversations, voice notes, rough ideas, or frameworks into executive briefs, compelling presentations, integrated project plans, communications, research summaries, and clear next steps.

This person will support both the COO and Chief of Staff, helping manage the day-to-day demands of the Executive Office while creating additional capacity to drive priorities, operating rhythms, cross-functional follow-through, and select projects. The core mandate is to make them both materially more effective by creating clarity, protecting time, accelerating high-quality work, and ensuring important commitments move from idea to completion.

Key Responsibilities

• Provide high-level executive support to both the COO and Chief of Staff, with exceptional discretion, judgment, and attention to detail.
• Own complex calendar management, travel planning, meeting coordination, expenses, and executive logistics.
• Understand priorities well enough to make thoughtful decisions about how executive time is allocated rather than simply scheduling requests.
• Anticipate upcoming needs, conflicts, deadlines, and decisions and proactively address them.
• Prepare concise meeting briefs, background information, outstanding questions, and desired outcomes.
• Create systems that ensure commitments, decisions, and follow-ups do not fall through the cracks.

Executive Communications & Presentations

• Turn conversations, notes, voice recordings, and rough concepts into structured executive communications and materials.
• Create compelling PowerPoint presentations from concept through final product, including storyline, structure, supporting content, and visual presentation.
• Draft and refine executive emails, leadership communications, meeting materials, talking points, and updates.
• Distill significant amounts of information into concise, decision-ready materials.
• Help the COO and Chief of Staff communicate complex ideas simply, clearly, and compellingly.

Executive Operations & Chief of Staff Partnership

• Partner closely with the Chief of Staff to maintain visibility into major priorities, commitments, decisions, and follow-ups.
• Drive alignment on complex, multi-stakeholder initiatives by tracking dependencies, owners, timelines, risks, and decisions across teams, and surfacing what requires executive attention.
• Maintain and continuously improve the Executive Office operating rhythm, including weekly and monthly reviews, leadership meeting preparation, offsite cadence, decision logs, and…