Senior Executive Assistant, Executive Operations

Senior Executive Assistant, Executive Operations

Reporting to: Chief Operating Officer & Chief of Staff

Department: Executive Office

Location: Boston, MA (Hybrid)

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

Executive Support & Effectiveness

• 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 follow-up.
• Build and maintain lightweight dashboards and tracking mechanisms for cross-functional priorities so progress, risks, and accountability are visible.
• Own select Executive Office projects end-to-end, including building the plan, coordinating stakeholders, tracking milestones and risks, and driving work through completion.
• Help prepare Executive Team meetings, leadership meetings, offsites, Board discussions, and other important forums.
• Coordinate across executives, leaders, and their teams to keep important work moving.

AI & Modern Ways of Working

• Use modern AI tools-including ChatGPT, Claude, Microsoft Copilot, and emerging platforms-as everyday productivity tools.
• Use AI to accelerate research, writing, analysis, meeting preparation, presentation development, project planning, and other Executive Office activities.
• Understand how to prompt effectively, iterate on AI-generated work, verify outputs, protect confidential information, and apply strong human judgment.
• Identify repetitive work that can be simplified, automated, or redesigned.
• Continuously test new technology and recommend better ways for the Executive Office to operate.
• Help the COO and Chief of Staff increase their own effective use of modern tools and AI.

Qualifications

• Exceptional organization and attention to detail combined with the pace and adaptability to operate in a fast-moving environment.
• Strong judgment and the confidence to determine when to act independently, when to push back, and when to escalate.
• Ability to navigate competing priorities between two senior leaders-and across the Executive Team-without requiring constant direction.
• Ability to listen to an executive talk through an idea and quickly create structure, clarity, and a high-quality first product from it.
• Excellent written and verbal communication skills.
• Demonstrated ability to create executive-quality presentations-not simply format slides, but build a compelling storyline.
• Strong program or project management capability, including plans, owners, dependencies, timelines, risks, and follow-through.
• Active and sophisticated user of modern AI and productivity tools.
• Intellectual curiosity and the ability to quickly learn new technologies, businesses, and ways of working.
• High standards for accuracy, discretion, confidentiality, and follow-through.
• Ability to comfortably interact with senior executives, external partners, and teams across the organization.
• Confidence to respectfully challenge, ask questions, and recommend a different approach when appropriate.
• Ability to remain calm, organized, and effective when priorities change quickly.
• Most importantly, this person closes loops. They anticipate rather than react, use judgment without waiting for perfect direction, and rarely need to be reminded twice.

Experience

We are intentionally open-minded about the traditional background of the person who fills this role. We expect approximately 8+ years of relevant experience, which could come from one or more of the following paths:

• Senior Executive Assistant or Executive Business Partner
• Executive Operations or CEO / Executive Office
• Program or Project Management
• Founder Associate
• Strategy or consulting
• Business operations or cross-functional transformation roles

Experience supporting senior executives is strongly preferred. Demonstrated judgment, learning agility, executive communication, project-management capability, and modern technical skills will be equally important.

What Success Looks Like

• The Executive Office has materially greater execution capacity and a stronger operating rhythm.
• Important commitments, dependencies, and follow-ups rarely fall through the cracks.
• Cross-functional priorities have clear owners, milestones, risks, and escalation paths.
• Meeting preparation and follow-up are consistently strong.
• Ideas move much faster from conversation to structured action.
• Executive presentations and communications improve in both quality and speed.
• AI and automation eliminate or significantly reduce repetitive Executive Office work.
• Select projects are independently driven from concept through completion.
• The Executive Office becomes more proactive, organized, and effective.

Total Rewards

The base salary range for this role is $140,000 - $170,000 annually for employees based in Boston, MA. Final compensation may vary and will be determined based on factors such as relevant experience, skills, internal equity, and geographic location. In addition to base pay, this role is eligible for an annual incentive bonus and first-class benefits, which include:

• Health & wellness: Comprehensive and heavily subsidized medical, dental, and vision plans, plus on-site gym access, holistic wellness sessions, and group fitness classes
• Time for you: Substantial Paid Time Off (PTO), and 11 paid holidays- including Juneteenth, Memorial Day, and Labor Day - and Summer Fridays. Plus- extensive parental leave, with up to 12-16 weeks paid leave at 100% base salary.
• Travel more, spend less: 50% off our trips for you and a companion, 25% for additional immediate family members, and exclusive quarterly associate travel deals
• Your future, secured: 401(k) with company match, life insurance, and disability coverage
• Continuous growth: Tuition assistance for both professional and personal development, opportunities for professional development through overseas travel, and direct access to Pinnacle Leadership & Team Development.
• Extra perks: Commuter benefits, FSA options, pet insurance, home & auto discounts, and paid volunteer time off to give back to the community

To learn more, please visit our websites at www.gct.com, www.oattravel.com and www.grandcirclefoundation.org.