Senior Executive Assistant, Executive Operations

Grand Circle Corporation•Boston, MA

2d•$140,000 - $170,000•Hybrid

About The Position

Grand Circle Corporation is seeking an exceptional, technology-forward Senior Executive Assistant, Executive Operations to support its Chief Operating Officer (COO) and Chief of Staff within a highly collaborative Executive Office. This role goes beyond traditional executive assistance, requiring a blend of strong executive support, organization, business judgment, program and project management capabilities, executive communication skills, presentation development, and fluency with modern technology and AI. The ideal candidate will manage complex executive logistics while also contributing to higher-leverage operating work, such as transforming ideas into executive briefs, presentations, project plans, and communications. This position aims to enhance the effectiveness of the COO and Chief of Staff by creating clarity, protecting their time, accelerating high-quality work, and ensuring commitments are fulfilled. The role involves supporting day-to-day demands of the Executive Office and driving key priorities, operating rhythms, cross-functional follow-through, and select projects.

Requirements

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.
Ability to close loops, anticipate needs, use judgment without waiting for perfect direction, and rarely need to be reminded twice.

Nice To Haves

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

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 to make thoughtful decisions about executive time allocation.
Anticipate upcoming needs, conflicts, deadlines, and decisions and proactively address them.
Prepare concise meeting briefs, background information, outstanding questions, and desired outcomes.
Create systems to ensure commitments, decisions, and follow-ups are managed effectively.
Transform 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.
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.
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.
Use modern AI tools (e.g., ChatGPT, Claude, Microsoft Copilot) as everyday productivity tools for research, writing, analysis, meeting preparation, presentation development, and project planning.
Understand effective AI prompting, iteration, output verification, and confidential information protection.
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 effective use of modern tools and AI.