Senior Executive Assistant, Executive Operations

Grand Circle•Boston, MA

1d•Hybrid

About The Position

Grand Circle Corporation is seeking an exceptional, technology-forward Senior Executive Assistant, Executive Operations to support its COO and Chief of Staff within a highly collaborative Executive Office. This role goes beyond traditional executive assistance, requiring strong business judgment, program and project management skills, executive communication, presentation development, and proficiency with modern technology and AI. The ideal candidate will manage complex executive logistics while also contributing to higher-leverage operating work, such as developing executive briefs, presentations, project plans, and communications. The core objective is 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 seen through to completion.

Requirements

Exceptional organization and attention to detail.
Pace and adaptability to operate in a fast-moving environment.
Strong judgment and confidence to act independently, push back, or escalate appropriately.
Ability to navigate competing priorities between two senior leaders and across the Executive Team.
Ability to listen to an executive's idea and quickly create structure, clarity, and a high-quality first product.
Excellent written and verbal communication skills.
Demonstrated ability to create executive-quality presentations with a compelling storyline.
Strong program or project management capability, including plans, owners, dependencies, timelines, and risks.
Active and sophisticated user of modern AI and productivity tools.
Intellectual curiosity and 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 different approaches.
Ability to remain calm, organized, and effective when priorities change quickly.
Proven ability to close loops, anticipate needs, use judgment without perfect direction, and require minimal reminders.
Approximately 8+ years of relevant experience, potentially from paths such as Senior Executive Assistant, Executive Business Partner, Executive Operations, CEO/Executive Office Program or Project Management, Founder Associate, Strategy or consulting, or Business Operations/cross-functional transformation roles.
Demonstrated judgment, learning agility, executive communication, project-management capability, and modern technical skills.

Nice To Haves

Experience supporting senior executives is strongly preferred.

Responsibilities

Provide high-level executive support to the COO and Chief of Staff, exercising discretion, judgment, and attention to detail.
Manage complex calendar scheduling, travel arrangements, meeting coordination, expense reporting, and executive logistics.
Proactively anticipate needs, conflicts, deadlines, and decisions, and address them.
Prepare concise meeting briefs, background information, and desired outcomes.
Create systems to ensure commitments, decisions, and follow-ups are tracked and completed.
Transform conversations, notes, voice recordings, and rough concepts into structured executive communications and materials.
Create compelling PowerPoint presentations from concept to final product, including storyline, structure, content, and visual design.
Draft and refine executive emails, leadership communications, meeting materials, talking points, and updates.
Distill large amounts of information into concise, decision-ready materials.
Partner closely with the Chief of Staff to maintain visibility into priorities, commitments, decisions, and follow-ups.
Drive alignment on complex, multi-stakeholder initiatives by tracking dependencies, owners, timelines, risks, and decisions.
Maintain and improve the Executive Office operating rhythm, including reviews, meeting preparation, offsites, and decision logs.
Build and maintain dashboards and tracking mechanisms for cross-functional priorities.
Own select Executive Office projects end-to-end, including planning, stakeholder coordination, milestone tracking, and driving work to completion.
Prepare for Executive Team meetings, leadership meetings, offsites, and Board discussions.
Coordinate across executives, leaders, and their teams to ensure work progresses.
Utilize modern AI tools (e.g., ChatGPT, Claude, Microsoft Copilot) for productivity, research, writing, analysis, meeting preparation, presentation development, and project planning.
Identify repetitive work for simplification, automation, or redesign.
Test new technology and recommend improvements for Executive Office operations.
Assist the COO and Chief of Staff in effectively using modern tools and AI.