Executive Assistant COO

This is not a traditional administrative role. The Executive Assistant to the COO serves as a trusted force multiplier protecting the executives time extending his reach across a complex multi-entity operation and ensuring the right things get done by the right people at the right time. Equal parts strategic operator and personal logistics expert this person handles everything from high-stakes board communications to monitoring a flights departure status before the COO even thinks to check.

The ideal candidate thinks two three and four steps ahead. They anticipate needs before they are voiced surface problems before they become crises and operate with the discretion and judgment required of someone trusted with sensitive business strategy family enterprise dynamics and personal matters alike.

What this role is not: If your goal is to manage calendars and book travel this is not the right fit. The COO needs someone who is energized by complexity capable of operating with significant autonomy and wired to think ahead rather than wait to be asked.

Scope of the Role

The COO oversees a fourth-generation wholesale insurance MGA/brokerage a resort and marina operation in the Bahamas and a marina in Charleston while managing board relationships active capital projects technology modernization programs and strategic planning across multiple business entities. This role supports him across all of it.

Core Responsibilities

1 Anticipatory Support & Time Protection

The single most important function of this role is staying ahead of the COOs world so that he is never caught off guard by something that was knowable. This means:

Monitoring upcoming travel logistics proactively flight status connections ground transportation weather and contingencies and flagging issues before they are asked about

Reviewing the upcoming weeks calendar each Monday and ensuring every meeting has necessary briefing materials context and preparation completed in advance

Tracking key deliverables commitments and deadlines across the COOs agenda and surfacing items at risk of slipping before they become problems

Knowing the COOs priorities well enough to make real-time judgment calls about what is urgent what can wait and what needs to be escalated immediately

2 Calendar & Schedule Management

Own the COOs calendar with strategic intent not just scheduling but protecting deep work time building in preparation windows before key meetings and avoiding overcommitment

Manage conflicting priorities and guard against time fragmentation; push back when the schedule is not working

Coordinate meeting logistics end-to-end: agendas attendees materials room or video setup and follow-up

3 Communications Management

Filter and triage all inbound communications calls correspondence and determine priority; handle route or hold as appropriate

Draft high-quality written communications on behalf of the COO including board correspondence executive memos partner and vendor communications and internal leadership messaging

Ensure the COOs voice and intent are accurately represented in all outbound communications; know when to write it and when to bring it to him

Represent the COO with professionalism and discretion in all external interactions

4 Operational & Project Coordination

Act as a project coordinator on COO-led initiatives: track milestones coordinate across teams follow up with owners and keep work moving

Attend leadership and board meetings; capture decisions and action items; distribute notes and follow up with owners to ensure commitments are met

Hold the COOs organizational commitments visible and accountable escalate gaps professionally when deliverables are not on track

Prepare briefing materials talking points decision summaries and board prep packages as needed

5 Travel & Logistics

Manage all corporate and personal travel end-to-end: flights hotels ground transportation itineraries and contingency plans for the COO and family as needed

Proactively monitor travel plans for disruptions and have solutions ready before being asked

Coordinate logistics for company events leadership offsites board dinners and corporate functions from start to finish

Maintain awareness of the COOs personal schedule cadence (hunting and fishing trips cycling events family travel) and coordinate logistics accordingly

6 Personal & Family Support

Handle personal errands returns and scheduling matters with the same efficiency and discretion as business matters

Coordinate family travel personal reservations and event logistics as requested

Assist with household-adjacent tasks that arise from time to time vendor coordination personal appointments and similar

Maintain full confidentiality on all personal and family matters; this is non-negotiable

7 Information & Document Management

Maintain organized systems for contracts licensing documents correspondence and executive records

Create and manage spreadsheets presentations reports and general business correspondence as needed

Ensure the COO has the right information at the right time not too much not too late

Education & Experience

Prior experience in a high-accountability EA role is a strong differentiator

Exposure to insurance financial services real estate or hospitality is a plus but not required

Skills & Attributes

Exceptional written and verbal communication able to write and speak credibly on behalf of a senior executive

Advanced proficiency in Microsoft Office Suite (Word Excel PowerPoint Outlook); comfort with project tracking tools (Smartsheet Asana or similar) and comfort using AI tools (Claude Chat etc)

High emotional intelligence reads the room builds trust quickly handles sensitive situations with care and composure

Proactive and self-directed doesnt wait to be told what to do next; anticipates and acts

Organized but not rigid able to build systems while adapting when priorities shift

Discreet and trustworthy handles confidential personal legal financial and succession-related information at the highest level

Comfortable managing up and across able to hold senior leaders and team members accountable to commitments professionally

Willing and able to travel and work flexible hours as business and personal needs require