Executive Assistant

The Mission of This Role 🎯

Protect the Founder’s time, attention, and energy so he can remain focused on the highest-value activities of the organization.

The Executive Assistant will take ownership of four primary areas:

Email . Phone. Calendar. Problems.

Success means fewer interruptions, fewer unnecessary decisions, a cleaner calendar, faster communication, and significantly less administrative work reaching the Founder.

Primary Responsibilities
📧 1. Executive Email & Inbox Management

Take primary responsibility for managing the Founder’s business email inbox.

Responsibilities include:📋

✅Review and organize incoming email throughout the business day.
✅Identify messages requiring immediate executive attention.
✅Separate important communication from routine requests and low-priority correspondence.
✅Respond to routine email s on the Founder’s behalf when appropriate.
✅Draft responses for executive review when personal involvement is required.
✅Delegate requests to the appropriate team member.
✅Follow up with employees, vendors, carrier representatives, clients, and business partners.
✅Archive, organize, flag, and categorize messages.
✅Maintain outstanding follow-up items so important communication does not fall through the cracks.
✅Reduce the number of email s the Founder personally needs to review or respond to.

Goal: The Founder should spend as little time as reasonably possible managing his own inbox.

📞 2. Phone Call & Voi cemail Management

Serve as the first line of defense for incoming calls and voi cemail s.

Responsibilities include:📋

✅Screen incoming business calls when appropriate.
✅Review missed calls and voi cemail s.
✅Determine the urgency and appropriate next action.
✅Return routine calls or coordinate responses when authorized.
✅Route callers to the appropriate member of the Legacy Insurance Group team.
✅Schedule calls requiring the Founder’s involvement.
✅Provide concise summaries before important callbacks.
✅Protect the Founder from unnecessary interruptions and unsolicited calls.

The Executive Assistant should become skilled at determining:

Does Sean actually need to handle this—or can I solve it, delegate it, or route it somewhere else?

📅 3. Executive Calendar Management

Own and protect the Founder’s calendar.

Responsibilities include:📋

✅Schedule and coordinate internal and external meetings.
✅Confirm appointments and meeting logistics.
✅Prevent unnecessary meetings from consuming executive time.
✅Resolve scheduling conflicts.
✅Create appropriate buffers between meetings.
✅Reschedule appointments when priorities change.
✅Ensure the Founder has the necessary information before important meetings.
✅Coordinate meetings with employees, vendors, carrier representatives, clients, recruits, and strategic partners.
✅Maintain dedicated time for strategic work and other high-priority responsibilities.
✅Anticipate scheduling issues before they become problems.

The calendar should reflect the Founder’s priorities—not simply other people's requests for his time.

🔥 4. Handle Small Problems Before They Become Big Problems

A major responsibility of this position is preventing minor operational issues from unnecessarily reaching the Founder.

When a problem arises, the Executive Assistant should first ask:

Can I solve this?

If not:

Who on the team can solve this?

Only issues that genuinely require executive authority, judgment, or involvement should be escalated.

Examples may include:📋

✅Coordinating with vendors.
✅Following up on outstanding requests.
✅Tracking down missing information.
✅Resolving scheduling conflicts.
✅Coordinating communication between team members.
✅Researching solutions to minor operational problems.
✅Following up with carrier representatives.
✅Handling routine administrative requests.
✅Identifying the appropriate person to own an issue.
✅Making reasonable decisions within established authority.
✅Ensuring delegated tasks actually get completed.

We want someone who does not simply report problems.

We want someone who solves problems.

Additional Responsibilities

The Executive Assistant may also assist with:📋

✅Preparing meeting agendas and executive summaries.
✅Tracking important commitments and deadlines.
✅Coordinating travel arrangements and itineraries.
✅Preparing documents and presentations.
✅Maintaining confidential executive information.
✅Conducting basic research.
✅Following up on delegated projects.
✅Coordinating recruiting interviews and candidate scheduling.
✅Organizing leadership meetings.
✅Maintaining executive task lists.
✅Documenting recurring processes.
✅Identifying opportunities to automate or delegate repetitive administrative work.
✅Supporting special projects assigned by the Founder.

What Success Looks Like

Within the first several months, the right person should create a noticeable reduction in the amount of administrative work reaching the Founder.

Success will look like:🏆

✅The executive inbox is consistently organized and under control.
✅Important email s receive timely responses.
✅Routine email s are handled without executive involvement.
✅Missed calls and voi cemail s are screened and appropriately routed.
✅The Founder receives concise summaries rather than having to investigate issues himself.
✅The calendar is organized around strategic priorities.
✅Low-value meetings and interruptions are reduced.
✅Minor problems are solved independently.
✅Delegated tasks are followed through to completion.
✅Important commitments do not fall through the cracks.
✅The Founder spends substantially more time on strategy, leadership, recruiting, systems, sales, marketing, relationships, and organizational growth.

Who We Are Looking For🔍

The ideal candidate is someone who is:

🥇Highly Organized

You naturally create order from chaos and can manage many moving pieces without losing track of details.

🥇Proactive

You don't wait to be told every next step. You anticipate what needs to happen and take action.

🥇Resourceful

When you encounter something you don't know, your instinct is to figure it out.

🥇Decisive

You are comfortable making reasonable decisions without constantly seeking approval.

🥇An Excellent Communicator

You communicate clearly, professionally, and concisely with executives, employees, clients, vendors, and business partners.

🥇Discreet

You understand that working directly with a Founder means having access to confidential business and personal information.

🥇Persistent

If someone owes you an answer, document, confirmation, or deliverable, you follow through until it gets done.

🥇Comfortable With Technology

You can quickly learn communication platforms, calendars, CRM systems, automation tools, AI tools, and other business software.

🥇Calm Under Pressure

When several things happen at once, you prioritize instead of panic.

🥇Ownership-Oriented

You don't say:

"Nobody got back to me."

You say:

"It wasn't resolved, so I followed up, found the right person, and got it handled."

The Most Important Question in This Role🎯

Before bringing something to the Founder, ask:

“Does this truly require the Founder’s time, authority, or judgment?”

If the answer is no, take ownership of getting it resolved.

If the answer is yes, bring the issue forward with the relevant information and a recommended solution.

Instead of:

“Sean, we have a problem. What do you want me to do?”

We prefer:

“Sean, here's the situation. I looked into it and see two options. I recommend Option A because of X. Unless you disagree, I'll move forward with that.”

Qualifications🥅

Preferred qualifications include:

✅3+ years of Executive Assistant, Administrative Assistant, Office Management, Operations, or similar experience.
✅Experience directly supporting a Founder, CEO, President, or senior executive strongly preferred.
✅Excellent written and verbal English communication skills.
✅Strong email and calendar management skills.
✅Excellent attention to detail.
✅Strong judgment and problem-solving ability.
✅Ability to prioritize competing demands.
✅Comfortable communicating with senior-level business professionals.
✅Experience working with Microsoft Outlook and Microsoft 365 preferred.
✅Familiarity with CRM and business communication systems is helpful.
✅Strong proficiency with modern AI and productivity tools is a plus.
✅Insurance experience is helpful but not required.

Our Culture

Legacy Insurance Group operates with a high-performance mentality.

We believe in:

🎯Taking 100% Ownership — Own the outcome, not the excuse.

🎯Making Decisions — Gather the information, make the best decision available, and move forward.

🎯Continuous Improvement — Get 1% better every day.

🎯Thinking Big — Look beyond today's problem and consider how the organization can operate better tomorrow.

🎯Being Resourceful — Find answers and solutions instead of waiting for instructions.

🎯Teamwork — The organization wins when everyone executes their role at a high level.

🎯Never Giving Up — Persistence and resilience are part of who we are.

Why This Role Matters

As Legacy Insurance Group grows, the Founder & Chief Risk Officer must increasingly focus on responsibilities that cannot easily be delegated:

✅Strategic vision and business planning
✅Recruiting and developing exceptional talent
✅Building scalable systems and processes
✅Sales and marketing strategy
✅Developing strategic relationships
✅Leadership and culture
✅Identifying new opportunities for growth

Every hour spent sorting email s, listening to routine voi cemail s, coordinating calendars, chasing information, or solving minor administrative problems is an hour that cannot be invested in those responsibilities.

Your job is to give those hours back.

The right Executive Assistant will become one of the most trusted and valuable people in the organization—not simply by helping the Founder accomplish more, but by progressively reducing the number of things that require his involvement.

The Ultimate G