Executive Assistant/Office Manager

THE ROLE

Legendary is looking for an exceptionally organized, proactive, and polished Executive Assistant & Office Manager to serve as the operational right hand to founder and CEO Tommy Breedlove and help keep the day-to-day rhythm of the Legendary organization running smoothly.

This is not a role for someone who simply waits for a list of tasks.

We are looking for someone who notices what needs to happen before being asked, keeps track of details others might miss, protects Tommy’s time and attention, and takes genuine ownership of making things easier, more organized, and more effective.

One moment may involve managing Tommy’s calendar and preparing him for an important meeting. The next may involve coordinating travel, communicating with a Legendary member, preparing materials for an event, organizing the office, or making sure a dozen small details are handled before anyone else realizes they needed attention.

The right person will become someone Tommy and the Legendary team can trust completely — with information, relationships, details, deadlines, and follow-through.

WHAT YOU’LL OWN

Executive Support

Administrative Support — Serve as the primary administrative partner to Tommy Breedlove, providing comprehensive administrative support including, but not limited to, scheduling, coordination, organization, documentation, and day-to-day executive needs.

Executive Calendar Management — Manage and protect Tommy’s calendar, including, but not limited to, meetings, calls, travel, speaking engagements, Legendary programs, events, and personal commitments that affect his schedule.

Task & Time Prioritization — Prioritize requests for Tommy’s time and attention, proactively identify competing priorities, and ensure his calendar and commitments remain aligned with the priorities of the business.

Meeting Preparation & Support — Prepare Tommy for meetings and engagements with the information, materials, schedules, and context he needs. Attend meetings when appropriate, take clear and actionable notes, document decisions and commitments, identify next steps, and ensure relevant information is communicated to the appropriate team members.

Travel Coordination — Coordinate and oversee travel logistics including, but not limited to, flights, accommodations, ground transportation, itineraries, reservations, schedule changes, confirmations, and other details necessary for seamless business and personal travel.

Project, Task & Follow-Up Management — Capture and manage action items, commitments, deadlines, and follow-up resulting from meetings, calls, events, and day-to-day conversations. Coordinate tasks across team members when appropriate, monitor progress, follow up on outstanding items, and help ensure projects and commitments move from conversation through completion.

Correspondence Management — Draft, coordinate, and manage correspondence on Tommy’s behalf when appropriate, including, but not limited to, emails, meeting follow-ups, introductions, confirmations, requests, and other professional communication.

Executive Gatekeeping — Serve as a trusted gatekeeper for Tommy’s time, attention, information, access, and resources. Exercise sound judgment in determining what requires Tommy’s direct involvement, what can be delegated or resolved independently, and what should be prioritized, deferred, or declined. Manage the flow of information to and from Tommy so he has the right information at the right time without unnecessary distraction. Protect confidential and sensitive information, appropriately manage access to Tommy and Legendary resources, and ensure requests are directed to the right person or solution whenever possible. This includes, but is not limited to, meeting and scheduling requests, introductions, communications, internal and external inquiries, information requests, member and partner needs, and the allocation of company time and resources. Maintain appropriate boundaries while representing Tommy and Legendary with warmth, discretion, professionalism, and sound judgment.

Office Management

Office readiness - Own the organization and daily readiness of the Legendary office which includes but is not limited to; maintaining office supplies, equipment, shipping, mail, vendors, subscriptions, and other operational needs.

Ensure the office is consistently organized, professional, welcoming, and prepared for members, guests, meetings, and team gatherings.

Vendor coordination - Coordinate vendors and service providers and follow through until issues are resolved.

File Management - Maintain organized digital and physical files, records, agreements, and important company information.

Process Improvement - Help establish and maintain simple systems that make the company easier to operate.

Legendary Member & Guest Experience

Legendary is built around relationships, and this role will often be one of the people behind the scenes making those relationships feel effortless.

Member support - Assist with communication and logistics for Legendary members, prospective members, speakers, partners, and guests.

Event Coordination - Help coordinate experiences connected to Legendary Live, The League, Inner Circle, masterclasses, retreats, events, and other programs.

Event Logistics - Manage details such as schedules, confirmations, gifts, materials, reservations, transportation, special requests, and follow-up.

Attendee and member experience - Know who is arriving, what they need, and what needs to happen next.

Professional excellence - Handle sensitive or high-level interactions with discretion, confidence, and genuine hospitality.

Meetings, Events & Special Projects

Coordinate internal meetings, leadership meetings, member gatherings, speaking engagements, and special events.

Prepare agendas, materials, presentations, meeting spaces, and other necessary resources.

Capture action items when needed and help ensure commitments move forward after meetings.

Work closely with vendors, venues, speakers, members, and team members on event logistics.

Take ownership of special projects that require organization, research, coordination, or persistent follow-through.

HOW YOU WORK

You anticipate.

You do not need someone to remind you three times that something needs to happen.

You are exceptionally organized but flexible enough to operate in an entrepreneurial environment where priorities sometimes change quickly.

You understand that protecting an executive’s time sometimes means saying no, rearranging priorities, or finding a better solution.

You communicate clearly and professionally.

You are comfortable interacting with successful entrepreneurs, executives, speakers, partners, and high-level clients without being intimidated or overly impressed by titles.

You understand discretion. You will have access to confidential business and personal information, and trust is non-negotiable.

You enjoy creating order.

And perhaps most importantly, when you say, “I’ve got it,” people know they no longer need to think about it.

WHAT WE’RE LOOKING FOR

The strongest candidate will bring:

• Experience supporting an executive, entrepreneur, business owner, or senior leader
• Exceptional calendar and scheduling management skills
• Strong written and verbal communication
• Excellent organizational skills and attention to detail
• Confidence managing multiple priorities simultaneously
• Strong judgment and the ability to make decisions independently
• High emotional intelligence and professionalism
• Comfort working with technology and learning new platforms quickly
• Experience coordinating travel, meetings, and events
• The ability to handle confidential information with absolute discretion
• A hospitality mindset and genuine desire to take care of people
• A bias toward action and follow-through

Experience in an entrepreneurial, consulting, events, hospitality, membership, or personal-brand-driven organization would be particularly valuable.

THIS ROLE IS PROBABLY NOT FOR YOU IF…

You need every task clearly assigned before taking action.

You prefer predictable days with very few interruptions.

You struggle when priorities change.

You consider something complete once you have sent the email rather than once the outcome has actually been achieved.

You are uncomfortable following up repeatedly when something needs to get done.

You dislike handling both high-level responsibilities and seemingly small details.

Or you believe being an Executive Assistant means simply managing a calendar.

At Legendary, the details matter.

WHAT SUCCESS LOOKS LIKE

Within the first several months, Tommy should spend significantly less time managing logistics, scheduling, administrative details, and follow-up.

The Legendary office should operate with greater consistency and organization.

Meetings and events should feel prepared rather than reactive.

Important commitments should be captured and completed.

Members and guests should experience thoughtful, seamless communication.

The details are handled, the priorities are clear, and Tommy and the Legendary team have more capacity to focus on the work only they can do.

ABOUT LEGENDARY

Legendary exists to help successful leaders build extraordinary lives — not simply successful careers.

Founded by bestselling author, speaker, and leadership expert Tommy Breedlove, Legendary works with entrepreneurs, executives, and leaders who have achieved significant professional success but know there is another level available to them personally, professionally, financially, and relationally.

Through experiences including Legendary Live, The League, Inner Circle, masterclasses, retreats, events, and private coaching, we challenge leaders to master themselves, lead intentionally, and create lives worthy of the success they have built.

Our work is personal. Our standards are high. Our community matters.

We believe how something is done matters just as much as whether it gets done.

And we are looking for someone who believes that too.

Pay: From $70,000.00 per year

Benefits:

• Dental insurance
• Health insurance
• Paid time off
• Professional development assistance

Work Location: In person

Salary : $70,000