Bryan Pennington
Doral,FL
Summary
Executive Assistant, Licensed Benefits Advisor, and Front Office Supervisor with 10+ years of experience providing senior-level administrative support, customer service, and operational leadership. Skilled in managing executive schedules, coordinating travel, handling confidential correspondence, and ensuring seamless operations in fast-paced environments. Licensed Florida 2-15 Life, Health & Variable Contracts Insurance Agent appointed with Aflac. Proactive, tech-savvy, and detail-oriented professional seeking to leverage extensive administrative and benefits experience in a fully remote Executive Assistant or Benefits Advisor role.
Overview
16
16
years of professional experience
1
1
Certification
Work History
Benefits Advisor (Licensed Agent)
Aflac
09.2025 - Current
- Licensed Florida 2-15 Life, Health & Variable Contracts Agent appointed with Aflac.
- Analyze / Evaluate employee benefits programs for businesses in the Miami region.
- Provide expert advice to clients on benefits options, compliance, and plan implementation.
- Develop and present benefit strategies tailored to client needs.
- Assist with open enrollment, employee communications, and ongoing account service.
- Work in hybrid capacity: field visits, office meetings, and remote consultations.
Front Office Supervisor (World of Hyatt Specialist)
Hyatt Place Miami Airport West/Doral
08.2023 - 01.2025
- Supported executive leadership with scheduling, reporting, and correspondence to streamline daily operations.
- Supervised front desk operations, ensuring smooth guest check-in and check-out processes.
- Balanced multiple priorities including guest relations, administrative tasks, and loyalty program coordination.
- Trained and supervised staff while optimizing scheduling and workflows to improve efficiency.
- Acted as liaison between executives, departments, and stakeholders to ensure service excellence.
Front Office Supervisor
CIRC Hotel
02.2018 - 01.2019
- Oversaw front desk operations for a luxury boutique hotel, frequently serving as acting department head.
- Created schedules, managed escalated issues, and coordinated directly with executives to maintain operational standards.
- Developed recognition and coaching programs to enhance staff performance.
Front Office Supervisor
Courtyard by Marriott Cadillac Miami Beach/Oceanfront
07.2016 - 09.2017
- Supervised 15–20 employees at a high-volume property, ensuring adherence to executive directives and company procedures.
- Managed cross-department communication and acted as escalation point for executive and guest concerns.
Night Auditor (Manager on Duty)
Holiday Inn
10.2015 - 07.2016
- Oversaw overnight hotel operations, acting as the executive point of contact for guests and staff.
- Balanced financial records and reconciled accounts for multiple revenue streams with accuracy and compliance.
Rooms Controller
Doral Golf Resort & Spa
12.2009 - 07.2013
- Allocated reservations and coordinated executive-level guest services for a 693-room luxury resort.
- Managed VIP requests, billing accuracy, and confidential information for dual management companies.
Education
Associate of Arts - Business Administration
Miami Dade College
Miami, FLAssociate of Science - Sign Language Interpretation
Miami Dade College
Miami, FLHigh School Diploma - Advanced Mathematics & Science
Ronald Reagan Doral Senior High School
Doral, FLSkills
- Executive Administrative Support & Calendar Management
- Travel Planning & Coordination
- Email & Inbox Management
- Customer & Client Relations
- Confidential Correspondence Handling
- Meeting Planning & Scheduling
- Process Evaluation & Improvement
- Team Training & Coaching
- Quality Assurance & Compliance
- Benefits Analysis & Employee Communications
- Proficiency in Google Workspace, Microsoft 365, Zoom, Opera, FSPMS/FOSSE, GuestWare, MEDALLIA
Certification
- Florida 2-15 Life, Health & Variable Contracts Insurance Agent License (Active)
- Appointed Benefits Advisor – Aflac, Miami Region
- Notary Public, State of Florida (Active)
- Cybersecurity Fundamentals, University of Miami (Completed)
Additional Experience
- Call Center Quality Assurance | Alorica, Miami Lakes, FL
- Reviewed calls, coached staff, and ensured compliance with service and communication standards.
- Executive Assistant to Owner | PhoneDoctor, Miami Shores, FL | 2022 – 2023
- Provided direct executive support to the business owner, managing calendars, scheduling appointments, and coordinating meetings.
- Drafted correspondence, drafted communications, and ensured timely follow-ups with clients and vendors.
- Managed travel arrangements, invoicing, and administrative workflows to streamline daily operations.
Timeline
Benefits Advisor (Licensed Agent)
Aflac
09.2025 - Current
Front Office Supervisor (World of Hyatt Specialist)
Hyatt Place Miami Airport West/Doral
08.2023 - 01.2025
Front Office Supervisor
CIRC Hotel
02.2018 - 01.2019
Front Office Supervisor
Courtyard by Marriott Cadillac Miami Beach/Oceanfront
07.2016 - 09.2017
Night Auditor (Manager on Duty)
Holiday Inn
10.2015 - 07.2016
Rooms Controller
Doral Golf Resort & Spa
12.2009 - 07.2013
Associate of Science - Sign Language Interpretation
Miami Dade College
High School Diploma - Advanced Mathematics & Science
Ronald Reagan Doral Senior High School
Associate of Arts - Business Administration
Miami Dade College
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