Personal Assistant (Executive Level)
Leesburg, Winter Park, and Daytona Beach, FL
Personal Assistant (Executive Level)
Leesburg, Winter Park, and Daytona Beach, FL
About Red Apples Media
Red Apples Media is a creative force in marketing — mixing digital smarts, bold storytelling, and scroll-stopping content to help brands grow and stand out. We build strategies that drive results, content that actually converts, and relationships that last.
As a boutique agency, we wear a lot of hats — but we do it with pride, personality, and purpose. We collaborate closely, move quickly, and care deeply about the work we put into the world. Now we’re looking for an Executive-Level Personal Assistant to help our President stay focused, efficient, and two steps ahead — across multiple office locations and fast-moving priorities.
The Role
This full-time, in-office role is more than admin work. It’s about high-level support, organization, discretion, and making the machine run smoothly. You’ll be the right hand to the President of Red Apples Media, helping manage schedules, streamline communications, coordinate between offices, and keep both professional and personal tasks on track. Think of it as executive ops meets concierge-level service.
What You’ll Do:
Executive & Administrative Support
Manage calendars, appointments, meetings, and travel logistics for the President
Draft emails, reports, presentations, and client correspondence as needed
Handle time-sensitive and confidential information with extreme discretion
Act as a liaison between the President and clients, partners, and team members
Monitor key action items, reminders, and follow-ups to ensure nothing slips through the cracks
Office & Operational Coordination
Help manage day-to-day needs at all three office locations (Leesburg, Winter Park, Daytona Beach)
Coordinate office supplies, shipments, and vendor relationships
Assist with internal events, staff meetings, and special projects
Maintain a polished, organized office environment and support logistics for team functions
Personal & Lifestyle Logistics
Assist with occasional errands, reservations, and personal scheduling
Coordinate personal and professional travel, appointments, and calendar alignment
Offer flexible support as needed — with the same professionalism across all tasks
What We’re Looking For:
Proven experience in a similar executive or high-level support role
A+ organizational skills, with the ability to juggle multiple priorities gracefully
High discretion, integrity, and emotional intelligence
Professional communication skills — written and verbal
Proficiency in Google Workspace and Microsoft Office
Problem-solver mindset with a can-do attitude and keen attention to detail
Valid driver’s license and willingness to travel frequently between offices
Schedule & Travel Requirements:
This is a full-time, in-person role with regular travel required between our offices in Leesburg, Winter Park, and Daytona Beach. A reliable vehicle and flexible availability are essential.
Perks of the Role:
Direct exposure to executive decision-making and operations
High-impact role within a fast-growing marketing agency
Diverse projects and a no-two-days-the-same work environment
A supportive team that values loyalty, initiative, and discretion
Red Apples Media Offers:
Flexibility in hours as situations dictate – we believe in “Family First”
Eight (8) paid holidays
Generous time off based on longevity
Why Join Red Apples Media?
Be part of a collaborative, fast-paced team where no one hides behind job titles
Help grow a dynamic, mission-driven business that makes a real impact for clients
Gain exposure to every aspect of creative marketing and business operations
Work closely with the leadership team to shape agency growth and culture
Think You’re the One We’re Looking For?
We don’t want just another resume. We want to find the one person who thrives in chaos, thinks three steps ahead, and knows how to get things done with style, discretion, and speed.
If that sounds like you — and not just something you say in interviews — then we’ve got a challenge for you:
Click below to begin the Red Apples Media Personal Assistant Challenge.