High-level Executive Assistant

We’re looking for a high-level Executive Assistant who will serve as a trusted partner to our leadership team. This role goes beyond traditional administrative support; you will play a key role in keeping the business organized, aligned, and operating efficiently.

You will help manage priorities, improve systems, and ensure day-to-day operations run smoothly so leadership can focus on growth, strategy, and high-impact initiatives.

Compensation & Benefits

• Base Salary: $55,000 to $65,000
• Bonus Opportunities: Expected total compensation $80,000+ annually
• Additional benefits may include reimbursement for business-related expenses, professional development, and operational leadership coaching.
• Paid Time Off

$55,000 - $65,000

Executive Support & Priority Management

• Manage complex calendars, meetings, and shifting priorities for leadership
• Act as a gatekeeper and strategic partner to protect leaders’ time and focus
• Prepare materials, agendas, and follow-ups for meetings and key initiatives

Operations & Systems Optimization

• Build and refine systems that improve efficiency and organization
• Identify gaps and proactively create solutions to streamline workflows
• Leverage tools, automation, and AI to improve productivity

Project & Initiative Management

• Track and drive progress on key projects and business priorities
• Ensure accountability and follow-through across the team
• Coordinate cross-functional initiatives and communication

Communication & Coordination

• Serve as a central point of coordination between leadership and team members
• Ensure clear communication, alignment, and execution across projects
• Assist with internal documentation and process clarity

Business & Administrative Support

• Support reporting, tracking, and organization of key business metrics
• Assist with light financial tracking, expenses, and vendor coordination
• Help maintain structure across day-to-day business operations

• 3+ years of experience as an Executive Assistant, Operations Coordinator, or similar role
• Strong organizational and time management skills
• Proactive mindset with the ability to anticipate needs
• Experience building or improving systems and workflows
• Comfortable using technology, automation tools, and AI platforms
• Strong communication and interpersonal skills
• Ability to manage multiple priorities in a fast-paced environment
• High level of discretion and professionalism

What Success Looks Like

• Leadership operates with clarity, focus, and fewer day-to-day distractions
• Systems and workflows are streamlined and scalable
• Priorities are executed efficiently with strong follow-through
• The business runs more smoothly because of your support

The Harlan Group, powered by Keller Williams Fort Myers and The Islands, is a growing real estate organization committed to delivering an exceptional experience for both buyers and sellers. The team combines strong market knowledge, proven systems, and a commitment to client service to help clients make confident real estate decisions.

As the business continues to grow, the team is focused on building strong operational systems that support both production and scalability. The Director of Operations will play a key role in helping the organization grow efficiently while maintaining the high standards of service the team is known for.