Business Support Specialist in South Portland, Maine at The Masiello Group

Overview:

The Masiello Group is committed to providing exceptional support to our real estate agents. The Business Support Specialist (BSS) is a cornerstone of that commitment. With 25+ offices across four states, this fast-paced and multifaceted role blends administrative support, technology troubleshooting, marketing coordination, and more.

You are the first face our clients and agents see—your professionalism and warmth will set the tone for the entire office. This role requires someone with a strong work ethic, exceptional organizational skills, and the ability to remain composed and productive amidst constant shifting priorities.

What We’re Looking For:

We value individuals who are proactive, solutions-focused, and dedicated to doing things the right way the first time. If you take pride in your work, enjoy organizing complex systems, and are driven by achieving excellence, you’ll thrive here.

This is a detail-heavy and knowledge-rich role that requires consistent learning, clear written and verbal communication, and an understanding that strong performance includes both day-to-day tasks and long-term growth. We’re looking for someone who takes initiative, thrives under responsibility, and consistently looks for ways to support the team. Flexibility to occasionally stay late to finish time-sensitive work is part of the expectation.

This in-person position will be based mainly in our South Portland office with one day in our Cape Elizabeth office, subject to business needs.

Candidates in the final stages of the interview process will be asked to provide three professional references.

We’re seeking someone who:

• Thrives in a support-focused role where helping others succeed is the primary mission
• Takes pride in doing things right the first time and never settles for "good enough"
• Has excellent written and verbal communication skills, including the ability to write and articulate professional, polished emails
• Is always willing to go the extra mile, including staying late to complete an important task when necessary
• Can juggle multiple responsibilities and requests with grace, accuracy, and follow-through
• Has a keen eye for detail and refuses to cut corners
• Is technically savvy with basic laptop/computer troubleshooting skills
• Presents themselves with professionalism, confidence, and a positive attitude
• Understands the importance of confidentiality, reliability, and showing up as a team player every day

Benefits of working at The Masiello Group:

• Paid time off
• Sick time
• Medical with company-paid HSA
• Dental and vision
• Parental Leave
• 401k with match
• And others!

Key Responsibilities

• Deliver high-level, reliable administrative support for the Sales Director and agents
• Serve as the primary liaison between the home office and agents, maintaining clear, timely, and professional communication
• Greet clients and advisors, manage inbound calls, schedule appointments, and oversee daily office operations
• Maintain office supplies and inventory, ensuring a clean, organized, and efficient work environment
• Handle sensitive and confidential information with the utmost discretion and integrity
• Manage listing data across platforms, coordinate signage logistics, and ensure timely listing updates and closures
• Support agents in using client transaction and lead management platforms and tech troubleshooting
• Track agent licensing status and manage renewal notifications
• Onboard and offboard agents from Masiello systems, ensuring seamless transitions and proper training on processes and tools
• Review listing and transaction documents for accuracy and completeness using digital back-office systems
• Enter and manage data in real estate accounting software with precision
• Collect and process escrow and closing commission checks
• Input/update listing information into the MLS system
• Update and distribute digital and print templated marketing materials using Canva
• Troubleshoot common tech questions on devices, printers, and laptops
• Provide both 1:1 and group training sessions—supporting agents at every knowledge level
• Take initiative, stay organized, and help create a smooth, efficient office environment

• Previous experience with Canva platform and social media/marketing
• Experience with Microsoft suite
• Excellent written and verbal communication skills
• Strong organizational skills and the ability to multi-task in a fast-paced, deadline driven environment
• Attention to detail, a must
• Ability to thrive in a team environment and work well with others
• Experience in the real estate industry, a plus