Executive Assistant to CEO – Business Development & Business Credit

Executive Assistant Trainee – CEO Support & Business Development

Company: D&J Properties
Location: Orlando / Davenport, Florida
Work Arrangement: Hybrid – Remote Work with Scheduled In-Person Activities
Job Type: Part-Time | Leadership Development Opportunity
Training Program: Six-Month Executive Assistant Academy
Executive Assistant Training Rate: $25.00 per hour beginning in Month 3, subject to successful transition requirements

About D&J Properties

D&J Properties is a growing, multi-service company specializing in property management, vacation rentals, hospitality management, residential and commercial cleaning, home services, and business development.

We work with property owners, real estate investors, business clients, and guests throughout Florida and select additional markets.

As our company continues to expand, we are seeking an ambitious, organized, dependable, and resourceful individual to join our executive team through our structured Six-Month Executive Assistant Training Academy.

This opportunity is designed for someone who wants more than a traditional administrative position. We are looking for an individual who enjoys learning how businesses operate, solving problems, building professional relationships, and helping executive leadership turn priorities into measurable results.

About the Position

The Executive Assistant Trainee will work directly with the Chief Executive Officer while developing skills across several areas of the company.

This is not an administrative-only position.

The selected candidate will receive structured training in executive operations, business development, lead generation, CRM management, Business Credit, hospitality, property management, networking, and company systems.

The ideal candidate is someone who can eventually become a trusted extension of executive leadership—helping protect the CEO's time, organize priorities, coordinate departments, communicate professionally, and ensure important assignments are completed.

Applicants with previous CRM, lead generation, appointment-setting, or executive administrative experience are strongly encouraged to apply and will receive priority consideration.

Key ResponsibilitiesExecutive Support & CEO Operations

• Assist with executive calendar management, appointments, meetings, reminders, and deadlines.
• Monitor and assist with company email, telephone communications, and correspondence.
• Research business matters and prepare information for executive decisions.
• Coordinate approved travel, business events, networking opportunities, and occasional field activities.
• Track executive priorities, assignments, and outstanding follow-up items.
• Prepare meeting agendas, notes, reports, and executive documents.
• Communicate with department managers regarding assigned projects and deadlines.
• Maintain confidentiality when handling company and client information.
• Anticipate upcoming executive needs and help the CEO remain organized and prepared.
• Help ensure that important tasks are completed rather than overlooked.

Business Development & Lead Generation

The first two months of the Academy emphasize lead generation and revenue development.

Responsibilities include:

• Complete D&J Properties' Lead Generation Specialist training and certification requirements.
• Learn and use HubSpot CRM and company sales pipelines.
• Make professional outbound prospecting calls to prospective clients.
• Conduct approved follow-ups by telephone, text, and email.
• Research property owners, real estate investors, business owners, and prospective clients.
• Qualify leads and schedule appointments.
• Maintain accurate CRM contact records, notes, tasks, and pipeline stages.
• Follow established sales scripts and communication procedures when appropriate.
• Track assigned activity and performance goals.
• Assist with property management, cleaning services, Business Credit, and other company growth opportunities.
• Participate in lead generation coaching, evaluations, and practical assignments.

Important: This position requires active participation in outbound prospecting and business development. Applicants must be comfortable communicating with prospective clients and learning sales-related responsibilities.

Business Credit & Client Support

• Complete training in D&J Properties' Business Credit programs and administrative processes.
• Assist with prospective Business Credit client inquiries.
• Coordinate consultations, appointments, and follow-up communications.
• Support approved student and client onboarding procedures.
• Maintain organized client records and progress tracking.
• Prepare information and documentation for executive consultations.
• Respond to routine administrative questions after completing appropriate training.
• Identify matters requiring executive review or escalation.
• Follow company confidentiality, documentation, and client communication procedures.

Networking & Professional Relationship Development

• Research local and virtual networking opportunities.
• Identify events involving real estate investors, Realtors, property owners, entrepreneurs, business professionals, and potential clients.
• Recommend relevant networking opportunities to the CEO.
• Assist with event registration, scheduling, and preparation.
• Attend selected networking events and company activities when assigned.
• Help organize new professional contacts and business opportunities.
• Enter appropriate contact information and follow-up activities into the CRM.
• Assist with maintaining professional relationships and identifying potential business partnerships.

Hospitality, Property Management & Company Operations

• Cross-train in D&J Properties' primary departments and business functions.
• Develop working knowledge of hospitality and property management operations.
• Learn owner onboarding, property evaluations, guest relations, and operational workflows.
• Become familiar with residential and commercial cleaning and home services coordination.
• Assist with cross-department projects, administrative assignments, and follow-ups.
• Help identify the appropriate department or manager responsible for an issue.
• Track assigned operational projects and deadlines.
• Support executive leadership in maintaining visibility across company activities.
• Recognize operational concerns and communicate them through established company procedures.

Systems & Technology

The Executive Assistant Trainee will receive training in company systems, including:

• HubSpot CRM
• Connecteam
• Microsoft Outlook and Microsoft Office
• QUO business communications
• ChatGPT and approved AI productivity tools
• Company dashboards, training portals, and internal systems

Candidates should be comfortable learning technology, maintaining accurate digital records, and using AI responsibly for research, drafting, organization, troubleshooting, and productivity.

Six-Month Executive Assistant Training Academy

The selected candidate will participate in a structured six-month professional development program while performing assigned responsibilities.

Months 1–2: Lead Generation, Sales & Revenue

Develop foundational skills in prospecting, professional communication, CRM management, lead qualification, appointment setting, sales follow-up, and business development.

Participants will complete required training, practical assignments, performance evaluations, and certification activities.

Month 3: Hospitality & Property Management Operations

Learn company hospitality standards, guest communications, owner relations, property management processes, home evaluations, and service coordination.

Begin transitioning into assigned Executive Assistant responsibilities after meeting applicable training and performance requirements.

Month 4: Business Credit & Student Support

Develop knowledge of Business Credit programs, client intake, administrative support, student coordination, consultation preparation, documentation, and follow-up procedures.

Month 5: Executive Operations & CEO Support

Focus on executive scheduling, communications, research, meeting coordination, project management, operational reporting, and cross-department follow-through.

Month 6: Live Executive Assistant Practicum & Certification

Apply acquired skills through supervised executive support assignments, real-world projects, independent problem-solving, and final competency evaluations.

The Academy includes training videos, company playbooks, systems instruction, practical assignments, assessments, and live work experience.

Successful completion of the Academy does not automatically guarantee certification, advancement, increased hours, or continued employment. Performance, reliability, communication, initiative, systems competency, and business needs are considered throughout the program.

Required Qualifications

• Strong organizational and time-management skills.
• Professional written and verbal communication.
• Comfortable speaking with prospective clients by telephone.
• Willingness to perform outbound calls, follow-ups, and appointment-setting activities.
• Ability to learn new technology and company procedures.
• Strong attention to detail and ability to maintain accurate records.
• Ability to manage multiple assignments and meet deadlines.
• Sound judgment, discretion, and respect for confidentiality.
• Ability to research unfamiliar problems and recommend practical solutions.
• Dependability, accountability, and willingness to accept coaching.
• Availability for required training, leadership meetings, and occasional in-person activities in Central Florida.

Preferred Qualifications

Candidates with demonstrated experience in one or more of the following areas will receive additional consideration:

• CRM software, particularly HubSpot, Salesforce, or similar platforms.
• Lead generation, outbound calling, sales, or appointment setting.
• Sales pipeline management, lead qualification, and customer follow-up.
• Executive assistance or senior-level administrative support.
• Office management, business operations, or team coordination.
• Hospitality, property management, or real estate.
• Business development, networking, or client relationship management.
• Business Credit or financial services administration.
• Entrepreneurship or small-business operations.
• AI productivity tools and digital workflow management.

Prior experience in every area is not required. However, applicants must demonstrate the willingness and ability to learn, follow through, and meet performance expectations.

What Makes a Strong Candidate?

We are looking for someone who is:

• Resourceful: Researches problems and identifies possible solutions before escalating routine matters.
• Proactive: Recognizes upcoming needs and takes appropriate initiative.
• Organized: Maintains accurate information and follows through on assignments.
• Professional: Communicates confidently with clients, team members, and business partners.
• Accountable: Takes ownership of assigned responsibilities and deadlines.
• Coachable: Welcomes feedback and applies new skills.
• Growth-Oriented: Wants to develop professionally and contribute to a growing company.
• Comfortable with Business Development: Understands that lead generation and relationship building are important parts of the position.

We especially value candidates who approach unfamiliar assignments with the mindset:

"Let me research this, determine what I can handle, and bring back a practical solution."

Schedule & Work Arrangement

This is a hybrid, part-time opportunity based in the Orlando/Davenport, Florida area.

The position includes remote work, scheduled virtual meetings, structured training, and occasional in-person business activities.

Expected scheduling:

• Month 1: Approximately 13 hours per week, including required leadership meetings.
• Month 2: Approximately 16 hours per week, including required leadership meetings.
• Months 3–6: Approximately 20 hours per week, subject to successful transition, training progress, and business needs.

Occasional in-person activities may include executive meetings, networking events, company training, and property visits.

Candidates must be able to attend scheduled meetings and complete assigned responsibilities within established deadlines.

Compensation & Advancement

This position follows a phased training and compensation structure.

Months 1–2: Lead Generation Specialist Training

During the initial training phase, compensation includes applicable pay for required training and meeting time, performance-based lead generation commissions, and any additional compensation required by applicable wage and hour laws.

The full initial-phase compensation arrangement, including commission terms, will be provided in writing before employment begins.

Months 3–6: Executive Assistant Training

Candidates who successfully complete the initial transition requirements are expected to move to an hourly rate of $25.00 per hour for authorized work while continuing their Executive Assistant Academy training.

The anticipated schedule following transition is approximately 20 hours per week.

Long-Term Growth

As D&J Properties expands, opportunities may become available for increased hours, additional executive responsibilities, advancement, and potential full-time employment.

Growth opportunities depend on performance, successful training, company needs, and available positions.

Why Join D&J Properties?

• Work directly with the CEO of a growing, multi-service company.
• Participate in a structured six-month leadership development program.
• Gain experience in executive operations, business development, hospitality, and property management.
• Develop practical CRM, sales, and professional communication skills.
• Learn about Business Credit programs and client support.
• Gain exposure to business networking and relationship development.
• Build experience coordinating projects across multiple departments.
• Pursue potential long-term career growth within the organization.

Our Standard

Protect the Time. Support the Vision. Help Drive the Growth.

If you are organized, ambitious, dependable, comfortable communicating with people, and interested in learning how a growing business operates, we encourage you to apply.

D&J Properties
BookDJProperties.com
800-684-0293

D&J Properties is an equal opportunity employer. Employment decisions are made without unlawful discrimination and in accordance with applicable law.

Pay: From $25.00 per hour

Benefits:

• Flexible schedule

Application Question(s):

• This Executive Assistant position begins with a structured training period. During Months 1–2, you will complete D&J Properties’ Lead Generation Specialist (LGS) training and will be compensated under the current LGS compensation and commission structure. The $25.00/hour Executive Assistant rate applies after successful completion of the training/certification requirements and formal transition into the EA role. Do you understand and agree to this compensation structure?

Answer: Yes / No

• The Executive Assistant role is expected to begin at approximately 20 hours per week once you formally transition into the position, with the opportunity for increased hours and eventual full-time employment based on performance, company growth, and business needs. Are you comfortable with this structure?

Answer: Yes / No

• Are you willing to complete D&J Properties’ structured six-month Executive Assistant Training Academy, which includes LGS/Sales, Hospitality & Property Management, Business Credit, Executive Operations, testing, and practical assignments?

Answer: Yes / No

• This is not an administrative-only Executive Assistant position. You will be expected to participate in outbound calls, lead follow-up, Business Credit support, networking, CRM management, research, and cross-department company operations. Are you comfortable performing these responsibilities?

Answer: Yes / No

• Are you comfortable making professional outbound calls, speaking with prospective clients, following scripts when appropriate, qualifying leads, and following up by phone, text, and email?

Answer: Yes / No

• Are you comfortable attending occasional in-person business meetings, networking events, property visits, or other company activities when scheduled in advance?

Answer: Yes / No

• Which areas do you have experience or knowledge in?

Select all that apply: Executive/Administrative Support; Sales/Lead Generation; Business Credit/Financial Services; Real Estate/Property Management; Hospitality; CRM Software; Networking/Business Development; Entrepreneurship/Business Ownership; AI/Productivity Tools; None of the Above.

• Tell us about a time you were given a problem without step-by-step instructions. What did you do to research the issue, determine a solution, and complete the task?

Answer: Written response

• The CEO is unavailable and a client contacts you with a question you have never handled before. Walk us through what you would do before deciding whether the issue needs to be escalated.

Answer: Written response

• Why are you interested in an Executive Assistant position that combines executive support, Business Credit, business development, networking, and company operations? What would you ultimately like to grow into professionally?

Answer: Written response

Work Location: Hybrid remote in Davenport, FL 33836

Salary : $25