ABOUT THE ROLE
We are seeking a highly capable, technology-forward Executive Assistant who can operate across multiple businesses and serve as the administrative and operational right hand to a busy entrepreneur and business owner.
This is not a traditional administrative assistant position.
- The primary objective of this role is simple: Protect the executive's time by taking ownership of administrative work, communication, scheduling, follow-up, coordination, and execution.
- The ideal person is highly organized, comfortable communicating with executives and customers, technologically advanced, sales-minded, resourceful, and capable of working independently.
- You will work across multiple businesses involving multifamily real estate/property management, mortgage lending, real estate investing, consulting/education, sales, and marketing. You must be comfortable switching between companies, priorities, software platforms, and responsibilities throughout the day.
CORE RESPONSIBILITIES
1. EXECUTIVE EMAIL MANAGEMENT
The goal is for the executive to spend as little time as possible managing email.
- Monitor multiple business email accounts.
- Organize and prioritize incoming communications.
- Identify what actually requires the executive's attention.
- Respond directly to routine emails when appropriate.
- Draft responses for executive approval when a personal response is necessary.
- Delegate emails and requests to the appropriate team member.
- Follow up on unanswered requests.
- Track commitments and deadlines created through email.
- Maintain an organized inbox and filing system.
- Reduce unnecessary email traffic and interruptions.
The executive should primarily see emails requiring a decision, approval, expertise, or personal response - not everything that enters the inbox.
2. CALENDAR & SCHEDULE MANAGEMENT
Own and protect the executive calendar.
- Schedule and reschedule meetings.
- Coordinate with clients, partners, employees, vendors, lenders, borrowers, and prospects.
- Prevent unnecessary meetings and protect focused work time.
- Create Zoom meetings and distribute invitations.
- Confirm appointments and prepare agendas or relevant materials.
- Identify scheduling conflicts before they become problems.
- Build travel and preparation time into schedules.
Coordinate personal and business calendars - You should be comfortable making reasonable scheduling decisions without requiring approval for every appointment.
3. MEETING MANAGEMENT & EXECUTION
Meetings should produce actions and results - not simply notes.
- Create and manage Zoom meetings.
- Prepare agendas and attend selected meetings.
- Take organized notes and use AI meeting tools when appropriate.
- Identify decisions, responsibilities, deadlines, and action items.
- Enter tasks into project-management systems.
- Assign action items to responsible team members.
- Distribute meeting summaries.
- Follow up until assigned items are completed.
A meeting is not complete when the Zoom call ends. It is complete when the resulting actions have been communicated, assigned, and tracked.
BUSINESS SUPPORT
BLACKSAND PROPERTY MANAGEMENT / MULTIFAMILY REAL ESTATE
Assist with administrative and operational coordination involving multifamily apartment communities.
- Property management administrative support.
- Vendor and team coordination.
- Tracking operational issues.
- Preparing reports and communications.
- Following up with property managers and team members.
- Organizing documents.
- Assisting with resident, owner, lender, and vendor communications.
- Using property-management software including AppFolio and EliseAI.
- Maintaining accurate property and business information online.
- Research and miscellaneous operational projects.
Real estate or property-management experience is beneficial but not required for a highly trainable candidate.
MORTGAGE OPERATIONS & ORIGINATION SUPPORT
Assist with mortgage origination and administrative responsibilities. You will gradually learn to:
- Navigate mortgage origination software.
- Assist with loan files.
- Request and organize borrower documentation.
- Track outstanding documents and conditions.
- Follow up with borrowers, real estate agents, title companies, and other parties.
- Assist with loan applications and file setup.
- Understand basic mortgage qualification concepts.
Executive Assistant Opportunity | Page 2 Learn basic Conventional, FHA, VA, and USDA lending concepts.
- Assist with mortgage prospecting and sales follow-up.
- Maintain CRM and prospect information.
- Help ensure loan files continue moving forward.
Mortgage experience is highly desirable but not required if the candidate demonstrates exceptional ability to learn regulated processes.
SALES & BUSINESS DEVELOPMENT
This is not purely a behind-the-scenes administrative position. The Executive Assistant must be comfortable communicating directly with prospects and clients.
- Answer and make phone calls.
- Follow up with leads and prospects.
- Schedule sales appointments.
- Maintain CRM information.
- Follow up after meetings.
- Re-engage older prospects.
- Assist with mortgage and Wheelbarrow Profits sales activity.
- Communicate professionally with business owners, investors, borrowers, real estate agents, vendors, clients, and partners.
You should sound confident, energetic, personable, and professional on the phone.
MARKETING COORDINATION
You will help coordinate another assistant responsible for social media and content execution.
- Help maintain the marketing calendar.
- Coordinate content deadlines.
- Provide direction and follow-up.
- Review work for completion and accuracy.
- Help turn ideas, meetings, videos, and business activities into potential content.
- Maintain accurate information across Facebook, Instagram, LinkedIn, Zillow, Google Business Profile, and other platforms.
- Understand basic branding, lead generation, sales funnels, and social media marketing.
- Help ensure marketing initiatives are actually implemented and completed.
You do not need to be the company's primary content creator, but you must understand marketing well enough to help
manage and coordinate the process.
AI & AUTOMATION LEADERSHIP
This is an extremely important part of the position. We are not looking for someone who is afraid that AI will replace their job.
We want someone who uses AI to dramatically increase what they can accomplish.
You should actively use and learn platforms such as ChatGPT, Claude, EliseAI, AI meeting assistants, AI research and writing tools, workflow automation platforms, and emerging AI applications relevant to our businesses.
- Stay informed about emerging AI capabilities.
- Identify repetitive tasks that can be automated.
Build or help implement AI-powered workflows.
- Create reusable prompts, templates, and processes.
- Connect AI with existing business systems where practical.
- Use AI for research, summarization, meeting preparation, communication, data organization, and process improvement.
- Train other team members on effective AI workflows when appropriate.
- Continuously evaluate new technology that could improve efficiency.
AI should make you more valuable, not less necessary. We want someone constantly asking: "How can we make this faster, simpler, automated, delegated, or unnecessary?"
PERSONAL EXECUTIVE SUPPORT
The position will also assist with personal administrative responsibilities when needed.
- Travel research and itinerary creation.
- Booking flights, hotels, transportation, and activities.
- Scheduling personal appointments.
- Bill payment coordination.
- Researching purchases and services.
- Making reservations.
- Coordinating personal scheduling.
- Calling businesses and service providers.
- Conducting research.
- Handling miscellaneous errands that can be completed remotely.
Confidentiality and discretion are mandatory.
SOFTWARE & TECHNOLOGY
Candidates should be technologically confident and able to learn new software quickly. Platforms may include:
- Monday.com
- Slack
- Zoom
- Google Workspace
- Microsoft 365
- AppFolio
- Mortgage origination software
- CRM platforms
- ChatGPT
- Claude
- EliseAI
- Zillow
- Google Business Profile
- Facebook
- Instagram
- LinkedIn
- AI and automation platforms
You are not expected to know every platform on day one. You ARE expected to be the type of person who can learn a new platform without needing someone to walk you through every button.
WHAT WE ARE LOOKING FOR
ORGANIZATION & EXECUTION
- Meet deadlines and respond promptly during working hours.
- Follow through without repeated reminders.
- Keep track of details and manage multiple companies and projects simultaneously.
- Understand priorities and recognize what is urgent versus what can wait.
- Take ownership instead of simply identifying problems.
- Work independently and follow projects through completion.
COMMUNICATION
- Excellent written and verbal communication skills.
- Comfort communicating with customers, borrowers, real estate agents, investors, business owners, executives, vendors, employees, prospects, and business partners.
- Professional but personable - not robotic.
- Lively, confident, and capable of carrying a conversation with prospects, clients, and business partners.
RESOURCEFULNESS
We want someone who attempts to solve problems before asking the executive what to do.
Instead of: "What do you want me to do about this?" We prefer: "Here's what happened. I researched it. These are our options. I recommend option B for these reasons. Unless you disagree, I'll handle it."
The ability to research, think independently, make recommendations, and execute is critical.
BUSINESS JUDGMENT
- Sales
- Marketing
- Customer service
- Real estate
- Multifamily property management
- Mortgage lending
- Business operations
- Basic financial concepts
- AI and automation
- Project management
THE STANDARD FOR THIS POSITION
Executive Assistant Opportunity | Page 51. HANDLE IT - If you have the authority and information necessary, complete it. Do not unnecessarily send work back to the executive.
2. DELEGATE IT - If another team member should handle it, assign it, communicate expectations, and follow up. Delegation does not mean forgetting about it.
3. AUTOMATE IT - If something repeatedly consumes time unnecessarily, determine whether technology, systems, or AI can eliminate or reduce the work.
4. ESCALATE IT - Bring something to the executive only when his decision, expertise, authority, relationship, or personal involvement is genuinely necessary. When escalating an issue, provide the relevant information and, whenever possible, a recommended solution.
THE ULTIMATE OBJECTIVE
The goal is not simply to make the executive more organized. The goal is to increase the amount of business the executive can operate without increasing the amount of administrative work he personally performs.
Your job is to protect the executive's time and attention. That means reducing administrative work, unnecessary meetings, email traffic, follow-up, coordination, and low-value decisions that reach the executive.
IDEAL CANDIDATE
- 3+ years of Executive Assistant, Operations, Chief of Staff, sales support, or similar experience.
- Excellent spoken and written English.
- Experience working remotely.
- Strong phone presence.
- Sales or lead-follow-up experience.
- Advanced comfort with technology.
- Significant experience using AI tools.
- Experience supporting entrepreneurs or multiple businesses.
- Real estate, mortgage, or property-management experience is a major plus.
- Strong project-management abilities.
- High discretion and confidentiality.
- Ability to work independently.
- Strong problem-solving skills.
- Ability to quickly learn unfamiliar industries and software.
SUCCESS IN THE FIRST 90 DAYS
- Take ownership of the executive inbox.
- Take ownership of scheduling and calendar management.
- Significantly reduce the executive's administrative workload.
- Understand the major businesses and key team members.
- Handle routine correspondence independently.
- Create reliable follow-up systems.
- Coordinate meetings and resulting action items.
- Become functional in the primary business software platforms.
Assist with mortgage files and sales follow-up.
- Coordinate effectively with the marketing assistant.
- Identify opportunities for AI and automation.
- Develop SOPs for recurring administrative processes.
- Become a trusted gatekeeper for the executive.
Our target is for 80-90% of incoming administrative work to eventually be handled, delegated, or automated without requiring executive involvement.
Success means the executive spends substantially more time on sales, relationships, strategy, leadership, growth, and high-value decisions - and substantially less time on email, scheduling, administration, follow-up, coordination, and repetitive tasks.
If you are someone who enjoys taking ownership, solving problems, learning new businesses, using technology, communicating with people, and creating order out of complexity, we want to hear from you.
Job Type: Full-time
Pay: $23,500.00 - $25,000.00 per month
Experience:
- High Level Executive Assistant: 3 years (Required)
Language:
- English fluently with neutral accent (Required)
Work Location: Remote
