Remote Chief Of Staff Jobs

About the Role

Ellestad Properties is a growing real estate investment and operating company with multifamily properties, hotels, vacation rentals, property management operations, mortgage lending, and other investments across multiple states.

We are looking for an Executive Operations Manager / Chief of Staff who can grow into a trusted operational partner to the owner.

This is not a traditional Executive Assistant position, but it is also not a purely strategic management position.

The right person needs to be equally comfortable getting into the details, building systems, following up with people, solving problems, and eventually taking ownership of major operational responsibilities.

During the first 60–90 days, a significant amount of time will be spent learning the portfolio, organizing information, building and updating trackers, making calls, following up with vendors and property managers, and learning our systems.

This initial work is important because it builds the foundation needed to understand and eventually help oversee a large and diverse real estate portfolio. As you learn the business, the position will transition toward greater ownership of projects, operational problems, cost savings, accountability, and process improvement. Ellestad_Executive_Operations_R…

What You'll Do

• Oversee projects and operational issues across a multi-state real estate portfolio
• Work with property managers, vendors, contractors, lenders, insurance agents, and team members
• Hold people accountable for commitments, deadlines, and follow-up
• Identify problems, recommend solutions, and drive issues through completion
• Build and maintain systems for properties, insurance, property taxes, mortgages, licenses, utilities, vendors, and renewals
• Identify opportunities to reduce expenses and negotiate better vendor agreements
• Assist with acquisitions, refinancing, inspections, due diligence, and special projects
• Attend meetings with the owner and make sure action items are documented and completed
• Improve processes and document procedures as the company grows
• Assist with executive priorities, communications, scheduling, and follow-up when needed
• Support Five Star Vacay and other affiliated businesses on operational projects
• Become the point person for projects that would otherwise require continued owner involvement

The position is intentionally broad and will evolve as you learn the businesses. The objective is to create leverage for the owner by improving operations and making sure things get done. Ellestad_Executive_Operations_R…

What We're Looking For

We are looking for someone who:

• Has experience in real estate, property management, operations, project management, or a similar role
• Is extremely organized and follows through without needing repeated reminders
• Enjoys walking into disorganized situations and figuring out how to make them work better
• Is comfortable with spreadsheets, tracking systems, phone calls, research, and detailed work
• Can communicate professionally with property managers, lenders, insurance agents, vendors, investors, and employees
• Is comfortable holding people accountable while maintaining good working relationships
• Can manage multiple projects and deadlines simultaneously
• Thinks like an owner and looks for ways to save money and improve performance
• Can identify a problem and bring forward possible solutions rather than simply escalating the problem
• Is comfortable working independently in a remote environment
• Wants increasing responsibility and ownership rather than a narrowly defined position

Communication & Accountability

This is a full-time position with flexibility in when some of the work is completed.

Clear communication and accountability are important.

We have short weekday morning meetings to review priorities, decisions, deadlines, and anything that is stuck.

A brief end-of-day report is also a standing requirement. It covers what was completed, what remains in progress, what you're waiting on, anything needed from the owner, problems or concerns, and priorities for the following day.

During the first 30 days, we also ask for a basic overview of hours worked and approximately where time is being spent. After the initial training period, the focus is primarily on results, ownership, communication, and follow-through rather than detailed time tracking. Ellestad_Executive_Operations_R…

Compensation

Base Salary: $50,000 per year

Additional performance incentives may include:

• Bonuses for documented recurring cost savings you create
• Bonuses for new property management business you generate
• Compensation reviews based on performance and increased responsibility
• Potential long-term incentive opportunities for successful long-term employees

What Success Looks Like

Success means fewer operational issues require the owner's direct involvement.

Over time, you should be able to take a problem, determine what needs to happen, coordinate the right people, follow through, and bring it back when it is completed—or when an executive decision is actually needed.

The long-term goal is for this person to help protect the owner's time, solve problems before they reach him, improve systems, hold people accountable, reduce expenses, support acquisitions and major projects, and become a trusted operational partner. Ellestad_Executive_Operations_R…

This Position May Not Be a Good Fit If...

• You are looking for a purely strategic role from day one
• You dislike spreadsheets, tracking, documentation, phone calls, or follow-up
• You need a narrowly defined list of responsibilities every day
• You are uncomfortable following up repeatedly until something is completed
• You don't enjoy working in a fast-moving environment where priorities can change
• You view administrative or detail-oriented work as being outside your role

Some detail and administrative work will always be part of this position. However, as you learn the portfolio and demonstrate ownership, the goal is for more of your time to shift toward operations, problem-solving, project leadership, cost savings, and higher-level responsibilities. Ellestad_Executive_Operations_R…

To Apply

Please submit your resume along with a short response to the following:

Tell us about a situation where you inherited a disorganized or underperforming operation, property, project, or process. What was wrong, what did you personally do to fix it, and what was the measurable result?

We are looking for someone who wants to grow with the organization, take increasing ownership, and become a long-term part of the team.

Pay: $45,000.00 - $65,000.00 per year

Benefits:

• Flexible schedule
• Paid time off
• Referral program

Work Location: Remote