Property & Operations Manager

Property & Operations Manager

Winter Park, Florida
$28–$35 per hour | Full-time, 40 hours per week

We are looking for an unusually capable, self-directed person to help manage a privately owned portfolio of residential rental properties and a small office property in Winter Park.

This is not a traditional administrative position, and it is not a large-company property management job. The person we hire will work directly with the owner and will have considerable independence and responsibility for keeping the day-to-day operation running smoothly.

The position is based in a beautifully restored historic office near Park Avenue in Winter Park. The owner travels frequently, so the ability to work independently, make good decisions and keep things moving without constant direction is essential.

What You'll Do

Approximately 60–70% of the position will involve property and real estate operations, including:

• Communicating with tenants and responding to their needs
• Coordinating maintenance and repairs
• Dispatching and overseeing our maintenance/home-repair person and outside vendors
• Walking properties and identifying maintenance issues before they become larger problems
• Meeting contractors and vendors at properties when necessary
• Inspecting completed work
• Showing available residential properties and office suites
• Coordinating turnovers, move-ins and move-outs
• Helping manage leases, renewals and tenant communications
• Obtaining estimates and helping make decisions about repairs and improvements
• Solving the inevitable unexpected problems that arise when managing real estate

The remaining portion of the job will involve working directly with the owner on a variety of business and professional matters. These may include correspondence, research, document preparation, scheduling, expert-witness consulting work, office operations and other projects.

A long-time accounting professional separately handles most bookkeeping, rent receipts, mortgage payments and other accounting functions, although this position may gradually assume additional financial and administrative responsibilities over time.

The Person We're Looking For

The most important qualifications for this position are not a particular age, degree or career path. They are judgment, initiative, integrity and follow-through.

We are looking for someone who:

• Naturally notices what needs to be done and does it
• Does not require frequent supervision or reminders
• Is exceptionally organized and follows things through to completion
• Is comfortable making decisions and accepting responsibility
• Communicates extremely well, both verbally and in writing
• Is technologically comfortable and learns new systems quickly
• Enjoys solving problems and helping people
• Can interact professionally and comfortably with tenants, contractors and professionals
• Has good judgment about when to make a decision independently and when to call the owner
• Is trustworthy enough to eventually be given substantial authority
• Has a sense of humor and enjoys working in a small, informal environment

Property management, real estate, construction, executive support or comparable operations experience is preferred, but we are open to an exceptional candidate from another background. A college degree is preferred but not required.

A valid driver's license, reliable transportation and the ability to travel locally between Winter Park properties are required.

Independence and Flexibility

This is an unusual working environment.

The owner expects to be in Winter Park approximately one week each month and will frequently be working or traveling elsewhere. Consequently, this position is best suited to someone who enjoys independence and does not need a busy corporate office or constant supervision to remain engaged and productive.

This is a full-time position, and 40 hours per week are available and expected for someone seeking a traditional full-time schedule. At the same time, we recognize that exceptionally talented people sometimes need flexibility in their working lives. For the right person, we are willing to discuss some flexibility in scheduling or, potentially, a somewhat reduced workweek.

There will be times when being physically present is necessary, but we care considerably more about reliability, communication, judgment and getting the work done than maintaining an unnecessarily rigid schedule.

Opportunity to Grow

We are looking for someone who wants more than a temporary job.

The right person will have an opportunity to learn virtually every aspect of managing a substantial privately owned real estate portfolio and, over time, assume considerably greater responsibility and autonomy.

If you are someone who enjoys being handed a problem, figuring it out and coming back with a solution rather than waiting to be told every next step, we would particularly like to hear from you.

Compensation: $28–$35 per hour, depending on experience and capability.

Schedule: Full-time, 40 hours per week. Some scheduling flexibility—and potentially reduced hours—may be considered for an exceptional candidate.

Location: Winter Park, Florida. Primarily on-site with some flexibility for remote work when appropriate.

Pay: $28.00 - $35.00 per hour

Expected hours: 40.0 per week

Work Location: In person