Assistant Property Manager

Job Details:

• Hourly Pay: Starting at $25/hour
• 30-40 hours/week based on need.
• Benefits: Health & Dental Insurance Paid Holidays
• The office and some properties are in Vancouver, WA, but you have to be able to drive to our property locations, such as Portland, Oregon City, and Salem, OR.

Reports to:

Jon Directo, CEO, who has been in the industry for 17 years and has worked in leadership for some of the biggest companies in the industry, including the Dinerstein Company. Jon is an incredibly chill guy with a crazy smart and innovative mind. We'd love someone who can balance Jon's ideas and brain by being his logical right hand, but who is also intuitive and able to pick up on next steps and learn quickly. Jon is a dream of a leader to work with, so we are looking for someone who complements him perfectly.

The Job:

Olive Tree Property Management (https://www.olivetreepm.net/) is seeking an Assistant Property Manager to support our CEO, Jon Directo, across multiple apartment communities throughout the Portland Metro and Salem areas.

This is not your typical office job. Every day can look different depending on the needs of the property, residents, and Jon/the team. One day you may be helping lease apartments and process applications; the next you may be stepping in to support a community during a staffing transition, assisting with resident concerns, coordinating maintenance needs, or helping a manager stay on top of operations.

Success in this role is less about having experience at a specific property and more about being adaptable, resourceful, dependable, and willing to jump in wherever needed. We're looking for someone who can handle change, think on their feet, and maintain a positive, professional attitude in a fast-paced environment.

What You'll Do

Support Jon as a Property Manager

• Serve as a trusted support partner to Community Managers across multiple apartment communities.
• Provide temporary coverage during vacations, employee absences, staffing transitions, and busy leasing periods.
• Step into different communities and quickly learn property-specific procedures and priorities.
• Help keep operations running smoothly when unexpected challenges arise.

Leasing & Resident Support

• Conduct apartment tours and assist prospective residents through the leasing process.
• Follow up on leasing inquiries through phone, email, and text communication.
• Process applications, prepare leases, and assist with move-ins and move-outs.
• Help maintain strong occupancy by delivering excellent customer service and leasing support.
• Respond to resident questions and concerns in a professional and timely manner.
• Assist with resident conflict resolution and policy enforcement when necessary.

Property Operations & Administration

• Assist with daily office operations and administrative responsibilities.
• Maintain accurate resident files, records, and documentation.
• Process resident paperwork, lease renewals, notices, and communications.
• Support compliance with company policies and Fair Housing regulations.
• Assist with property inspections, audits, reporting, and special projects.

Financial Administration

• Collect rent and accurately post payments.
• Assist with delinquency follow-up and resident communications.
• Support Community Managers with financial and administrative reporting.

Maintenance Coordination

• Coordinate with maintenance teams regarding service requests and unit readiness.
• Help ensure work orders are completed promptly and residents receive appropriate follow-up.
• Assist in preparing vacant units for leasing and move-ins.
• Support property walks and inspections to maintain community standards.

Who We Are Looking For

In the Workplace:

We are looking for the Mike to a Harvey here (except Harvey here is Filipino and works in property management, but is just as genius and talented).

We are looking for someone with a raw talent for organizational and administrative excellence in the property management space who will grow with us. If you have property management experience too, that's a real win.

You are someone who is incredibly detail-oriented (not just a cliché word we're using) — this is the #1 thing we are looking for — and someone with a natural eye for improving processes. You have the courage to speak up, share your ideas, and think logically enough to process Jon's ideas, ask "okay, what does it look like to get this done?", and already envision the process in your mind.

You are someone your boss can bounce ideas off of, and who can take an abstract idea and turn it into concrete steps and a process.

Personality-wise:

• #1: a team player with a good heart (respectful and full of integrity).
• We are looking for someone who is a beast in the workplace and gets things done, but who also has that underlying "nothing is too serious, nothing is personal, nothing we can't solve" type of personality — someone who can stay relaxed and have a good conversation.
• • • Ideal TV characters who would fit this role: Donna and Mike from Suits.
    • TV characters who would absolutely not fit this role: Louis from Suits, April Kepner from Grey's Anatomy.

What Makes Someone Successful in This Role

We're looking for someone who:

• Is highly adaptable and comfortable working in changing environments.
• Can shift priorities quickly and stay productive when plans change.
• Demonstrates resilience and professionalism when handling difficult situations or resident concerns.
• Is a natural problem-solver who focuses on solutions.
• Takes initiative and doesn't wait to be told what needs to be done.
• Is dependable, resourceful, and self-motivated.
• Can walk into a new property and quickly assess how they can help.
• Maintains a positive attitude during busy or stressful situations.
• Has a strong work ethic and takes pride in following through on commitments.
• Communicates effectively with residents, vendors, maintenance teams, and management.

Qualifications

• Minimum two (2) years of professional work experience.
• Previous experience in property management, leasing, customer service, hospitality, retail management, office administration, banking, or another service-oriented environment is preferred.
• Demonstrated history of reliability, accountability, and strong attendance.
• Strong organizational and time-management skills.
• Ability to work independently when needed.
• Comfortable learning new software systems and processes.
• Valid driver's license, reliable transportation, and willingness to travel between properties throughout the Portland Metro and Salem areas.

Who We Are

We put people over work, first and foremost, and if you need anything, we have your back. We aren't just saying this — we care about our people like family. We go on retreats, invite you over to the owner's house for holidays, and hang out outside of work (this isn't expected, but it's always welcome).

Everyone here is a team player and has each other's back. It's a small team, which means that when someone is struggling or has too much on their plate, there's no "that's not in my job description."

The company is growing and ever-changing, which might feel daunting to some people who want something set in stone, with processes that have been in place for decades. You will have more say in this job than in any other organization you've been part of, and because of that — and because you'll be taking on so many different responsibilities — it's a 110% guarantee that you will grow, and grow fast, not just as a worker, but as a person.

At Olive Tree Property Management, we believe great communities are built by great people. We value team members who are proactive, adaptable, and willing to step in wherever they're needed. If you enjoy variety, solving problems, helping people, and making a meaningful impact across multiple communities, we'd love to hear from you.