WHY US?

From One Family to Another

The founder started in the business locally in Vancouver, WA over 25+ years ago, raising four kids who grew up doing community work, while developing new construction and historically kept apartment buildings.


Loyalty, integrity, and deep care have always been at the core and will continue to be the core.


We value the community, and that’s why we will always hire local historians. While big corporations in this industry make money managing properties, our company makes money by owning the property. We care, go the extra mile, and have stakes in this—because once you join us, it’s no longer your business we manage; it’s ours. 

What Makes Us Different

Over time, it became clear that while Vancouver, WA is a strong, growing market for long-term property investment, it is not considered a major hub for attracting top-tier talent. Because of that, our principal, made a deliberate decision to look beyond our local borders—nationally and internationally—to bring in the best talent, technology, and practices in the U.S., all with the goal of competing at a higher level locally. 


This was done while maintaining the core values that defined where we started.


After a rigorous search process, that commitment led to the appointment of Jon Directo as CEO of Olive Tree Property Management. His leadership reflects exactly what we believe in: honoring our roots while building a company equipped to operate at the highest standard. 

We have the ultimate Avengers team, on your side

International Talent to Compete Locally with One Mission: Your Success

JON: CHIEF EXECUTIVE OFFICE

πŸ“Former Manager of Project Innovation at The Dinerstein Companies | Santa Monica, Austin, and Denver.

We hired Jon for his award-winning leadership and consistent track record of turning properties into top-performing assets, backed by 15+ years in multifamily operations and a history of driving 8% YoY rent growth.


A previous Manager of Project Innovation at The Dinerstein Companies; led Class A lease-ups and managed portfolios of 1,100+ units, including the #1 ranked student housing property in Texas.


  • Scale & Sales: Managed 1,100+ units and contributed to a landmark $199M asset sale.
  • Operations: Maintained 95%+ occupancy during stabilization and repositioning while achieving the fastest lease-ups in the portfolio.
  • Reputation: Delivered the #1 online reputation in the state and ranked #5 nationally for Millenium Rainey Street.


CALEB: OPERATIONS

πŸ“Previous Franchise Performance Leader

at Tim Hortons & Chick-fil-A | Toronto, Canada

We brought Caleb on after he spent years operating large, complex businesses at scale — leading hundreds of locations and thousands of team members across the U.S. and Canada — to bring that same discipline, accountability, and steady leadership to Olive Tree.


Before joining us, he held franchise performance leadership roles with Tim Hortons and Chick-fil-A, overseeing 100+ locations and more than $300M in annual revenue.


He’s the person companies call when operations break down — stepping into underperforming locations, stabilizing teams, tightening systems, and getting performance back on track.


At scale, that meant:

  • 114 locations under his oversight
  • 2,600+ employees led
  • distressed sites turned around
  • #1 system-wide ranking for speed and efficiency


Here, it means properties that simply run better — cleaner operations, tighter systems, and fewer things slipping through the cracks.

ADALINE: MARKETING

πŸ“Former Marketing Manager for International Brand Launches, PR Exposure, and Executive Education Operations | Orange County, CA

We hired Adaline  to modernize  how we lease — using data, AI, and real-time marketing  to generate qualified leads and fill units faster.


A previous Marketing Manager launching Korean Conglomerates in America & Program Manager of Executive Education at UCI.

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  • Operational Impact: Drives stronger NOI by creating data-driven workflows that align marketing strategy with operational execution.
  • Lead Generation: Focuses on high-intent systems that generate qualified traffic and result in faster lease-ups rather than just visibility.
  • Strategic Partnerships: Extensive experience managing multimillion-dollar programs and securing national PR coverage through high-level brand launches.
  • Scale: Expert at building scalable systems that bridge the gap between national brand presence and property-specific leasing results.


DEBI: CHIEF FINANCIAL OFFICER

πŸ“An accomplished financial executive with more than 25 years of experience in land acquisition, development, construction, and asset/property management, combined with 15 years of expertise as an International Accounting Business Liaison.

Throughout her career, she has built a reputation for strategic financial leadership, operational excellence, and the ability to navigate complex business environments across domestic and international markets.

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As a Chief Financial Officer, Debi specializes in financial planning and analysis, budgeting, risk management, operational oversight, and long-term growth strategy. Her extensive background in real estate development and construction management provides her with a unique ability to align financial performance with large-scale project execution and organizational objectives.

Debi is known for fostering strong business relationships, streamlining financial operations, and driving sustainable growth through sound fiscal management and collaborative leadership. Her global accounting and business liaison experience has enabled her to successfully support cross-functional teams, improve financial processes, and strengthen organizational performance in dynamic industries.


Outside of her professional career, Debi is also a passionate glass artist whose creativity reflects her appreciation for craftsmanship, beauty, and innovation. She is a devoted mother, an avid world traveler, and a nature enthusiast who finds inspiration through exploring diverse cultures and the natural world. Her balance of executive leadership and artistic perspective brings a unique and thoughtful approach to both her professional and personal life.