Meet the Team
Jamison Sessions
President
Real estate has been a part of Jamison’s life for as long as he can remember. Born and raised in Clark County, he grew up around his parents rental properties and his father’s real estate business, giving him an early look at both the opportunities and challenges that come with owning investment property.
Today, Jamison serves as President of Utmost Property Management, where he focuses on the company’s growth, operations, and long-term direction. He has a particular interest in using better systems and technology to make property management simpler and more transparent, without losing the personal service and local knowledge that owners expect from a family-run company.
As a rental property owner and real estate investor himself, Jamison understands the business from an owner’s perspective. He believes good property management comes down to clear communication, consistent standards, and making sound decisions that protect an owner’s investment over the long term.
Outside of work, Jamison enjoys golfing, following the Portland Trail Blazers, and spending time with his wife, Ashley, and their two children.
Shelley Roll-Ragusa
Senior Property Manager
Shelley brings more than 26 years of property management experience and has been an integral part of Utmost Property Management for more than a decade. Before joining Utmost, she managed large multifamily communities of up to 900 units, giving her extensive experience across nearly every aspect of residential property management.
Shelley is exceptionally detail-oriented and plays a central role in Utmost’s day-to-day operations, particularly with resident relations, accounting, and the more complex situations that inevitably arise in property management. After more than 10 years with Utmost, she has an incredible depth of knowledge about our properties, owners, residents, and internal operations.
More than anything, Shelley cares deeply about doing right by both owners and residents. She is thorough, persistent, and willing to dig into the details until an issue is resolved. Her combination of experience, compassion, and attention to detail has made her a major part of what makes Utmost work and someone our clients and team have come to rely on.
Grace Lanning
Vacation Rental Manager
Grace oversees Utmost Property Management’s vacation rental portfolio, helping ensure every stay runs smoothly for guests and property owners. She manages guest communication, coordinates with cleaning teams and local hosts, and keeps owners informed about their properties.
With experience managing short-term and long-term rentals, single-family homes, and commercial properties, Grace brings a broad understanding of property operations to her role. Vacation rentals are where she has found her passion: creating welcoming, memorable experiences for guests while giving owners confidence that their properties are in good hands.
Grace believes thoughtful details, responsive communication, and consistent care make the difference between a good stay and one guests remember and want to repeat.
Outside of work, Grace enjoys exploring parks and hiking trails with her dogs. Her ideal weekend includes a quiet beach, iced coffee, a good book, and time with her husband and their two pups.
Vincent Joe Ragusa
Broker / Senior Property Manager
Vincent “Joe” Ragusa
Joe brings more than 25 years of experience in many aspects of real estate, mortgage lending, and property management and has been a key part of Utmost Property Management for more than a decade.
As one of Utmost’s senior property managers, Joe works closely with property owners on everything from bringing new properties into management to rental strategy and the day-to-day decisions that come with owning investment property. His extensive experience gives him the perspective to work through complicated situations while keeping the owner’s long-term goals in mind.
What has made Joe such an important part of Utmost, though, is how much he genuinely cares about the people he works with. He has built long-standing relationships with owners and residents over the years and takes personal responsibility for helping solve problems when they arise. His experience, judgment, and commitment to our clients have played a significant role in Utmost’s growth over the past decade.
Ashley Sessions
Leasing Manager
Ashley serves as Utmost Property Management’s Leasing Manager, helping oversee the leasing process and ensuring our policies and procedures continue to keep pace with Washington’s changing landlord-tenant laws.
With a background in real estate and property management, Ashley brings a careful and thoughtful approach to leasing. She works with the team on leasing standards, resident screening, documentation, and policy changes, with a focus on creating a process that is consistent, fair, and well understood by both property owners and prospective residents.
Ashley also keeps a close eye on changes to state and local rental regulations and helps Utmost translate those changes into practical policies for our team and clients.
Ernesto Lopez
Leasing Specialist
Ernesto has been with Utmost Property Management for more than two years and serves as one of the first points of contact for prospective residents. He helps guide applicants through the showing and application process, makes sure application files are complete, and coordinates the transition from approval through move-in.
Ernesto also works with current residents on lease renewals and requests involving roommates, pets, parking, and other lease changes. His background in customer service, sales, technical support, and operations management helps him troubleshoot issues and find practical solutions for both prospects and residents.
What Ernesto enjoys most about his role is helping people navigate the leasing process and finding solutions that fit their situation. He values clear communication and teamwork and believes both are important to creating a smooth experience for residents.
Outside of work, Ernesto enjoys spending time with his family and his dog, Bruno. He also enjoys cooking, going to the beach, watching movies, and following car racing, basketball, and soccer.
Carlos Santiago
Maintenance Coordinator
Carlos serves as Utmost Property Management’s Maintenance Coordinator, overseeing service requests, vendor coordination, and maintenance projects for our managed properties. He works closely with residents, property owners, and vendors to keep repairs moving and make sure the right people are involved when an issue needs to be resolved.
Carlos brings more than five years of experience in real estate and property management, with a background that includes property acquisitions, trusts, rental property operations, and maintenance. He also holds degrees in both Law and Computer Engineering, giving him a unique combination of technical knowledge and problem-solving experience that he brings to his role at Utmost.
What Carlos enjoys most about his work is building relationships with residents, owners, and vendors and finding practical solutions when problems arise. He believes good maintenance coordination comes down to communication, follow-through, and connecting people with the right resources to get the job done.
Outside of work, Carlos enjoys spending time with his family, traveling, technology, gaming, and fishing.
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