About Us

Raina Pratt has over 10 years of experience as a licensed property manager and leads the operational, administrative, and strategic side of Enjoy Montana Vacation Rentals. She built the company’s internal systems, workflows, and business infrastructure from the ground up, laying the foundation for long-term growth and operational clarity.

Raina brings a rare blend of strategic oversight and creative insight to the business. With years of experience in home staging, optimization, and presentation, she helps properties perform at a high level by balancing functionality, aesthetics, and strong online visibility. She plays a hands-on role in photography direction, listing descriptions, and marketing strategy.

In her CEO role, Raina oversees office operations, owner relations, and business planning, ensuring the company runs efficiently while maintaining a high standard of care for both properties and people.

Brian Pratt brings over 20 years of experience in home care, maintenance, and property oversight and is a licensed property manager. He leads the hands-on operations of Enjoy Montana, overseeing property readiness, maintenance planning, and on-the-ground problem solving across the portfolio.

Brian’s deep understanding of home systems, construction, and preventative maintenance allows him to proactively address issues before they become problems. His practical, steady leadership ensures each property is safe, functional, and consistently maintained to a high standard for owners and guests alike.

Alisha Shilling has worked with Enjoy Montana Vacation Rentals for several years and has a well-established understanding of the company’s homes, standards, and internal processes. A fifth-generation Montana resident, she brings a grounded sense of place and connection to the community she calls home.

In her prior role with Enjoy Montana, Alisha helped shape internal communication and tracking systems used across the housekeeping and property support department. That experience informs how she works today and supports clear expectations, consistency, and alignment across her role with Enjoy Montana.

Today, Alisha works with Enjoy Montana in a housekeeping support role through her professional cleaning company, bringing consistency and care to the work she does. She is known for her attention to detail and her ability to organize and clarify systems, drawing on both her experience running her own business and her long-standing relationship with Enjoy Montana, and her work reflects a shared understanding of Enjoy Montana’s standards and expectations.

Krista Putnam oversees accounting for Enjoy Montana Vacation Rentals and has over nine years of experience in the accounting field, with a specialization in property management and trust accounting. She brings a strong understanding of the financial structures and compliance requirements unique to vacation rental management.

Krista previously owned and operated her own vacation rental property in Minnesota and has lived in Montana for 14 years. She now resides near Lake Superior and operates her own bookkeeping and payroll firm, Rising Earth, outside of her work with Enjoy Montana. Her long-standing relationship with the company and attention to detail provide consistency, accuracy, and trusted financial oversight for both the team and property owners.