Our Team

Guardian Association Management

At Guardian Association Management, a woman owned business, we understand the power of good employees and their values in creating a thriving company. Our dedicated team, led by the experienced Madeline Osborne, brings a wealth of association and property management expertise. With a deep commitment to excellence, our associate managers deliver exceptional service, drawing on their extensive knowledge and passion. Together, we serve our clients to improve Association relationships and efficiency.

Madeline Osborne

Madeline Osborne, AMS, CMCA


Guardian Association Management’s President, Madeline Osborne, comes with extensive experience in all aspects of association and property management.   During her career, she and her team have managed the day-to-day activities of small, well-established communities, as well as directed the successful transition of a $100M development from Developer to Association. 

Most recently, Madeline managed the community operations of a 1500-unit portfolio consisting of eight individual properties while overseeing a team that manages over 50 Associations.  Guardian’s experience at all levels, can help your homeowners and building owners realize their communities’ fullest potential.

Madeline is a member of the Community Association Institute and has been for over 10 years.  She is a designated AMS, Association Management Specialist, and CMCA, Certified Manager of Community Associations.  Madeline holds a Bachelor’s degree in Business Administration from Cleveland State University.

Sue Bene - Guardian Association Management

Sue Bene
Association Management Specialist

She is a seasoned professional with vast knowledge and experience in Association Management Accounting, Corporate Accounting, Association Banking and Procedures, and property management technologies. She is also a Professional in Human Resources (PHR). She earned her certification via HRCI in 2011.

Her experience includes a 50+ association accounting portfolio, all facets of managing Accounts Payable, Accounts Receivable, Vendor relations, and client-facing.

After working as an HR Director for an accomplished Cleveland IT Consulting firm for 18 years, she decided to pursue an association accounting role. While working as an association accountant she fell in love with the work and never looked back. She enjoys the challenges of accounting and loves the people she works with inside Guardian and with all association owners and members.


Bob Guarino
Property Manager

Guardian Association Management’s Property Manager, Bob Guarino, brings decades of Property Management experience. He holds an Associate’s Degree in Business Management; a Real Estate Sales License in the State of Ohio; a Certified Occupancy Specialist in the National Center for Housing Management; a CPM (Certified Property Manager) candidate with IREM (Institute of Real Estate Management); and has extensive knowledge of the Construction and Restoration industry.

Most recently, Bob has managed a portfolio of 600+ Residential Apartments, 20+ Condominium Associations (1,000 units), 3 Homeowner Associations (approx. 600 units), as well as additional Commercial Properties totaling 150,000 sq. ft.

Katie Thomas

Katie Thomas

Associate Manager

Katie Thomas is an accomplished individual with a passion for helping homeowners and residents in the property management business. Katie has always been driven by a relentless curiosity and a desire for personal growth and has achieved numerous milestones and accomplishments.

She holds a bachelor’s degree in Early Childhood Education from Cleveland State University, which has provided her with a strong foundation in communication and multitasking skills. With a strong commitment to personal growth and a drive to make a positive impact, Katie continues to strive for excellence in the property management business. She looks forward to new challenges, opportunities, and experiences that lie ahead.

Denise Cavallaro

Denise Cavallaro
Associate Manager

Denise Cavallaro is an Associate Manager at Guardian Association Management. She brings an abundance of experience and knowledge to the company in many aspects of property management.

Her experience includes working with 50 plus properties, made up of Homeowners Associations, Commercial Buildings, and Apartments. These interactions provided her with a strong, broad knowledge base which she taps into to assist our clients.

She manages day-to-day activities in accounts receivable, and accounts payable, assisting property managers and coordinating monthly and annual meetings.