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, AMS, CMCA

​President

 Madeline Osborne is a seasoned leader in community association and property management, recognized for her strategic oversight, operational expertise, and ability to manage complex, high-value assets. With a career spanning over 20 years, she has successfully directed the management of a diverse portfolio ranging from established residential communities to large-scale, planned developments.

Madeline has played a pivotal role in the transition of a $100 million development from developer control to homeowner association governance, ensuring a seamless and financially sound turnover while establishing strong operational frameworks for long-term success. Her experience extends to overseeing highly specialized and infrastructure-intensive assets, including a private water treatment plant, a marina and boating community with dock systems, protected wetlands, and a dam supporting lake management demonstrating her depth in regulatory compliance, risk management, and capital asset stewardship.

In 2020, Madeline founded Guardian Association Management, positioning the company as a forward-thinking, service-driven organization focused on elevating the standard of association management. Under her leadership, the company has built a reputation for delivering tailored management solutions, financial discipline, and exceptional client service.

A dedicated industry professional, Madeline has been an active member of the Community Associations Institute for more than 15 years. She holds designations of AMS (Association Management Specialist) and CMCA (Certified Manager of Community Associations), reflecting her commitment to continued education and professional excellence. She earned her Bachelor’s degree in Business Administration from Cleveland State University.

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
Associate Manager

Katie is an accomplished association management professional serving as an Associate Manager, where she brings a strategic, solutions-focused approach to community operations. Partnering closely with senior managers, she plays a critical role in guiding boards through complex governance, financial, and maintenance decisions while ensuring communities operate with efficiency, transparency, and fiscal responsibility.

As a trusted liaison between boards, residents, and service partners, Katie is dedicated to fostering thriving, well-managed communities that protect and enhance property values. Katie holds a Bachelor’s degree in Early Childhood Education from Cleveland State University.

Hannah Hildebrandt

Association Manager

Hannah brings years of proven expertise in property management, overseeing everything from large-scale roof and landscaping projects to navigating complex developer and owner lawsuits. She excels at anticipating challenges, resolving issues proactively, and ensuring properties run smoothly and efficiently.

Holding a bachelor’s degree in business administration from Cleveland State University and drawing on a strong background in the restaurant industry, Hannah combines exceptional customer service skills with a deep understanding of association and owner needs. Her unique blend of operational know-how, communication skills, and commitment to excellence makes her a trusted advocate for the associations she serves.

Lisa Humphrey

Associate Manager

Lisa Humphrey is a senior property management leader with over 20 years of experience overseeing luxury high-rise and mixed-use communities across Washington, DC, Northern Virginia, Maryland, New York City, and Cleveland. She has held executive-level roles, including Regional Portfolio Manager, Director of Property Management, Director of Leasing, Executive Concierge Director, Asset Manager, and Director of HR and On-Boarding Advisor. After relocating to Cleveland, Lisa transitioned into community association management, where she served as a Portfolio Manager. She brings a results-driven, service-focused approach to every organization she supports.

Lisa is a nationally recognized industry professional, having earned multiple National Apartment Association (NAA) Property of the Year awards and consecutive Best Sales honors. Her leadership style blends operational excellence, team development, and innovation in customer experience to deliver exceptional results.

She holds bachelor’s degrees in Business Administration and Applied Science, as well as dual master’s degrees in Human Resource Management and Organizational Behavior & Development from New York University (NYU). Lisa also earned her Certified Apartment Manager (CAM) designation through the NAA. She is known for building high-performing teams, elevating brand standards, and driving sustainable growth.

Outside of work, Lisa enjoys spending time with her husband and two young children, traveling, and discovering new destinations and restaurants.

Chrissy Cavotta

Association Manager

Chrissy Cavotta began her career in property management in 2020 as a Leasing Manager for a student housing community. From 2020 to 2022, she specialized in leasing within the downtown Cleveland market, where she developed a strong foundation in resident relations and client service. She later transitioned into association management, expanding her expertise in community operations and stakeholder engagement.

Chrissy is highly customer-centric and takes pride in delivering excellent, timely service. Her commitment to creating positive experiences makes her a valuable asset to any team or community she serves.

Outside of work, Chrissy enjoys staying active through cycling, swimming, Pilates, and rock climbing. She also loves experimenting with her grandmother’s Sicilian recipes and baking. With a passion for fashion and event planning, Chrissy brings creativity and energy into both her personal and professional life.

Candace Clark

Associate Manager

Candace brings a dynamic blend of experience in luxury sales, customer service, and retail management to their role in association management. With a proven track record of delivering exceptional service in high-end environments, she is skilled at building strong relationships, anticipating client needs, and creating seamless, positive experiences.

In addition to their background in client-focused industries, Candace became a licensed real estate agent in the past year with Howard Hanna, further strengthening her understanding of property management, market dynamics, and the needs of homeowners and communities. This added expertise allows her to approach association management with a well-rounded, informed perspective.