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Cari O'Leary

Associate Vice President, Operations

About
  • Leadership Team

      Marshall Bleiweis

      Jack Beaton

      Sebastian Russo

      Lily Bejleri

      Cari O'Leary

      Kyrsten Lingenfelter

      Mark Jules

      Patricia Sgandurra

      Ian Phillips, PMP

      Elena Candeloro, CHRL

      Christina Basanti, CPA, CA

  • Why SKPM?

Cari O'Leary is the Associate Vice President, Residential Operations at Sterling Karamar Property Management. In her role, she provides strategic leadership for residential operations, driving operational excellence, team development, client satisfaction, and portfolio performance. She works closely with property teams and ownership groups to implement best practices, improve resident experiences, and deliver consistent, high-quality service across the organization.

Having advanced through every stage of the property management profession, Cari brings a practical, hands-on perspective to executive leadership. She is passionate about mentoring future leaders, building high-performing teams, and fostering a culture of accountability, collaboration, and continuous improvement.

Cari is a three-time nominee for Property Manager of the Year and was recognized as a finalist for the 2023 Property Manager of the Year Award presented by the Canadian Federation of Apartment Associations. She is also a dedicated advocate for Autism and ADHD awareness, believing that strong leadership is built on integrity, empathy, and a commitment to helping others succeed.

More Leadership Team Members

  • Marshall Bleiweis

    Marshall Bleiweis

    President & CEO

  • Jack Beaton

    Jack Beaton

    Executive Vice President, Operations

  • Sebastian Russo

    Sebastian Russo

    Executive Vice President, Operations

  • Lily Bejleri

    Lily Bejleri

    Associate Vice President, Operations

  • Cari O'Leary

    Cari O'Leary

    Associate Vice President, Operations

  • Kyrsten Lingenfelter

    Kyrsten Lingenfelter

    Director, Residential Property Administration

  • Mark Jules

    Mark Jules

    Associate Vice President, Commercial Operations

  • Patricia Sgandurra

    Patricia Sgandurra

    Director, Commercial Property Administration

  • Ian Phillips, PMP

    Ian Phillips, PMP

    Director, Capital Projects

  • Elena Candeloro, CHRL

    Elena Candeloro, CHRL

    Vice President, People and Culture

  • Christina Basanti, CPA, CA

    Christina Basanti, CPA, CA

    Vice President, Finance

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