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Maria Oliva | Connect CRE

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Maria Oliva


Pathway to Living

Three decades' experience in the senior living sector

COO of Pathway to Living since 2005

Puts an emphasis on promoting resident wellness

In the course of Maria Oliva’s 16 years at Pathway to Living—the senior housing arm of Chicago-based investor and operator Waterton–and 29 years in the senior living industry, she has been a respected leader, accessible mentor, and savvy strategist. From creating a wellness-focused operating model, to developing a multi-brand portfolio under the Pathway to Living umbrella and leading her teams through an unprecedented global pandemic, Oliva has set new benchmarks in the senior housing sector.    

As Pathway to Living’s COO, Oliva always puts an emphasis on promoting resident wellness. Under her leadership, the firm implemented its signature VIVA! operating guidelines in 2009 in order to provide a holistic cultural approach to senior living, focused on resident wellness and care while catering to individual residents’ desires and abilities.  

While VIVA! was created in a much simpler time, its tenets held strong through what was a period of historic change in the seniors housing sector. After the monumental challenges created by the pandemic, Oliva and her team navigated uncharted territory by taking care of not only the organization’s vulnerable residents but went above and beyond for the Pathway to Living teams. 

These are just a few of the reasons we chose Oliva as one of the Chicago & Midwest 2021 Women in Real Estate Award winners. Connect CRE’s Women in Real Estate Awards honor the achievements and inspirational stories of women who have reached respected positions of leadership and play key mentorship roles for others. 


Inside The Story

Pathway to Living's Oliva

About Paul Bubny

Paul Bubny serves as Senior Content Director for Connect Commercial Real Estate, a role to which he brings 13-plus years’ experience covering the commercial real estate industry and 30-plus years in business-to-business journalism. In this capacity, he oversees daily operations while also reporting on both local/regional markets and national trends, covering individual transactions across all property types, as well as delving into broader subject matter. He produces 15-20 daily news stories per day and works with the Connect team and clients to develop longer-form content, ranging from Q&As to thought-leadership pieces. Prior to joining Connect, Paul was Managing Editor for both Real Estate Forum and at American Lawyer Media, where he oversaw operations at both publications while also producing daily news and feature-length articles. His tenure in B2B publishing stretches back into the print era, and he has served as Editor in Chief on four national trade publications. Since 1999, Paul has volunteered as the newsletter editor of passenger rail advocacy groups (one national, one local).