From humble beginnings to industry leadership, John Olivieri’s professional journey is a masterclass in vision, grit, and transformative leadership. As a third-generation entrepreneur with over 45 years of experience in architecture, construction, real estate, and property management, John’s name is synonymous with integrity, innovation, and enduring success in the southwest suburbs of Chicago. Rooted in a legacy of craftsmanship and fortified by decades of strategic enterprise building, his life’s work reflects the values of perseverance, excellence, and service to community.
John’s story begins with industrious roots. While still in high school, he worked as a maintenance man and co-founded a successful sealcoating company at just 17 years old. He wasn’t merely laying asphalt—he was laying the foundation for a career defined by enterprise and leadership. Managing the marketing and bidding for over 200 residential driveways and several commercial lots, John quickly proved that entrepreneurship was not just in his blood—it was his calling.
Motivated by a desire to combine creativity with structure, John pursued a degree in architecture at the University of Illinois at Chicago. After graduation, he refined his architectural talents under the tutelage of two prominent Chicago firms before taking a pivotal step alongside his brother: buying out their father’s partners in the family’s general contracting business. This marked the genesis of their leadership era, where John’s architectural insight and business acumen transformed a traditional construction company into a premier architect-led design-build enterprise.
Throughout the 1990s, John and his brother steered their company into becoming a regional force, averaging over 35 design projects and constructing three to five major buildings annually. Their unique model merged the creative precision of architectural design with the operational efficiency of in-house construction. This synergy led to landmark projects like Frankfort Public Library, North American Spine Society headquarters, and multiple high-profile banks and commercial centers that continue to define the region’s architectural landscape.
Never content to rest on past successes, John responded to market fluctuations with strategic foresight. During economic downturns, he and his brother personally invested in office and industrial developments, resulting in a diversified portfolio of income-generating assets. His leadership ensured not only the sustainability of his business but also its evolution into a robust ecosystem of complementary ventures—spanning design, construction, property management, and maintenance.
In 2020, amid a nationwide commercial real estate slowdown prompted by the COVID-19 pandemic, John made the difficult but calculated decision to close his architectural firm. Yet even this transition exemplified his adaptability. Retaining his license, he continued to design for his own properties while pivoting his focus entirely to the growth of his three remaining companies: Olivieri Real Estate LLC, Olivieri Association Management, and Olivieri Maintenance Inc. Each company is a testament to his ability to identify market needs and deliver targeted solutions with precision.
Today, John oversees more than 43 property management contracts and services over 200 commercial tenants across suburban Chicago. Under his guidance, Olivieri Real Estate has become a premier provider of commercial leasing, management, and development services. His Association Management firm plays a critical role in board governance and long-term financial planning for office condominiums, while his Maintenance company ensures properties remain functional and future-ready.
John’s leadership style is both hands-on and visionary. He inspires his team through clear strategic direction and a commitment to excellence. His employees—many of whom have been with him for years—describe a leader who mentors, delegates, and empowers. John’s capacity to cultivate relationships, manage risk, and execute ambitious plans has made him a trusted advisor to investors, a mentor to emerging professionals, and a steward of community-focused development.
Beyond the boardroom, John is an active civic leader and public speaker. He has served as President of the Mokena Chamber of Commerce and the Mokena Park District Foundation, and has delivered construction and entrepreneurship seminars for Purdue Northwest University. His passion for giving back is fueled by a belief in education, mentorship, and sustainable development—values that have informed every aspect of his business and personal life.
As he begins to taper his day-to-day involvement in business operations, John is looking to extend his impact by serving on advisory boards. With unmatched experience as a CEO, developer, and strategist, he is poised to offer his insights to companies and organizations seeking visionary guidance, operational excellence, and growth-focused leadership.
Character:
John embodies integrity and perseverance, drawing on a multigenerational legacy to uphold high standards of ethics and service. He leads with humility and determination, earning trust through consistent delivery and honest communication.
Knowledge:
With over four decades of experience in architecture, construction, and real estate, John’s domain expertise is vast and deeply practical. He applies this knowledge to create value in both stable and volatile markets.
Strategic:
John has an exceptional ability to anticipate market trends and adjust business models accordingly. His strategic foresight has allowed him to grow and adapt his companies while maintaining profitability and resilience.
Communication:
A natural communicator, John excels at translating complex ideas into actionable strategies for clients, teams, and stakeholders. His approachable demeanor and thoughtful leadership foster collaboration and long-term loyalty.
