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Recognizing 100 CEOs & C-level Executives

Andy MacGregor


Skyline Construction

Location: Cook County

Founded: 2019

Industry: Construction - Construction Staffing

Andy MacGregor’s roots in the construction world run deep, nurtured by his architect father’s legacy. With three decades of experience, he swiftly transcended the role of consultant to become the president and founder of Chicago’s new outpost for parent company Skyline Construction.

Skyline Construction brings together a team of seasoned construction professionals with extensive backgrounds in large-scale, complex projects. The firm partners with clients to construct corporate tenant improvements, life sciences facilities, as well as hospitality, industrial and building repositioning projects.

“In the dynamic landscape of construction, Andy stands as exemplars of visionary leadership, adaptability and unwavering dedication,” said his colleagues. “His journey is a testament to the power of strategic foresight, deep-rooted industry knowledge and a steadfast commitment to both clients and employees, ensuring he and Skyline’s Chicago office remain a significant force within the Chicago construction scene.”

In a city where barriers to entry are high and competition is fierce, MacGregor and his team astutely identified the burgeoning tech sector as a key growth opportunity. He began by forming strategic alliances with major players and established an impressive roster of clients. Noteable projects include headquarters for tech giant Google, the cutting-edge innovation hub 1871 and Motorola Mobility at the Merchandise Mart.

With the rebranding to Skyline Construction, MacGregor balanced the pursuit of business growth with safeguarding the interests of the workforce, fostering a sense of ownership and pride among the employees at the firm’s 100% employee-owned construction company.

“Andy’s leadership style is a force to be reckoned with,” said his staff. “His dynamic approach, collaborative spirit and out-of-the-box thinking have earned him a reputation that is second-to-none.”

In order to reignite his passion as a leader, MacGregor said it’s exciting to push people outside their comfort zone and empower them to lead new initiatives. “It’s exciting to see people work through new challenges on their own and to develop the confidence that goes along with that,” he said. “I enjoy coaching through the personal growth it takes to move tactical and strategic balls forward.”

His true superpower is the ability to distill large, complex, messy challenges down to a concise group of action items and milestones and to get a team organized, inspired and moving toward resolution. With work on more than 250 projects in Chicago, MacGregor’s list of accolades continues to grow and includes being named to the Engineering News-Record Top 400 National General Contractors List and the CoreNet Chicago Innovation Real Award in Construction.

For his continued impact on his team and the Chicago’s skyline, MacGregor has been named a titan.

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What is your superpower?

I have 2 superpowers, and the first is totally superficial – ordering food for large groups of people. I’m truly the Michael Jordan of that.
However, my true work-related superpower is my ability to distill large, complex, messy challenges down to a concise group of action items and milestones and to get a team organized, inspired and moving towards resolution.


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