Recognizing 100 CEOs & C-level Executives
Dennis Cooley Bridgely Key Options, Llc

Dennis Cooley

COO, CFO | President

Bridgely Key Options, LLC | Securehr

Location: Bradenton, FL

Founded: 2013

Industry: Payroll and HR

Dennis Cooley’s entrepreneurial story began in 1996 when he joined forces with his brother to launch Prostaff Human Resources. However, after one year in business, Cooley’s life changed completely when the business was sold, and shortly after, his brother was killed in a motorcycle accident. While his intentions were to continue with the company that acquired the firm, he wasn’t sure if it was the right move for him at the time.

Cooley found himself working at other professional employer organizations instead, including a startup where the company grew from 2,000 worksite employees to nearly 20,000. By 2013, with like-minded partners, Cooley found his fit when he formed Bridgely Key Options. He and his partners went on to found Secure HR, a payroll services company, too.

Bridgely Key Options LLC, is an insurance agency specializing in the PEO (professional employer organization) industry. In addition to direct sales, the firm works with PEO brokers and insurance agents to reach customers and help business owners with their payroll, human resources, workers’ compensation, health benefits, 401(k) and other supplemental services by leveraging the services of a PEO.

Under Cooley’s guidance, Secure HR expanded its offering last year with Secure HR Pro to include advanced human resources consulting. “Leveraging our broad scope of experience with comprehensive, integrated HR solutions, we began offering professional services for large, complex organizations, including municipalities,” he said. “We found that large organizations find it challenging to re-organize, leverage technology and utilize partners without outside expertise to help them along the way.”

Helping others has been a key part of Cooley’s leadership style during his 30 years in the industry and as an active board and committee member within the community.

“Integrity is more than just doing the right thing when no one is looking; it’s also about helping others when it’s the right thing to do, even without personal gain,” he said. “I believe this philosophy is what has led to my company’s longevity; without integrity and trust, my business would not survive.”

Empathy is a necessary skill for a leader, Cooley said. “Understanding and addressing the needs of employees and the community is crucial,” he said. “As an engaged member of my community and a small business champion, I have seen firsthand the positive impact of empathetic leadership. Leaders must listen actively and foster a supportive environment.”

Presented by:

What is your secret superpower?

My secret superpower is my ability to seamlessly integrate technology with human-centric solutions. I have consistently leveraged this superpower to drive innovation and efficiency while maintaining a strong focus on the people at the heart of any organization.
As an early adopter of technology, I stay ahead of industry trends and continuously explore new tools and platforms. This enables me to identify and implement solutions that streamline processes, reduce costs, and enhance overall productivity. I use data analytics to gain insights into various aspects of the business as this data-driven approach ensures that decisions are well-informed and effective.
Despite my strong focus on technology, I never lose sight of the human element. I prioritize understanding the needs and concerns of employees and clients, ensuring that technological solutions enhance their experience rather than complicate it. The interface between the user and the tool is more important than the tool itself.
My ability to balance cutting-edge innovation with practical, actionable strategies helps in navigating complex challenges and achieving long-term goals. I can see the big picture while paying attention to the details that matter. This superpower also includes adaptability, allowing me to pivot quickly in response to changing circumstances and find creative solutions to new problems.

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