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Recognizing 100 CEOs & C-level Executives

Chip Cresswell

Chief Financial Officer & COO

Independent School Management

Location: Wilmington, DE

Founded: 1975

Industry: Education Management

Chip Cresswell is a seasoned entrepreneur with a passion for building and growing companies. From his early ventures as a teenager to his current role as chief financial officer and chief operating officer of Independent School Management (ISM), Cresswell has demonstrated unwavering dedication to helping businesses thrive and sharing his knowledge with others.

Cresswell joined ISM in 2019 with a mission to foster positive change in education management that would have a lasting impact on future generations of students. Taking on the dual roles of CFO and COO, Cresswell set out to achieve three key goals: develop a robust financial and accounting infrastructure, restructure the company for operational efficiency and increased profitability, and identify initiatives to drive organic growth and expansion through acquisitions.

Since then, Cresswell has implemented a reliable financial reporting system, enabling the company to make informed investment decisions and secure capital for long-term initiatives. “Through strategic restructuring and a focus on empowering associates, Cresswell has fostered a culture of inspiration and collaboration, resulting in increased revenue, the launch of new products and services and successful acquisitions,” the company said.

“Promoting change and not being worried about whether or not it will succeed is the most important risk that I’ve taken and will continue to take,” Cresswell said.

ISM is a leader in the education management services industry, dedicated to advancing school leadership through extensive research, proven management techniques, cutting-edge products and personalized service. ISM plans to invest in research, education technology and solutions tailored to the needs of private and independent schools. “By leveraging data and analytics, ISM aims to double its revenue over the next five years,” the company said.

Cresswell led the transition at ISM to a fully virtual model and co-founded a business incubator. Despite the challenges posed by the COVID-19 pandemic, he guided ISM to maintain profitability and reinvest in its people and services.

“No one could have fully predicted how the 2020 pandemic would change the business world, and from our perspective at ISM — the education system. And still, I dove head first into leading the development of a fully virtual company model that performs to the highest standards and that we still use today,” Cresswell said. “That said, organizational change can be difficult and intimidating for some. There will be wins and there will be losses, but making those changes and taking those risks enables us to create and deliver better products and services for our schools, increasing our competitive advantage and profits, but most importantly helping our schools create sustainable legacies as they educate future generations.”

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Did you know?

Chip is a foodie who enjoys trying new combinations and creations whether fine dining or the local hole-in-the-wall. In fact, Chip has been known to try to recreate a favorite restaurant dish, approaching it with the same passion and creativity that he uses in his everyday job. There are only a few things that Chip won’t eat, but you’ll have to share a meal with him to find out what they are.


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