Insight-Driven Leadership and Entrepreneurial Resilience

Cindy Estis Green shares her career path, including writing books to stay connected to the hospitality industry after selling her first analytics business while raising children. After corporate and General Manager roles at Hilton International, she became an entrepreneur, recognizing growing demand for analytics as the digital and distribution landscape evolved. She built on her interest in digital technology during a major transition in the marketplace, starting companies to create solutions for emerging needs.

She explains the challenges of fundraising as a woman entrepreneur and the importance of early investors, such as real estate owners, who supported the launch of Kalibri Labs. She highlights champions in her career who advocated for her at Hilton by giving her access to senior executives and enabling property-level leadership roles. She discusses support systems built through mentors with varied skills and shares her experiences advocating for herself by asking despite hesitation and pushing past uncertainty.

Notable Quotes/Highlights

• “I had a strength in seeing patterns in data…apply them to real world situations.”
• “It is hard…there’s an element of . . .  grit and perseverance.”
• “Entrepreneurs don’t see a wall. They see a ladder to climb.”
• “What’s the worst thing that can happen?… You’re never going to get anything if you don’t ask.”
• “The reason that people are successful is not because the path was easy…it was because they were resourceful and scrappy and figured it out.”

Closing Reflection

Success, Cindy notes, comes from resourcefulness, grit, and the willingness to keep moving forward despite setbacks. She encourages others to build personal development plans, understand their aptitudes, and pursue growth areas with confidence.

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