Maile Keone
CEO | Listen Technologies
What has been a significant challenge you’ve faced? How did you overcome it?
One of the most challenging things in my leadership journey was guiding the integration of two long-standing, founder-led companies while continuing to grow the business. These organizations were built with care, pride and deep personal investment. Asking people to let go of familiar ways of working, while asking them to trust a new direction, was not easy. What carried us through was a commitment to lead with respect, transparency and patience. I spent a great deal of time listening, explaining the “why,” and making sure we didn’t lose sight of our technology or customers during the transition. Some decisions were difficult, but avoiding them would have been harder in the long run. That experience reinforced for me that strong leadership isn’t about avoiding discomfort — it’s about navigating it thoughtfully and with integrity.
How do you define success for yourself and your company?
Personally, I define success as building something that lasts, while making decisions that are thoughtful and principled — even when they’re hard. Success for me is knowing the company is stronger because of the leadership choices we’ve made, and that the people here feel supported, challenged and proud of their work. My success and the success of the business come from the hard work of our employees and partners. For the company, success means steady, responsible growth, strong leadership at every level and a reputation for doing what we say we’ll do. If our customers trust us, our people are growing, and the business is positioned well for the future, we’re succeeding.
Describe the growth of your company in recent years. What other major achievements did the company accomplish under your leadership?
In recent years, the company has grown well beyond our original plans, expanding both revenue and global reach. That growth happened alongside a complex integration, leadership transitions and a significant evolution of how we operate as a business. We successfully brought two companies together into one aligned organization, transitioned out of founder-led governance, established a clear executive and operational structure, and were first to market with a new product that expanded our market opportunity well beyond our expectations. Just as importantly, we invested deeply in our culture, leadership development and customer experience, ensuring that growth was not only strong, but sustainable.
