Randy Otto

TEC Canada Speaker | Actor | Playwright | Vice President of Wealth Management – Stifel Financial Corp. | Vistage Speaker

Randy Otto, CEO & President of Winston Churchill LLC, is a leading authority on Winston Churchill, with over four decades of academic and performance experience. As a one-man tribute to Churchill, Otto delivers humorous, poignant, and highly relevant keynotes and workshops, inspiring positive action through interactive portrayals of Churchill’s leadership. His customized presentations, including “Winston Churchill: CEO” and “Dining with Churchill” events, have garnered acclaim worldwide from corporate and association audiences. Otto’s accolades include being the Honorary Archivist at the Churchill Archives Center and creating the “Painting as a Pastime” exhibit for the National Churchill Museum. He is the only Churchill endorsed by the Churchill family and has a background in private investment management.

Randy Otto

TEC Canada Speaker | Actor | Playwright | Vice President of Wealth Management – Stifel Financial Corp. | Vistage Speaker

Randy Otto, CEO & President of Winston Churchill LLC, is a leading authority on Winston Churchill, with over four decades of academic and performance experience. As a one-man tribute to Churchill, Otto delivers humorous, poignant, and highly relevant keynotes and workshops, inspiring positive action through interactive portrayals of Churchill’s leadership. His customized presentations, including “Winston Churchill: CEO” and “Dining with Churchill” events, have garnered acclaim worldwide from corporate and association audiences. Otto’s accolades include being the Honorary Archivist at the Churchill Archives Center and creating the “Painting as a Pastime” exhibit for the National Churchill Museum. He is the only Churchill endorsed by the Churchill family and has a background in private investment management.

Randy’s Topics

In this program, Randy Otto brings Winston Churchill’s eight timeless leadership principles to life, offering an interactive “AskWinston” Q&A with the leader admired by CEOs worldwide. Otto, the only Churchill endorsed by the Churchill family, weaves four decades of academic and performance experience into a presentation that shares Churchill’s visionary, action-oriented leadership style. Participants gain valuable insights into why Churchill’s courage, eloquence, and optimism led to victory during the darkest hours of history, and how these lessons are applicable to 21st-century leaders. The program has been praised for increasing productivity, team communication, and enthusiasm, and leaving lasting takeaways for all ages. Otto’s portrayal of Churchill is both entertaining and deeply impactful, providing an unforgettable leadership lesson.

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