In this episode of the '30 Minutes with Insurance CEO Podcast,' host Raution Jaiswal, CEO and co-founder of InsuredMine, sits down with Jackson Rollo, President of Rollo Insurance, to discuss the nuances of running and expanding an insurance agency. As a second-generation agency owner, Jackson shares insights on his journey from being a producer and director of sales to becoming the president of the company. He delves into the importance of serving local communities, the agency's growth from a single office to 62 locations across six states, and the critical role of building relationships in the insurance industry. Jackson highlights how embracing technology, maintaining a focus on clients rather than customers, and the significance of balancing personal life and work contribute to sustained agency success. Throughout the conversation, the themes of staying true to company values, the power of networking through platforms like LinkedIn, and the influence of mentors, particularly his father, are explored. This episode provides valuable lessons on leadership, the impact of technology and data on agency operations, and the continuous pursuit of improvement.


00:00 Welcome to the Podcast with Jackson Rollo
01:09 Getting to Know Jackson: Breakfast Habits and Agency Insights
03:52 Jackson's Journey: From Law School Aspirations to Insurance Agency President
07:27 The Importance of Relationships in the Insurance Industry
13:55 Balancing Work and Family Life: Jackson's Personal Philosophy
16:49 Challenges and Growth: Steering the Agency Towards Success
17:04 Introducing the Rollo Rules: A Guide to Perfection and Innovation
17:49 Balancing Success and Challenges: The Journey of Continuous Improvement
22:33 Embracing Technology and Client Relationships for Growth
25:37 The Power of Data in Shaping Business Strategy
30:05 Mentorship and Personal Growth: Learning from Experience
33:53 The Importance of Networking and Building Personal Connections