Jay Esterson: 37 Years of Leadership, Ethics, and Excellence in Insurance

In this powerful Ask the Experts conversation, host Andy Arter sits down with Jay Esterson, one of the most respected agency owners in the Allstate network, to discuss what it really takes to lead with integrity, adapt to change, and build a winning culture that lasts.

With over 37 years of experience in both corporate and agency leadership, Jay shares lessons learned from his journey through HR, sales management, and entrepreneurship. From the importance of ethics to building non-negotiables in your business, this episode is a masterclass in leadership that every agency owner needs to hear.

In this episode:

• Why ethics is the foundation of all long-term business success
• How HR shaped Jay’s leadership style and people-first philosophy
• The importance of establishing non-negotiables in your agency
• How to lead through change and stay adaptable in a shifting market
• Why agency owners must invest in growth, not just survive the day-to-day
• How to manage fear and replace it with consistent action
• The mindset needed to build and protect company culture
• Why firing one wrong person can unlock exponential growth
• How to create trust-based relationships that fuel referrals

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