Taking the High Street: Molly Stewart on Leading with Vulnerability

In this episode, I interview Molly Stewart, Regional Sales Operations Leader at High Street Insurance and Financial Services. Molly brings a rare 360-degree view of the insurance world, having worked across frontline operations, outside sales, agency ownership, and sales leadership. Her holistic experience informs a leadership style grounded in purpose, strategy, and heart. We dive into how she empowers agents to lead with integrity, reminding them that selling insurance isn't about pushing products; it's about protecting people and businesses from life’s worst moments.

Molly shares powerful insights on what it means to truly serve clients, including when to walk away from the wrong fit and how vulnerability and storytelling can strengthen relationships. She challenges the outdated stigma of insurance sales and offers a compelling vision of what happens when agents ask the hard questions and stand confidently in their expertise. Molly proves that real impact in our industry comes from showing up with authenticity, courage, and care.