Growing and Leading in a Family Agency with Ashley Winebrenner

In this episode of the Insurance Perspectives Podcast, host Brad Boldt sits down with Ashley Winebrenner, a third-generation insurance professional at Dwyer Insurance Agency in London, Ohio. Ashley shares her winding path to insurance — from working for a CRM company and traveling the world, to nursing school, to stumbling into her dad's agency "just temporarily" and never leaving. Now 14 years in, Ashley is an inaugural member of HawkSoft's Taking Flight Program and is preparing to one day take over the agency her great-grandfather founded in 1931. She opens up about the joys and challenges of working with a parent, navigating a paper-vs-digital standoff, and what it means to carry the weight of a nearly 100-year family legacy.

Takeaways

• Your path doesn't have to be straight. Sometimes you stumble into your purpose.
• Working with family is a gift, even when it's hard.
• Change takes patience. Move the agency forward without leaving people behind.
• Solve the problem before buying the tool.
• Community closes the knowledge gap. You don't have to figure it out alone.
• Legacy is both a burden and a privilege.

Learn more about Dwyer Insurance Agency:
https://www.dwyerinsuranceagency.com/
https://www.facebook.com/DwyerInsAgency

To get in touch with today's guest, reach out below:

• Ashley Winebrenner (click here)
• Brad Boldt (click here)

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If you’re looking to reach out to HawkSoft, please email marketing@hawksoft.com.

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https://www.hawksoft.com/
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https://x.com/HawkSoft
https://instagram.com/hawkSoft

Music by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/