Municipal Leaders: Develop Faster, Lead Stronger, Build Better

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Episode 308 of The HaltingWinter Podcast
Brought to you by Tyler Technologies

What prepares someone to become a city manager?

For Jessica Leavins, it wasn’t a straight line…it was a calling.

Raised in Crestview, Florida on land her family has stewarded for generations, Jessica didn’t set out to lead a city. She started in social work, helping families navigate some of the darkest moments of their lives. That experience shaped something critical: the ability to absorb emotion without becoming hardened by it.

In Episode 308, Jessica shares her journey from child welfare caseworker to becoming Crestview’s first HR director and eventually city manager.

But this conversation goes deeper than titles.

We talk about:

  • What social work taught her about public criticism
  • The emotional weight of becoming the public face of a city
  • Leading through COVID without panic
  • Why empathy is both a strength and a burden
  • And how to keep doing good work when it isn’t always applauded

One moment stands out: realizing that when criticism shows up online, it’s not just you who sees it — your family does too.

That’s the part few people talk about.

Municipal leadership is public. It’s personal. And at times, it’s heavy.

But as Jessica says, if you’re doing good with good people, you keep going.

If you serve in local government, this episode will feel familiar.
If you aspire to lead, it will prepare you for what the role really requires.

Listen to Episode 308 here:

Tyler Technologies

This episode is sponsored by Tyler Technologies, the leader in empowering the public sector with software solutions that connect data, streamline operations, and improve service delivery. From civic services to public safety, Tyler helps local governments build stronger, more resilient communities. 
Learn more at tylertech.com/winter →

The Municipal Leadership Development Circle (MLDC)

The MLDC is where local government leaders go to grow, together. It’s the fastest-growing leadership development community designed specifically for the public sector, now paired with a comprehensive 9-month Leadership & Culture Program for those ready to elevate their leadership and their organization.
Learn more at haltingwinter.com/mldc →

The HaltingWinter Podcast celebrates and elevates the people who power local government. Through in-depth conversations with leaders from cities, counties, and communities of all sizes, host Seth Winterhalter explores the journeys, challenges, and innovations happening in municipal leadership across America.