Breaking Barriers in Property Management · Episode 6

From Regional to Director: Leading Bigger While Becoming a Mom

What does it take to grow into a bigger leadership role while becoming a mother and carrying responsibilities others may never see?

May 1, 2026 · 38 minutes

About This Episode

Growth does not require you to leave your whole life behind.

Sheila sits down with Jessica Dimas, Director of Operations at Rainey Property Management, for an honest conversation about motherhood, career growth, caregiving, burnout, and taking risks.

Jessica’s story shows what can happen when a leader recognizes potential and builds a role that allows someone to grow without pretending life outside work does not exist.

This episode is for women who feel stretched between ambition, family, and the pressure to keep saying yes.

Leadership Takeaways

Three things to carry forward.

Support Changes Careers

The right structure and support can unlock leadership potential that pressure alone never will.

Growth Requires Courage

Moving forward often begins before you feel completely ready.

Whole People Lead Better

Strong leadership makes room for the realities people carry outside work.

You do not have to choose between meaningful leadership and being present for the life you are building.

Keep breaking barriers. — Sheila