Helping Lawyers Find the Right Fit Firm with Jennifer Gillman

In this episode of the Mastering Business Skills podcast, hosts Erin Alli and Sharon Savage sit down with Jennifer Gillman, founder and CEO of Gillman Strategic Group.

A former lawyer turned candidate-facing recruiter, Jennifer specializes in helping attorneys find their “exact right perfect fit” law firm opportunities that align not only with their professional goals but also with their personal well-being.

Jennifer shares how she quickly identifies whether lawyers need a career shift, a new firm, or simply better resources to thrive. She also debunks the myth that attorneys only move for money, highlighting instead the importance of balance, culture, and the ability to serve clients effectively.

Other highlights from this conversation include:

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  Jennifer’s superpower of spotting career misalignment in under 15 minutes

  
  


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  Why most lawyers leave firms for better resources or balance—not just compensation

  
  


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  The power of focus: how adopting the Entrepreneurial Operating System (EOS) transformed her business

  
  


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  Why taking imperfect action beats waiting for perfection every time

  
  


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  The concept of the “Happy Rainmaker” and her six pillars for building a fulfilling legal career

  
  


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  A sneak peek at Jennifer’s upcoming book, inspired by The Go-Giver, launching in 2026

  
  

Whether you’re a lawyer searching for happiness in your career, a professional struggling with perfectionism, or a business owner trying to master focus, Jennifer’s story offers practical insights and inspiring advice.

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  Gillman Strategic Group Website

  
  


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  Connect with Jennifer on LinkedIn