JENNIFER PHILBROOK

I grew up in New England but have lived in Chicago long enough that I’m not sure which place counts as home anymore—my accent keeps people guessing. My road to HR was a winding road. I started out running my first business, a small fashion company called Stitch Method. What I loved most wasn’t the fashion itself, but the people: creating a workplace where our team felt valued, supported, and excited to show up every day. That realization sparked a new passion and ultimately led me into a career in HR. Over the past decade, I’ve taken on leadership roles where I’ve guided culture initiatives and helped organizations align their people practices with their business goals. HRoadmap was born from this journey, with the mission of helping other small businesses lay the foundation for compliance, culture, and growth.
 

Outside of work, I share my life with my husband and an elderly cat named Kitty. I spend my free time exploring Chicago’s museums, discovering new restaurants, traveling whenever I can, and balancing my love of food with a focus on fitness and health. Along the way, I’ve added a few tattoos that mark different chapters of my life. 
 

When you work with me, you’ll get a practical, collaborative partner who loves strategizing with new businesses—especially those planning to hire or growing teams of up to 50 employees. I’m passionate about helping founders build compliant, people-first workplaces where employees thrive and businesses can scale with confidence.