Speaking Engagements

Jessica D. Winder brings raw honesty, humor, and real-world expertise to the stage, making complex workplace topics not just accessible, but unforgettable. As an HR executive, career strategist, and unapologetic truth-teller, she shares powerful stories and actionable insights on leadership, diversity, workplace equity, and navigating the modern corporate landscape.

Whether she’s delivering a keynote, hosting a workshop, or joining a panel, Jessica blends research, personal experience, and straight talk to leave audiences inspired, informed, and ready to take action. Her style is equal parts motivating and disruptive, perfect for organizations that want to challenge outdated thinking and spark meaningful change.

Popular Topics Include:

• The Audacity to Interview Pregnant – Breaking hiring bias and rewriting the rules for working parents

• The Corporate Cheat Code – How to build a career without losing yourself

• Workplace Truths HR Won’t Tell You – What really drives promotions, pay raises, and retention

• Building a Personal Brand Inside (and Outside) the Office – Stand out, get noticed, and own your career

If you’re looking for a speaker who will make your audience laugh, think, and take notes furiously - look no further!