I’m Jenny Holaday, aka Bossy Skirt. With over 30 years of leadership experience in the male-dominated hospitality industry, I’m what some have called a “goddamn force of nature.” I started my career as a call center representative and worked my way up. Before pivoting to give Bossy Skirt my full attention, I was the Senior Vice President of Operations for a $500 million-dollar business. 

Now my passion is helping the next generation of young professionals get where they want to be. That’s why I’m here to give you actionable, no-nonsense career advice. 

My extensive experience in corporate, entrepreneurial, and family-run operations creates a uniquely broad understanding of the workplace and its dynamics. If the young professionals in your organization can use a little guidance or you’re in the market for some generational leadership work hacks, book Bossy Skirt for your next event.