Jenny "Bossy Skirt" Holaday

Witty, actionable advice to help Millennials to Boomers navigate the workplace!
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Program Descriptions

  • Career Development for Millennials

  • Tackling Generational Biases in the Workplace

  • Re-Establishing the Ground Rules in a Post #MeToo Workplace

  • Improving (For Real This Time) Your Corporate Culture
  • Why Book Jenny?

  • Jenny has enjoyed an expansive career as a marketing and operations executive. Her extensive experience in corporate, entrepreneurial, and family run operations, creates a uniquely broad understanding of the workplace and its dynamics.

  • Jenny followed her passion for mentorship into a career dedicated to professional development, initially as the president of a digital media company offering work inspiration for millennials, and now as the emerging on-line media personality: Bossy Skirt

  • Jenny's deep, real-world understanding of complex work cultures allows her to create custom messaging and actionable advice for any organization looking to motivate, educate and inspire current and next-generation leaders.
  • Videos

    Biography Read more

    Jenny Holaday is an experienced executive, an insightful commentator and a force of nature! She has over 30 years of leadership experience in the hospitality industry, many of them in male-dominated, executive level positions. She began her career as a call center representative, and exited the industry as a Senior Vice President of Operations, leading a $500+ million-dollar business. Jenny is now the President of Fuel Leadership, where she dedicates herself full-time to the career advancement and professional development of our next generation of leaders.

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    "Just had the pleasure of listening to your presentation. I have to say, you were nothing short of amazing. Thank you for being an experienced professional that took the time to understand our younger generation. I look forward to following Bossy Skirt.” - Michelle C.

    "Good morning Jenny, I totally enjoyed your talk! Almost wish I was a millennial just so I could hire you! By far the best of the day, and we talked at our table, you should have come back up and spoke more after the snoozer who spoke last! ThanksTerry D.

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