Rachel Ackerman, Director of People Operations at Barstool Sports, shares her journey and the common thread of helping people that has led her to her current role. She discusses her transition from wanting to be a teacher to working in HR, and the impact of mentors in her career growth. Rachel also talks about the unique challenges and responsibilities of being the Director of People Operations for two different divisions within Barstool Sports. She emphasizes the need for HR to be more creative and adaptable in implementing policies and communicating with employees. Rachel predicts that HR will continue to evolve with the integration of AI and the changing expectations of the younger workforce. In this conversation, Rachel Ackermam discusses the need for positive changes in FMLA policies, the importance of managing expectations in the workplace, the culture at Barstool, her career aspirations, and the future of Barstool. She also talks about mentorship and the potential for employees to switch between the business and content creation sides of the company. Rachel shares advice she would give her younger self, emphasizing the importance of listening and allowing others to learn and grow.