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Be all in. That’s the philosophy of Intraprenista Kasey O’Leary, Vice President of Global Marketing for what she calls “a 100 year old startup”, one of the biggest names in hospitality and hotels: Hilton. From her start in a family ad agency business to marketing books and music for Borders, to being an agent of positive impact, Kasey has been working toward shattering the view of who Hilton is, feels proud to be a spokesperson, and mentors other women within the organization to also be all in. Kasey joins Socialfly Co-founders Stephanie Cartin and Courtney Spritzer for a conversation about her executive role in an iconic company and her journey to success, including about the emphasis Hilton puts on people who want to make an impact and have ideas, and as an inclusive place for women; why it is important to be mindful of how you show up every day, and to make mistakes and be OK with that; the value of reading the room, and understanding the usefulness of letting your guard down, and short conversations; why it matters to get the DNA of the company you work for; why Hilton chose, and how they recruited, Anna Kendrick as a powerhouse voice of Hilton; and, why seeing the world through her daughters eyes has transformed the way she sees the world.
Guests
Kasey O'Leary
Vice President of Global Marketing for what she calls
Hosts
Stephanie Cartin
Co-founder of Socialfly and Entreprenista.
Stephanie Cartin is the co-founder and CEO of Entreprenista, an all-in-one platform – which includes a private community & business membership called The Entreprenista League that's made up of over 2,000 women founders at all stages of business, a weekly newsletter received by 60,000 readers, two podcasts, in-person educational & networking events, and an award program – that women founders at all stages can turn to for everything they need to grow.
Stephanie is also the co-founder of Socialfly (acquired by Truform Media Group in 2024), Markid, and Pearl Influential Capital. She has won countless awards, including the SmartCEO Brava award, which recognizes the top women CEOs in New York, and a Stevie Award for Women-Run Workplace of the Year. She has also appeared in Bloomberg, Forbes, Entrepreneur, Refinery29, and more.
Courtney Spritzer
Co-founder of Entreprenista.
Courtney Spritzer is a serial entrepreneur, angel investor, author, and community builder with a passion for creating brands and platforms that empower women to lead, grow, and thrive.
In 2012, she co-founded Socialfly, a leading social-first digital and influencer marketing agency. Over the course of a decade, she helped scale the business into an award-winning agency working with Fortune 500 brands and emerging startups, building a powerhouse team and culture along the way. In 2024, Socialfly was acquired.
In 2018, Courtney launched the Entreprenista Podcast to spotlight the stories of inspiring women founders. That passion evolved into Entreprenista Media in 2021, a media platform and community supporting women entrepreneurs at every stage of growth. She now co-leads the continued expansion of The Entreprenista League, a membership-driven community and ecosystem for founders.
As an angel investor, Courtney supports female-led and mission-driven startups aligned with her vision for a more inclusive and equitable business landscape.
She is the co-author of Like, Love, Follow: The Entreprenista’s Guide to Using Social Media to Grow Your Business (2015), a strategic guide for leveraging social platforms to drive business success.
Her work and ventures have been featured in Bloomberg, Forbes, Inc., Entrepreneur, and The New York Times. She is committed to championing visionary founders and helping build the next generation of impactful, community-driven businesses.
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