Made for More: Toby Myles & Caroline Pennington on Owning Your Brand and Taking the Leap
Caroline Pennington shares her journey from executive recruiter to LinkedIn marketing expert, plus how launching a wine product and following her instincts led to a powerful personal brand and a business built on bold moves.
Her Origin Story · Guest: Caroline Pennington, Original Cover Art: Isabel Paterson, Host: Toby Myles, Editor: Ilorah Dela Cruz
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Show Notes
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Caroline Pennington spent 15 years climbing the corporate ladder, placing C-suite executives and mastering the art of communication on LinkedIn. But when the work stopped feeling meaningful, she listened to the voice in her head saying, “You were made for more.” In this episode, Caroline shares how she launched a wine product during the pandemic, built a powerful personal brand from scratch, and turned her skills as a recruiter into a thriving LinkedIn marketing agency.
We talk about her shift from side hustler to full-time entrepreneur, why consistency on LinkedIn pays off, and how she uses podcasting and visibility to grow her network and impact. Caroline also opens up about handling skeptics, taking imperfect action, and why you should never wait for permission to start.
About Caroline Pennington:
Caroline Pennington is a LinkedIn marketing expert, founder of The Feminine Founder Podcast, and creator of ChilledVino. She helps female entrepreneurs and executives build personal brands that get noticed, while keeping it real, strategic, and fun.
Connect with Caroline:
🌐 Website: https://femininefounder.com/
💼 LinkedIn: https://www.linkedin.com/in/caroline-pennington/
📸 Instagram: https://www.instagram.com/cpennington55/
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About Me: https://tobymyles.com/about/
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Her Origin Story is produced by Toby Myles Copywriting, and podcast editor Ilorah Dela Cruz
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