Takin' Care of Lady Business®
The Women Who Get Ahead Aren't Smarter. They Ask. — with Caroline Dell
Your biggest career opportunities may not come from what you know, but from who remembers your name. Takin' Care of Lady Business Episode 169 On this episode of Takin' Care of Lady Business, Jennifer Justice sits down with Caroline Dell , Co-founder and CEO of Goodword , to explore why your network is one of the most valuable assets you'll ever build, and why its real power comes from knowing how to activate it. Drawing on her experience helping scale Chief and now building Goodword, Caroline shares why relationships, not resumes, algorithms, or AI alone, continue to create the biggest career opportunities. From finding her co-founder through a single introduction to raising her first $500,000 almost entirely through her personal network, she explains why the people who advocate for you behind closed doors often shape your future more than any application or pitch ever could. Jennifer and Caroline also unpack why women are often more hesitant to ask for introductions, support, and opportunities, how understanding the realities of fundraising creates leverage rather than limitation, and how AI can strengthen, not replace, the human relationships that move careers forward. This conversation is a reminder that your network isn't just who you know. It's the trust you've built, the people willing to vouch for you, and the opportunities that become possible when you're willing to make the ask. What You'll Learn: How relationships become a real source of career leverage Why asking for an introduction doesn’t require turning every contact into a friendship How Caroline used her own network to find her co-founder and fund her company How AI can help preserve the context that makes professional relationships valuable Highlights: (00:00) Meet Caroline Dell (01:39) Why your network is your most powerful asset (06:08) The gap Goodword fills that communities can't (06:53) Why our brains can’t keep up with our networks: The Dunbar number (13:52) Why women hesitate to ask for favors (19:53) Leaving Chief and deciding to found a company (23:56) Finding her technical co-founder Chris (24:59) The hard truth about women raising venture capital (34:38) The worst advice Caroline ever received About Our Guest: Caroline Dell is the co-founder and CEO of Goodword, a modern relationship management platform designed to help professionals manage, cultivate, and leverage their networks. Before launching Goodword, she spent nearly a decade building communities and creating access for women in leadership, including serving as an early employee and executive at Chief. Drawing from her experience scaling a professional network to thousands of members, Caroline recognized that while relationships drive career-changing opportunities, people struggle to maintain the context and connections needed to use those networks effectively. Today, she is using AI to transform how people understand and activate their relationships, helping professionals turn their networks into a powerful source of opportunities, introductions, and growth. Caroline Dell’s LinkedIn: https://www.linkedin.com/in/caroline-dell/ Caroline Dell’s Instagram: https://www.instagram.com/foundercaroline/ Explore Goodword: https://www.goodword.com/ Get $25 off (1 free month) of Goodword with the code: FRIENDOFJJ About Jennifer Justice and The Justice Dept. JJ’s LinkedIn: https://www.linkedin.com/in/jennifer-justice-354a0b99 The Justice Dept: https://www.thejusticedept.com/ JJ’s Instagram: https://www.instagram.com/jenniferjusticel/ Newsletter: https://tkolb-newsletter-a50814.beehiiv.com/ JJ’s YouTube: https://www.youtube.com/@TakinCareOfLadyBusiness The Justice Dept. is a female-focused advisory, consulting, and law firm advocating for female founders, talent, execs, and brands. We represent bo$$ ladies to make them . If you love what you hear, please subscribe and share with a friend. This is a Lady Business LLC Production.
