Ever wondered how an aerospace engineer transitions into a financial services powerhouse? Or how the landscape of female leadership in finance has evolved over the decades? In this episode, we sit down with the incredible Darlene Flagg to uncover her unique journey and the transformative changes in the industry.
Join us as Darlene shares her inspiring story, from building databases at Prudential to becoming a VP at National Life Group. We delve deep into the rise of self-educated investors and how financial professionals must adapt to this new era. Discover why trust and genuine relationships are paramount in financial services, and how involvement in professional associations like WIFS can shape your career.
Plus, get tailored financial advice for every generation and learn how aligning personal values with company culture can lead to authentic success. Don't miss Darlene's lightning round of quick financial tips!
Tune in for an episode packed with wisdom, practical advice, and a whole lot of inspiration.
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Darlene Flagg's Bio:
Darlene Flagg is a Vice President and Head of Retirement at National Life Group leading their institutional sales division for retirement plans creating and managing institutional marketing strategies for 403(b), 457, 401(a), and 3121 plans. Darlene has over 20 years of senior management experience and 27 years of financial services and marketing experience.
Darlene has also served as Chief Marketing Officer and Head of Annuity Marketing at National Life. Prior to joining National Life in 2015, she worked at AIG VALIC (CoreBridge), where she last served as Vice President of Institutional Marketing. She previously served on the Women in Insurance and Financial Services (WIFS) National Board as President partnering to attract, develop, and advance women in financial services. She is also a Past President of the National Tax-Deferred Savings Association (NTSA). Additionally, for six years, she served as an adjunct professor for the University of Phoenix, Houston Campuses.
Darlene received her Bachelor's (BA) degree in Communications from Seton Hall University in South Orange, NJ, and a Master’s (MA) degree in Strategic Communications from the same institution.
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What is Women of Wealth?
Women of Wealth is where generational wisdom meets entrepreneurial ambition.
Hosted by Hawley Woods Gray and Allie Ramo, the podcast brings two generations - and two distinct perspectives - to conversations about money, business, leadership, and building a life on your own terms.
Hawley brings the Gen X perspective, shaped by decades of experience in business, finance, leadership, and wealth building. Allie brings the Millennial perspective of a modern entrepreneur navigating growth, opportunity, and what success looks like for the next generation. Together, they prove that some of the best lessons happen when women at different stages of life learn from one another.
Each week, Hawley and Allie sit down with powerhouse founders, executives, entrepreneurs, and changemakers for candid conversations about the wins, challenges, pivots, and lessons behind their success.
Expect powerful stories, practical advice, different perspectives, and honest conversations about money, entrepreneurship, career, confidence, leadership, and creating lasting wealth.
Because wealth is about more than money. It’s about freedom, opportunity, impact, and creating a life on your own terms.
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