InsHER

In this episode, I interview Mary O’Leary Dronson, Managing Director, Corporate Segment Team Leader, and Senior Account Executive at Marsh, to explore her inspiring journey from starting as an accounting clerk with tuition reimbursement to leading corporate segments. Mary shares how growing up as the middle child taught her to continually advocate for herself and adopt the powerful mindset of "why not me?" when pursuing career growth. We unpack the systemic barriers and societal conditioning, from traditional media tropes to passive expectations, that often hold women back from speaking up or stepping forward for major professional opportunities. Balanced with humor, Mary also recounts memorable career milestones, including completing her degree at Temple University in just 18 months while working full-time and turning a nerve-wracking interview moment featuring a severe cold sore into an ice-breaking triumph. Mary emphasizes the vital roles that authenticity, mentorship, and proactive sponsorship play in reshaping the insurance industry. 

In this episode, in collaboration with ISC Group, I interview Margaret Resce Milkint, Managing Director and Global Insurance Practice Leader at DSG Global and U.S. Chair of ISC Group. We share an insightful conversation on leadership, community, and industry evolution. We explore the transformative growth of the ISC Group as a vital "sanctuary" that fosters deep personal and professional connections for women in insurance. Margaret shares powerful perspectives on the power of mutual support, breaking traditional molds, and the shifting dynamics of female leadership where women actively lift and amplify one another. Margaret also dives into the future of work, examining how women can leverage artificial intelligence as a strategic coach to enhance executive communication, bridge technological gaps, and shape industry standards. Margaret offers actionable advice on building personal gravitas, establishing a diverse personal advisory board, and redefining success on one's own terms.

In this episode, I interview Danielle Clifford, Vice President and Head of Sales and Marketing at Openly, for an insightful conversation on career paths, sales leadership, and finding authentic purpose within the insurance industry. Danielle shares her unique transition from molecular biology to insurance, explaining how she discovered a deep appreciation for the industry’s complexity, its problem-solving capacity, and the profound meaning of helping policyholders recover during life's most challenging moments. Building on her extensive leadership experience, Danielle dives deep into practical strategies for modern sales and communication, including the power of relationship-building over purely transactional sales. She shares how to overcome common communication habits, such as over-explaining and using hedging language, while embracing the strategic power of silence, "breadcrumb conversations" for building consensus, and intentional sponsorship infrastructure to drive true workplace equity.

In this episode, I interview Shanna Sweeney, SVP of Excess Casualty at Upland Specialty Insurance and co-founder of Women of Wholesale (WOW). Shanna shares how an unexpected start in insurance through an Enterprise Rent-A-Car internship led to a 15-year career in reinsurance, proving that you don’t need a traditional risk management degree to find your place and thrive in this space. We also talk about the power of community building and why Shanna created WOW to give women a safe, non-judgmental space to build authentic relationships before they need them. Shanna offers refreshing, practical insights on moving past workplace competition with an abundance mindset, the importance of sponsorship over mere mentorship, and how designing for diversity can genuinely reshape the C-suite. Plus, she shares why her favorite part of the industry has been the lifelong friendships forged along the way.

In this episode, I interview Megan Bock, Chief Operating Officer at Federato, to discuss her fascinating 20-year career journey across traditional commercial P&C insurance and her leap into the AI-native InsurTech space. Megan shares why she ultimately stayed in the insurance industry, driven by the profound impact and promises we keep to people during their most challenging moments, and what motivated her to seek out an early-stage startup environment where her voice could be heard more loudly and her impact could be felt faster. We also dive into the realities of leadership in male-dominated industries, why authenticity always outperforms trying to fit in, and how AI is actively augmenting underwriting by handling complex data so humans can focus on relationships and strategy. Megan offers incredible, practical wisdom on building core values through employee collaboration, prioritizing high emotional intelligence and soft skills when building a dream team, and learning to delegate effectively to avoid burnout and create a more equitable playing field.