InsHER

In this episode, I interview Angela Ripley, President of VW Brown Insurance Service and national chairperson of the Big I, who shares her journey growing up around an insurance agency and later rising to lead a 130-year-old organization. Angela shares the evolution of leadership styles, the power of mentorship, and why she believes in focusing on true talent and skill development across the board rather than siloing demographic groups.
Angela also shares the special connections she has made with female agency owners across the country in states like Alaska, Montana, and Maine. We also explore exciting industry topics, from breaking away from gimmicky insurance advertising to attract the next generation of professionals to the positive impact of technology and AI on our daily work. 

In this episode, in partnership with the National African American Insurance Association (NAAIA), I interview Susan Johnson, Chief Culture Officer at The Hartford and Vice Chair of NAAIA's Board of Directors, for a deeply insightful conversation about what it truly means to build sustainable, value-driven inclusion within the insurance industry. Susan shares her unique journey into insurance from outside the traditional mold, offering a refreshing perspective on why we need to look beyond the same talent sources, rethink job descriptions, and tell a much broader, more compelling story about the diverse career paths available in our industry.
Susan also shares how organizations can move past surface-level checklists and embed cultural belonging directly into everyday business operations, leadership behaviors, and talent systems. Susan provides incredible wisdom on navigating organizational transformation without putting culture on hold, fostering non-judgmental curiosity among all employees, and how executives can leverage strategic partnerships with organizations like NAAIA to drive real business and talent results. 

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.

In this episode, I interview Layla Farivar, Employee Benefits Consultant at IMA Financial Group. Layla shares her inspiring career journey from the mortgage industry to finding her true passion in employee benefits. Layla opens up about transitioning from marketing to sales, sharing her refreshing perspective on why true confidence is built over time and how supportive leaders and powerful brand representation paved the way for her success.
Layla also talks about redefining modern leadership, and candidly explains why she chose to step away from people management to focus on individual contributions, and why it is vital to normalize that leadership doesn't always mean managing a team. Layla also shares her advice for women entering male-dominated spaces, the impact of IMA's women's network, and her take on what it takes to create a more equitable playing field in insurance.

In this episode, I interview Stephanie Miles, Senior Vice President, Producer, and Practice Leader at Marsh McLennan Agency, for an incredible conversation about family legacies, authenticity, and redefining leadership in insurance. Stephanie shares her unique journey to the industry, stemming from a deep-rooted family history starting with her grandfather's agency in 1910, and how pivoting from retail and underwriting eventually led her to build a multi-million-dollar book of business.
We dive into what it’s like being a triple threat in a male-dominated field, why selling insurance is a lot like selling a commodity like red lipstick, and how the industry can create its own "Caitlin Clark effect" by focusing on storytelling rather than changing its core. Stephanie also opens up about the realities of protecting family time as a working mother, building a true 50-50 partnership with her wife Taylor, and why ambition and prioritizing your home life can happily coexist. It’s a powerful, heartfelt discussion on ditching the corporate box, betting on yourself, and opening doors for the next generation.

In this episode, I interview Jennifer Kapp, Partner at Cruser, Mitchell, Novitz, Sanchez, Gaston & Zimet, LLP, to talk about her unique journey into the insurance industry, the realities of working motherhood, and why flexibility is the ultimate key to retaining top talent. Jennifer shares how she originally graduated from law school in 2008 during the economic downturn with the intention of pursuing public interest work, only to find herself stepping into the insurance world through a family connection. From there, she built a thriving career spanning claims, complex litigation, and thought leadership, proving that career paths do not need to follow a rigid, linear trajectory.
We discuss the challenges of navigating corporate return-to-office mandates, the power of authentic social media connections, and how her firm fosters an equitable environment by prioritizing autonomy and remote work. Jennifer also opens up about the beautiful mess of balancing a demanding legal career with raising three children, sharing why she believes women shouldn't feel pressured to do it all perfectly.