InsHER

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.

In this episode, I interview Candace Steele, Group Risk Director at Canopius Group Limited, for a conversation that spans continents and decades of resilience. Candace shares the fascinating story of how a manager’s recommendation to move to Bermuda during Hurricane Ivan accidentally launched her into the insurance industry. This path that eventually took her from her professional foundations in Canada to building a life and career in Bermuda and, most recently, the UK. We dive into what it truly means to navigate international moves with small children, the importance of maintaining your core values while adapting to new cultures, and why building a network is more critical than ever in an era where AI is changing how we approach hiring.
Candace also offers a refreshing perspective on the delicate balance between hard work and professional visibility. We unpack why women shouldn't wait to be noticed, but rather advocate for themselves with intention, and how external coaching can be a game-changer for building confidence early in one's career. From the necessity of genuine human connection in our global industry to the power of taking professional leaps before you feel "perfectly ready," Candace’s insights on sponsorship, mentorship, and self-advocacy are incredibly empowering.

In this episode, I interview Rajni Kapur, CEO of one of California’s largest independently owned insurance agencies, All Solutions Insurance. We discuss her inspiring path from CPA to insurance leader. Rajni opens up about the resilience required to launch her agency in 2003 while navigating the complexities of new motherhood, explaining how those early years shaped her leadership philosophy. She shares her powerful perspective on why working mothers don't need reduced responsibilities, but rather the trust and flexibility to excel while managing their family lives.
The conversation also dives deep into Rajni’s commitment to building a workplace culture that normalizes real-life challenges, including her policy of welcoming children into the office when needed. Rajni also emphasizes the "clear but kind" feedback approach and the need for intentional support systems that foster growth rather than discourage. Rajni also details her ambitious vision for the future, including her plans to create educational programs and measurable pathways to help more women secure equitable leadership roles within the insurance industry. 

In this episode, I interview Rachel Druckenmiller, Keynote Speaker + Founder, UNMUTED, and former Director of Well-Being and Employee Engagement at a benefits consulting firm. Rachel opens up about her unexpected 13-year journey in the insurance industry, which began as a simple summer administrative role and evolved into pioneering an award-winning corporate wellness initiative from scratch. Facing tight budgets and early resistance, Rachel shares how she and a colleague eventually built a national exemplar of workplace wellness by experimenting with innovative ideas internally before offering them to clients. She dives into the art of service differentiation, detailing how providing unique, personalized value not only cements client retention but also positions insurance professionals as indispensable industry leaders.
Rachel also introduces me to the concept of "internal muting", the ways professionals, particularly women, silence their own voices due to internal, relational, or structural fears. Drawing from her own raw experience with burnout and health challenges while at the height of her corporate career, Rachel breaks down how authentic self-confidence is fundamentally rooted in self-trust. She shares actionable leadership strategies for overcoming self-silencing, including the "Reflected Best Self" feedback practice and the transformative shift of asking "what if it were just right?" instead of focusing on the worst-case scenario. What resonated most is her perspective on championing ambitious talent, not to be threatened by it.
 
Rachel also shared these original songs!
Somebody: https://song.link/somebody-rachel
Believe In You: https://song.link/believeinyou

In this episode, I interview Natina Berry, Senior Underwriter at Freberg Environmental, with over 20 years of expertise in commercial insurance and strategic account management. Natina shares her fascinating career journey with me, which began with a specialized training program through The Hartford. Beyond her corporate role, Natina discusses her extensive leadership in the industry, including serving as president of the NAAIA New York Tri-State Chapter and on the board of RIMS New York, explaining how getting involved in committees builds genuine confidence and visibility. Natina is also a single mother of four boys, and opens up about the "five-shift" daily structure she used to approach parenting and her career.
Our conversation goes deep into the true meaning of professional development, moving past surface-level networking to focus on building authentic relationships, mentorship, and sponsorship. Natina highlights how unexpected skills, like learning to play golf, opened unique doors for connection. From inspiring the next generation at a local Girl Scouts event to preparing diverse teams for the impact of AI, Natina defines leadership as actively opening doors for others.