Arrive early, connect with peers, and step into the room with intention. 

Transformation isn’t theoretical for insurance leaders—it’s happening in real time, shaped by market pressure, evolving risk, and rising expectations from clients and capital providers. From M&A to portfolio shifts, leaders are making decisions while the ground is still moving. This conversation explores how senior leaders read the environment, make strategic calls, and lead through both planned change and unexpected disruption. 

• The external forces actually driving change—from capital pressure to emerging risk and client demand 
• How leaders read signals and translate them into clear strategic moves 
  
• When M&A and structural change become growth plays—not just reactions 
• Keeping teams aligned and moving forward when direction isn’t fully clear 

From complex claims and fraud to regulatory scrutiny and reputational risk, senior leaders are increasingly required to make high-stakes decisions with incomplete information. This conversation brings together experienced insurance leaders to share real-world examples of navigating complex situations where judgment and values are tested. This session focuses on how those decisions play out in real-world scenarios—where stakes are high, timelines are tight, and outcomes are visible.

• Sharing high-pressure scenarios that challenged executive judgment
• Understanding how to weigh competing priorities when the path forward isn’t clear
• Identifying where silos and legacy processes increase risk—and how collaboration improves response
• Supporting teams through emotionally demanding and high-stakes work

Reflect on the morning’s sessions, recharge with coffee, and make a new connection. 

This is where the real exchange happens.

Join senior leaders for focused, peer-driven conversations on the issues shaping strategy, leadership, and growth across the insurance industry. Exchange perspectives, challenge assumptions, and leave with ideas you can put into practice.

Choose a table aligned to your priorities and join discussions on:

• Cyber risk & emerging exposures
• AI & digital transformation
• Talent, retention & succession planning
• Claims transformation & rising cost pressures
• Distribution & evolving client expectations
• Underwriting discipline in a volatile market
• Climate & catastrophic risk
• LinkedIn, visibility & building influence in insurance
• Perimenopause, menopause, & performance at work
• Mentorship, sponsorship & career growth

Join us as an industry leader shares the defining moments, risks, and lessons that shaped her career in insurance — offering a candid look behind the title and the path it took to get there. 

At the senior level, leadership is defined as much by influence and presence as it is by expertise. This panel brings together accomplished women in insurance to share how they’ve learned to articulate their value, command senior rooms, and shape pathways to executive and board-level roles, often before they felt fully “ready.”

• Highlighting how women have crafted and communicated narratives that clearly link their experience to business outcomes and strategic value
• Showcasing what presence and authority look like in executive, client, and board-level conversations, and how to continue development over time
• Practical ways to elevate “behind-the-scenes” contributions into visible, valued impact without self-promotion fatigue

Connect with peers, trade ideas and discuss opportunities. 

Strong organizations are built by people who choose to stay—but too often, high-performing talent disengages, stalls, or leaves altogether. This panel focuses on how senior leaders can better understand retention challenges and intentionally build cultures where people grow, contribute, and stay invested.

• Exploring the real drivers behind disengagement and turnover across career stages
• Identifying what leaders often get wrong about retention—and how to course-correct
• Diving into how development, sponsorship, and meaningful feedback shape long-term commitment
• Highlighting leadership behaviors that turn teams into communities people choose to stay in

Technology and AI are no longer side conversations—they are core to enterprise performance and risk management. This fireside chat explores how insurance leaders approach technology decisions through a business lens, including where investments deliver real value—and where they fall short.

• Showcasing where AI and automation have delivered measurable business impact—and where expectations haven’t matched reality
• Understanding where to invest, where to pause, and how to align tech bets with strategy
• Navigating governance and people considerations, including risk, bias, vendor complexity, and keeping human judgment in the loop
• How leaders can challenge assumptions, ask better questions, and take a more active role in technology decisions

Step away from sessions and reconnect with peers in a more intentional way. This break is designed to help you reflect on key insights, share challenges, and exchange practical ideas with others navigating similar decisions. 

A single conversation can change the course of a career. In this quick-hit session, an industry leader shares a pivotal conversation, piece of advice, or unexpected moment that shifted her perspective, leadership style, or next move.

The most effective leaders don’t rely on a single leadership style—they adapt how they communicate, make decisions, and lead based on the people and situations in front of them. In this interactive session, certified Myers-Briggs instructor and Ladder Down founder, Beth Fitch guides participants through a practical exploration of personality preferences—and how they can create alignment or friction within teams.

• Explore personality preferences and how they show up in everyday leadership moments
• Identify your strengths—and where they may work for or against you—through guided self-reflection and group exercises
• Learn practical strategies for flexing your style to communicate, motivate, and collaborate more effectively across differences

Close the day with a fast-paced, candid conversation where senior leaders share quick lessons and perspectives that have shaped how they lead today. Through a series of rapid-fire questions, speakers reflect on what they’ve learned over time—what they’d do differently, what matters most now, and what they wish they knew earlier.

Short answers. Honest reflections. No scripts.

Not ready to end the day? Keep the conversations going while experiencing some of the best food Chicago has to offer. Join fellow attendees for curated small-group dinners at local restaurants across the city. Dinner groups will meet at 6:30 PM, with sign-ups available at the registration desk throughout the day. Reservations will be coordinated by our team, with attendees paying individually at the restaurant.