Kristin Guglielmo | Digital Insurance Summit

Digital Insurance Summit 2026

May 18 - 19, 2026

Westin Copley Place - Boston, MA

Kristin Guglielmo

Kristin Guglielmo

Founder and CEO Strategic Intelligent AI Solutions LLC
Kristin Guglielmo
Kristin Guglielmo is the Founder and Principal of Strategic Intelligent AI Solutions LLC and a 30-year insurance industry veteran with over two decades as a business owner. She previously led and successfully exited a 160-year-old insurance agency, giving her firsthand experience navigating legacy systems, regulatory complexity, and operational risk. Today, Kristin advises insurance organizations on how to modernize responsibly using AI. Her approach centers on her framework, Clarity to Automation to Intelligence, ensuring that technology aligns with people, compliance, and long-term trust. She specializes in helping agencies and carriers identify operational bottlenecks, strengthen knowledge systems, and implement AI to improve decision-making without introducing new risk.

Transforming Modern Insurance Models with Data and AI

10:00 AM Keynote Panel: Building and Uniting Data – New Challenges and Opportunities

Insurance organizations are drowning in data from countless sources, leaving insights fragmented and hard to act on. This disconnection slows decision-making, hampers customer experiences, and limits growth. This panel will illuminate how to turn scattered data into a cohesive, organized source to draw upon for decision-making and AI. We will spotlight practical strategies for integrating diverse systems, improving data quality, and unlocking real-time insights that drive smarter decisions. By creating a seamless flow of information, insurers can streamline operations, anticipate customer needs, and respond faster to market shifts. Attendees will leave with clear approaches to transform disconnected data into a powerful tool for engagement, efficiency, and growth.

Participants will leave the session equipped to:

  • Unify fragmented data sources into a cohesive, accessible framework for faster, smarter decisions
  • Boost data quality and governance to ensure insights are reliable and trusted
  • Turn scattered information into actionable intelligence that drives measurable business results

3:20 PM Track A: Fireside Chat: Staying Relevant in the Age of Generative AI & AI-Driven Search

AI tools and AI-driven search are changing how customers buy and interact with their insurance companies, including how they discover and evaluate options, get answers to their insurance-related questions, and even how they get quotes. This panel brings together industry leaders to explore how generative AI and AI-driven search are influencing the insurance landscape. Panelists will share ideas for how engagement signals, content relevance, and data feed into recommendation engines and AI algorithms. They’ll also discuss implications for brand perception, trust, and customer acquisition. We’ll explore the need to understand AI as a gatekeeper rather than just a marketing channel. We will also talk about leveraging generative AI tools and search to drive customer engagement and improve search results. The discussion will provide ideas for: 

  • Optimizing digital content and metadata to align with machine learning factors
  • Monitoring how your own company is referenced on popular AI search platforms
  • Designing digital engagement strategies that feed favorable recommendation patterns
  • Maintaining relevance, building trust, and upping ‘discoverability’ in a loud digital world 

Innovation for Efficiency: Streamlining Insurance Experiences and Operations

11:20 AM Panel: Building Trust in AI-Driven Insurance

Trust in AI is becoming a defining factor for insurers as they integrate advanced technologies across underwriting, claims, and customer engagement. This panel will explore the critical question: how can insurers implement AI responsibly while maintaining confidence among customers, regulators, and internal stakeholders? By bringing together leaders from across the insurance ecosystem, the discussion will highlight practical approaches to AI governance, transparency, and risk management, emphasizing the importance of a multi-stakeholder perspective. Participants will gain insights into not just the “how” of deploying AI, but the “why” behind building trust and accountability in these systems. Panelists will share real-world strategies and lessons learned to ensure AI initiatives are ethical, compliant, and customer-centric. They will explore the frameworks, policies, and cross-functional collaborations that help organizations navigate regulatory expectations, mitigate biases, and maintain credibility in an AI-driven environment. Attendees will leave with actionable ideas for integrating AI governance into everyday operations, ensuring technology strengthens rather than erodes stakeholder confidence. Takeaways from this session will include how to:

  • Establish governance frameworks that balance innovation with accountability
  • Identify and mitigate potential biases in AI models
  • Engage internal and external stakeholders to build transparency
  • Align AI deployment with regulatory and ethical standards
  • Foster an organizational culture that supports responsible AI use

Check out the incredible speaker line-up to see who will be joining Kristin.

Download The Latest Agenda