A featured contribution from Leadership Perspectives: a curated forum reserved for leaders nominated by our subscribers and vetted by the Retail Tech Insights Advisory Board.

SterlingRisk
Leading Risk Management with Data and Judgment


Stevi Siber-Sanderowitz
A Holistic Approach to Risk
My background in insurance, litigation and analytics lets me assess risk from multiple perspectives. Insurance grounds my understanding of coverage and risk transfer. Litigation gives practical insight into dispute resolution, defense strategy, settlement pressure, venue risk and trial realities. Analytics connects these, transforming information into actionable strategies.
Bringing these areas together has made me proactive in my approach to risk. I identify trends early, realistically assess exposure and help organizations make informed decisions to prevent issues from escalating into larger legal or financial problems. I integrate analysis of claims data, policy language, contractual obligations, litigation history and operational trends to provide a comprehensive understanding of risk.
It also strengthens my communication with business leaders. Executives want practical impacts and clear options, not a law school lecture. I translate complex legal and insurance issues into clear business recommendations that support operations while minimizing exposure.
A Strategic Approach to Risk Management
A major challenge is that risk is often managed in silos. Legal, finance, compliance, claims and operations can view the same issue from different angles, leading to inconsistent strategies and missed early opportunities to address it.
In addition to siloed risk management, unpredictability is a significant challenge. Among evolving case law, nuclear verdicts, regulatory changes and complex coverage disputes, organizations must navigate a constantly shifting risk environment. Balancing litigation strategy with financial and reputational costs is more complicated than ever.
“Early exposure analysis and clear reporting help organizations make better legal and financial decisions.”
I take a cross-functional, data-driven approach. I align stakeholders on claims trends, policy analysis, litigation developments or operational risks. Early exposure analysis and clear reporting help organizations make better legal and financial decisions.
Frame issues using business metrics, provide decision-makers with facts on probability, cost, impact and tradeoffs, and maintain consistent documentation and analysis to support successful outcomes in litigation or negotiations.
Turning Data into Better Decisions
Analytics strengthens judgment but does not replace it. Legal and insurance decisions need experience and context, but data reveals trends and exposures that might otherwise be missed.
I start by defining the specific business or legal question. Then, I use data to evaluate patterns like claim frequency, severity, defense costs, settlement timing, venue exposure and operational risks. This helps in forecasting, reserve decisions, settlement strategy and risk transfer choices.
I emphasize that data must be interpreted in context. In litigation and insurance, outcomes depend on factors like jurisdiction, policy wording, industry and claim type; numbers alone rarely tell the whole story.
Analytics should clarify, not complicate. Leaders need clear, useful metrics. If a report is confusing, it is not serving its purpose.
Leading through a Changing Risk Landscape
Several trends are reshaping the industry. Social inflation and nuclear verdicts drive up claim severity, especially in high-exposure areas. Cyber, privacy claims and regulatory scrutiny are rising across industries. AI and predictive analytics are also changing how organizations handle claims and assess exposure.
Insurers now underwrite more cautiously and scrutinize claims more closely, increasing the need for strong documentation, consistent controls and solid risk analysis.
I stay informed on litigation, claim trends, coverage issues, and focus on data quality. Predictive tools are only as good as their data. Technology can help, but sound judgment and practical insight are still required.
More than anything, adaptability matters. The risk landscape changes quickly, so strategies must evolve. Continuous learning, cross-departmental collaboration and reassessing assumptions are essential to staying ahead.
Advice for Emerging Leaders
Do not specialize too early. Standouts in this field know the law but also understand the business and financial drivers of risk. Learn insurance practice, litigation realities and be comfortable with data.
Communication and technical skills are equally important. Even the best analysis loses value if you cannot clearly explain it to executives, clients or teams. Translating complex issues into business guidance sets strong advisors apart.
Stay adaptable and curious. This field evolves quickly with technological advances, regulatory changes and shifts in litigation. Those who learn about new risks and build cross-functional skills succeed.
Finally, never underestimate the importance of judgment. Data and legal analysis matter. But the ability to evaluate risk in context, draw on experience and make sound decisions under uncertainty drives strong outcomes.


