Jason Gesser on Why Clear Communication Is a Risk Advisor’s Greatest Asset

Jason Gesser on Why Clear Communication Is a Risk Advisor's Greatest Asset
Photo Courtesy: Jason Gesser

By: Natalie Johnson

Clear communication is the most essential part of a Risk Advisor’s approach to business. The key to serving clients well is making sure that what is at stake is translated plainly. If stakeholders cannot openly see how risk translates into real financial, operational, and strategic consequences, they will not take action.

ā€œClients don’t need abstract theory. They need to understand what’s at stake, where they’re exposed, and what happens if something goes wrong,ā€ says Jason Gesser, Sr. Vice President of Commercial Lines at USI Insurance Services.

This philosophy underpins Gesser’s approach to risk communication in commercial insurance on behalf of his clients in the Pacific Northwest, particularly in the construction sector, where he designs and structures comprehensive Commercial Lines programs for contractors, including Project Specific insurance and Builders Risk placements. Below, he shares how to translate risk into business language that drives action.

Turning Risk Into Real-World Impact

Effective risk communication starts with the ability to make exposure tangible. Gesser frames conversations around outcomes that matter most to construction executives, CFOs and Project Managers.

ā€œI anchor every discussion to money, time, and accountability,ā€ he says. ā€œWhat would a 30-day delay cost your project? What happens if a loss hits your balance sheet today? Who owns the problem at 7 a.m. when something goes wrong?ā€

This storytelling-driven method reflects a broader shift in risk advisory. Gesser uses real-world scenarios that mirror a client’s operations to align with how mid-to-large contractors manage and evaluate construction risk. This leads to a comprehensible understanding of exposure across key areas such as Business Interruption, Professional Liability, and contractor insurance programs. It also allows decision-makers to connect insurance strategy with operational and financial outcomes.

Translating One Risk Into Multiple Business Languages

A defining feature of Gesser’s client-first advisory model is his ability to tailor risk communication to different stakeholders without changing the underlying message. ā€œThe core risk doesn’t change,ā€ Gesser says. ā€œJust the framing.ā€ The same construction risk can carry very different implications depending on who is in the room.

For CFOs, the conversation centers on financial volatility, capital preservation, and the impact on enterprise value. Discussions focus on how coverage solutions mitigate balance sheet surprises and reduce the total cost of risk. For project managers, the lens might shift to operational realities such as downtime, subcontractor disputes, and schedule pressure.

By aligning risk communication with each stakeholder’s priorities, Gesser turns insurance program design into a shared business issue rather than a technical exercise. This results in adding direct value to his clients’ decision-making around Project Specific insurance, Builders Risk coverage for complex projects, and broader commercial lines strategies.

Exposing Hidden Gaps Before They Become Losses

One of the most pressing challenges in construction risk today is the impact of rising project costs. Tariffs and inflation continue to push valuations higher, yet many insurance programs remain static. The result is a growing gap between insured values and actual replacement costs.

ā€œMost uncovered losses don’t come from negligence,ā€ Gesser notes. ā€œThey come from outdated assumptions.ā€ His strategy is to make that gap visible. By comparing current insured values with real-time placement costs, he surfaces discrepancies that might otherwise go unnoticed. ā€œOnce clients see the delta in black and white, the conversation becomes urgent on its own.ā€

From Reactive Broker to Proactive Risk Advisor

The future of commercial insurance is shifting toward proactive insight, driven by data and emerging technologies. Gesser sees this transformation already underway, particularly in how risk advisory services are delivered to construction firms.

ā€œThe biggest shift is from reactive explanations to proactive insights,ā€ he says. ā€œInstead of explaining what happened and how we’ll help handle it, we’re moving to preemptively advising on what is likely to happen and what clients should do about it.ā€

Through pre-renewal analysis, benchmarking, and data-driven underwriting strategies, Gesser helps clients evaluate commercial insurance gaps before they become costly issues. The integration of AI and real-time data further enhances this process, enabling more responsive and flexible insurance program design. Even as technology evolves, Gesser maintains that communication remains the defining factor.

ā€œThe brokers who add the most value won’t be the best policy readers,ā€ he says. ā€œThey’ll be the clearest communicators.ā€

Clear Risk Communication Drives Better Decisions

The role of a risk advisor in construction extends beyond placing policies. It involves coaching clients through complex insurance decisions and building structured insurance programs for contractors that evolve with their business. Gesser’s background, from leading on the football field to advising in the boardroom, reinforces this mindset. Preparation, accountability, and clarity remain central to both disciplines. His approach highlights a critical truth for risk-ready businesses: communication is a strategic capability that influences coverage decisions, financial outcomes, and long-term resilience.

Follow Jason Gesser on LinkedIn or visit his website for more insights.

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