Federal labor projections put roughly 400,000 insurance roles at risk of going unfilled over the coming decade.¹ Replacing 400,000 people is a recruiting challenge. Preserving the knowledge and judgment behind them is a different task, one that will be critical to maintaining business stability.
The Real Exposure
Veteran professional knowledge is immense and not often captured in writing. Their decisions are made in part by instinct based on both experience and historical client performance. This may look like an underwriter giving extra time to a submission when the numbers pass but something in the file does not. It can also be a claims professional who sees a loss pattern forming before it compounds. Judgment of this kind is critical in insurance, yet its value can be difficult to quantify and even harder to capture.
Close to one in four insurance professionals is 55 or older.² The commercial underwriting judgment needed typically takes years to develop, and that assumes access to an experienced mentor. The window in which a role handoff can happen is set by retirement dates, not by planning cycles. Leadership that names successors early and builds the bench years before a retirement date turns a fixed deadline into a planned transition.
The Automation Question
With automation absorbing routine work, underwriter headcount is expected to shrink over the coming decade. At the same time, the work itself is becoming more complex, creating new demands on the leaders and professionals who remain. Leadership needs are evolving alongside the work itself. Across the insurance industry, executive search activity reflects continued demand for leaders who can pair deep underwriting judgment with data and technology fluency.
Automation may absorb some volume, but it does not absorb discretion. The complex, ambiguous work where experienced judgment carries the most weight still needs people. That creates a sequencing challenge carriers will increasingly need to navigate. A model learns from the bench that remains. Train one on a thinned, more junior group and the output reflects their choices, not the judgment of the practitioners who left. AI is a workforce multiplier, not a replacement.
Succession Planning in Practice
Preserving judgment is an operational discipline, not a documentation exercise; proximity does most of the work.
Strategically pairing professionals within a few years of retirement with their anticipated successors creates the conditions in which tacit judgment moves. Ensure the reasoning behind difficult decisions is captured on paper, not simply the outcomes, because the reasoning is exactly what a junior team member lacks.
With about a quarter of the workforce under the age of 35, the internal bench may not be large enough to replace what is leaving, which means looking beyond the current team. Graduate programs, apprenticeships, rotational assignments and mid-career hires from adjacent fields all widen the intake. Whether that talent can carry the work depends on that same pairing discipline and years of investment. Additionally, offering a phased retirement, where compensation structures and culture allow, converts a departure date into a transition period.
Combined, these efforts buy time against a clock that cannot be slowed.
The Opportunity Within the TransitionThe pattern intensifies at the leadership level, where the loss is harder to replace and the runway to develop a successor is longer. Below the executive line, a retirement removes a practitioner. At the top, a retirement removes the individual who set the bar, arbitrated the exceptions and held the reinsurer and broker relationships through which pricing gets negotiated. A retiring Chief Underwriting Officer or Head of Claims carries not only technical judgment, but the institutional memory of how the organization weighs risk: which classes the carrier has walked away from and why, which exceptions proved costly and where appetite was quietly tightened after a bad year. Succession at that level cannot be improvised in the quarter a resignation arrives. A turnover of this scale is a loss of expertise and an opportunity that rarely comes twice. Organizations rebuilding their bench have license to reexamine assumptions that tenure made permanent, structure knowledge in ways never done before and hire for capabilities the previous generation was never asked to hold. The external market can provide important options, especially when every competitor is recruiting from the same short list of proven executives. Organizations best positioned to turn the transition into a talent advantage will begin the work while industry veterans are still in the building. |
SOURCES
¹ U.S. Bureau of Labor Statistics projections, cited by the U.S. Chamber of Commerce, 2026.
² U.S. Bureau of Labor Statistics workforce data, via industry reporting, 2025–2026
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