Retiring Underwriters Are Creating An Insurance Talent Shortage 

The industry is about to lose decades of underwriting expertise. Here’s why addressing the knowledge bridge matters more than filling open enrollment.  

What is the operational impact of this talent shortage? 

The insurance talent shortage is already reshaping daily operations for carriers—and the impact reaches well beyond headcount. 

The Bureau of Labor Statistics (BLS) projections estimate that nearly 400,000 insurance professionals will retire by the end of 2026. That’s 400,000 seasoned professionals with decades of hands-on experience—and carriers, MGAs, and brokerages have seen this approaching on the horizon and are feeling the pressure 

According to Convr’s 2025 Insurance Talent and Tech Trends survey, 82 percent of insurance leaders say staffing limitations are negatively affecting their growth and/or expense ratio—and underwriting remains the single hardest area to staff with quality candidates. Worse, 72 percent say understaffing has already led to inaccurate information informing their quotes, and 83 percent tie understaffing to more negative customer experiences. 

With significantly more people retiring and churning versus onboarding, insurance leaders are feeling the operational strain and trying to figure out what’s next. 

This is the insurance industry’s emerging “silver tsunami”—a term for the wave of baby boomer retirements sweeping through carriers. It’s ripple effects extends across headcount and the apprenticeship model that’s built underwriting expertise for generations. 

Knowledge shouldn’t leave with your experienced underwriters 

When most people hear “talent shortage,” they think about open enrollment and time-to-fill. But what makes the insurance industry talent crisis different is what’s leaving with the people who retire. 

BLS also highlighted that one in four underwriters is over 50. The average insurance professional is in their mid-50s. Over the next decade, roughly half of the workforce will retire—and they’ll take decades of tacit knowledge with them. On the other hand, less than 25 percent of the insurance workforce is under 35. 

The imbalance alone would already be a point of concern, but coupled with the fact that the knowledge isn’t being transferred, creates a challenge that insurers are still struggling to solve. 

According to the American Productivity and Quality Center (APQC) The Great Retirement: Knowledge Loss, AI and the Workforce Shift Survey Report, 93% of insurance CxOs say they’re genuinely concerned about knowledge loss from departing employees—yet that same percentage are not consistently capturing knowledge before those employees walk out the door.  

This expertise rarely lives in a manual or a playbook. It lives in the veteran underwriter who instinctively knows which risks warrant a second look. The claims adjuster who spots fraud patterns before losses spiral. The senior analyst who can read a submission and feel something’s off before the data confirms it. 

Skills like judgement and discernment are refined through experience. Training decks and AI can only do so much without it. 

Why AI Alone Won’t Close the Gap 

As most other industries, AI is making its waves in insurance operations. And just like other industries, automation can unintentionally replace mechanisms and processes that were previously used to learn and build knowledge.  

The entry-level tasks that junior underwriters cut their teeth on—data gathering, submission intake, preliminary risk review—are typically the tasks being automated first. And while it does create efficiencies, it removes the on-ramp that junior talent reaps the most value from—building pattern recognition and judgment that mentorship is designed to sharpen. 

That gap matters because AI is not yet preserving the knowledge those early career experiences used to pass down. In fact, APQC notes that 87% of carriers have yet to operationalize AI for knowledge capture and management. Until that changes, automation can make work more efficient while still weakening the path junior talent needs to build judgment. 

AI can codify some of what experienced underwriters know, but it isn’t yet in a place where it can replicate how they teach. And when you automate the on-ramp and don’t have enough people in the building to learn, the insurance mentorship gap can compound fast. 

4 ways to preserve institutional knowledge 

If APQC found that 83% of insurance organizations are still relying on manual, people-to-people methods to transfer knowledge—and those people are leaving—it stands to reason that a priority for insurers would be investing in onboarding the right people before it’s too late. 

And 95% of insurance leaders agree their company’s performance could improve with process efficiencies in underwriting, highlights Convr. Hiring support roles is one of the fastest ways to unlock those efficiencies—and create the space for insurance knowledge transfer to actually happen. 

Here are four levers you can use that treat talent as both a recruiting discipline and a knowledge preservation strategy: 

1. Staff underwriting support roles to free up senior underwriters for mentorship. Your most experienced people can’t transfer knowledge if they’re buried in data entry and administrative work. Bring in support staff to handle the low-value tasks so your senior underwriters can do what only they can do: teach. 

2. Build contract-to-hire pipelines that double as learning pathways. Bring junior talent in on flexible engagements. Pair them directly with senior underwriters during the contract period. You’re assessing fit and absorbing institutional knowledge simultaneously. The best performers convert to full-time with months of mentored experience already under their belt. 

3. Recruit mid-career professionals from adjacent industries. Analytical thinkers from finance, risk consulting, and data science already speak the language of risk. They can be trained in underwriting fundamentals by the very veterans who are about to retire—but only if you get them in the door fast enough. 

4. Design phased retirement around staffing and knowledge transfer. Breaking down retirement into phases gives senior underwriters a gradual off-ramp while they share what they know. But it only works if there’s someone on the other side of the desk ready to absorb it. A prepared, proactive staffing plan is equally crucial to successful knowledge transfer. 

Protect your expertise while you can 

The insurance talent shortage is real, and so is the risk of decades of underwriting judgment walking out the door before anyone captures it. 

We’ve seen the most successful carriers are the ones already preparing and empowering their people for it. 

Insight Global helps insurance companies cross the knowledge bridge and fill open enrollment with a strategy built around preserving expertise. Whether you need underwriting support teams, contract-to-hire pipelines, or mid-career talent from adjacent industries, we can help you move fast enough to preserve what matters most.