How To Overcome The Insurance Staffing Crisis

When we talk with Outmarket customers, we regularly hear about the challenges they are facing with staffing, particularly commercial line CSRs. These challenges are pervasive across the industry, and they are painful for brokerages of all sizes. 

This is a two-pronged crisis. On the front end, there is a staggering lack of interest from the next generation of workers. Despite a challenging job market for recent graduates, a 2025 Cake & Arrow study found that 79% of Gen Z have never even considered an insurance career, with nearly half stating they have zero interest in the field. 

However, the challenge isn't just getting talent through the door. The second prong of the crisis is keeping talented employees there long enough to see a return on investment. The industry is currently trapped in a high-stakes hiring and training loop. If a new hire burns out or leaves within their first year, the agency loses its entire investment and starts from square one — but only after many months of searching for a new hire. 

It’s incredibly difficult to break this cycle, because the risk of burnout is higher than ever. According to Liberty Mutual and Safeco, 51% of frontline staff feel burned out, largely because 87% have seen their workloads spike over the last year. 

What we’re hearing from insurance leaders is that this entire crisis has made it impossible to grow their businesses without growing headcount. 

If brokerages want to break this cycle, we need to reframe the problem. 

The Staffing Crisis Isn’t An HR Problem 

The staffing crisis in insurance is not an HR problem, it is a work problem. Insurance professionals are not leaving the industry, they are leaving endless data entry, 400 page PDFs, and workflows that turn experienced operators into human middleware. When high stakes decision making is paired with tedious, repetitive tasks and outdated systems, burnout becomes inevitable. Stress compounds, errors rise, and retention falls, not because people lack commitment, but because the work itself is unnecessarily hard.

The most common workflows in the insurance industry are fueling the staffing crisis. If we can fix the workflows, we can put an end to the staffing crisis altogether. 

Can Insurance AI End the Crisis?

Insurance AI is already rewriting the rules of burdensome insurance workflows. We built the world’s #1 insurance AI by focusing relentlessly on how brokers work each and every day. The results are transformative when brokerages strategically select and deploy the right AI for their business. 

Kevin Hawkinson at Commercial Insurance Associates made a bold bet on insurance AI with Outmarket, and he reported “It pays for itself in terms of not having to hire additional service staff. Our agency is more agile, and we can bring on more clients.” 

Hawkinson estimates that Outmarket is already saving his staff 17,160 hours per year. The immediate time savings fuels growth without growing headcount. 

To get started down a similar path, take a phased approach including:

1. Identifying workflows and processes that are the biggest choke points and resource drains for your team. 

2. Evaluating AI solutions to determine if their workflows work like your people work. Are they compatible and adaptable to your mission-critical processes, or would the AI force you to change how you operate? 

3. Testing solutions in real-world scenarios. Empower your team by giving them an opportunity to experiment, evaluate and buy into these solutions. 

4. Deploying AI to your most burdensome workflows first — because brokerage-wide adoption is much easier when you solve the most common pain points for your team. 

5. Measuring impact. When you can quantify early success with AI, you begin a virtuous cycle that fuels ongoing innovation and growth. 

The staffing crisis will not be solved overnight. But brokerages that invest in AI designed to work the way their teams work will reduce friction, restore focus to high value work, and emerge on the other side of the staffing challenge stronger, faster, and more resilient than the rest.