Posts by Amy Simpson
Why Top Insurance Talent Leaves, Even When They’re Paid Well
Compensation matters. Insurance professionals know their market value, and employers know competitive pay is necessary to attract and retain experienced people. When someone leaves, salary is also one of the easiest explanations to point to. They received a better offer. They wanted more money. A competitor was willing to pay more. Sometimes, that is exactly what happened. Other times,…
Read MoreThe Leadership Gap Nobody Talks About: Preparing Your Next Generation of Insurance Leaders
The insurance industry has spent years talking about its talent gap. Experienced professionals are retiring. Specialized expertise is difficult to replace. Organizations are competing for people who understand increasingly complex markets, technologies, products, and client expectations. There is another gap that deserves just as much attention. The leadership gap. Many insurance organizations have strong individual contributors and…
Read MoreThe Cost of Staying Comfortable: When Growth Requires a Change
Comfort is not a bad thing. In a career, it can mean stability, confidence, strong relationships, and a deep understanding of the work. For employers, it can mean experienced people who know the business, support the team, and perform consistently. The problem begins when comfort turns into stagnation. For professionals, that can look like staying in the same…
Read MoreWhat Insurance Professionals Should Know About AI in Hiring
Artificial intelligence has become impossible to ignore. Whether you are applying for a new role, updating your resume, or preparing for an interview, you’ve probably heard someone say, “Make sure your resume is AI-friendly.” The advice isn’t wrong, but it is often incomplete. AI is changing how companies recruit. Applicant tracking systems are becoming more sophisticated, automation is helping hiring teams manage…
Read MoreAI Can Screen a Resume. It Can’t Spot Leadership.
Artificial intelligence has become one of the biggest topics in recruiting. Every week, there seems to be a new platform promising faster hiring, better candidate matching, or more efficient recruiting processes. Organizations are investing in automation to save time, reduce administrative work, and improve hiring outcomes. Some of those tools are genuinely valuable. Others promise…
Read MoreWhy Strong Insurance Candidates Are Losing Momentum in Long Hiring Processes
There is a frustrating reality many insurance professionals are facing right now. They apply for a role, have a strong conversation, receive positive feedback, and feel confident about the opportunity. Then things slow down. Days turn into weeks. Weeks turn into months. Communication becomes sporadic. Interview rounds multiply. Timelines shift. Eventually, many candidates find themselves…
Read MoreThe Cost of Waiting: When Delayed Hiring Decisions Start Hurting the Business
Most hiring managers believe they are being careful. They want to evaluate every option. Compare candidates thoroughly. Make the right decision. On the surface, that sounds responsible. But in today’s insurance hiring market, there is a growing difference between being thoughtful and being slow. And that difference can be expensive. Over the past few years, hiring…
Read MoreSuccession Is Not a Plan: How Insurance Companies Should Be Thinking About Leadership Before It’s Urgent
Most insurance organizations know succession planning matters, but very few approach it with the urgency it deserves. Instead, succession conversations tend to happen reactively: At that point, the organization is no longer planning; it is responding under pressure. And in insurance, where leadership stability directly impacts teams, clients, operations, and long-term growth, reactive leadership hiring is one of…
Read MoreHiring Leaders Who Change Trajectory: What Sets High-Impact Insurance Executives Apart
There is a difference between hiring an executive who maintains a business and hiring one who changes its trajectory. On paper, both candidates may look qualified. Both may have years of experience, recognizable employers, and technical credibility within the insurance industry. But over time, the outcomes look very different. One leader keeps the organization operating. The other elevates it. One…
Read MoreFrom Technical Expert to Strategic Leader: Making the Shift in Insurance
At some point in an insurance career, the question changes. Early on, success is about learning the role, building expertise, and becoming someone others rely on. You develop technical depth. You understand the details. You become the person people go to when something needs to be done right. Then the opportunity for leadership appears. And suddenly,…
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