Posts by Amy Simpson
The 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,…
Read MoreCompensation Reality Check: Why Insurance Searches Stall When Budget and Expectations Don’t Align
There is a moment in almost every stalled insurance search where the conversation shifts. It usually sounds like this: “We just are not seeing the right candidates.” Or: “The market must be tighter than we thought.” But after working across underwriting, claims, brokerage, and leadership hiring, we can say this with confidence: Most stalled searches are not…
Read MoreThe Counteroffer Trap: What Insurance Professionals Should Consider Before Staying
It is a familiar moment in the insurance industry. You decide to leave. Not impulsively, not emotionally, but after thinking through your role, your growth, your compensation, and your long-term direction. You accept a new opportunity that feels like a step forward. Then the counteroffer comes. A raise. A new title. A renewed sense of urgency from…
Read MoreWhy Your Retention Problem May Actually Be a Hiring Strategy Problem
When insurance organizations talk about retention challenges, the conversation usually starts in the same place. “We need better engagement.” “We need stronger onboarding.” “We need better leadership development.” “We need to improve culture.” Those conversations are important. Retention does matter. But after years of working closely with insurance carriers, brokerages, MGAs, and agencies, we have noticed something consistent: …
Read MoreThe Interview Is a Two-Way Mirror: How to Evaluate Fit Before You Accept the Offer
Most insurance professionals walk into interviews focused on one thing: How do I prove I am the right candidate? That instinct makes sense. Interviews can feel like evaluations, and in many ways they are. Hiring managers are assessing experience, judgment, communication style, and technical knowledge. Candidates want to make a strong impression. But here is what many…
Read MoreBeyond Qualifications: Why Alignment Is the New Competitive Advantage in Insurance Hiring
For decades, insurance hiring followed a familiar formula. Find someone with the right experience, the right credentials, and the right technical skill set, then move quickly before another company does. That approach worked when talent was plentiful and career paths were predictable. But, today, it falls short. Insurance organizations are discovering that even the most qualified hires can struggle,…
Read MoreHuman vs. Automated Hiring: How Insurance Professionals Can Navigate an Evolving Interview Landscape
Hiring in the insurance industry has changed, but not always in the ways people expect. Technology has made its way into nearly every part of the hiring process. Online applications, automated screenings, virtual interviews and AI-driven tools are now common. For candidates, this shift can feel confusing, impersonal or even frustrating. For employers, it can feel efficient but disconnected. What has…
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