Posts by Amy Simpson
Compensation 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…
Read MoreStop the Search Spiral: Why Insurance Roles Stall and How the Right Alignment Gets Them Moving Again
Every insurance organization has experienced it. A role opens with urgency. The need is clear. The team agrees it is important. Recruiting begins with momentum and optimism. Then weeks pass. Interviews slow down. Feedback gets vague. Candidates drop out. The search drags on longer than anyone expected. Eventually, frustration sets in, and the conclusion sounds something like this: “There just aren’t any…
Read MoreStanding Out Without Shouting: How Insurance Professionals Can Showcase Impact in a Noisy Market
The insurance industry has never lacked smart, capable professionals. What has changed is how crowded the conversation has become. Today’s job market is loud. Everyone seems to be talking about personal branding, optimizing resume leveraging LinkedIn, and “selling yourself.” For insurance professionals, especially those in underwriting, claims, brokerage and operations, that advice often feels misaligned with reality. Many of the most effective people in insurance…
Read MoreWhere Great Hiring Breaks Down First: How Early-Stage Process Mistakes Repel Top Insurance Talent
Companies often assume that their biggest hiring challenge is a lack of strong candidates. But after years of working with professionals across underwriting, claims, brokerage, risk and specialty lines, we’ve learned something different: Most organizations aren’t struggling because great candidates don’t exist. They’re struggling because great candidates never make it past the first step of the hiring process. And here’s the catch—most companies never know it’s happening. The candidates…
Read MoreYou’re Stuck, Not Broken: Navigating Mid-Career Pivots in Insurance
The feeling is familiar to countless professionals in their late 30s, 40s and early 50s. You’ve achieved seniority, your salary is stable, and your career in insurance is solid. Yet, every Monday morning brings a profound sense of inertia. You’re no longer growing, you’re merely maintaining. It feels like you’ve hit a professional plateau. This feeling of professional stagnation is often misdiagnosed as burnout or…
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