What a "Best Place to Work" Award Doesn't Tell You

Best Place to Work awards measure how employees feel after they're hired. What they don't measure is how candidates are treated before they join. And sometimes those two experiences aren't even close. So here's the question worth asking every time one of those "Best Place to Work in Insurance" press releases goes out. Sure, but what's it actually like to try to get in the door?

Here's a real story. Fully deidentified. Completely true.

A well regarded insurance firm, badge proudly displayed on the careers page, recently put a candidate through this.

The first meeting was with the a Business Unit President. They canceled. An opportunity came up to attend the Masters. Going to Augusta isn't a crime. It's April, it's insurance, client entertainment is part of the business. Keep reading.

The next meeting was in person with a unit Sr. manager. Except no conference room had been reserved. The candidate sat down, got bumped when someone else claimed the room, moved, got bumped again, moved a second time, and spent the whole interview being shuffled through whatever space was open in a building that was supposedly deciding whether to hire them. 3 rooms total.

A second meeting with that same manager got scheduled, then canceled because he was sick, then rescheduled again. It was going around!

Then came what was supposed to be a close to final conversation. A Zoom call with a sr. member from the sales team, who asked to push the start time back fifteen minutes. He joined wearing a backwards baseball hat and mentioned it was his vacation day. He was in the middle of doing yard work. Four interviews in, and the company still couldn't find fifteen uninterrupted minutes that didn't compete with somebody's landscaping.

An email followed. Good news, a final round was in order! The final round never got scheduled. Two weeks passed with no interim word at all. Then the message came through. We've decided to go in another direction.

You might read all that and think, that's extreme, that's not us. Fair enough. But before you let yourself off the hook completely, ask yourself a few honest questions. Has anyone on your team ever walked into an interview without reading the resume first? Promised a decision by Friday and then gone quiet for two weeks? Taken a candidate call half distracted, answering emails the whole time? Let a senior leader push back an interview and never circled back personally to apologize? Those are smaller versions of the same problem, and they happen far more often than the extreme version above.

None of this is really about the recruiting team. TA can build the process, set the timeline, prep the interviewers, and follow up on the firm's behalf. What they can't do is make a senior leader choose a candidate call over a trip to Augusta. They can't make a manager book a room. They can't make a sales rep step away from the mower for a final round.

The numbers back up just how common this is. 80% of hiring managers admit to ghosting candidates at some point in the process. Not coordinators. Not recruiters. Hiring managers, the same people whose feedback fills out the engagement survey and helps earn the badge in the first place.

Every moment in that story was owned by a hiring leader. Three different people, three different levels, one consistent message about how much the candidate's time was actually worth.

That message is the culture. Just not the side anyone bothered to survey.

It helps to understand what these rankings actually measure. The Business Insurance Best Places to Work program, the most recognized one in our industry, scores firms on a self-reported employer questionnaire plus an employee survey. The employee survey makes up 75% of the total score, covering pay and benefits, role satisfaction, work environment, culture, communication, and engagement. Companies have to register and pay a participation fee just to be considered, which means the entire pool is self-selected. Firms that never opt in are invisible, no matter how they actually operate.

No candidate has ever been surveyed. Not once, in any version of this award. The people rating the culture already work there. They have a desk, a manager, a paycheck. They're not the one getting bounced through a third borrowed conference room.

And on the candidate's side of the desk, only 26% of North American job seekers say they had a great candidate experience. One in four, across companies of every size, reputation, and award history. 61% report being ghosted after an interview, up nine points from the year before, and post interview ghosting is the most damaging communication failure a hiring process can produce, because it lands after the candidate has already put in real time and energy.

So, here's the actual question worth sitting with, badge on the wall or not. Would the last person you didn't hire say your process respected their time? Not your best process. Your actual, most recent one.

Patterns at the top don't stay at the top. A senior leader who skips a call for a golf tournament, a manager who can't book a room in his own office, a rep who logs onto a final round from the backyard, that's three levels of leadership showing a candidate exactly how the place runs, probably without even realizing it.

So if you're a hiring manager reading this, and there's a decent chance you are, here's the ask, and it isn't complicated. Show up to the meeting you booked. Reserve the room. If you need to reschedule, do it yourself instead of letting an assistant handle it three days later. Give the candidate an honest timeline, even when the honest answer is I don't know yet. None of that costs a dollar or needs anyone's permission. You don't need an award to get this right. You just need to do better, starting with your next first round call.

Your recruiting team can only run the process you're actually willing to show up for. The award measures how employees feel once they're already in. The candidate experience measures how you behave when you think nobody's grading you. Those two things should match. Most of the time, they don't.

Bror David Johnson
Founder & Executive Recruiter, Retention Search
773-573-5942 | bdjohnson@retentionsearch.com
www.retentionsearch.com

The Cow, the Milk, and the Quiet Crisis: What Insurance Leaders Get Wrong About AI Hiring

Wednesday Insights — from the desk of Bror David Johnson, Founder & Executive Recruiter, Retention Search

The 400,000-person problem nobody scheduled

There is a number that should be sitting at the top of every insurance leader's strategic plan — whether you run a retail brokerage, a wholesale operation, or a carrier — and for most of them it isn't. By the end of 2026, an estimated 400,000 insurance professionals will have retired from the U.S. industry since 2021 — a figure drawn from Bureau of Labor Statistics projections and repeated, with increasing urgency, across nearly every workforce study in our sector. One panel of industry veterans put it more bluntly than the reports do: this is not a looming crisis, it is a crisis that is already here.

I have spent my career inside insurance talent, and I can tell you the statistics undersell the lived reality. The average insurance employee is now in their mid-forties. Roughly one in four workers in the industry is 55 or older, against a sliver of new entrants in their early twenties — a retirement-age-to-newcomer ratio that runs as steep as six to one. Insurance is aging faster than tech, faster than finance, and it has not yet rebranded itself as a place a twenty-five-year-old dreams of building a career. Meanwhile the industry's unemployment rate hovers near 1.6 percent. There is no slack in the system. Every producer, underwriter, claims professional, account manager, and client-service specialist who walks out the door takes relationships and institutional memory that took decades to build — and the replacement pipeline has thinned to a trickle.

For the largest national players in every segment, this is a budget line. The biggest carriers, the national brokerage platforms, the major wholesalers — they have embedded talent-acquisition teams, employer-brand machinery, and the balance sheet to pay a thirty to fifty percent premium in a bidding war and absorb it. For the firms I spend most of my time with — the strong regional and mid-market shops across all three segments, the ones without a national recruiting apparatus behind them — it is something closer to an existential question. They feel the retirements just as acutely, but they are fighting for the same scarce talent without a full-time recruiting function to do it. That asymmetry is the single most important thing happening in insurance hiring right now, and it is the lens through which everything else — including the AI conversation — has to be read.

Everyone is selling AI. Almost no one is telling you what works.

If you have attended a single industry event in the last eighteen months, you have been pitched "AI-powered" hiring so many times it could be a drinking game. I say that with affection, because I live in this market — and the honest truth is that the noise has become its own obstacle. Virtually every applicant-tracking system, sourcing platform, and HR tool now has "AI" stamped somewhere on its marketing. The genuinely difficult task, even for specialists, is telling the difference between a tool that delivers measurable efficiency and one that has quietly renamed a keyword filter as "AI matching."

The market hit peak hype somewhere around 2024 and has not fully come down. What that means for an insurance leader is simple and frustrating: more options has not produced more clarity. It has produced overload. More application volume does not equal more qualified candidates — it usually just means more noise. And here is the part the vendors do not advertise: most AI recruiting implementations fail for the same unglamorous reason. The technology was ready before the organization was. Tools get bought; processes never get redesigned around them; the promised time savings evaporate into yet another dashboard nobody owns.

This is precisely the work I have done so that my clients don't have to. I have evaluated, tested, and waded through the landscape — the proven, the promising, and the glorified spreadsheet — and reduced it to a tight, integrated handful of capabilities that actually move the needle for a mid-market insurance organization, whether it's placing producers, underwriters, or claims talent. That curation is the service. Anyone can hand a firm a list of thirty tools. The expertise is in knowing which two or three belong together, in what order, configured around the realities of insurance hiring. This is agentic.

Because the deeper point is that there is no such thing as an "insurance recruiting platform." The AI tools are industry-neutral; they screen a producer the same way they screen a software engineer. The differentiation is never the software — it is the person configuring generic software around the things the software does not understand. No off-the-shelf system understands that a retail or wholesale role often hinges on the right property-and-casualty or life-and-health license across the specific states it covers. No generic tool knows that the best people in this industry — a top producer, a seasoned underwriter, an experienced claims lead — are passive, rarely apply to a posting, and will accept an offer inside of seven to ten days if you move with intention. That judgment layer is not a feature you can buy. It is the cow. The tool list is the milk.

Where AI actually earns its keep — and where it never will

Let me be specific, because specificity is what separates an advisor from a pitch deck. There are a few places where AI delivers real, defensible return in an insurance organization's hiring process.

The clearest win is automated résumé screening and ranking. For any role drawing a meaningful volume of applicants, manual screening is the primary bottleneck — and semantic matching against actual job requirements, rather than crude keyword filtering, can cut screening time by roughly seventy to eighty percent while surfacing strong candidates a keyword filter would have missed. The second clearest win is interview-scheduling automation: eliminating the endless back-and-forth of finding a time is pure friction removed, with no judgment lost. Job-description generation, candidate-communication automation, and pipeline tracking round out the set. These are the capabilities with proven ROI. Everything else warrants healthy skepticism until proven in your environment.

But notice what every one of those wins has in common: it removes administrative drag. It does not make the hiring decision. And that distinction is the whole ballgame in 2026. The most telling data point I have seen recently comes from a Harvard Business Review Analytic Services survey of small and midsize businesses: when asked which single candidate they would prioritize, fifty-two percent chose deep, relevant industry experience, while only seven percent chose a candidate strong in AI skills. That is better than a seven-to-one preference for domain expertise over AI fluency. In the same research, seventy percent said AI is driving the need for people with the creativity, intuition, and discernment to work alongside it — not to be replaced by it.

The recruiters and the firms pulling ahead understand this instinctively. They use automation to eliminate the noise so that scarce human attention lands where it actually matters — early conversations, judgment calls, relationship-building, closing. Survey after survey now ranks critical thinking above AI skills as the most-needed capability in talent work, and demand for relationship-building skills in recruiter roles has surged dramatically over the past year. The machines got better at the busywork, which made the human part more valuable, not less. That is not a comforting story I am telling to protect my profession. It is what the data says, and it is what I see in every search I run.

What this means if you're leading an insurance organization right now

Here is the strategic posture I would urge on any leader reading this, in any segment of the business. First, stop treating "should we use AI in hiring" as the question. That question is settled; the answer is yes, for the administrative layer. The real question is where it helps you most and who owns it — because AI in recruiting works only when there is a clear owner accountable for the workflow, not just a license sitting unused.

Second, right-size the solution to your actual hiring volume. A firm making a handful of senior hires a year has a fundamentally different problem than one making dozens of similar roles — the first is a sourcing-and-judgment problem best solved by a light tool set and an expert; the second can justify heavier automation and a database that compounds in value over time. Buying enterprise-grade machinery for a ten-hire year is how firms waste money on AI. So is hand-screening four hundred applicants for a role that automation could triage in an afternoon.

Third, and most important: protect the human layer ruthlessly. In a market where résumés and cover letters are now trivially easy to optimize with AI, where both candidates and employers are leaning on the same tools and producing the same fatigue and distrust on both sides, the firms that win are the ones who keep a sharp, experienced human in the early conversations and the final decisions. The tools are the great equalizer of administrative speed. Your judgment — or the judgment of an advisor who lives in insurance talent — is the only thing left that competitors can't simply buy a license for.

That is the work I do: cutting through the noise so insurance firms — brokerages, wholesalers, and carriers alike — get the proven tools, properly configured, with the human expertise that makes them worth anything at all. The retirements are not waiting. Neither, frankly, is your competition.

Bror David Johnson is the Founder and Executive Recruiter of Retention Search, specializing in insurance and risk talent acquisition. He works exclusively in insurance talent and advises brokerages, wholesalers, and carriers on recruiting strategy, fractional and embedded recruiting, and retained and contingency search. 📞 (773) 573-5942 · 📧 bdjohnson@retentionsearch.com · 🌐 www.retentionsearch.com

Additional Resources & Further Reading

A curated set of sources behind this week's analysis, for principals who want to go deeper:

• U.S. Bureau of Labor Statistics workforce projections — the source behind the widely cited 400,000-retirement figure and the industry's sub-2% unemployment rate. The foundational data on the insurance talent gap.

• Industry workforce-demographic analyses (2025–2026) — reporting on the mid-forties median age, the ~6-to-1 ratio of retirement-age workers to young entrants, and how insurance is aging faster than tech and finance.

• Harvard Business Review Analytic Services — talent practices pulse survey of small & midsize businesses (2025) — the source for the 52%-vs-7% industry-experience finding and the 70% figure on demand for human discernment to work alongside AI.

• 2026 AI-recruiting market analyses — independent, hands-on tool evaluations that separate genuine efficiency gains (résumé screening, scheduling automation) from "marketing noise," and document why most AI implementations fail on process rather than technology.

• Recruiter-skills research (2026) — survey work ranking critical thinking above AI skills as the most-needed recruiting capability, and tracking the surge in demand for relationship-building skills.

Insurance Recruiting Trends in 2026 The Talent Market Is No Longer Forgiving Average Hiring Processes By Bror David Johnson, Founder & Executive Recruiter, Retention Search

Insurance recruiting in 2026 is not simply about filling open seats.

It is about whether insurance organizations can identify, attract, assess, and close the right talent before their competitors do.

Across the United States, the insurance industry continues to face a complicated talent equation: an aging workforce, increased specialization, more complex risk, technology disruption, and a candidate market that is far more selective than many hiring managers realize.

The firms winning talent in 2026 are not necessarily the firms with the biggest names. They are the firms with the clearest story, the fastest process, the strongest leadership alignment, and the most realistic understanding of what top insurance professionals actually want.

Here are several recruiting trends I am seeing across the national insurance market.

1. Passive candidates still drive the market

The best producers, underwriters, claims leaders, account executives, benefits consultants, wholesale brokers, program professionals, and specialty insurance executives are rarely sitting on job boards waiting to apply.

They are working. They are busy. And they need to be approached with credibility, market knowledge, and a compelling reason to listen.

Posting a job and hoping the right person appears is not a talent strategy. It is a lottery ticket.

2. Speed is now part of the offer

Slow hiring processes are costing firms strong candidates.

In 2026, top insurance talent is not waiting through six rounds of interviews, vague compensation conversations, unclear reporting structures, and delayed feedback.

A slow process sends a message. It tells the candidate the organization may be indecisive, misaligned, or not serious about the hire.

The best firms are defining the role upfront, aligning internally before the search begins, communicating clearly, and moving quickly when the right person is identified.

3. Specialization is commanding a premium

The insurance market continues to reward true specialists.

This is especially clear across wholesale and E&S, professional liability, cyber, construction, healthcare, surety, captives, stop-loss, employee benefits consulting, complex commercial lines, program business, underwriting leadership, and technical claims roles.

General insurance experience is valuable, but deep specialization is what moves the market.

The harder the role is to explain to a general recruiter, the more important it is to use someone who actually understands the insurance vertical.

4. Compensation clarity matters more than ever

Candidates are asking better questions.

They want to understand base compensation, bonus opportunity, commission structure, renewal income, book ownership, service support, noncompete language, equity opportunity, leadership access, and realistic first-year expectations.

Vague answers create doubt. Clear answers create confidence.

The firms that are transparent early in the process are building trust faster than the firms that wait until the end to discuss economics.

5. Employer brand is no longer just marketing

Candidates are evaluating the whole opportunity.

They want to know who the direct manager is, whether the service team is stable, whether the book is real, whether leadership is investing in growth, whether the technology is current, and whether the culture is collaborative or political.

They also want to understand whether the role is a true growth opportunity or simply a cleanup project with a better title.

Insurance remains a relationship-driven industry. Reputation travels quickly. The internal employee experience and the external recruiting message need to match.

6. AI is changing the work, but judgment still wins

AI, automation, data analytics, and workflow tools are reshaping insurance roles. But insurance is still a judgment business.

Technology can improve process, speed, and insight. It cannot fully replace technical underwriting judgment, producer credibility, client trust, claims expertise, relationship management, or leadership presence.

The strongest candidates in 2026 are not simply “tech savvy.” They know how to combine insurance knowledge, commercial judgment, and modern tools.

7. Succession planning can no longer be delayed

The industry has talked about the retirement wave for years. It is no longer a future issue. It is here.

Many firms still have key client relationships, underwriting expertise, leadership responsibilities, and institutional knowledge concentrated in a small number of senior people.

That creates business risk.

Recruiting is not only about growth. It is also about protecting revenue, relationships, and continuity.

Bottom line

The insurance organizations that win talent in 2026 will be the ones that treat recruiting as a strategic growth function, not an administrative task.

The market is not forgiving unclear roles, outdated job descriptions, slow feedback, weak compensation communication, or passive hiring strategies.

In a specialized, relationship-driven industry, the right hire can protect revenue, open markets, strengthen client relationships, and change the trajectory of a team.

That is why recruiting in insurance needs to be handled with precision.

Hiring in Insurance in 2026?

I work nationally with insurance organizations looking to hire excellent talent across virtually every insurance vertical, including retail brokerage, wholesale/E&S, employee benefits, commercial lines, professional lines, carriers, MGAs, MGUs, program business, claims, underwriting, operations, and leadership roles.

If your organization is making critical insurance hires in 2026, I would be happy to be a resource.

Bror David Johnson

Founder & Executive Recruiter | Retention Search

Phone: 773-573-5942

Email: bdjohnson@retentionsearch.com

Website: www.retentionsearch.com

LinkedIn: https://www.linkedin.com/in/bror-david-j-b422462/