Chris Winterboer

Chris Winterboer
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Recent Posts

Is The Job Market Like The Stock Market?

A very common question I get, especially this time of year, is what the job market looks like. Candidates want to know. Clients want to know. Heck, even our bankers and accountants want to know as they put together company financials and prepare our annual tax return. Many times my answers sound like I am also referring to the stock market. There are quite a few similarities:

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Insurance Agencies Targeting Niche Candidate Profiles

For many years insurance agencies have targeted producers that can build a vertical market within a particular niche. The reasons for this strategy are obvious and plentiful, but we have now seen a push for agencies to hire all positions within a niche. Sometimes even a niche within a niche. As producers build out these niche markets, the expectation from the client is higher that tools, resources, products, and client service will come at a higher level. Firms have responded by pro-actively hiring people to build out that story. Here are some recent projects we have worked on that are a testament to that fact:

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How to Interview a Millennial Account Manager

What is the best way your agency can interview account managers when 50% of the workforce is comprise of Millennials and 25% the current workforce (i.e. hiring managers and seasoned mentors) are Baby Boomers? 

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Planning Ahead - Tips for 2019 Hiring Needs

As you set goals and agendas for hiring in the new year, we wanted to provide a cheat sheet as a guideline of what is trending in the coming year. Everywhere you look you can find articles regarding tips for the job seeker, but less information is available for employers. With that in mind, here are six helpful tips to guide your hiring process and strategies in 2019:

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Incorporating Your Agency’s Character Into The Recruiting Process

We work with a broad spectrum of clients, from small agencies in rural areas to large national firms in the biggest cities. They all have their unique cultures and workflows, but some do better than others when describing it to potential employees. Who you are, what you do on a daily basis, and how you conduct your business is going to be at the core of the recruitment process in a perfect world. If you have difficulty outlining that or explaining it early on, it will put you at a distinct disadvantage with your competitors when it comes to attracting top talent.

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What season are we in for hiring?

Q4: A Love/Hate Season for Insurance Agencies to Recruit

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How To Achieve Age Diversity in Recruiting

It doesn’t take much online browsing to find articles about how to recruit Millennials, or the “next generation”, or how recruiting strategies have evolved for new candidates entering the workforce. Yet there are far fewer articles or “how-to guides” regarding how to hire Baby Boomers, experienced hires, or someone looking to apply 25+ years of working experience in a new career adventure. More and more studies, however, are finding that there is going to be a huge talent gap upcoming in the insurance industry. Nearly a quarter of the workforce is at or nearing retirement age.

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Your Next Insurance Hire: 'Time Kills All Deals'

Not even one full week in May and the insurance market is already sounding the "mission critical" alarm. Organizations that move quickly get the candidates they want. Insurance professionals know they are in demand. Just take a look at job boards. There are so many job openings. To them it's like shooting fish in a barrel.

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The ABCs of Interviews

I may be dating myself here, but how many of you remember the infamous scene in Glengarry Glen Ross when Alec Baldwin talks about ABC standing for Always. Be. Closing. My spin on that for today’s blog is a different idea:

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2018 Insurance Industry Recruiting Trends

While we are early in the New Year, we are already beginning to see trends that we believe will hold true throughout a good portion of 2018. Some are good and some are bad...so it is going to be important to pay attention if you want to stay ahead of the curve.

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Do People Still Value Thank You Notes After a Job Interview?

Yes. Yes. Yes, a million times over. A thank you email is the minimum and expected. The handwritten note or card is a lost art. The tendency in an email is to write too much or ask lingering follow-up questions. The gesture of a thank you card sent through the mail is more of a true sign of gratitude. You expect nothing in return other than the good vibes that it creates when the reader opens up that card and sees your name on it.

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Spooked To Start The Insurance Job Search?

The Halloween season brings about lots of change: the leaves on the trees, the cooler weather, and literally even the clothes you wear as you attend parties and Trick-or-Treat nights. It also brings about change in job seekers as the fourth quarter is a time to reflect upon your career.

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Insurance Recruiting: Balancing Long Term vs. Short Term Hiring

A study from McKinsey & Company found that 25 percent of professionals in the insurance industry will retire by 2018, leaving a large talent and experience gap in the industry. So how do you plan for that alongside any and all current openings for immediate hires?

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Insurance Recruiting: Do You Have To Spend More To Get More?

For the casual observer of the NBA playoffs, it may appear as though the Golden State Warriors are a good team playing well together at the right time. If you really dig into it, though, you will find that a big part of the reason this team is even together is a discussion that happened a few years ago. The league met with the players’ union to discuss a new salary cap. That was the true trigger point to a path for the Warriors to open up enough cap space to sign Kevin Durant, who is likely their best player right now on a loaded line-up.

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How to Avoid Draft Day Mistakes With Insurance Producer Recruiting

It always strikes me curious how people react to their team’s draft choices in the NFL. The armchair QB suddenly knows more than the executives on a team who have put weeks and weeks of research into their draft choices. It often comes down to basic decisions that can also relate to producer recruiting in the insurance industry.

  1. Do you hire the seasoned vet who is going to come with a high price tag and possibly past the twilight of their career?

  2. Do you take a huge risk with organic hires that have little or no proven experience?
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How to Brand Your Organization to Attract Top Insurance Talent


Just as an insurance candidate needs to a brand themselves during a job search, it is equally important for an insurance organization to think strategically about their branding: 

The Image You Project: Old and Studgy or Up Close and Personal?

For those companies that think it doesn’t matter, the world is changing daily and will quickly pass you by if you’re not careful. Some companies spend a tremendous amount of time, energy, and money to create their unique brand in the public eye. Here are 4 steps to enhance your branding strategy.

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How to Brand Your Insurance Job Search as a Candidate

Everything these days is about branding, marketing, social media, and how to “project” who and what you are online and in person. It can become complicated quickly and even overwhelming. We often counsel candidates regarding how to polish their resumesmanage their social media platforms throughout the insurance job search, communication, and much more.


What you are and have become in your insurance career can be difficult to sum up in a one-page document or online profile. Here are a few quick tips to make that process easier:

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Is Your Insurance Job Search in #LaLaLand?

As everyone knows, the #Oscars2017 ceremony provided one of the biggest gaffes in its illustrious 89 year history. One so big it just might make us forget about Steve Harvey’s mishap at the Miss Universe pageant. The explanations for what went wrong keep coming out of the woodwork, but the bottom line is that something went terribly, terribly wrong on live television in front of a national audience.

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How to Be The MVP of Your Insurance Job Search

It was the NBA All-Star weekend in New Orleans, so Anthony Davis figured to play a prominent role in the proceedings. He wanted to show off the NOLA pride and represent his community as well as his team. The youth basketball coach in me really didn’t like the lack of defense in the actual game, but I suppose that's by design for the most part. I doubt anyone is emphasizing defense in the huddles or pre-game film sessions. However, there were 5 things about Anthony’s quest for the MVP that I felt ran parallel to guidance I give candidates throughout their insurance job search.

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Are You Collaborating Throughout Your Insurance Job Search? 

I have to admit I don’t keep up with music as much as I used to. Most of what I know about popular music these days comes from my teenage daughter. But I decided to watch part of the #GRAMMYs last night and saw several artists collaborating, sometimes even crossing genres. It made for some interesting combinations, and some could argue it was an evolution of how we listen to music. How does collaboration in your insurance job search process benefit candidates and companies alike?

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