Have You Ever Asked Your CEO to Apply for One of Your Insurance Jobs?

Here's a challenge for every insurance company CEO: Grab your phone and apply for one of your company's open jobs. No help from HR. No special treatment. Just you, your phone, and a job opening.

Pretend you're an experienced claims adjuster, underwriter, or account manager looking for your next opportunity. Find the job. Click Apply.

Now the fun begins.

Create an account. Verify your email. Upload your resume. Wait. Where exactly is your resume stored on your phone? How do you even upload it? Just recently I was speaking to a group of TA and HR leaders in Melbourne, Florida and asked them if they could upload their resume to an email or ATS from their phone, and only about 50% of the room could. They were sincerely shocked because none of them have applied to jobs on their phones.

If it doesn’t work for them, it doesn’t work for thousands of job seekers to figure it out every day! Then, once you've conquered the resume upload, in many cases you're asked to type in all the information that's already on your resume. Then come the questions, assessments, passwords, and maybe another login.

Still interested?

Remember, many candidates are doing this on their phones during lunch, after work, or between family responsibilities. Here's something worth considering. According to Monster's 2026 Application Black Box Report, 43% of surveyed job seekers would abandon an application within 15 minutes. Finding talent in the insurance industry is hard enough, and if that one qualified job seeker has a long application process, you will never meet them.

But Making It Too Easy Isn't the Answer Either.

In the AI era, someone can generate a polished resume and apply to dozens of jobs with little effort. That's not necessarily good for employers or serious job seekers.

You don't need thousands of applications from people who barely know what job they applied for. We need a little friction that creates commitment, not frustration. So how do we do that?

Three Ways to Make Applying Smarter in the AI Era

1. Make the first step mobile-friendly.

Allow candidates to upload a resume, connect a professional profile, or enter basic information without creating an account. Ask only what's necessary. Save the complicated paperwork for later. Capture their name, email and job title and let them know if they don’t have time to apply, you will follow up with them later (this can be automated).

2. Ask three great questions instead of thirty unnecessary ones.

For an underwriting position, ask about lines of business, years of experience, and relevant underwriting authority. For claims, ask about claim types, licensing, and experience. Use AI to organize and summarize responses but make sure people remain involved in hiring decisions.

3. Verify interest and communicate like a human.

A short, job-specific follow-up question, text confirmation, or brief screening conversation can help identify serious candidates. Tell applicants what happens next and when they should expect an update. Don't leave them wondering whether anyone received their application.

After more than 30 years in insurance recruiting, I've learned something pretty simple. Technology should make connecting people easier, not create another obstacle course.

We should expect candidates to put some effort into pursuing a career opportunity. That's reasonable. But that effort should help us understand their qualifications, experience, and interest, not test their patience or technical skills.

So, CEOs, here's your assignment.

Take 15 minutes. Grab your phone. Apply for one of your own jobs. Then answer two questions.

Would you finish the application?

And if you did, would you still want to work for your company?

You might discover your biggest recruiting problem isn't finding qualified insurance talent. It's what happens when qualified insurance talent finds you.