Hiring the Right Way: How to Onboard New Insurance Agency Team Members Successfully
Hosts of The Insurance Dudes Podcast — 1,000+ episodes helping insurance agents build elite agencies
The hiring decision is the beginning. Most agency owners treat it as the whole thing, they pour their energy into finding the right person and then largely leave that person to figure out the agency on their own. The result is a retention problem disguised as a performance problem. People leave not because the job was wrong for them but because nobody made them feel like the agency was right for them. Jason's solo conversation is about fixing that.
The Gap Between Finding and Keeping
Jason has watched the pattern play out in agency after agency: the hiring process is thorough, the person selected is genuinely qualified, and within ninety days there is already a question mark over whether it is working. Not because the hire was wrong but because the onboarding was absent.
Onboarding in most insurance agencies consists of some combination of: here is your login, here is the carrier portal, these are your goals, good luck. The new person is dropped into a functioning operation and expected to figure out the norms, the culture, the unwritten rules, and the specific way this agency expects things to be done by observing and asking questions until they stop feeling lost.
Some people succeed in that environment. They are the ones who have strong enough fundamentals and high enough tolerance for ambiguity to build their own map of the territory. But the agency owner who is selecting only for people who can succeed without guidance is narrowing their hiring pool dramatically and accepting a development timeline that is longer and more expensive than it needs to be.
The alternative is an onboarding system that does the job the agency owner intends but does not have time to deliver personally every time someone new joins the team.
What a Memorable Onboarding Actually Looks Like
Jason's definition of memorable onboarding is specific: it is an experience that makes the new team member feel genuinely welcomed, clearly oriented, and invested in the agency's success within the first week. Not comfortable, invested. The goal is not to remove all discomfort from the new-person experience. It is to ensure that the discomfort is the good kind, the challenging, learning kind, rather than the demoralizing, invisible kind.
Memorable onboarding has a few specific elements that most agencies are missing.
The first is intentional cultural orientation. Not a values poster on the wall, an actual conversation about what the agency believes, how it operates, and what excellence looks like in this specific context. New people should hear this directly from the owner or a senior leader in the first two days. Not in a brochure. In a real conversation where they can ask questions.
The second is assigned connection. The new person should not have to find their way into the social fabric of the team alone. Assign them a buddy, a specific, tenured team member whose job for the first thirty days is to be the person the new hire can ask the dumb questions to without feeling judged. This one structural move dramatically reduces the anxiety of the early weeks and accelerates integration.
The third is early wins by design. Build the first month of tasks so that the new person experiences genuine accomplishment before the end of week two. Not fake wins, real ones, appropriately sized for their current capability. The feeling of early success is emotionally important and motivationally durable in a way that nothing else in the onboarding sequence matches.
The Hiring Side of the Equation
Jason also spends time on the hiring process itself, because good onboarding cannot rescue a bad hire. The best onboarding investment in the world cannot make someone the right fit if they were fundamentally the wrong fit from the beginning.
The dimension Jason emphasizes most in hiring is the values alignment piece. Skills and knowledge can be trained. Values cannot be installed after the fact. Someone who does not share the agency's actual values, not the posted ones, the real ones, will produce friction with every interaction and eventually either leave or degrade the culture by their continued presence.
He recommends a specific approach to values assessment in interviews: behavioral questions designed to surface how the candidate has actually behaved in situations that require the values the agency cares about. Integrity questions: tell me about a time when doing the right thing cost you something. Accountability questions: tell me about a time when something went wrong that was your responsibility and what you did about it. Commitment questions: tell me about something you worked at for a long time before it paid off.
The stories people tell about themselves are the most accurate signal available for who they actually are.
The First Ninety Days as a Test of Fit
Jason frames the first ninety days not as a trial period for the new hire but as a diagnostic for the agency. If someone strong leaves in ninety days, the agency needs to examine what happened in those ninety days more honestly than it examines the person who left.
Most agency owners do the opposite: they attribute early attrition entirely to the employee's performance or attitude and move on to the next hire without examining what the experience was like for the person who did not stay. That is expensive and self-reinforcing. The agencies with the lowest early attrition are the ones that have examined their onboarding honestly and fixed the things that make good people leave.
What This Means for Your Agency
Walk through the first seven days of a new team member's experience in your agency right now. Not the intended experience, the actual one. What do they see? What do they learn? Who talks to them and what do those conversations consist of? If that picture is not one that builds commitment, it is worth the few hours required to redesign it.
The Bottom Line
Hiring right is both a selection decision and an onboarding commitment. Jason's solo is a clear articulation of why the second half of that equation matters as much as the first, and a practical framework for building an onboarding experience that makes good people want to stay and build something. The agency that masters both is the one that retains exceptional talent instead of cycling through it.
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About Jason Feltman: Jason Feltman is co-host of The Insurance Dudes podcast and co-author of The Million Dollar Agency. He runs a high-performance P&C agency and coaches agency owners on building retention-oriented teams through deliberate hiring and onboarding systems.
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