Last Updated on: January 5, 2026

From Executive Leadership to Field Underwriting: Lessons Producers Can Learn from Aaron Puchbauer’s Transition into Middle-Market Insurance

The most successful producers in the middle market did not get there because they quoted faster, smiled bigger, or knew how to talk longer. They got there because they learned how to differentiate themselves so clearly that prospects had no choice but to see them as trusted advisors. They learned to operate like businesspeople first and insurance technicians second. They learned how to tie operational mechanics to insurance outcomes. They learned how to control their time, their pipeline, and their future.

That mindset was on full display during my recent podcast conversation with Aaron Puchbauer, a former healthcare CEO who transitioned into commercial insurance and is already making waves as a contestant on Season Three of The Protege. His story is not only compelling, it is a blueprint for the exact mindset and disciplines producers need to adopt if they want to win bigger and win faster.

This blog breaks down the most important lessons producers can learn from his career transition, the insights he gained as a former buyer, and the tactical risk management strategies that immediately differentiate you at the point of sale.

A Career Shift Built on Disruption and Opportunity

Aaron spent fifteen years rising through the ranks of hospital leadership inside the HSHS system. He served as President and CEO at multiple facilities and oversaw operations, finance, people, and outcomes in a highly regulated, highly stressful, and increasingly margin-compressed industry.

Then, in one hour, everything changed.

The organization made sweeping financial decisions. His entire layer of management was eliminated. After fifteen years of commitment, results, and leadership, Aaron suddenly found himself like many mid-career executives who get caught in the wrong place at the wrong time inside a corporate restructuring.

Instead of rushing back into the same cycle, he took time to reflect on what he wanted the next twenty-five years of his career to look like. He knew three things:

  1. He wanted more control over his future.
  2. He wanted to stop relocating his family every few years.
  3. He wanted a career with unlimited upside based on effort rather than politics.

Like many who have transitioned successfully into commercial insurance, he discovered that this industry creates a pathway for all three.

But there was something else. Something that far too many producers overlook.

He understood what it felt like to be on the other side of the table.

The Buyer’s Perspective: The Advantage Most Producers Never Have

Aaron’s inbox was always filled with vendors. He spent years sitting in meetings with salespeople pitching software, services, staffing, equipment, and yes, insurance.

He could tell within five minutes whether the person walking into his office had done their homework or whether they were regurgitating the same tired script he had already heard dozens of times.

Here is the part most producers never understand:

Executives can smell unpreparedness immediately. They can feel when you are winging it. They know when you are guessing. They know when you are just trying to quote something without understanding how their business works.

And because they are busy, they mentally check out the moment they realize you do not respect their time.

Which is why this quote from Aaron should grab every producer by the collar:

“Those who did their research always stood out.”

That is the difference between getting five minutes and getting the keys to the kingdom.

Differentiation Is a Discipline, Not a Slogan

When Aaron looked at the insurance landscape, he saw something that most outsiders notice immediately but most producers ignore for far too long.

On the employee benefits side, he saw a handful of dominant players and very little room to differentiate as a new producer.

On the property and casualty side, he saw unlimited opportunity to stand out.

Not because the work is easier.

Because the work is more strategic.

Producers who know how to talk about risk, operations, loss drivers, safety culture, hiring practices, financial impact, and total cost of risk automatically rise above the quoting crowd. They sound like businesspeople. They speak the language of the buyer.

Aaron was drawn to P&C because he knew he could differentiate. He knew he could bring an executive mindset that most producers do not have. And he knew that his ability to understand decision-making processes inside middle-market companies would give him a powerful advantage.

But differentiation does not happen in theory. It happens in preparation.

Preparation: The Secret Weapon Everyone Says They Have and Almost No One Uses

Insurance

Buyers do not want more quotes. They want better conversations.

They want confidence that you understand their business, their structure, their problems, and their priorities. They want evidence that you are thoughtful. They want proof that you respect their time.

The simplest way to demonstrate all of that before the first meeting even starts is also the tactic almost no producer uses.

Send a proposed agenda before the meeting.

Not a list of coverages. Not a list of forms. Not a renewal timeline.

A business conversation agenda.

Bullet points that show the prospect you understand their industry. Questions that relate to their operations. Topics that matter to their financial picture. An invitation to add or remove items so they feel ownership in the conversation.

Nobody does this. When you do, you stand out instantly.

And there is something else producers should be doing that the average producer still ignores.

Use AI to prepare like a true consultant.

Aaron shared how he used ChatGPT before a meeting with a restaurant owner. Not to write copy. Not to generate marketing ideas.

He told ChatGPT to simulate the owner and give him the exact questions the owner was likely to ask.

It was spot on.

This matters for one simple reason. The best producers know what objections are coming before they walk in the room. The best producers understand the operational concerns of a CFO before that CFO ever speaks. The best producers prepare for reality instead of reacting to it.

And in today’s world, AI makes that preparation faster, easier, and more precise than ever.

Field Underwriting: The Skill That Separates Professionals from Quoters

Differentiation is not theoretical. It is practical. It is physical. It happens when you walk the floor, touch the risk, evaluate the operations, and ask questions that uncover gaps, exposures, and opportunities.

Field underwriting is the difference between being an insurance salesperson and a risk manager.

I told Aaron on the podcast that two things are non negotiable for every producer in my agency:

  1. Attend every audit.
  2. Attend every loss control visit.

You cannot understand risk if you never see how it operates in real life.

Producers who don’t walk operations are trying to write business they do not understand. Producers who do walk operations gain knowledge that shows up in better submissions, better underwriting results, better pricing, and better close ratios.

Aaron learned this early when he walked through a restaurant kitchen and asked about fire suppression, grease buildup, cooler storage, dating systems, and workflow. These are questions very few producers ask. Yet they matter more than almost anything on an Accord form.

Because when you understand the story behind the operation, you can tell the story the underwriter needs to hear.

And sometimes, field underwriting reveals something even more important.

Sometimes it reveals that the prospect should not be your client.

Time, Alignment, and the Discipline to Walk Away

Insurance

New producers often chase anything with a pulse. They feel pressure. They feel urgency. They feel desperation. And that desperation leads them straight into accounts that waste time, drain energy, and produce nothing.

Bob Paskins said it perfectly:

“Your prospects will never love you as much as you love them.”

Producers must stop chasing opportunities that will never close.

Aaron learned this the hard way early in his career. He put time into accounts that looked good from the outside but had no intention of making a change internally.

Every producer has been there. What separates average producers from exceptional ones is discipline.

Exceptional producers walk away early.

Exceptional producers protect their time.

Exceptional producers only pursue prospects who align with their process and values.

Exceptional producers know that they can only serve clients who want to be served.

The Power of Coaching, Community, and Vertical Focus

When Aaron applied for The Protege, his motivation was not fame or competition.

His motivation was growth.

He wanted to learn from the best. He wanted to challenge himself. He wanted to accelerate his sales trajectory. He wanted to be vulnerable. He wanted to immerse himself in a community that forces him to operate at a higher level.

That mindset is why he will succeed.

Coaching compresses time. Vertical specialization increases speed. Community increases accountability. And The Protege environment exposes contestants to high-level producers, wholesalers, subject matter experts, and operational thinkers from across the country.

By the time Season Three ends, each contestant will have gained more insight, strategy, and perspective than most producers acquire in their first five years.

And that is why the real win is not the final result. The real win is the producer you become along the way.

What Producers Can Learn from Aaron’s Journey

Aaron’s story is not unique. Many producers come into the business mid-career seeking stability, autonomy, and control. Many come from industries where they sat on the buying side and saw firsthand how weak most salespeople really are.

But Aaron did something most producers never do.

He brought his buyer mindset with him. He brought his operational awareness with him. He brought his leadership experience with him. And he learned quickly that winning in commercial insurance is not about quoting better. It is about asking better questions, telling better stories, and preparing better than anyone else.

Here are the biggest lessons his story reinforces:

  • Preparation is the most overlooked form of differentiation.
  • Field underwriting is the fastest way to build trust.
  • Buyers reward producers who understand operations, not insurance forms.
  • Vertical specialization accelerates credibility and results.
  • Coaching and community create exponential growth.
  • Producers must protect their time and walk away when alignment is missing.
  • Telling the underwriting story correctly is more important than quoting quickly.
  • Vulnerability drives growth.
  • Action creates clarity.
  • Effort compounds over time.

Aaron’s transition into insurance demonstrates an important truth.

Commercial insurance is not a sales job. It is a business consulting role disguised as a sales job.

The sooner producers understand that, the sooner they will win.

Conclusion

The path from healthcare CEO to commercial insurance producer is not a traditional one. But it is a powerful reminder that success in this industry belongs to the producers who think like executives, prepare like professionals, and operate like partners.

Aaron’s story is a masterclass in how to differentiate, how to approach risk, how to prepare for meetings, how to use AI, how to learn quickly, and how to position yourself as a trusted advisor in the middle market.

He is still early in his insurance career, but the mindset he brings is the same mindset every producer needs if they want to dominate the middle market.

Prepare intentionally. Walk the floor. Understand operations. Tell the story. Protect your time. Commit to coaching. Specialize. And always put yourself in the buyer’s shoes.

Because the producers who master those disciplines do not just win more business.

They own their future.

Insurance

From Med Device to Middle Market: Lessons on Sales, Risk Management, and Reinventing Yourself in the Insurance Industry

Reinvention is one of the most powerful themes in the insurance industry. Some of the best commercial producers in the country did not grow up wanting to sell insurance. They did not study risk management in college. They did not come from an agency family. They found this industry after they tried something else. They found it after life pushed them toward a career where performance, autonomy, and mindset determine the outcome.

Read More »

From Executive Leadership to Field Underwriting: Lessons Producers Can Learn from Aaron Puchbauer’s Transition into Middle-Market Insurance

The most successful producers in the middle market did not get there because they quoted faster, smiled bigger, or knew how to talk longer. They got there because they learned how to differentiate themselves so clearly that prospects had no choice but to see them as trusted advisors. They learned to operate like businesspeople first and insurance technicians second. They learned how to tie operational mechanics to insurance outcomes. They learned how to control their time, their pipeline, and their future.

Read More »
Commercial

From Newcomer to Contender: What Commercial Insurance Producers Can Learn from Pam Seidler’s Middle-Market Journey

The commercial insurance industry is one of the few professions where someone can enter with no experience, no connections, and no background in risk management and still build a long, lucrative career. But success is never automatic. It requires hunger, humility, curiosity, and the willingness to keep showing up even when the process feels overwhelming. That is why the story of Pam Seidler has already started making waves among new and aspiring commercial producers.

Read More »
Insurance

How AI and Automation Are Reshaping Independent Insurance Agencies

In an industry where tradition often outweighs innovation, artificial intelligence and automation are slowly but steadily reshaping how independent insurance agencies operate. The push toward smarter, more efficient workflows is no longer a matter of if—but when. While many agencies are still evaluating how AI fits into their operations, early adopters are already reaping the benefits of streamlined submissions, faster processing, and actionable data insights.

Read More »
Producers

Coaching, Competition, and Consolidation: Inside the Protege Mindset That’s Reshaping the Future of Insurance Producers

The commercial insurance industry is changing faster than ever—and not always for the better. Consolidation is accelerating. Service levels are declining. Private equity is pushing agencies to scale in ways that strip out the personal touch that once defined the independent channel. But for the producers willing to do the work, lean into mentorship, and sharpen their craft, this isn’t a challenge—it’s an opportunity.

Read More »

Responses

Test Message

Killing Commercial Login