The commercial insurance world isn’t for the faint of heart. It’s unpredictable, chaotic, and constantly demanding producers to manage competing pressures—client needs, renewal deadlines, life events, prospecting goals, and agency responsibilities. And if you’re a middle-market producer, multiply that by ten.
On a recent episode of the Power Producers Podcast, I sat down with Heather MacKinnon of Horizon Insurance Services—an unexpected but incredibly impressive producer whose path into the industry was anything but traditional. What followed was a candid conversation about confidence, time management, buyer psychology, referral ecosystems, and what it really takes to succeed in a high-stakes sales career.
This blog distills the biggest takeaways from that conversation, giving producers at every level a blueprint for how to grow with intentionality instead of accident.
Before we even got into the business talk, Heather and I spent several minutes doing what every producer in America can relate to—talking about the chaos of family life, travel, home repairs, and the never-ending surprises that seem to happen at the exact moment you don’t need them.
Coming home from a family vacation and diving back into work would have been enough, but life had other plans: broken appliances, unexpected delivery issues, IT failures, alarms blaring, and all the typical “you’ve got to be kidding me” moments that seem to come in clusters.
It’s funny, but it’s also a perfect metaphor for what producers deal with daily.
Commercial insurance sales reward people who can:
The chaos doesn’t stop. But your ability to operate inside of it is a competitive advantage.
Heather’s background is one of the most surprising I’ve heard:
She didn’t grow up in insurance. She didn’t plan for it. And if you had told her ten years ago she’d become a commercial producer, she would have told you that you were nuts.
But once she entered the industry, something clicked.
Insurance became the ultimate puzzle.
She described it perfectly: every policy is a puzzle where the pieces either fit together—or leave the client exposed. Seeing that 70% of businesses are underinsured by 40% or more only intensified her drive to learn the craft and do it the right way.
Her analytical brain loved it. Her business background enhanced it. And her willingness to learn made her dangerous—in the best possible way.
One of the biggest mistakes producers make is assuming that prospects understand how insurance works. They don’t.
They don’t know:
And they certainly don’t know how to assess coverage properly.
Yet producers often treat questions like challenges—when in reality, the buyer is simply asking for clarity.
Your job is to educate, not defend.
If you reframe the conversation through this lens, everything changes. The producer stops responding with insecurity or impatience, and the prospect gains confidence in the process.
Education is your differentiator.
Transparency is your weapon.
Patience is your closing tool.
One of the most powerful parts of the conversation was the story of a prospect who had:
Four.
For most inexperienced producers, that sounds like an opportunity.
But the truth? It’s a trap.
When underwriters receive submissions from multiple wholesalers, multiple times, from multiple agents, they don’t think:
“Wow, this buyer is thorough.”
They think:
“This buyer is unorganized, desperate, and price-shopping.”
And underwriters respond to desperation with defensive pricing—or no pricing at all.
So I told the prospect plainly:
“I’m going to excuse myself from competing. You aren’t helping yourself, and you aren’t helping me.”
And that moment of scarcity—of walking away—changed everything.
Scarcity increases perceived value.
Clarity increases trust.
Control increases win probability.
And when the prospect finally removed the other agents and provided full transparency, the entire opportunity shifted into alignment.
Nearly every new producer faces the same internal battle:
“Do I really belong here?”
Heather admitted it openly—and honestly. Coming into an industry full of people boasting 20- and 30-year careers intimidates anyone who’s only been in the game for a year.
But here’s the truth every producer needs to internalize:
If a prospect agrees to meet with you, they already believe you can bring value.
They wouldn’t waste their time otherwise.
Confidence isn’t something you magically get.
It’s something you build through repetition, preparation, and intentional action.
And even when you’ve been around for decades, the game still involves talking yourself up before the big meetings—just like athletes psych themselves up before stepping onto the field.
The butterflies never leave.
You just learn to fly with them.
Most producers don’t fail because they lack talent.
They fail because they lack structure.
Heather openly shared her struggle coming from the corporate world where her schedule was managed for her. Suddenly she had full freedom, and without a system, days often became overwhelming.
So I explained the method that saved my productivity:
The 50/10 Sprint Method
Followed by:
This approach:
It’s simple.
It’s sustainable.
And it changes the game.
Especially if you have ADHD or struggle with traditional time blocking.
Most producers believe referral partners are something that magically appears over time.
Wrong.
Referral networks must be built intentionally.
But not with the usual suspects.
People automatically think:
These can be great eventually—but they’re slow to warm up and slow to refer.
The real goldmine is B2B sales reps calling on the same clients you want:
And when your partnership is well-structured, you both win.
The key?
Clarity and Accountability
Not:
“When you think of me, send me someone.”
Instead:
And reciprocity is automatic when you help others first.
One of Heather’s biggest goals for 2026 is going heavy into content:
And it’s exactly the right move.
Content is the modern salesperson that works:
24 hours a day
7 days a week
365 days a year
Before a prospect ever talks to you, your content has already:
By the time they meet you, they already feel like they know you.
That is a massive strategic advantage.
One of the most meaningful stories Heather shared was about her first full-cycle win—a construction and excavation contractor referred through a friend at church.
It wasn’t easy:
But she leaned in.
She researched.
She learned.
She asked deeper questions.
She solved the puzzle.
And she wrote the account.
Not because she was the most seasoned producer.
But because she was the most prepared.
This is what newer producers need to understand:
Curiosity can beat experience when curiosity is paired with effort.
Commercial insurance is not a game of perfection.
It’s a game of intentionality.
The lessons from Heather’s journey and our conversation can be distilled into six guiding truths:
Producers who embrace these truths don’t just survive in the middle market.
They thrive.
They build reputation.
They build confidence.
They build trust.
They build book.
And they build a career they can be proud of.
If Heather’s story proves anything, it’s this:
No one knows you’re out of your comfort zone unless you tell them.
So step forward boldly—because your next win is waiting.
The commercial insurance world isn’t for the faint of heart. It’s unpredictable, chaotic, and constantly demanding producers to manage competing pressures—client needs, renewal deadlines, life events, prospecting goals, and agency responsibilities. And if you’re a middle-market producer, multiply that by ten.
In the middle market commercial insurance space, the role of the producer has never been more critical—or more misunderstood. Too many producers still view their job as selling policies instead of what it truly is: protecting the assets and livelihoods of the businesses they serve.
The middle market rewards depth, not breadth. Yet many producers still approach it like a volume game, quoting everything that moves, chasing price, and hoping activity turns into production. From the outside, it looks like hustle. From the inside of the underwriting and wholesale world, it looks like noise.
Personal lines has quietly become one of the most competitive segments in the insurance industry. Agencies that once dominated their local markets are now fighting to differentiate themselves against direct writers, digital-first carriers, and large brokers with massive content machines.
The cyber insurance market has always been unpredictable. Over the past decade, we’ve seen it move from an emerging line of coverage to one of the most volatile, swinging rapidly between soft and hard market cycles. But today, cyber has entered one of the softest markets in recent memory—and that presents a rare opportunity for both agents and clients.
For most of my 20-year career, captives felt like something reserved for the insurance elite—the jumbo accounts, the Fortune-level operations, the companies with multimillion-dollar manual premiums and entire departments dedicated to risk management. If you had asked me ten or fifteen years ago whether a $250,000 account was a legitimate captive candidate, I would’ve laughed. I thought captives were reserved for companies so complex and so large that the only rational way to insure them was to build an insurance company around their risk.
Please confirm you want to block this member.
You will no longer be able to:
Please note: This action will also remove this member from your connections and send a report to the site admin. Please allow a few minutes for this process to complete.
Responses