I've spent more than fifteen years broking middle market, upper middle market and national accounts. I've sat on the broker side of plenty of RFPs. I had never run one until now. It was fascinating.
I just wrapped up leading an RFP, start to finish, for a very sizable upper middle market organization. I'm not claiming to be an expert. This was my first time on that side of the table. But I learned more in a few weeks than I expected to, and I want to share it while it's fresh, because I think it could be really beneficial for you to see the RFP process through your buyer’s eyes.
Here's how I set it up
I worked with the client to define what mattered most to them, wrote the questions around those conversations, and built a 100-point scorecard. Then we ran a pretty traditional process: the invitation went out, firms elected to respond, written answers came in, and finalists came in for interviews. My goal was to keep it broker friendly while shaking up the parts of the process that felt more like habit than common sense.
I read all six written responses front to back. That's a lot of reading. Here's what my big takeaways are.
1. Kill the stock answers and AI slop
Every RFP has the usual questions. Tell us about your firm, tell us what makes you different as an agency, and as a broker, etc. Mine had some of those too, and if I did it again I'd change the written part. But here's what matters for brokers.
Three or four years ago it was fine to pull the closest answer from your agency's library, hit Ctrl+F, swap in the client's name and move on. Nobody was on the lookout for canned content. Now everybody is. Buyers are already asking whether what they're reading from someone trying to impress them is authentic. Whether AI wrote your response or you're still pasting from the library, it's time to flip that on its head.
Of the six responses I read, the one that was clearly written by hand, specifically to answer our questions, was the shortest. It was also the most compelling.
If you use a stock answer or an AI draft to get started, be ready to rework it heavily until it fits this client. And stop treating the written response as a hurdle on the way to the meeting. Everybody says "I just need to get in the room, that's where I’ll shine." Maybe. But your written response is your director of first impressions. I reread every one right before the finalist meetings, and a response full of slop shaped how I felt walking in.
2. Bring fewer people, and bring the right ones
The instinct, especially in the middle market when you're going up against the big boys, is to flex your bench and bring a specialist for every line. I'm telling you that six, seven or eight people in a time-boxed finalist meeting is overwhelming, especially when the buyer brings one or two.
All you're doing is cutting everyone's speaking time. The buyer wants to get to know you. They want unscripted back and forth so they can picture working with you. If seven people each talk for four rehearsed minutes, there's no time for questions, and I can't get a read on whether I like any of them. Less is more. The best interviews we had were small, and they included the people we'd actually work with day in and day out.
Two more things on this:
A great communicator beats the expert. You might have the best claims person in the business, someone who can out-hustle and outmaneuver anyone. If they're a behind-the-scenes operator who isn't comfortable talking about their work, leave them home. I'd rather hear someone who communicates well describe how good that person is. If they're stumbling in front of me, all I see is the stumble, not the skill.
Give the service team a real speaking part. In this business the service team matters as much as the throat to choke. Let your account manager tell a story about how they handle annoying certificate requirements or work through a loss payee issue. That's the experience the client lives with every day, and it gets overlooked far too often.
3. Only flex the tools that fit
We all love our tools and gadgets. I saw plenty: PML calculations, risk quantification models, benchmarking platforms, and I lost count of how many times I heard about TCOR. Middle market buyers have every right to expect those things, and I love me some gadgets. But if you flex them, show me why they matter for this client.
If you walk me through how you help quantify loss picks on retro-rated comp programs, and the client has a $150,000 guaranteed cost comp program with no chance of ever going loss sensitive, the gadget is cool. It's just not applicable.
And if the tool runs on data and you have the client's data, use it. Don't show me ABC Company. Don't give me a tutorial with a sample account. The strongest presentations I saw loaded the client's own data and ran a live demo in the finalist meeting. They didn't show me every gadget they own. They picked the one they thought would land, and it did.
4. Examples carry the water
Prepared statements about what you can do only get you so far. Real examples are what stick. How do you get involved in claims? Tell me about a tough account you marketed. Tell me how you handle two markets against each other, how you manage TIV, what your special sauce looks like when you go to market.
I think people get nervous here. Nobody is asking you to name clients under oath. But "I just went through a renewal and here's how we handled it" lets me put myself in your client's shoes. If you did it once, you can do it for me. That's how I understand your skills, and it's how you separate yourself from everybody else at the table.
5. Quick hitters: the meeting is its own step
Don't bring the printed RFP. Here's the conundrum. You sent the written response, you got the meeting, now what? Do not show up with a printed copy and ask what I'd like to talk about. Unless you're the best conversationalist in the world, flipping through it page by page is not a plan.
Send an agenda. I told every participating broker what we wanted to focus on, which I think made me a little unusual. If the buyer doesn't do that for you, build your own agenda and send it ahead of time.
Change the medium. The ones who stood out brought something different, whether that was an interactive website built for us or a deck with a real twist on it. The written response is step one. The meeting is a different step, so treat it that way.
Create the follow-up. This is pure salesmanship, and it surprised me most. In every finalist meeting there's a moment where you can create a reason to meet again. "We didn't get to cyber. Let's set up a quick virtual call." That extra touch comes after everything has sunk in, and it gives you another shot at whatever you want to revisit. I budgeted time for a virtual follow-up with every finalist, and not everyone took it. When the window to make an impression is this short, extra touches matter.
I could go on and on
It was an unbelievable experience, and I got to meet an unbelievable crop of brokers, including the ones who weren't selected. But these are the things that separated the best from the rest. Write for this client. Bring the people they'll actually work with. Show tools that fit, run on their data. Tell real stories. And find your wedge to get one more conversation.
If you want the full breakdown, catch this episode of The Wolf of P&C on the Max Revenue Podcast Network.
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