Why Dealerships and Fleet Customers Keep Missing Each Other — and How to Connect

By: Casilyn Lund

Commercial Sales Strategist | Creator of the Commercial BDC Model

Ever ask yourself, “Why do we keep missing each other?” If you’ve ever tried to connect a dealership with a fleet customer and felt like the conversation just didn’t land, you’re not alone. Every day, good dealerships and good fleet customers pass right by one another, not because there isn’t opportunity, but because we’re often speaking different languages. I am up for the challenge of translating.

Fleet buyers aren’t retail buyers. A retail customer walks in wanting a vehicle that fits their lifestyle. A fleet buyer wants a tool that fits their business. They’re thinking about uptime, total cost of ownership, fuel strategy, and resale value, not heated seats or trim packages. (But please, at the very least have Bluetooth.)

But too often, dealerships approach fleet customers with the same playbook they use for retail buyers. That’s where the disconnect begins. Fleet buyers don’t want a sales pitch; they want someone who understands their operation and can bring real business value.

* A customer with 27 units was shown a retail quote for two half-ton trucks and a last minute delivery van. These were to replace 4 units that were high mileage and they only had the budget for 3 at 2025’s price. After being warm-transferred to a commercial account manager, they agreed to getting two in Q3 of 2025, and two in Q2 in 2026. Because after three conversations, a tour of the customer’s business, and a meeting with the CFO, the commercial account manager confidently gave a valid business plan that met their very real budget with their business goals.

Generally speaking, dealerships often don’t realize how much fleet opportunity is right in front of them. Most stores already have local companies buying one or two vehicles at a time — landscapers, contractors, delivery services, municipalities. These are fleet buyers in disguise.

What’s missing is a little fact-finding. When a salesperson takes the time to find out how those vehicles are being used, how long they’re kept, and what they cost to maintain, it opens the door to something bigger: a fleet strategy. Suddenly, with some finesse and sometimes multiple conversations, that “one-truck buyer” becomes a multi-year customer with a plan.

* Last month, I heard a customer say, “If the {other dealership down the road} would have taken this time to consult with me, I wouldn’t have even taken this meeting.” Their business (96 unit fleet) was earned at a dealership with a commercial and fleet staff of two.

Fleet data tells a story. Now we need to listen. I believe that every business running vehicles has data. The challenge is, most of it sits untouched in spreadsheets or service logs. The run-of-the-mill commercial and fleet salesperson doesn’t know to uncover this data. When we analyze that information, we can uncover the story behind the numbers.

And that’s where the real conversation begins. Instead of asking (that terrible) question, “How many trucks do you need this year?” we can say, “Here’s how we can reduce your fleet costs by 15% over the next five years.” That’s the difference between selling a product and offering a partnership.

*After three months of communication, a customer recently handed in a fleet list of 31 that was missing mileage, full vehicle description, and driver assignments. Instantly, I could tell they were embarrassed. They operated a multimillion dollar company that had earned the trust of their local town and surrounding area, yet the disorganization was going to drown them. After setting them up with a free trial of our OEM’s telematics program, they came back to the commercial salesperson and said, “I didn’t know this could be that easy.” Imagine, the ROI that comes in the form of a free trial!

It’s time for a mindset shift. I will say it plainly. Fleet customers don’t need another quote, they need real and individualized insight. When dealerships position themselves as consultants who help businesses make smarter decisions with their fleet data, trust follows. That’s how partnerships grow, and that’s how dealerships build lasting fleet portfolios.

When fleet customers and dealerships miss each other, it’s rarely for lack of effort. I’ve found that it’s for lack of alignment. Because at the end of the day, this isn’t about who sells more trucks — it’s about who creates more trust.

The dealerships that learn to speak the fleet customer’s language, and the customers willing to share their story, are the ones who will shape what the next era of fleet partnerships looks like.

Fleet sales may start with vehicles — but the real win is when both sides drive forward, together.

Let's connect on LinkedIn! https://linkedin.com/casilyn-lund

Casilyn's Bio:

Helping Dealerships Grow Their Fleet & Commercial Sales—One Strategy at a Time

I partner with dealerships to unlock new revenue through smarter commercial sales strategies, better appointment-setting processes, and long-term customer retention tools.

From building high-performing Commercial Business Development Centers (CBDCs) to training your team on how to present value—not just vehicles—I help your sales department close more deals with the right buyers, faster.

I also work hands-on with dealers to implement modern cycling strategies and fleet-focused software solutions that don’t just win new business... but keep it. If you're ready to grow your fleet operations with systems that actually stick, let's connect.

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