I didn’t start out in a hard hat as an outside sales representative. My degree is in education, and for a while I thought I’d spend my life in a classroom. Then I found the construction world and realized there was a massive need for someone who could teach people about products, jobsites, and opportunities. The first time I walked onto a site it was intimidating. People were busy, machines roared, and I felt like an outsider. I took notes, lots of them. Over time those notes turned into a playbook that helped me build confidence and connect with customers who trusted me.
This is my outside sales representative playbook.
An outside sales representative is a salesperson who meets with prospects and customers in person. But they’re also far more than that. They’re problem solvers and solution providers. They average 5 customer and prospect visits on the road, but many top-performing reps can hit 25+ stops daily.
When most people imagine an outside sales representative, they picture someone dropping off brochures or shaking hands at a trade show. That’s not how it works. In the equipment rental world you must be a problem solver on wheels. You’re moving from jobsite to jobsite with solutions that keep projects on schedule.
Confidence comes from knowing your product and understanding the environment your prospects and customers live in. I’ve seen reps freeze when they don’t trust what they’re selling. And customers sense that hesitation instantly. One way to avoid that is to study your equipment and ask questions until you can explain why your solution matters in plain language.
The other way is to practice. Role‑play objections with a colleague. Walk yourself through a pitch aloud in the truck. When you’ve had those conversations before, they’re easier in front of a real customer.
Confidence isn’t innate. It’s built by doing. The old adage, “leaders aren’t born, they’re made” rings especially true in outside sales.
In my early days as an outside sales representative, I’d get flustered when a customer asked a question I couldn’t answer. Instead of bluffing, I learned to say “I don’t know, but I’ll find out.” Many people don’t understand the value this creates. The trust it builds. But you have to follow through.
I’d call the manufacturer. Talk to a technician. I’d test the equipment myself when necessary. Over time those experiences stacked up. I also embraced who I am and didn’t pretend to be something I’m not. I’m the guy who shows up in a polo shirt and work boots. I listened more than I talked. I genuinely want to help. People respond to authenticity.
One of the best confidence builders is preparation. Before visiting a jobsite, I research the company, look at photos of the jobsite or pull up the Street View on Google Maps. I think about what challenges the trades on-site might face and how my products and services could provide solutions. I jot down questions and a loose agenda so I don’t wander aimlessly. When you’re prepared, you walk in with purpose. When you’re unprepared, you talk about the weather.
The world is now filled with video calls and automated emails. It’s unavoidable. It might be tempting to think you can sell from behind a screen (and certainly in many industries you can). But not in outside sales.
Research from hospitality company Accor underscores how much money is left on the table when you rely solely on digital channels. A study of 9,000 professionals around the world found that people expect to generate 36% more revenue and close 37% more deals if they conduct important meetings face‑to‑face. 85% of respondents believed their business outcomes would improve if they could prioritize in‑person interactions. That doesn’t mean you need to spend your life on airplanes, but it means human connection is irreplaceable when trust and nuance matter.
My own experience as an outside sales representative echoes those numbers. When I meet a foreman in his trailer, we talk about more than equipment. I learn about his challenges, his deadlines. I learn the quirks of his crew. He sees that I’m not just looking for a quick sale, but that I’m there to help him succeed. Those conversations turn into repeat business. They also uncover problems I didn’t know existed that create new business opportunities. A piece of gear he didn’t realize I could provide or a service his current supplier can’t offer. None of that happens over a cold email.
Relationships are everything when you're an outside sales representative. In the equipment world, you don’t rent once and move on. You see the same contractors at the new hospital getting put up across town, the school reno, or the new housing development. Being present means showing up at the right time, not just when you need to hit quota. It’s remembering the superintendent’s name, calling the project manager after a shipment arrives, and following up when you say you will. Trust is built over multiple visits, not after one handshake.
I spend hundreds of hours on ride-alongs with reps every year. I’ve lost count of how many times I’ve seen the ball get dropped after a promising first meeting. Reps get busy, lose the business card, or forget which site they promised to revisit. Don’t be that person. Use a tool (like RepMove). Keep an organized list of your contacts and commitments. Track sales and plan routes. Remind yourself when to swing by again with an app. Organization isn’t optional. It frees mental space so you can focus on people rather than spreadsheets.
One reason reps fail is poor time management and disorganization. They spend half the morning in traffic or show up at jobsites at lunch when nobody’s there. Plan your route the night before. Group nearby sites together. Leave space for unexpected opportunities. If a crane is going up on the other side of town, go introduce yourself. If you hear about a new development breaking ground, stop by and see who’s in charge. The best reps are opportunistic but structured.
I like to think of a day as a series of intentional moves. Everything on my calendar has a purpose: prospecting, delivering equipment, checking on existing accounts, or building new relationships. When you finish a visit, log notes immediately. Use talk-to-text to get it done on the way back to the truck. Note what equipment is on site, what follow‑up is needed. That way you don’t rely on memory and can pick up where you left off. Tools like RepMove can help you organize these tasks, but the core principle is to be deliberate with your time.
Finally, don’t confuse confidence with ego. Confidence is quiet, steady. It’s open to learning. Ego is loud and brittle. Customers can tell the difference. When you admit what you don’t know, ask good questions, and follow through, people will respect you. They’ll also refer you to others. The equipment rental world is surprisingly small and word travels fast. Be the rep who makes life easier for your customers. That’s the role of an outside sales representative. It’s someone who delivers results and builds relationships. They do it with confidence born from experience.
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Interested in having Elliott coach your sales team? Send him a message or buy his onboarding and sales 101 training video series.
