Every career in sales has an origin story. Mine started in Kyle, Saskatchewan, population about 480 at the time, with a Chevy Corsica, a yellow pages phone book, and a one-sheeter for the upcoming Kyle Rodeo. That first trip down a gravel road to sell radio spots for a small-town rodeo is where I learned that selling media is really about one thing: adapting to what the customer actually needs.
The Kyle Rodeo and the One-Sheeter
When I started in radio, the sales manager handed me the yellow pages and said, here is your account list. That was the entire onboarding. A one-sheeter is an eight-and-a-half-by-eleven piece of paper with the products you are selling and the price. Nothing fancy.
I drove to Kyle, pounded the pavement, and learned fast that the one-sheeter was just a starting point. The local businesses did not want a radio spot. They wanted someone who could help them figure out their whole marketing plan. The radio was part of the answer, not the whole answer.
Always Be Learning
If there is one thing I have taken from 30+ years of selling media, it is that you have to commit to lifelong learning. Every quarter something changes. Every year a new channel shows up. Every few years an entire business model gets disrupted. The sellers who survive are the ones who treat themselves as a student for life.
For more on this theme, see my post on why lifelong learning is the only career strategy that works.
A Sales Process That Actually Wins
The process I landed on after years of refining is not complicated. The discipline to use it every single call is what separates pros from amateurs.
- Research before you walk in the door
- Open with something other than a pitch
- Find the pain, but do not interrogate for it
- Let the customer do most of the talking
- Agree on a mutually clear next step before you leave
How to Differentiate Yourself from the Competition
Every market I sell into has more competitors than it did five years ago. The differentiation is almost never in the product. It is in the experience around the product.
Three tactics that still work in 2026:
- Prepare more than anyone else expects
- Bring insights the buyer cannot Google on their own
- Build a personal brand that travels ahead of the meeting
That last point matters more every year. Your prospects are researching you before they pick up the call. They check LinkedIn. They check your company page. They check social. The seller whose online presence tells a clear story wins the meeting before it starts. I unpacked that idea more in my post on Dennis Yu on why personal brand beats any platform drama.
Selling Digital Media in 2026
The tools have changed a thousand times since that Chevy Corsica hit the Kyle rodeo grounds. The fundamentals have not. Do the research. Help the customer before you sell them. Earn the right to ask about pain. Keep learning. Build a personal brand. Show up.
If you sell digital media today, ask yourself two questions this week. What am I learning that my competitors are not? And what does a prospect find when they Google me before the first meeting?
The answers to those two questions will tell you everything about your next twelve months.