How to Sell Print for Decades

A client asked me to evaluate a candidate for a job in print sales. I’ve had conversations like this many times over the years. I ask typical questions and get typical answers. Ordinarily, I find expectations to be a long way from reality. Ask any legacy sales rep and they will say some version of, “If I’d known how difficult it was going to be to become successful, I might not have chosen the profession!” So imagine my surprise when I asked the question, “What are your goals?” and heard the answer, “I want to build a career in sales.”

Boom! Mic drop!

The conversation got me thinking about what it takes to stick around for decades in this crazy, challenging, rewarding, frustrating career. I started in sales in the prehistoric era: A time before AI, internet, cell phones, fax machines, caller ID, and voicemail (pause for effect). Forty-three years have passed. There have been countless evolutions and revolutions. The industry has been declared dead multiple times, and yet here we are.

Looking ahead, the keys to this young candidate’s success are not unlike taking a look back to see what it took for someone starting in 1982 to still be standing in 2025:

1| Keep it simple — Your job is to uncover a need and solve it using your various products and services. Your target market will change. Change with it. Things will get chaotic and scattered. Remember to return to the basics and fundamentals of sales and problem solving. The tools and toys will change. Technology will innovate. But don’t overthink the job: Solve the problem, earn the order.

2| Keep learning — The job itself might have a finish line (read: retirement) but keeping up on what’s next is endless. Attend trade shows. Participate in local educational opportunities. Review webinars on current topics. As one printing industry CEO in the early ’80s said, “Ten years from now, 70% of our business will come from customers we do not currently have, selling products we do not currently offer.” You need to stay relevant, and that starts with learning about and following trends in our industry.

3| Keep ahead of your customers — At several times in your sales career you’ll wonder, “Where do I go from here?” The answer is always, always, always in the heads of your customers. That is both a relief and a challenge. You need to take a lesson from Wayne Gretzky’s success when he said, “I skate to where the puck is going to be, not where it has been.” This advice is especially relevant during turbulent, uncertain times such as recessions and extended dips in sales when panic sets in. A quick check-in call with a few of your better customers can provide direction and great comfort.

4| Keep humble — When you first start out in sales, humility is not a problem. You are well aware of how little you know, and everything is new. Any bravado you possess is ill-conceived and brief. As time goes on, experience builds, success ensues, and confidence can wipe out the humility that was an important part of your success to date. The best of the best never believe they know it all. Not even close. They listen more than they talk. They ask questions and benefit from the expertise of others. As such, their services are sought out and they are able to avoid the price objection entirely.

5| Keep a curious outlook — Pay. Attention. Opportunities for new sales abound. They are in newspaper articles. Read, and then read between the lines. They are in conversations. Engage, and then be engaging. Bring curiosity to every situation. You never know who you are sitting next to or playing golf with. (Case in point: A few years back I was playing with a retired gentleman who told me he was part of the team that invented the barcode. Wait, WHAT?)

6| Keep innovating — Every print job represents a solution, but is it the right solution? And when it comes to repeat orders, is it still the best solution? Your ability to maintain customer relationships for decades rests on the constant and unending habit of questioning the status quo. Not only can that process result in a new and better way to solve the problem, but it shows the customer you are still working to earn their business.

7| Keep it fun — If it’s not fun, quit and go find something that is. Nuff said.

8| Keep networking — One of the many lessons in Dale Carnegie’s “How to Win Friends and Influence People” is to develop a deep, genuine interest in other people. Networking is a craft. It’s an art form. LinkedIn wants you to believe networking is about how many connections you have, but I’m here to tell you it’s the depth of those connections that matters. Have you ever heard an interview where some famous person talks about how they were once a waitress or worked the counter at a car rental agency? Today’s bonehead entry-level employee is tomorrow’s CEO. Make contact and stay close.

9| Keep reaching for the next level — I’m likely being generous when I say 50% of all print salespeople are happy to maintain their existing level of sales volume. They’ve stopped growing and, regardless of what they tell their sales managers, they are in maintenance mode. If you think there is a finish line, then there is. Reach it and get out of the way. If you think there is no finish line, you’ll always stay motivated, you’ll stay engaged, and you’ll get to the next level, the level after that, and the level after that.

10| Keep adapting — This last one sums up the first nine. Your target market, your sales pitch, your communication style ... it will all change. The 21-year-old version of me is 100% unrecognizable to the present version of me. You make it 40-plus years in this industry seeing the future as a Polaroid picture that gets clearer only when the future becomes the past. Everything around you is in flux. You must change with it.

My dad had two careers and three jobs. I had one and three. Today, people change jobs more often than they change their socks. No judgment. There is nothing wrong with that. Assuming the intention of a new print sales rep is to one day become an old print sales rep, the path to get there is not a straight line. But with all the change one can encounter over a, say, 43-year-career, the connection from Aug. 8, 2025 to Aug. 8, 1982 is fundamental: Solve the problem, earn the order.