An interview with a Director of (Sales) Content Strategy who got his start in theater ticket sales

Derek Johnson has called New York City home for the past decade, where he works with Fortune 500 companies to achieve their (sales) content marketing goals. Outside of his professional life, Derek is active in the arts and entertainment scene, always with a concert ticket in hand. He enjoys escaping to New England to visit friends and family during the city’s oppressive summer heat.

You made the move from actively selling to leading a team at a content writing agency team that produces B2B sales content. What made you want to make the switch from selling to writing about selling? 

I still actively sell which I believe is important for sales leaders to continue to do. When you have CRMs and other reporting tools you may think you have a good sense of what’s going on, but that firsthand experience may tell you otherwise. Following the sales cycle yourself will uncover unnecessary friction or hurdles that prohibit your team from doing their best work.

I’ve written a little on the side for ContentWriters, the content writing agency I work for that specializes in organic content. I also help manage our blog and social media. I highly recommend subscribing and following us for news and best practices in content marketing!

You started your career running the box office for a prominent theater company in NYC. What was it like being responsible for ticket sales and filling seats for live events every week? What were some of the challenges? 

Every day had a new challenge. NYC patrons, donors, and subscribers are a unique cast of characters so there’s always entertainment even in the simple task of selling a ticket. 

Forecasting ticket sales and working to get houses filled 6 days a week meant planning ahead and solving issues before curtain time. A show with a bad review in The New York Times meant a different strategy compared to a sold-out show with New Yorkers' insistence on getting in at whatever cost (“do you know who I am?!”).

Has your theater background helped you in sales? If so, how?

When you’re managing a box office, you have to solve issues quickly and publicly. That means keeping your composure, learning to dissolve situations elegantly, and keeping theatergoers’ trust. It’s a skill worth mastering in sales.

Theater also taught me how to think creatively about partnerships, promotions, and subscriptions that support the bottom line. Timing these launches with the season, production, and competition required solid planning and project management skills.

What’s one thing you see a lot of salespeople do that you think is counterintuitive? OR What’s one piece of conventional sales wisdom you don’t subscribe to? 

Don’t rely on your script. 

If you’re dependent on it, you haven’t fully understood the product or services you're selling or prepared your conversation for the unique prospect. A script is an important resource to ensure you’re qualifying and informing your contact(s) efficiently, but you’re missing out on relationship building and deeper discovery if you’re limiting yourself to a one-size-fits-all document.

When I’m a buyer, I’m bummed when I notice this happening. AI can follow a script, but I don’t want to talk to a machine. I want to talk to a human.

What advice would you give to someone who is just starting out and is considering a career in sales?

Invest in sales education consistently. Engage with sales coaches, learn different approaches, and refresh your sales training regularly.

When you’re new to sales, you might think, like I once did, that you can learn on the fly. With some great (lucky) wins early in my career, I thought I was innately skilled at sales, but that ego got in the way of building the right habits and learning new strategies. I wasn’t seeking help or actively fine-tuning my skills causing new business acquisition to feel more like a stressor outside of my control than a challenge I could face head-on. 

Committing to learning new tips, experimentation, and retraining will hone your skills, jumpstart motivation, and improve knowledge retention. Education, refresher training, and coaching are essential at all stages of your sales career and there are so many resources available to provide that support.

Subscribing to sales courses, video channels, and weekly newsletters (like this one!) pulls me out of bad habits or a negative headspace and builds the valuable skills that are key to exciting wins, more money, and a career that’s fun!

What is your favorite sales movie?

Not really a sales movie per se but the first thing that came to mind: Fargo. Don’t be a Jerry Lundegaard sales manager.

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