Adventures in sales

I missed the opportunity for an anniversary post. It’s now been three years since I began The Rebooting. Over the next few weeks, I’m going to write about different aspects of the business because, while self-referential, it is informative to how I view the next chapter for the media business. This week, I’m with an evaluation of sales. First up, a message from Hashtag Labs

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Thanks to John Shakman and HTL Labs for the support.

Adventures in sales

Sales might solve everything, but it’s notoriously difficult to get right. I spent my career on the editorial/audience side. I tend to think in terms of leverage. What are the advantages I bring that have a high VORP? I could make the product myself, and have deep experience in the field. That was a big one. I was “more than a content guy” in my last job because tech, product and memberships were part of my remit. One glaring weakness: I never sold, outside hawking papers in front of Orlando’s Bakery in Avalon.

I’ve now sold over for three years, so I’ve dispensed with the disclaimer I don’t know sales. I’ve learned a lot, and I’ve developed an appreciation for sales acumen that isn’t like the caricature of a big personality who knows enough to be dangerous and is adept at simultaneously kissing babies and petting dogs.

Sales is a lot like reporting: It rewards persistence. I noticed over the years in an open newsroom that the reporters with the most well-sourced stories, I heard on the phones all day. The ones with thinly sourced stories, who told me they “reached out but didn’t hear back,” were far quieter. More is not always more, but in sales, more activity tends to correlate with more results. You have to be competitive.

But more clients isn’t necessarily better. To build a nano-publishing operation, you need to have bigger partnerships, because otherwise you’ll end up needing a sales infrastructure to support a churn-and-burn approach of many small clients. The leverage in small operations is in being small. That doesn’t mean turning down small deals, but it does mean being realistic about which ones can become true partnerships.

Many well-meaning people encouraged me to find a “business partner” to handle sales. I thanked them, but never considered that path because I wanted to run the business myself but that would also eliminate a piece of leverage. The person making the product is going to be the best at selling it. I don’t care if they’re not a stereotypical sales person – this is usually a bonus, actually – but they will develop a different level of connection with clients.

David Hansson reflected on this with the example of two key partners for 37signals, and how “modern commerce” is evolving. There’s a human premium that small business owners can use to have clients “buy the seller.”

“This in-person encounter made me reflect on modern commerce. How impersonal it is most of the time. Which is probably more efficient, and, as an introvert, preferable much of the time. I usually would rather deal with a web form than a salesperson, but it's different when you can establish a connection to someone actually running the show.”

Too many people think of sales as being a gladhander.  But it’s really about establishing a human connection with other humans. Kayvan Salmanpour, chief commercial officer at the Boston Globe, told me a key trait he looks for is self-awareness.

“Having self awareness gives you space to not be defined as someone selling but more as someone who is helping to solve a problem,” Kayvan told me. “It also gives you the skill  to read whether the client is responding or not and to adapt.”

You only learn about your customers by talking to them over and over again. Actually, scratch that. You learn by listening. The good part about being a non-traditional seller is you don’t have any bad habits. You tend not to be the “who needs another drink” person, and most people outside sales are intimidated by it because they think of sales as the home of the aggressive extroverts.

That’s not the case. The best sellers are close listeners and act more like consultants by identifying a problem and matching solutions to the problem with what the selling company does well and uniquely. “You have to be able to understand what the client’s business challenges are and then figure out how your solutions can be the solution,” Puck COO Liz Gough told me.

The nature of sales is shifting. The talking-a-dog-off-a-meat-truck stuff is from a bygone era. There’s a reason people dreaded going to a car dealership. Sales is more consultative and less transactional. Many sellers are stuck in a bygone era of hand-to-hand combat for transactions. This is sometimes called “coin-operated.” Those sellers are the ones who get replaced by programmatic and AI.

I don’t know if the 20x sales person exists, but the 5-10x one certainly does. The more-with-less era will see a lot of sales functions automated. The hand-wringing about the impact to editorial is mostly because editorial people are writing the stories. The sales function has felt the impact of automation for a generation now. It will only accelerate as companies no longer can deploy the “feet-on-the-street” playbook of overwhelming the market with a big sales force like meat-grinder assaults on Bakhmut. That doesn’t work in a more-with-less era.

“If you start hiring like crazy, you have to hire an ecosystem around sellers with account managers and marketers,” Liz said. “You’re adding a lot of operating costs.”

Like most areas, the sales function will do more with fewer people. This favors a niche approach. The verticalization of sales organizations is a decade old, even if some legacy players are just getting around to it. That speaks to the need for expertise – and the realization that in some narrow but deep markets you can cover a lot of ground without a ton of people. Puck has all of three people selling. That’s because it mostly sells into concentrated markets like corporate affairs and for-your-consideration efforts. It helps if your customers are also consumers of your products, needless to say.

Again like other areas, sales will favor doers over strategists. You’ll need to carry a bag. I always liked the FedEx commercial of the fresh-faced, overconfident MBA called on at his first day in the office to address a problem. He cracks his knuckles and is ready to strategize, only to be told he’s to create shipping labels and not to worry, it’s easy to pick up. “You don’t understand, I’m an MBA,” he tells the woman. Her response: “Oh, in that case I’ll show you how to do it.”

I’ve seen sales leaders who never talk to clients or even fully understand the value of the products. You have to walk the floor. You can’t be a general in a tent with a whiteboard or, worse, PowerPoint. You’ll never get a true feel for the market without talking to customers and truly understanding their challenges. It’s not rocket science. As one longtime exec advised me, “Don’t overthink it.”

Reporting carries over here, because you’re always listening closely to understand what the real story is and making connections in your head while carrying on a conversation. This type of parallel thinking – I’ve compared it to being bilingual – is needed in sales. You start to process things faster the better you get.

Drew Schutte, who has held top sales positions at places like Condé Nast and who worked with me at Digiday, told me, ”Sales people should have two ears, one mouth, emphasizing the importance of listening over excessive talking. By actively listening, you gain insights into the clients challenges and problems.”

The challenge of sales is solving problems in ways that benefit clients, ideally adds to the product value and, by the way, are good for the business. Solving for all three is an art form.

A lot of editorial people think sales is distasteful rather than this kind of Rubik’s Cube. That’s mostly because there’s a moralistic streak that runs through editorial, and for good reason. And in its crassest form, sales can be somewhat adversarial. We’ve all been on the other end of transactions where we have felt ripped off – I mean, I’ve lived in Miami – and that breeds distrust. Trust will only get more valuable.

“Don't try and convince someone of buying into a deal that truly isn't there,” Jason Krebs, a longtime digital media veteran, told me. “It's short term thinking and it damages long-term prospects.”

Finally, I think a lot of sales is doing the basics well. Be upfront, be confident but realistic, and above all else, do your job. You don't need to overwhelm someone with the greatest idea ever,” Jason advised. “Be accurate, be available, be respectfully persistent. Make the calls, do the follow up, act like a human (not a bot or a miscreant) and good things will follow.”

Thanks for reading. Send me a note with your sales tips by hitting reply. If you want to have a sales conversation, check out the packages we’re selling for 2024. (I don’t see the point in keeping media kits secret. This game is about execution and delivering results, not a secret formula like the Coke recipe.)