Content & Entrepreneurship: Office Hours with Walter Chen
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All content is bought or sold long before it's written, edited and published. But even some of the best content marketers don't really understand why and how— and therefore can't fully grasp their own place in its lifecycle.
Selling content is the best learning experience of my nearly 15 years in this business. I know that not every content marketer wants (or needs) to sell content, but I can't emphasize enough how useful it is. I know plenty of content folks with an entrepreneurial itch. My own experience selling is what gave me the confidence to start Superpath, and it's the thing I spend the most time on today.
Between Animalz and Superpath, my deals have accounted for north of $10 million in lifetime revenue. That's a lot of content marketing services.
I don't consider myself a "real" salesperson but this was no accident either. This post will cover some of my best sales tips, but first, I'll tell a quick story about my very first sale.
Back in 2016, I was an early employee at content agency Animalz. Founder Walter Chen had started bringing me on sales calls, something I was hesitant to do at first. But I was close to the client work and he wanted me to talk to talk process, brainstorm content ideas, share examples of other client work and just generally try to give people good content advice. Just free consulting, that was all.
But Walter still did all the sales. He was the one to handle the conversation about pricing, negotiate deals, close them, get the contracts signed, etc. As a longtime content marketer, all of that felt foreign and intimidating. I knew how to strategize, write and distribute—sales felt uncomfortable.
As Walter and talked more about my own career path, we came up with an analogy that really resonated with me. Legendary basketball player Jerry West—his silhouette is featured on the NBA's logo—played, coached and later managed. He participated, elevated others and then learned the business side. This spoke to me—and ended up being the exact path I've followed in my content marketing career.
Business is nearly all sales, so it was time to learn. Walter and worked towards my first solo sales call, which was scheduled with a prominent company in our industry. If I closed it, it would be the biggest deal in Animalz' then-short history. I was really nervous. And to add to the pressure, we'd decided to raise prices just a few days before the call.
So, the day came and I jumped on the call. I was prepared with all kinds of questions and ideas. We had a fluid, easy conversation and then they asked, "So how does work? What's the cost and what are the deliverables?" I answered as calmly and nonchalantly as I could, even though I was cringing inside. And to my amazement, the person on the other side of the Zoom call didn't even blink. "Sounds great. When can we get started?"
I learned two things on that call. The first is that sales is really just free consulting. If you help people out, it comes back around. Some percentage of them will want to work with you. The ones that don't probably aren't a great fit anyway.
The second thing I learned is that business people get that this stuff costs money. Of course a high-end content service is kind of expensive. I wanted to play on that field too, and over time learned to treat business as business.
Those are the two frameworks I still lean on heavily today, but I learned a lot of other little things too. I've collected as many of them here as I can think of.
Research people ahead of a sales call and try to find some common ground. I suggest looking for details like the city they live in or other places they've worked. If you can make a connection in the first few minutes, you're setting yourself up for a friendly conversation. Stuff like, "Oh, you live in San Diego. Do you surf?" or "I see you used to work at [Company], do you know [person]?" are great prompts.
You won't always find obvious common ground, so small talk is the next best thing. "How was your weekend?" or "Did you catch the World Series game last night?" or "Any fun plans this summer?" are good ones to kick off a conversation with someone you don't know well. Remember that getting on a face-to-face Zoom call with a stranger can be uncomfortable for both parties, so use these kinds of questions to create a comfortable environment.
Later, you should use the small talk as hooks in your follow-up. "Hope your family vacation was great" or "Can't believe the Phillies blew it" make it much harder for people to ignore your follow-up emails.
Meet a qualified lead anywhere and anytime that is convenient to them. I know productivity gurus suggest things like "no meeting Mondays" which I generally agree with, but I've gotten on sales calls at 5am and 10pm to accommodate people around the world.
Here's my rough agenda:
I always like to ask a bunch of questions about the business and product. Things like, "Who is the target persona?" and "How big is your marketing team?" warm things up. Then I like to ask things like, "What's your best acquisition channel?" and "What's been the hardest thing about building a content program?"
I'll even say something like, "I can't make good content recommendations without really understanding the business." This helps ease any skepticism about all my questions.
When it comes time to talk specifics about content, ask specific questions based on your research before the call. If you are prepared enough to ask something like, "It looks like you're all-in on product-led growth but I don't see much middle or bottom of funnel content on the site. Do you have plans to create an academy or tutorials?" then you'll earn yourself instant credibility.
I know that many vendors have NDAs but you have to be able to cite specific examples. At Animalz, we actually built a library of customer stories that we could use on sales calls and in follow-ups. I had this memorized and could pattern-match during a call. This meant I could say things like, "We worked with another customer on a very similar problem and here's how we solved it."
In every good sales call, there's an "aha" moment. It's the moment when the prospect starts to feel like you can really help them. They might say, "Wow, it seems like you really understand our challenges" (though it's unlikely). They might also say, "Tell me more about that" which means you've piqued their interest. When you jot down notes after your call (which you should always do), make a note of that moment so you can work with it on future calls and emails.
Talk about a happy future together. This helps the prospect envision how wonderful it will be to work with you. I like to do this by saying something like, "I'm getting ahead of myself but say we work together. I think we can have that ebook, two guides and six blog posts done in three months. If you want, I'll put together a timeline and send it over."
This starts to make things feel concrete and will hopefully make your prospect feel excited. My experience on sales calls is that most people have tried something before contacting me. They're frustrated and want to move on. If you can be the one to show them what a brighter future looks like, you're the one to get the deal.
I've sold $100,000 deals in a single 30-minute call. Don't overcomplicate a sale just because there's a lot of money involved. Use the call to understand the business, understand the content need, explain a solution, and talk next steps. Watch the clock to make sure you have time to make your pitch. And never skip the pricing/packaging talk. You'll send it an email later, but have the conversation live so you can gauge their reaction and even ask them what they think.
About 2/3 of the way into a call, I always say something like, "If you'd like, I'll send you an email with a summary of this conversation, plus pricing, examples and next steps so you can look it over with your team." This is the exact moment in the call when the prospect starts feeling like there's a lot of info to absorb, so I use this as a way to (1) keep them present in the conversation and (2) set the expectation that there will be a follow-up.
A follow-up email should include a few things, like a personal note, an overview of the service, info about pricing/packaging and a clear next step. But most importantly, it should include something that the prospect can easily say "yes" to. That "yes" should result in a deal.
For example, if you say, "Let's schedule another time to go through what a custom package would look like" then you're killing the deal. But if you say, "I thought more about our call I think the best way to handle is for us to deliver [the deliverables] by [date]. We can do it for [price] and start on [date]. What do you think?" There's no gray area here. It's a clear plan and "yes" means you've got a deal.
You also don't need to use fancy proposal software. Just talk to the person like you'd want to be talked to. Simple, direct, and informal.
I think sales decks can be useful if they are focused on social proof. A proper sales deck isn't just the same info from your email in a PowerPoint. Ideally, it's chock full of examples, case studies, testimonials and other social proof. You want to give the prospect the feeling that they'll be in very good company when they become a customer.
Ideally, the next step after a call is a contract, but it could also be a smaller commitment that keeps a deal moving:
Find creative ways to give your prospects a little bit of homework. But make sure that effort is rewarded. It should cut time from onboarding if they do become a customer, or it should give them information (remember, sales is free consulting) that they can use whether they convert or not.
You absolutely must make sales personal. Get to know these people, work hard to close good deals, handwrite a thank you note, check in with them once they've become customers, stay in touch if they leave for a new job, send a happy birthday note, connect on LinkedIn. This is corny but sales is a way of life. The people who really excel at it live it every day.
And all that said, don't take it personally when prospects don't convert. Assuming you've done your best work, move on to the next one. There's always a next one!
One last thing. Content marketing is a field rich with opportunity. Many people go on to lead marketing teams, manage people, build freelance businesses, and so much more. I don't think many consider it a foundation for a career in sales but...
If you love the craft of writing or the rhythm of running a content team, then you should pursue it. But if you're interested in the business side, and you want to understand how and why billions of dollars a year are invested in content, then sales is for you. It really helps to have done it. It makes you a subject matter expert, which makes the free consulting a breeze.
Want to chat about it? Shoot me a DM in the Superpath Slack group.
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Jimmy is the cofounder and CEO of Superpath. You can follow him on Twitter here.
