Buffer’s Tamilore Oladipo: Mature Content Teams Must Experiment More

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New businesses love to experiment. Facebook famously told its employees to “move fast and break things.” Elsewhere in the tech space, there’s hardly a company that hasn’t pivoted its product, go-to-market, or both.

But as organizations mature, their willingness to innovate wanes.

Success increases the stakes. Fresh rounds of funding up the ante. New customers double the blinds. (Okay, enough gambling metaphors.) The reality is, when jobs and fortunes rely on stability, you can’t encourage your employees to break things. That’s a problem. When businesses stop experimenting, they stagnate.

Tamilore Oladipo’s seen this challenge first-hand at Buffer. She joined the 12-year-old social media scheduling platform in early 2022. The company was stable and secure, but they were looking for new ways to grow. For its marketing team, that meant breaking out of their SEO-focused niche and exploring more journalistic-style stories.

I caught up with Tami to learn about Buffer’s culture of creativity and how it’s motivated her to experiment with new writing styles and formats.

This interview has been edited for length and clarity.

Marketers adore Buffer’s content strategy. It’s prolific and impactful and joyful. What was it like coming in as a new writer?

Oh, man! It was such a big adjustment. After I joined Buffer, I got to see their backlogs, documentation, and processes. Buffer has a long history and a lot of content. Whenever I want to publish an article, I have to check to see if they've done it. If it's an SEO piece, seven times out of 10, someone has tackled it already.

[Joel] wants us to test new things. If something doesn’t work, try something else.

That's why we've shifted towards more original content ideas. We're in the maintenance phase for SEO content. We're always refreshing something. But we’re experimenting with original ideas and trying out new things.

It's part of the overall company vibe. Joel, our CEO, wants us to operate like a small business. While Buffer isn’t a small business, he wants us to stay agile and ship new features frequently. He wants us to test new things. If something doesn’t work, try something else.

Before Buffer, you worked at an agency on SEO content. Was it tough to switch from SEO-focused writing to more journalistic pieces?

With SEO content, it can feel like you’re churning out articles. Someone has probably covered the topic before you. You’re using the same resources, but putting your company’s spin on it.

Starting with SEO influenced how I write everything. We had the principles of SEO usefulness hammered into us: develop a structure, split up your content into these formats, add H2s or Google will hate your piece.

Moving into more experimental pieces felt like discovering a new world, but I didn’t feel part of it. Even though I went to school for media and communications, I don’t consider myself a journalist. I don’t know if I’m good enough to be a journalist.

Your readers will disagree with that. You recently launched Social Proof, a series profiling how people built their personal brands. It’s amazing. It'd feel at home in Slate or Fast Company. How did that come about?

Getting Social Proof approved internally was the easy part. After that, it was one thing after another.

I was like, “Oh no! This is probably the worst interview she's ever done.”

For example, I forgot how hard cold pitching is. I don't have a big enough online presence for someone to look at my bio and think, “Oh, she’s legit.” Cold pitching was the most difficult part. I say that as someone who had zero experience interviewing people.

I reached out to like 10 people and three got back to me: Jack Appleby, Steph Smith, and Fadeke Adegbuyi. My first interview was with Steph. I was so intimidated because she's done so much stuff. I was like, “Oh no! This is probably the worst interview she's ever done.”

I created some standard questions for each interview, but I’ve found it’s better to let the story flow. I’ve had a couple of interviews go a different way than what I was expecting. Those were the most fun interviews.

An SEO-focused content team probably wouldn’t have greenlit Social Proof. After all, there’s no traffic for the keyword What does Fadeke Adegbuyi think of personal branding? Is it liberating working in a more experimental marketing team? 

That’s one thing that I don't miss about working at an agency. You have very tight numbers and hitting them means success.

We try not to put too much pressure on numbers. Right now, we're looking at pageviews. How many people are coming to the blogs? That's what we're tracking. But there is no pressure.

This was such a relief because I don't care about the numbers. I know that’s not what you’re supposed to say as a content marketer, but when you start focusing so hard on numbers, you lose so many options and ideas.

Is there anything you miss about working at an agency?

My last job was the first time I was heavily edited. The first three months of being edited were some of the worst in my career. It hammered home that I’m not writing for myself. I’m not writing an article so I understand it. I’m writing for my audience. I had to understand my audience and their challenges. That can be tough.

For context, my first client was an eCommerce provider. I knew nothing about eCommerce going in. It was a totally new experience writing for an unfamiliar industry.

The first three months of being edited were some of the worst in my career.

Having an editor improved my writing so much. They weren’t just looking at line editing and proofreading. They challenged the arguments I made and the article structures I created. They asked soul-crushing questions.

At Buffer, we peer edit. Everyone writes. My co-worker reviews my work and I review theirs, but we don’t have an editor whose job is just editing. I miss having that. Not having a dedicated editor feels like I’m missing a limb.

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