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Don't be boring

Idle thoughts on marketing technical software to skeptical developers
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Ned O'Leary
X GitHub
Cofounder and CEO, SSOReady

Several weeks ago, I received an invitation from our Y Combinator group partner Dalton to speak to companies in YC’s Fall 2024 batch. It ended up being a bit of a general Q&A session.

Me talking to people at YC

I talked a lot about the mistakes we made in the first year of running this company. Now, I could literally talk for hours about all the things I did wrong. It really did take us a while before we found our current business.

But before long, someone asked about the current business: hey you guys are doing really well with marketing; what’re you doing right? I didn’t have an especially coherent answer at the time. I’m not sure I have an especially coherent answer now.

Even still, it’s clear to me that people find our approach to marketing interesting, so I thought I’d put pen to paper and share our thinking more publicly.

What this isn’t

This is not advice

Some number of people have bristled at previous blogs I’ve written, seemingly taking objection to a tone that feels like advice. That’s not really my intent.

I am explicitly not trying to give advice here. Please don’t interpret this as what you should do. I’m just a guy that’s trying to figure shit out.

This is not a how-to manual

Let’s briefly inhabit a fantasy world in which our company does everything right. In this fantasy world, therefore, you have chosen to mimic all of our sales and marketing tactics.

This blog post will not help you very much. I’m just not going to live that deeply in the details. The details are really, really boring, and I’m pretty sure we’re just making things up anyway. I’m not sure I could write an instruction manual if I really wanted to.

This is not the last word

We’re still just figuring stuff out and trying different things. Sometimes we’re right, but we’re usually wrong. I’m pretty sure that I’ll look back on this post and wonder how I was so profoundly incorrect. In other words, I’m definitely going to change my mind in the future.

Making B2B marketing more human

Management by dashboard

At some point in the last decade, it became fashionable for professional managers in SaaS to consider themselves data-driven. That seems fine on its face, doesn’t it? But that impulse gives life to a pernicious affinity for beancounting. Everything needs a KPI. Everything needs a dashboard.

Taken too far, the data-driven approach crowds out qualitative data and hardens companies against the squishy, artful decisionmaking that they also need.

My friends are tired of hearing me talk about Starbucks. But I promise: it’s really instructive. For years, Starbucks management made disastrous choices. If you’ve been to a Starbucks in the last few years – at least in the USA – you probably know what I mean. The stores feel positively sterile. The operations feel very mobile-centric. It doesn’t feel like a place for humans. And Starbucks knows it – it’s shown in their financial results. The new CEO, Brian Niccol, has made clear his intent to unravel virtually all of the preceding regime’s data-driven initiatives. He’s instead prioritizing a reversion to a more human flavor of hospitality.

We in the SaaS industry have undoubtedly fallen victim to this flavor of management science. We’ve literally adopted scientific language. We’ll talk about hypotheses and growth experiments. We’ll obsess over best practices and benchmarks and fuss over micro-optimizations.

Such sterile management has a well-documented tendency to enshittify products. We shouldn’t be surprised that it acts similarly on marketing, stripping it of joy, identity, and excellence.

B2B buyers are humans

When I first started selling our company’s first product, I mistakenly thought that selling a B2B product meant that … well … I was going to sell to businesses. And to sell to businesses, I thought, I’d rely on a concrete ROI pitch. I was thoroughly wrong.

Businesses are just loose confederations of human beings. No business makes decisions; people make decisions in their roles as employees. Showing up to work doesn’t turn a human being into a calculating automaton. The same principles that govern consumer marketing apply to business marketing.

I hadn’t internalized that “selling to businesses” entailed the following subtasks:

  1. Earning a particular person’s attention
  2. Helping that person understand what we do
  3. Supporting that person’s efforts to communicate our product’s value to colleagues

I hadn’t internalized that my pitch to the business only became relevant in step (3) above. And before I hit step (3), I needed some particular person to care. That’s the hard part. Until presented with evidence to the contrary, no reasonable person should care about our little startup. Our marketing exists solely to help people care; we trust that product quality wins the deal.

The humans that buy our software

Pressed to describe a target customer, most SaaS vendors will rattle off a list of easily observable characteristics that they can associate with companies in third party data. They might mention something like healthcare providers with 1,000+ employees in the United States. In some cases, you might get a job title: we tend to sell to the CISO, someone might say.

To be clear, that’s great. I take absolutely no issue with that. In fact, we do exactly the same thing. We market to developers who work at certain kinds of business software companies.

But I think it’s important to go a step further, to anticipate the unobservable preferences of an ideal customer.

Our ideal customers are curious. They enjoy esoteric trivia. They genuinely enjoy writing code. They’re the kind of people who read the docs. They dislike big companies – or at least dislike big companies’ bureaucratic sprawl. They’re a little irreverent. They care deeply about security. Technically capable enough to know they could build a version of our software themselves, they’re experienced enough to know that they really shouldn’t.

That’s the customer profile we build for. That’s our market, our audience. Now of course, we make our money by closing sales with executives, but we only get there once we’ve earned trust from a particular kind of developer.

We need to find these people, earn their attention, and then help them see what we’re up to. We trust that our product serves their needs sufficiently well that they’ll figure out the rest.

What do people want?

It should be clear, then, that we need to orient our marketing around this kind of person. Our marketing should appeal to their curiosity, their affinity to trivia. It should probably feel a little irreverent, maybe even a little bit brash. It should be a little wonky and a little technical. It should be transparent and honest.

In the same way that we need to make something people want with respect to our product, so too should we develop marketing that people want. It should be intrinsically interesting. We should treat our marketing seriously enough that it feels like its own output – and not just as a soulless, obligatory utility.

We should recognize a very important truth here: what we want to say bears little resemblance to what people want to hear. We can’t just occupy people’s space and shout at them about how great our product is. No one wants to hear our spiel.

Consumer-facing brands basically always understand this.

Consumer brands – or at least the ones that stick around – excel at marketing, because they have to. They have little room for competitive differentiation. Consumer brands know to build marketing programs that resonate emotionally with human beings.

Often they try humor, as with the below Cheez-Its advertisement that has blanketed football broadcasts for years.

Unclear why one of these cheese wheels wears shoulderpads while the others wear helmets

Sometimes B2B marketers think they’re above this kind of marketing. It is pretty silly, after all. A locker room full of animated cheese wheels won’t help you sell a seven-figure data warehouse contract. But that’s not really the point. There’s still plenty that they can learn.

Consumer marketing tends not to pitch products’ core merits too hard. The folks advertising Cheez-Its aren’t really trying to convince consumers that they’ve optimally arranged salt crystals on a crispy cheese cracker. The marketers want their product feel fun and indulgent. They want to inculcate specific feelings in prospective customers. It’s not above being objectively better, faster, cheaper in a comprehensive evaluation. It’s about being subjectively desirable.

As I mentioned before, we don’t want to mimic consumer brands too closely. We just need to remember that we’re marketing to humans. We need to invest in marketing content that makes people feel something. We can’t be boring.

An aside on being boring

We should acknowledge briefly that boring is subjective. We’re trying hard not to bore our target audience, which emphatically isn’t everyone. As long as our target audience likes our stuff, we’re happy.

Our target audience actually likes stuff that most people would consider boring. Our top-performing blog post dedicated over 3,000 words to the minutiae of timezones. Honestly. It was a big hit.

And I should add – we are ourselves basically our target audience. When we invest in not-boring content marketing, we’re effectively asking ourselves would I find this interesting?

People don’t always like what we write. I’m reminded of my defense of the “SSO tax” as a pricing practice. People really didn’t like that. But it was definitely interesting.

On appeal and relevance

A friend recently asked me about our timezones blog post. “Why do you guys post so much random stuff?” He was totally right to be skeptical. How on earth does a post about timezones help us sell authentication software?

Well, it doesn’t – at least not directly.

For any given piece of content, we can evaluate its general appeal to our target audience and its relevance to our product offering. A highly appealing post captures people’s attention and drives a lot of traffic. A highly relevant post delivers our sales pitch.

Ideally, every post would share both high appeal and high relevance.

But every post cannot be both highly appealing and highly relevant. There’s only so many ways we can dress up a veiled sales pitch. We usually have to accept a trade-off, accepting that we’ll have to compromise on either the appeal or relevance of our marketing.

I couldn't help myself and needed to go all ECON101 here

Most B2B marketers seem strangely unwilling to compromise on relevance. They choose almost solely to sacrifice the appeal of their messaging. They trot out tedious regurgitations of the same basic ideas over-and-over. I guess no one gets fired for recycling proven messages in familiar formats.

My congratulations to Cisco

The way we see it, a coherent content marketing strategy should just try hard to avoid the origin. That is, we should avoid anything that’s simultaneously irrelevant and unappealing.

Content that’s appealing but only distantly relevant still serves a few ends. Most mechanically, low-relevance content still drives traffic – which helps with awareness, search engine optimization, and actually a surprising amount of downfunnel conversion.

But low-relevance content also gives us an opportunity to fortify the brand. We can prove things about our company – instead of telling everyone what we’re about, we can show them.

Let’s take the timezones blog post from before.

Among other things, it helps us prove that we care about the details, that we’re the kind of people that actually read technical specifications. It helps us prove that we find software intrinsically interesting and that we’re serious about building a developer-first company. It hints that we’re the kind of people that care about documentation. For our target customer, this stuff matters. And its the foundation of our brand equity.

Wrapping up

I’ve been told that I can’t just end blog posts when I feel like I’m done. So here’s a conclusion.

B2B marketers shouldn’t be so boring. They’re marketing to humans. Humans don’t like boring stuff. And stuff that’s not boring lets you communicate subtle ideas in a credible way.