Don’t worry, we all do. So how can we get better? Let me give you the lens of someone who’s built a business, someone with strong beliefs around what does and doesn’t work, but otherwise has no clue what they’re talking about. This is all grounded in what I’ve seen at Sentry over the years, so let me take you through our go-to-market journey a little bit.

The biggest question people ask me is how we found product market fit. Often what they’re asking is how we attracted our first customers. That’s a marketing question. My answer has generally been that I’m not really sure, but I do have some ideas on what worked. You see, early days Sentry we weren’t trying to build the business. Instead I was working on things for other companies, and most of Sentry’s market presence was seen through social interactions, often at conferences. You might say we were an early adopter of DevRel tactics, but there was a key difference: there was no fluff.

I wasn’t speaking about some bullshit topic at a conference, or giving a terrible demo of a half-assed product. I was building a brand. That brand was centered around trust and authenticity. It was represented when I - just like with this blog - gave my honest point of view on challenges. I would talk about how I approached scaleability issues with duct tape-esque hacks, or how we were building an open source business out of Sentry. I was giving people genuine value alongside interesting content. I was doing it all from real world experience, not manufactured, make believe stories about how things work. That’s marketing.

I did that for many years early in my career. I traveled around to various events, often within the Python community, talking to colleagues and speaking about things I had learned in my career. That meant when we started charging for Sentry, many people already knew who I was, as well as what Sentry was. Many were already using the open source project, and more than happy to pay the affordable price tag we had set. That happened because we had achieved what many fail to understand about marketing: we had created awareness.

You see, when we buy ads - that is, we as in Sentry - we’re not actually buying conversions. That’s not true for all businesses. When I scroll Instagram and buy whaetver junk I run across, I’ve probably never seen the brand before, and its a one-time impulse buy. When you buy Sentry however you’re buying a brand, and what that brand has promised you. In our case, we think of our brand as a number of things, but particularly important are product quality/excellence and trust/authenticity. Some of you are probably rolling your eyes right now, but consider where you spend money in life. Why do you eat up everything Apple has to offer? Why do people spend money on a Rolex? Why do I have a Red Bull in my hand right now? This $10 can of still water from Liquid Death? You’re buying into something more than a product, you’re buying into a brand.

When we acquired Syntax a lot of people were confused. One of our board members, someone who trusts our decision making, asked with an extremely serious face how this made sense for the business. You see, most people while they believe in brand, they still have a hard time actually committing to it. Syntax is a brand investment for Sentry. It’s not an advertising channel. It’s not a podcast. Its a brand, both in name as well as via the hosts, that people trust to inform them about a set of technologies. That brand trust, that brand loyalty, we invest into that. We invest into that because if you value a brand, you will give them a shot to earn your money. It’s often hard to measure, but the results are everywhere if you look.

Billboards are no different. Our CFO, rightfully so, is highly skeptical of billboards. What makes them valuable? Just like digital advertising, you cant put up a billboard and pretend thats going to instantly convert to leads. Its just another touch point. I was at my wife’s holiday party two year ago. It’s a larger company with executives who are much more seasoned than me, and more importantly, a place where everyone was a stranger. She wanted to introduce me to their CTO, who she didn’t know, which meant an awkward bump-into-them-and-start-a-convo. The CTO was clearly expecting it, as is their job at a party like this, but what he wasnt expecting what happened next. I mentioned that I started a company called Sentry many years ago, and the CTO’s partner immediately interjected: “Like those bilboards?“. Yep, like those billboards. She recognized our billboard because it was interesting. The CTO’s ears immediately perked up, and that got the conversation started.

Aside, if you don’t understand what the point of our billboard campaign was, you wouldn’t be alone! We’re not pitching, or even explaining our product. We’re aiming for intrigue. What is Sentry? What can’t Sentry fix? Why is there a minotaur playing in VR? Even if you know about Sentry, you’d know Sentry doesn’t fix anything, we just tell you what’s wrong!

Now that precise scenario is not high value for Sentry - the CTO isn’t our customer - but you can imagine a world where he’s reviewing a contract put in front of him by his engineering teams, and that contract says Sentry on it. He will (ideally) recognize the name, and either immediately let his guard down, or even better, have a point of contact that he trusts. Brand is all about market awareness. It’s about making sure people know who you are, what you stand for, and eventually what you’re offering them. That means that no matter the touch points, all we’re trying to do is reenforce “hey we exist and we do cool shit”. If you have a need for what we sell, you’ll evaluate it when the time comes.

So all of this said, you should invest into your brand. If you’re building a real business, and you actually give a shit about your product (rather than just making a buck), brand is the strategic investment that will pay dividends for the rest of time. It’s not going to solve for bad product-market fit, and it certainly won’t help if your brand values are not represented in your product, but if you solve for that, brand can be your marketing strategy too.