Adding subscription billing to your SaaS product seems simple at first, but implementing it well can be harder than it looks. It’s easy to end up with an over-complicated and leaky subscription flow if you’re not careful.

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Even with developer-friendly tools like Stripe, it’s still on you to do a lot of heavy lifting. I’ve spent a considerable amount of time building and rebuilding subscription management logic. I’ve talked with other founders about the pains they are experiencing with their billing stacks. Here are some of the big mistakes I’ve made personally or seen others make:

Complicated Pricing Model

I’ve fallen victim to this one multiple times, and I’m sure I will make this mistake again at some point. Pricing is hard to get right, and it’s also one of the most powerful levers in a SaaS business. As a result, SaaS founders tend to tweak pricing frequently and often end up with complicated pricing models as a result. Don’t let this happen. You are deterring customers and complicating your subscription management logic — a losing combination. …

There’s no arguing it — Slack is a great product. Everyone seems to be raving about the magical team chat app that boosts productivity overnight. If you’re not using Slack you are missing out on an easy productivity boost, right? I mean, NASA seems to be using it to put robots on Mars and it’s making their lives simpler, more pleasant, and more productive.

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A snapshot from the Slack homepage.

A few weeks ago I attended the first “Basecamp Way to Work” workshop hosted by Jason Fried of Basecamp — collaboration and project management software. He is also the New York Times Bestselling author of the business book Rework. In short, he’s a smart guy when it comes to productivity and software.

The workshop was mainly attended by project managers and team leads from startups. Naturally, the concept of team chat and Slack were mentioned frequently throughout the day. It was clear that many of these teams were using Slack as their main form of communication. Jason raised some great points as to why this structure doesn’t scale and actually hurts productivity. …

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Photo by Rohit Padmanabhan

I check on our signup funnel every couple days. It only takes me a few minutes and helps bring me back to our critical path — growing revenue. I care about how many new signups rolled in, and of those how many are active and likely to convert to paying customers.

Knowing how many signups our competitors capture has always been a question I’ve wanted the answer to. This number is the key to estimating revenue growth and understanding which marketing efforts are working. Without actually hacking into our competitor’s analytics tools I didn’t think this number was possible to get. After a bit of digging I realized it was right in front of me! …

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Photo by TJ Holowaychuk

Ever since I started programming I’ve been dreaming in code. Talking to other programmers I quickly learned I was not alone. Initially I embraced these dreams as if they were a result of my focus and dedication. I get a sense that other developers feel this way as well. I’ve come to realize these dreams are not natural, and most importantly not healthy. They result in restless sleep and deprive my mind of the time it needs to be at rest. I want to trade logic and classes for rainbows and unicorns.

Why such analytical dreams?

It’s not a coincidence that “in the zone” or “wired in” is used to describe a programmer who is working. For most developers it takes a block of undisturbed time to get focused and work on a problem. I’ve heard programming compared to building a glass house in your head. Every time you start working you need to construct a map of the environment and the steps you need to take to solve the problem. This process takes time, and if you get distracted or take a break the house falls down. This level of focus makes it difficult to step away or “unwire.” You might be physically away from your screen, but your mind is still consumed. Whatever your mind is consumed with will drive what you dream about. …

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I went into college quite adamant on entering the investment banking world after school. I have no idea what I was thinking at the time besides the fact that it would pay well. (If that isn’t a big red flag I don’t know what is.) Fortunately, I realized that I wanted something else from a career and lifestyle early in my studies. I graduated from Marquette University with a degree in Finance, but this ended up being more of a formality than anything.

After switching gears before graduating I quickly became enamored with web development and the idea of web-based software. Today everyone knows this as SaaS, but this term wasn’t widely adopted at the time. The entrepreneurial culture, creative outlet, and joy of building something from scratch was what sold me. After reading Getting Real by Jason Fried and DHH I was truly hooked. The following 6 years of my life have been a journey in self-taught development and bootstrapping businesses. …


Ben Bartling

Now — searching for my next venture. Past — built, grew, and sold ZoomShift. Full-stack developer, believer in product-led growth, somewhat of a designer.

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