Lessons from scaling SaaS

When I started in sales, working commission-only at a PR agency in Stockholm against the advice of everyone I knew, the feedback loop was brutal. You either closed the deal or you did not eat. I met Fredrik Bage at that agency, and he convinced me I had a knack for this. We eventually left to co-found Mediapilot, spending roughly seven years growing the company and creating more than a hundred jobs. We figured out how to sell services the hard way. Years later, when I joined Happeo on the commercial side, I assumed the mechanics of selling software would be cleaner. The truth is, scaling SaaS is much messier than moving agency hours. It involves a lot of moving parts that you only learn how to fix by breaking them first. If you are building a software company right now, let me save you a few of the mistakes I made repeatedly.

You are charging too little

Your first pricing model is almost certainly too low. I get why this happens. When you look at your own product, you see the missing features. You see the bugs that your engineers have not patched yet. You feel slightly guilty asking a stranger to pay top market rates for something that feels unfinished to you. So, you heavily discount it to compensate for your own insecurity. But buyers do not see your internal bug tracker. They see a tool that either solves their headache or fails to do so. Buyers have budgets they need to spend to fix specific, painful problems in their daily operations. If your solution costs significantly less than the perceived size of their problem, they will actually doubt if your software works. I spent years thinking a low price was a competitive wedge into the market. I realise now it is usually just a lack of commercial confidence. Double the price on your next ten prospects. See if they even blink.

The single-rep trap

Eventually, you decide you need a dedicated sales team. The logical, financially conservative approach is to hire one account executive, train them, watch them hit their quota, and then hire a second one. This is exactly what I used to think made sense. It is entirely wrong. You need to hire the second rep before the first one is fully ramped. Let me explain how the single-rep strategy usually goes. You hire someone smart and driven. Six months later, they have closed almost nothing. Now you have to guess why. You have to wonder if you hired the wrong profile, if your onboarding is terrible, or if the software is currently unsellable. You have no data to answer those questions. You are back at square one, but six months older and quite a bit poorer. When you have two people pitching the same software, you establish a baseline. If one fails and the other succeeds, you have a rep problem. If they both fail, you have a product or positioning problem. It feels expensive upfront, but losing half a year of runway on a bad hire costs much more.

Churn is a product problem

Then there is the issue of keeping the customers you fought so hard to win. In the early days of any recurring revenue business, when customers start leaving, the immediate reaction is to blame the relationship. We assume we did not hold their hands enough during onboarding. We hire customer success managers, give them playbooks, and ask them to save accounts that are already walking out the door. Your customer success team ends up acting as a human shield for your product team's missing features. They spend their days apologising, offering manual workarounds, and trying to save face.

Your customer success team cannot out-smile a fundamentally broken workflow.

I got this wrong for a long time. I treated churn as a customer success failure when it was almost always a product failure being reported as one. If a user logs into your software every day to do their job, they will tolerate a mediocre relationship with your team. They might never reply to your check-in emails, but they will keep paying. If the software is confusing, slow, or fails to deliver on the initial promise, the most charming account manager in the world will not save the renewal. When churn spikes, stop yelling at your commercial team and go sit with your product team.

I sit in Marbella now, trying to apply these lessons to the new tools I am building, like Anchor and Substrat. I review my own progress against the written life plan I update every year, tracking my work and personal time out of ten. I would love to tell you that knowing these rules means I execute them perfectly every time. But building businesses is stubbornly difficult, and theory rarely survives contact with a Tuesday morning crisis. I still catch myself underpricing early iterations of a product. I still play tennis terribly. I still have not figured out a foolproof way to scale a commercial team without a few sleepless nights. But at least now, when I make a mistake, it is usually a new one.