What building Happeo taught me

I spent years on the commercial side of Happeo, selling employee experience software. When you are building and selling a product that technically anyone with a workforce could use, you feel a certain kind of optimism. You look at an office block in central Stockholm or London and think the people inside are all potential buyers. I will be honest with you: that optimism is a trap. If I look back at the hardest lessons from that period, the biggest one was how much time we wasted simply because we were not entirely sure who we were supposed to be talking to.

When I started my career in sales at a PR agency back in Sweden, I worked on commission only. Everyone around me told me it was a terrible idea, but my future co-founder Fredrik Bage convinced me I would be good at it. When you eat what you kill, you develop a habit of talking to anyone who will listen. You pitch hard. That mentality helped me build Mediapilot with Fredrik and grow it to over 100 people. But when you apply that same scattergun approach to complex software sales, it breaks.

The danger of anyone

Ambiguity in your ideal customer profile is an expensive luxury. It costs you years. In the early days, if a mid-sized logistics firm wanted a demo, we gave them a demo. If a massive retail bank showed interest, we spent weeks preparing a pitch. Because our software connected employees and managed internal communication, we convinced ourselves our market was simply companies with employees. It sounds ridiculous now, but when you are trying to hit commercial targets and keep morale high, you find a way to justify taking every single meeting.

What happens is that your sales cycles stretch into infinity. You spend months doing the dance with companies who genuinely like your product but have no actual urgency to buy it. They nod at your features. They tell you the interface is very clean. Then they disappear. You end up with a bloated pipeline of 'maybe', which is much worse than a pipeline of 'no'. A flat rejection lets you move on. A maybe eats your Wednesday afternoons for six months.

People buy, not companies

The shift happens when you realise how big companies actually buy software. I got this wrong for a long time. I used to think enterprise sales was a battle of feature lists. If we just had a slightly better integration, or a smoother interface, or a faster search function, the deal would close. But companies do not buy software. People do. And inside a large organisation, buying a new platform is a massive headache for the person championing it. They have to fight with their IT department, argue with procurement, and sit through endless security reviews where people whose entire job is to say no try to find reasons to block the purchase.

Enterprise sales is rarely about having the best software. It is about finding one person inside the building willing to spend their political capital on you.

If you do not have that person, an internal champion who actively wants you to win, your deal is dead. It does not matter how much sense the financial numbers make. It does not matter how pretty the dashboard is. Deals in large corporations do not usually die with a dramatic rejection. They die in silence. Emails go unanswered. The procurement review gets pushed to next quarter because someone was on holiday. The champion is the only mechanism you have against that silence. They are the ones walking down the hall to ask the legal team why the contract is stuck on a desk. Our commercial success did not come from suddenly building a flawless product, but from getting much better at identifying the specific human being who felt the pain enough to fight for us.

What I took with me

I moved my family from Sweden to Marbella in 2018. We meant to stay two years, and somehow I am still here, playing tennis badly and building new things. I keep a written life plan that I update every year, rating my family and friends, health, finances, work and personal time out of ten. I have done this since around 2010. It forces me to look at reality rather than what I hope is happening. I try to apply that same harsh scoring to the companies I build and invest in today.

With Anchor, where we are building AI for alienated fathers, the customer profile is painfully specific. There is no ambiguity. I know exactly who I am talking to, and I know exactly what kind of pain they are in. The same goes for Substrat. We are building infrastructure for AI builders. If you are not building AI, I have nothing to sell you. It is a massive relief to operate this way.

Saying no to a broad market feels unnatural when you first start out, especially if you have ever lived on commission. I still catch myself occasionally slipping back into that mindset, thinking maybe a product could be tweaked to fit a slightly different customer type. But then I remember sitting in endless meetings with massive companies who were never going to buy, and I stop. I haven't got everything figured out when it comes to building companies, but I do know this. If you do not know whose political capital you are asking for, you are wasting your time.