Twelve years ago Stefan walked into an empty office. No colleagues, no handover, no manual.
Two of our three customer-facing people had left within six weeks of each other. One fired at the end of May. The other resigned at the end of June. Stefan started August 1st to a blank desk and a list of 15+ enterprise customers we'd just signed during a brutally strong Q2, all waiting to be onboarded and get started with Upsales. Immediately.
I was in a kind of floating "executive chairman" role at the time while Johan Nilsson was CEO. We agreed I'd step in and run the accounts together with Stefan.
What followed was eight of the most intense weeks I can remember.
Four travel days a week. Trains, flights, customer sites. Back to back. We were running so hard that I was best man — toastmaster, actually — at a friend's wedding in late September and fell asleep right after dessert. Not the champagne. Just the pace.
Apprenticeship is the only onboarding that actually works.
There are a hundred ways to onboard someone. Documents, product training, shadowing calls. Most of it is theater. What actually works is sitting next to someone who knows what they're doing and doing real things together.
By week two Stefan was leading parts of our customer meetings. By week three he was running most of them himself. We split the workload fast because he's sharp, driven, and has the strongest sense of accountability I've ever encountered in a colleague. Not the performative kind. The quiet, internal kind that doesn't announce itself but shows up every single time.
That kind of trust is hard to build sitting in an office. It comes from grinding together. You learn how someone thinks when things go sideways. You learn their judgment. You stop second-guessing each other. What Stefan and I built in those eight weeks would have taken two or three years to build in a normal working environment.
He's been head of our solution engineering team for a while now, and that foundation is still there.
The thing nobody tells you about people like Stefan.
When you have someone on your team with that level of accountability, someone who would rather work themselves into the ground than say they can't do something, you have a responsibility as a leader to watch them. Closely.
Two years ago we signed a large contract with a client. It became a nightmare almost immediately. The scope was 15 to 20 times larger than the client was willing to acknowledge. The timeline was nearly impossible. Stefan was the lead.
We had a walk-and-talk one afternoon. I asked how the project was going. He said: "I think we can get there, even if it's almost impossible. My health might be slightly at risk though."
He said it without a trace of complaint. Completely matter-of-fact. It is what it is.
That sentence scared me.
No contract is worth your best people. We'd written an opt-out clause into the agreement at the start because both sides knew there were real uncertainties in the scope. When the client pushed to extend that clause and keep moving the goalposts, we faced a straightforward question: do we absorb unlimited risk on a project we already knew was deeply complex, or do we make a clean exit while we still can? We exercised the clause. The client was unhappy. The conversation was uncomfortable. But it was the right call.
At the end of the day, it's just business.
I believe you win in the long run by holding your moral compass even when it costs you. When you own 44% of the company you built from scratch, the calculus is different than when you're a line item in a VC's spreadsheet. One of the real benefits of bootstrapping is that you never have to betray your own judgment to hit someone else's number.
Stefan is now 12 years in. I'm building Aira.app alongside running Upsales, and the honest answer to how I manage both is: people like him. Exceptional colleagues who want responsibility and can carry it. That's the only real answer.
I've never forgotten those eight weeks in the fall of 2013. Four travel days a week, bad train coffee, a wedding I barely stayed awake for, and the beginning of one of the best working relationships I've ever had.
Apprenticeship. Real work. Side by side. Still the only onboarding that works.
.png)
