I spent eleven years being the person who had to use the system.

I read European Studies at King's College London, which prepared me for none of this. What did was a summer job: I went to upstate New York as a counselor at a Fresh Air Fund camp, for children from parts of the city that don't get many trees.

I meant to do one summer. I stayed eleven years, through camping, human resources, youth programming, and eventually communications and PR. In each of those roles I was one of the people the systems were supposed to serve. That turns out to be the most useful thing on my CV.

Because I was the one filling in the forms. I knew which fields nobody understood, which report took two days to produce and got read by no one, and exactly how many times a family's address was typed into a computer before anyone acted on it. When I built the organization's database, I wasn't guessing at the workflow. I was the workflow.

More than a decade after I left the staff, that system lives on as the live archive of all of the organization's data. The real test of this work is whether it keeps serving people after the person who built it has gone.

I started Solve IT Simply in 2013 to do that for other organizations, and it grew into Simply360, a platform for the parts every mission-driven organization needs and nobody should have to rebuild. Since then: two hundred and fifty-odd projects, a hundred-plus organizations, and a fairly clear view of how technology decisions go wrong.

Mostly they go wrong early, quietly, and for understandable reasons. Somebody chose a system in a hurry three years ago, and everything since has been an accommodation. Nobody was negligent. It's just that no one was in the room whose job it was to ask the awkward question.

That's the job now.

Away from the software

The Creators Social

For five years I ran something that had nothing to do with software. Small gatherings (brunches in Harlem, workshops, one long weekend retreat) for freelancers, founders and creative people who were mostly working alone and feeling it. It was open to everyone and deliberately built around people who don't find other rooms welcoming.

I mention it because it explains something the case studies don't. The systems are the visible part of this work. What I'm doing, most days, is getting a group of people to agree on how their organization should work. It's the same skill, in a smaller room.

The companies

Solve IT Simply since 2013 — the studio side of this, with a small team. Simply360 — the platform underneath much of the work.

How I work

Remotely, with clients on both sides of the Atlantic. I'm English, based in the States, and I do still say “quite good” when I mean it.

Elsewhere

LinkedIn, if you want the chronology. jake@solveitsimply.com if you'd rather just write.

Come and tell me what's not working.

Thirty minutes. I'll ask a lot of questions and give you my honest read at the end.