After Business of Software Conference, we got a lot of messages.
Not about the after-party. About one talk – Tim Barker’s session on building an AI operating system for your business. Founders wanted to know where to go next. How to start. Whether there was somewhere to actually work through this with people taking it as seriously as they were.
So we built two workshops. Here’s what they are.
What these workshops are not
They are not a survey of AI tools. They are not a keynote stretched into a webinar. They are not a vendor pitch with an agenda stapled to it.
There will be no magic prompts. No breathless forecasting about where AI is heading. No frameworks being sold, no sponsor content.
That’s not us, and it’s not Tim Barker.
Who Tim Barker is, and why it matters
Tim has founded five startups and seen the startup journey from every angle. He sold his first company to Salesforce. He’s taken companies through scale to IPO and led them to several hundred people. He’s been a member of the BoS community for fifteen years.
About nine months ago, he made a deliberate decision: to build his current company, Attain IP, as an AI-native business from day zero. Not AI-assisted. AI-native. He rebuilt how his organisation makes decisions, how it coordinates work, how it delegates and reviews – everything – around a documented operating system that AI agents can actually run inside.
His talk at BoS Europe 2026 was the distillation of that nine-month experiment. The reaction from a room full of founders who had heard every AI pitch going: “someone actually doing it.”
That reaction created these workshops.
The Two Workshops
Workshop 1: AI in Your Business: Where to Start
Two sessions. One week. A first-version OS written down for the first time.
This is for founders who know AI matters and haven’t yet built anything systematic around it. You may be using tools here and there. You may have played with Claude. But nothing has compounded. Every session starts from scratch. You’re still the one holding it all together.
In two sessions across one week, you’ll see exactly how a company OS gets built in practice – then build a first version for yours. Not a template to fill in. A first draft, built from your own business context, challenged by eleven other founders doing the same work in parallel.
By the end of Session 2 you’ll have: a bootstrapped Agent OS, a correction list (the context your tools need that no public source contains), a revised CLAUDE.md (the standing brief your tools read at the start of every session), and a clear path forward – whether that’s building independently or joining the four-week cohort.
- Format: 2 live sessions with Tim Barker and Mark Littlewood
- Cohort: Max 12 founders — no observers, no spectators
- Dates: 13 May + 16 May 2026 · 11am UK
You’ll need Claude Desktop and a Claude Pro or Team plan (required for Cowork mode). If you’re not already using Claude in some capacity, this workshop isn’t the right starting point.
Questions about fit? Email mark@businessofsoftware.org
Workshop 2: Build Your AI Company Operating System
Four weeks. One operating system each.
This is for founders who are already in motion – already using AI tools, already tinkering – and have hit the ceiling that only a documented OS can break through. You’re not getting less done. You’re amplifying a mess instead of a system.
Over four weekly sessions, with Tim and eleven other founders at exactly the same ceiling, you’ll build yours. Not in theory. Live, in the sessions, challenged each week by the group.
By the end you’ll have: your AI company operating system (the documented rules, constraints, and decision boundaries your agents read at every session), five to eight strategy documents ready to delegate, one fully specified agent (decision boundary, escalation triggers, evaluation framework – ready to run), and a Phase 1 mission your agent can start executing the Monday after the workshop ends.
- Format: 4 live sessions, weekly, with Tim Barker and Mark Littlewood
- Cohort: Max 12 founders – no observers, no spectators
- Dates: Starting Wednesday 20 May · Weekly · 11am UK
You’ll need Claude Desktop, a Claude Pro or Team plan, and to already be using Claude in your business. If you haven’t started yet, Workshop 1 is the right first step.
Questions about fit? Email mark@businessofsoftware.org
Why a cohort?
The cohort format is deliberate. Peer quality is part of what you’re paying for – a room where almost every conversation is worth having.
You’re not just learning from Tim. You’re learning from eleven other founders who are grappling with the same problems from different angles, with different businesses, at the same stage. That friction is where the most useful thinking happens.
Both cohorts are capped at 12. That’s not a marketing tactic. It’s how you keep the quality of the room.
The BoS No Quibble Guarantee
If you attend either workshop and feel you didn’t get value, we will refund your fee. No questions asked. This is the same guarantee that applies to every BoS event.
Which one is right for you?
- AI in Your Business: Where to Start is the right choice if you haven’t yet built anything systematic with AI in your business – or if you’ve been using tools but nothing has compounded.
- Build Your AI Company Operating System is the right choice if you’re already using Claude or similar tools regularly and want to build the governing structure underneath them – the documented OS that lets everything else finally run without you holding it together.
If you’re genuinely unsure, email Mark: mark@businessofsoftware.org
AI in Your Business: Where to Start – 13 + 16 May · 12 seats
Build Your AI Company Operating System – From 20 May · 12 seats
Business of Software has connected founders and operators with the people who can actually help them build better businesses since 2007. These workshops are built on the same principle as every BoS event: real practitioners, honest conversation, and work that compounds.