Your company already has an operating system.
In two sessions, you’ll write it down.
Sessions
2 × 2 hours
Flexible scheduling
Format
1-on-1
Live, online
Access
Workshop skill suite
Provided on enrolment
Not templates. A first-version OS built entirely from your own business context, with Mark working through it alongside you.
The cohort workshop is built on peer challenge, and that format works well for most founders. This is the same curriculum, the same framework, the same rigour, with every question, example, and decision boundary grounded in your company specifically. Mark does what he does in the cohort room: asks the questions that make the vague specific.
Why 1-on-1
The same OS. Built around your specific business.
The cohort workshop is built on peer challenge, and that format works well for most founders. But some businesses are too specific, too sensitive, or too far along for a shared room to be the right context.
The 1-on-1 version runs the same curriculum: you build a first-version AI company operating system across two sessions. The difference is that every example, every challenge, and every decision boundary you write is grounded in your company’s actual context, not a general framework. Mark works through it with you directly.
This is not coaching and it is not consulting. It is a structured working session where you do the building and Mark does what he does in the cohort: asks the questions that make the vague specific.
The sessions
What you will do across the workshop.
Session 01 – Scheduled via booking link
See how a company OS gets built, in your context
Surface the rules, constraints, and decision boundaries already living in your head. Document them roughly. Mark challenges, sharpens, and identifies what is vague. You leave with a real first draft, not a template.
Between sessions
Run the bootstrap on your own business
Run the AI bootstrap on your company using the workshop skill suite (provided on enrolment). Review what it gets right and what it misses. Write your correction list: the context your agents need that no public source contains. Approximately 1.5–2.5 hours.
Session 02 – Scheduled via booking link
Sharpen, correct, and map what’s next
Bring your correction list back. Work out what your tools actually need from you and whether the right next step is building independently or joining the full four-week cohort. You leave with a clear path forward, not homework you will not do.
Who this is for
One seat. The right fit matters.
Same audience as the cohort workshop. This is for founders who know they need to act on AI but have not found the right starting point, and want to work through it directly with Mark rather than in a group setting.
This is for you if…
Probably not for you if…
Who’s in the room
One facilitator. You.
Mark Littlewood
Founder, Business of Software
One facilitator. You.
Mark has run Business of Software for 19 years, two annual conferences, more than 400 practitioner talks, and a community of founders building software companies that last. He has spent that time working out what actually separates the businesses that make it from those that do not.
BoS now runs its own operations on an AI company operating system, the same framework this workshop is built on. The difference in coordination, work quality, and team efficiency has been significant. This workshop is Mark sharing what is actually working, so your company can achieve the same.
Registration
Your company already has an operating system. In two sessions, you’ll write it down.
$500
First 5 registrations only · Regular price: $2,500
Common questions
Before you register.
What do I need before Session 1?
Claude Desktop and a Claude Pro or Team plan (required for Cowork mode). The workshop skill suite is provided on enrolment, no additional setup needed before your first session. If you are not already using Claude in some capacity, this workshop is not the right starting point. If you hit any issues before Session 1, email mark@businessofsoftware.org.
How does the pilot pricing work?
The pilot price of $500 is available for the first 5 participants to register and pay. After that, pricing will be set based on what we learn from the pilot sessions. If you are considering it, the time to register is now.
How is this different from the four-week cohort?
The four-week cohort is for founders already using Claude and Cowork who want to build a complete governing system: strategy documents, a fully specified agent, and a first mission. It requires roughly 24–30 hours of work. This 1-on-1 workshop is the step before or alongside that. In two sessions you will have a bootstrapped start and a clear direction. If you leave ready to go deeper, the full cohort is the natural next step.