JANUARY 26, 2025
The Challenges and Issues of AI
Some ideas on why AI will cause more problems than it solves in the short and medium term.
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SIMON CONWAY
AI-native Product Manager. I ship products with Claude Code daily.
20 years of senior product across consulting and scale-ups. The last year I've rewired how I work, learning to ship with Claude Code, Cursor, n8n and context engineering. I build the AI tools my own PM practice runs on, then take what works to product teams.
Now building: OS-Intelligence, an open-source PM system for Claude Code →
Currently building
OS-INTELLIGENCE
An open-source PM operating system, built in Claude Code.
The product manager's job is mostly context work: synthesising meetings, writing PRDs, tracking decisions, briefing stakeholders. OS-Intelligence handles all of it. Skills, layered memory, sub-agents for review. Clone it, point Claude Code at it, and your PM workflows compound across sessions.
40+
custom skills
Stakeholder synthesis, PRDs, decision docs, status updates, planning.
15 hrs
saved per week
Measured on my own PM work across synthesis, docs and filtering.
Open
source
Apache 2.0. Clone into any repo, point Claude Code at it.
The proof
I run my own product career on a private fork called PM-OS. Every PRD, status update and stakeholder brief in this portfolio came out of it. OS-Intelligence is what I'm releasing once I'm sure it works in real conditions.
Case studies
Three pieces of work, one per pillar
Companies
Where the 20 years happened
Beyond product
Public work and conversations I'm part of
Meetup series · Barcelona
Sobremesa Tech
A meetup at the intersection of tech, philosophy and society. Conversational format, deep questions, no need to find the answer. Two events run, third on May 19: "The Quiet Coup - how power moved while we scrolled."
See on Luma →Writing
Substack
Notes on AI product management, Claude Code, context engineering and the future of the PM craft. New writing dropping through 2026 as OS-Intelligence and PM-OS evolve in public.
Read on Substack →Latest writing
JANUARY 29, 2025
From "I Do" to "Wow"
A Brotherly Side Hustle to redesign my brother's wedding photography website.
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JANUARY 30, 2025
Align CJM & OKRs for CX success
A 4-part series on bridging the gap between CX, Product, and Delivery.
Read more →Testimonials
From colleagues and clients I've worked with
"He is understanding and inspirational - the sort of person you simply want to work for and go the extra mile with."
Edwin Groenenndaal
CEO, Harness Intelligence
"As I've grown in my career Simon's coaching was and remains invaluable. Moreover, he cares much more about people over process and genuinely is a great great individual."
Jason Burin
Product Director, Diageo
"Simon is one of the 'go to' people in AND Digital for Product centric knowledge."
Stuart Munton
Chief for delivery, AND Digital
"Simon is a valued member of my leadership team. His contribution has helped make Newton the successful club it is today."
Shan Beerstecher
Club Executive, AND Digital
"Simon not only is one of the best Product principals I have come across in all my years of professional services, but also has a keen commercial awareness and business development acumen."
Fahad Ansari
Business Development Manager, AND Digital
"Simon is exceptionally knowledgeable on modern product, agile and experience design, with a sharp commercial and business awareness."
Mary Ahern
CEO, Alps Education
"Simon is a brilliant Product consultant. He faces into big-picture problems, quickly understanding the wider scope of what's really going on. He is remarkably action-oriented."
Tom Rooney
Product Director, Primark
"A stand out quality is Simon's genuine passion about supporting other people's growth and championing their successes."
Nick Simm
Squad Lead, AND Digital
"Simon is a collaborative leader and strong listener who brings people together and creates space for open dialogue. He champions the design process and fosters an environment where teams can think, contribute and grow."
Natalia Boestad
Director Research & Design, User Experience, IFS
"One of those rare people who makes difficult product and operational challenges feel genuinely solvable. Thoughtful, measured, and relentlessly pragmatic."
Pete Trainor
Digital Service & Product Director, IFS
Where I'm strongest
The conditions, the work, the way
Start-ups and scale-ups
I do my best work in fast-paced, high-growth environments where vision and product practice are still being shaped. I move fast, take ambiguity in stride, and care about outcomes more than process.
AI-native product, shipped with Claude Code
I work in Claude Code every day. Not for slide decks. For shipping. Three AI-native systems built on it: PM-OS (40+ skills, 10X faster workflows), a stakeholder intelligence app, and an automated job search pipeline (200+ roles screened weekly, 87% time saved).
Most senior PMs talk about AI. I build the systems, ship the code, measure what changes, then bring the workflows into product teams.
Context engineering and memory systems
The thing that separates AI products that work from ones that don't is context. I design the memory layers, the skills hierarchy and the eval loops that make Claude Code agents reliable in production. PM-OS is my proving ground; OS-Intelligence is the open-source version.
Small, cross-functional teams that ship fast
Small teams with real problems and short feedback loops beat large teams with long roadmaps every time. I ship to customers often and let their signal drive the next decision.
The value I add
AI-native builder, hands-on with Claude Code
I ship AI-native product workflows with Claude Code, Cursor and n8n. Not slides. Working systems.
- PM-OS (40+ skills, 10X faster workflows)
- OS-Intelligence (open-source)
- Context engineering, evals, memory design
Product operations at enterprise scale
I set up product practice that holds. Op-model transformations at Fortune 500 (Constellation Brands) and FTSE-listed (Primark), AI-native discovery at IFS.
- Op-model design and roll-out
- Discovery, OKRs, communities of practice
- Product coaching at scale
Strategic direction and narrative
I align organisations behind product direction. At IFS I set the North Star for AI in industrial software and aligned a global engineering organisation behind it.
- North Star definition
- Customer and market research at industry scale
- Company-wide activation alongside technical leadership