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Articles by Simon
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2026 CPO Insights: The Problem With the Product Builder Prediction
2026 CPO Insights: The Problem With the Product Builder Prediction
As you may have already spotted, there's a report doing the rounds that is causing considerable consternation at the…
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AI Bugs: How to Triage for Non-Deterministic Systems?Aug 27, 2026
AI Bugs: How to Triage for Non-Deterministic Systems?
Effective triaging of bugs is table stakes for any well-run product team. Historically, the typical process for…
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AGAPO: A Framework for the Question Your Rubric Can't AnswerAug 14, 2026
AGAPO: A Framework for the Question Your Rubric Can't Answer
I've already published two frameworks on LinkedIn, serving two different purposes: Convergent/Divergent/Judgement asks…
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Stop Building a "Claude Code Second Brain". Build a Shared AI Brain Instead. (Part 2 of 2)Aug 11, 2026
Stop Building a "Claude Code Second Brain". Build a Shared AI Brain Instead. (Part 2 of 2)
You made the LLM swappable. That was the easier part.
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Stop Building a "Claude Code Second Brain". Build a Shared AI Brain Instead. (Part 1 of 2)Aug 4, 2026
Stop Building a "Claude Code Second Brain". Build a Shared AI Brain Instead. (Part 1 of 2)
Your team doesn't have an AI problem. It has a consistency problem.
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Your AI Eval Rubric is in Place - What Next?Jul 23, 2026
Your AI Eval Rubric is in Place - What Next?
An AI workflow that cleared its launch gate isn't done being tested. It's just done being tested for the first time.
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Where Most AI Evaluation Rubrics Quietly FailJul 14, 2026
Where Most AI Evaluation Rubrics Quietly Fail
Every AI-first product team I talk to claims to evaluate their agentic workflows before implementing them. When pressed…
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The Hidden Downside to "Frictionless" AI OnboardingJun 30, 2026
The Hidden Downside to "Frictionless" AI Onboarding
Every growth tool selling AI right now has the same pitch. Fewer signup steps, faster verification, less drop-off…
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Your build/partner/buy decision is broken before it begins. Here's how AI can help.Jun 16, 2026
Your build/partner/buy decision is broken before it begins. Here's how AI can help.
I've sat in a lot of rooms where a build/partner/buy decision was supposed to be worked through and agreed upon. More…
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The Smartest AI Move Right Now? Seeing Through the PitchJun 1, 2026
The Smartest AI Move Right Now? Seeing Through the Pitch
Many organisations rolling out AI right now are going to look back in three years and realise that the gains they…
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Simon Freedman shared thisIf you're in the Reading area next week, I'll be giving a ProductTank talk on applying AI in Product responsibly - do come along if you can! 🗓️ Wednesday 30 September 📍Pentahotel Reading ⌚️ 6:30pmSimon Freedman shared thisLess than a week to go! Here is our line up of fantastic speakers from within the Reading ProductTank community. Sign up on Meetup to join us at Pentahotel Reading next Wednesday 30th September and hear their ⚡ Lightning Talks ⚡ Franz Vitulli, MBA Ayo Adisa Suhas Ganjare Santosh Kumar Simon Freedman
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Simon Freedman shared thisMost PMs by now are capable of writing decent AI prompts, but not necessarily fully comprehensive ones. How do you know if yours covers all bases? I've built a tool to help you determine just that - as always, any feedback welcome! https://lnkd.in/e85g_aYK
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Simon Freedman reposted thisSimon Freedman reposted thisA few people kindly asked if they could share my earlier post, but I hadn't realised it was restricted to my connections. So, making this one public: I'm currently exploring senior architecture and technical leadership opportunities, particularly across Technical Architecture, Solution Architecture and technical leadership roles. My background spans cloud platforms, enterprise integration, distributed systems, identity and access management, SaaS ecosystems, platform modernisation and technical delivery. I'm open to remote opportunities across the UK, as well as hybrid roles across Liverpool, Greater Manchester and the North West. If you know of a suitable opportunity, I'd be very happy to connect — and please feel free to repost this. #OpenToWork #TechnicalArchitecture #SolutionArchitecture #TechnicalLeadership
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Simon Freedman shared thisThere's a lot of noise at the moment about the supposed impending extinction of PMs by 2030, following the 2026 CPO Insights Report. I disagree wholeheartedly with this conclusion, and in this article I lay out specifically why.2026 CPO Insights: The Problem With the Product Builder Prediction2026 CPO Insights: The Problem With the Product Builder PredictionSimon Freedman
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Simon Freedman shared thisLooking at the World Economic Forum's Future of Jobs report, there's a couple of things I found both insightful and hopeful. Unsurprisingly, AI is the fastest-growing skill, but look at what it says about the human element: Analytical thinking, resilience, leadership and creative thinking dominate the skills that employers value today. By 2030, AI, big data, cybersecurity and technological literacy shoot up the rankings, but creative thinking, resilience, curiosity and leadership rise with them, the latter ranking in 6th place among the fastest-growing skills. Perhaps the most future-proof capability isn’t a specific technical skill at all. It’s the ability to keep learning, adapt and think critically about how to use the technology available. The choice facing the future workforce isn’t either humans or machines, it's humans who know how to apply what only they can bring to the table to the machines they work with.
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Simon Freedman shared thisHistorically, bug triage has been based on the assumption that if you can't replicate it, it doesn't pass. AI features have thrown that out of the window, but our backlog management hasn't yet caught up. The issues we can't replicate may be the ones with the highest stakes. So what to do instead?AI Bugs: How to Triage for Non-Deterministic Systems?AI Bugs: How to Triage for Non-Deterministic Systems?Simon Freedman
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Simon Freedman shared thisGartner predicts that by 2028, AI inference costs per agentic workflow will rise by more than 5x. There's a paradox here. Token costs are falling, whether due to being subsidised, or actual efficiency gains, or both. Those falling costs however are resulting in AI being used for ever more complex work, which means that overall spend continues to rise. Question to anyone running agentic workflows in production, given the above economic realities: are you matching the level of LLM capability to the complexity of the task or are you just defaulting to your most capable model? If the latter, why is that? https://lnkd.in/ejK_rpKzGartner Predicts AI Inference Costs Per Agentic Workflow Will Increase More Than Fivefold Through 2028Gartner Predicts AI Inference Costs Per Agentic Workflow Will Increase More Than Fivefold Through 2028
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Simon Freedman shared thisI've published two frameworks here already. One for whether AI belongs in a task, one for checking if a specific output is good enough. Neither one answers a question that matters just as much, i.e. is the system itself in a fit state to be running at all? That gap is where many AI failures hide. Here's the third check I've not addressed before, and why you need it alongside the other two, not instead of them.AGAPO: A Framework for the Question Your Rubric Can't AnswerAGAPO: A Framework for the Question Your Rubric Can't AnswerSimon Freedman
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Simon Freedman posted thisGiven that Claude's new watermark is based on word choice bias, rather than hidden characters etc, I'm curious - and more than a little concerned - how many false positives are going to be flagged on truly human-written content. Add that to the purely subjective 'seems like AI slop' reaction that LinkedIn recently introduced and I feel like we're headed for a proper mess. I was actually about to use an Oxford comma there and didn't, for that very reason! 🤦♂️ Thoughts?
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Simon Freedman liked thisSimon Freedman liked thisOne year at Propel Recruitment🙌🏻 Today marks one year since I joined Propel, which somehow feels like it’s flown by! ❤️ (Honestly I keep going to say I've been here a few months😊) I joined with the ambition to continue my career in Tech recruitment and immerse myself in the world of start-ups and scaleups. 🚀 It's hard to pinpoint exactly when Product became my world but I've had the opportunity to work with some incredible businesses building out their teams, from founding Product hires through to senior leadership, and build a network of some genuinely brilliant people across the Product space. Reflecting back, it’s really solidified the importance of consistency, being authentic and genuinely being invested in the people you work with. Building relationships takes time, and I’ve learnt that the best ones come from being honest, showing up consistently, adding value where you can and actually caring about the people on the other side of the conversation.🤝🏻 Propel has given me the space to really find my niche within Product, build something I’m genuinely passionate about and surround myself with people who have made the last year a lot of fun. I’m really excited to keep building on that in year two, continue growing within Product, meet more great people and see what the next year brings. 🚀 A huge thank you to everyone I’ve worked with, spoken to, met for a coffee or connected with over the last 12 months and of course to everyone at Propel for making the first year what it’s been. A big shout out to Ben Dalzell and Amy Somers for making it possible! Bring on year two 🥂
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Simon Freedman liked thisSimon Freedman liked thisAn unexpected update and I’m reaching out to my network. I was due to begin an exciting new chapter in two weeks, moving into a Project Manager position after making the decision to transition my career into Project Management. Unfortunately, following an unexpected change in business strategy, I’ve been informed that the position I was due to start is no longer proceeding. To say im absolutely gutted is an understatement, I only received the phone call yesterday afternoon explaining the situation, I am extremely shocked and disappointed. I worked incredibly hard to secure the role and to have it taken away like this is devastating. Having already left my previous position in preparation for the move, this means I’m now immediately available and looking for my next opportunity. I’m interested in Junior/Project Manager, opportunities, ideally within insurance, financial services or related professional-services environments, where I can combine my project management training with my existing industry experience. I’m PRINCE2 Agile Foundation certified and bring extensive experience working within the insurance market, including several years working closely with project and change professionals. If anyone in my network is hiring, knows of an opportunity, or would simply be willing to make an introduction, I’d massively appreciate hearing from you. Any help here would be really appreciated, I just need a chance. Many Thanks Henry #ProjectManagement #ProjectManager #ProjectManagementJobs #PRINCE2 #PRINCE2Agile #ChangeManagement #CareerChange #OpenToWork #Hiring #LondonJobs #FinancialServices #Insurance
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Simon Freedman liked thisSimon Freedman liked thisThe best way to learn a new tool is to build something with it, so I spent a day taking a small app through GitHub's Spec-Kit workflow with Claude Code, from constitution to a working app on my iPhone. It worked well. Spec-Kit kept the agent on track between sessions, made tests the definition of done, and turned a licence condition I stumbled on into a rule every later step had to follow. The downsides were a lot of documentation for a small app and specs that were confidently wrong in places, but neither would put me off using it again. It would be interesting to point it at a brownfield project next. An agent can work out what a system does, but not why it was built that way unless someone wrote it down, and on some of the legacy systems I've worked on, those reasons left with the people who made them. If you're thinking about trying Spec-Kit, my full post covers what I did and what I learned: https://lnkd.in/g-Gia7vg I've recently moved to Sydney with my family and hold Australian permanent residency. I'm looking for my next role leading engineering teams or driving AI adoption, so if your organisation is working out how to build with AI agents, I'd love to talk. #LearningInPublic #EngineeringManagement #SpecDrivenDevelopment #AIAgents #ClaudeCode #SydneyTech
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Simon Freedman liked thisSimon Freedman liked thisLess than a week to go! Here is our line up of fantastic speakers from within the Reading ProductTank community. Sign up on Meetup to join us at Pentahotel Reading next Wednesday 30th September and hear their ⚡ Lightning Talks ⚡ Franz Vitulli, MBA Ayo Adisa Suhas Ganjare Santosh Kumar Simon Freedman
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Simon Freedman liked thisSimon Freedman liked thisWell, here we are again. 🫣 Today I left HeliosX. Both Product Ops, and everything else I have been doing with AI Transformation, were deemed to be ‘no longer needed’ and I have been made redundant. I’m not going to hide my feelings on this, clearly, but that is that, and my 2 years come to a sudden close. 😔 I am sad to leave many of the colleagues I have worked with during that time, and sad to have left many of our projects without the expertise and support they dearly need at this time, I genuinely hope these do continue, that you individually thrive and that we have the opportunity to work together in the future. If we got on well, please keep in touch. If we didn’t… don’t! 🫠🤣 Almost 3 years to the day when this happened to me before, back then at the height of the ‘big tech layoff’, and this was a particularly difficult time for me. But this time I feel much wiser, with a better profile and brand, and an amazing, supportive network of product professionals around me. 🙌🏻 What comes next… I don’t know. But with the messages of support, the conversations, the referrals, the shock from colleagues already, I am hopeful. As well, I know more than ever that Product Operations has a big future (with a lot of AI Building thrown in too) in the tech world. It IS needed… let’s see where next. 🤔
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Simon Freedman liked thisSimon Freedman liked thisI dont post very often, so it must be important 🙃 Very proud to announce our partnership with Engine by Starling. Thanks to Sam Everington Anton Fortunatov Tom Beresford. Looking forward to going on the journey with you all! 🚀 FF News | Fintech Finance https://lnkd.in/epWaiVjREngine by Starling Taps Build Circle to Accelerate Global SaaS Banking DeploymentsEngine by Starling Taps Build Circle to Accelerate Global SaaS Banking Deployments
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