About
Over 30 years of experience delivering modern software engineering, architecture…
Services
Articles by Phillip
Activity
1K followers
-
Phillip Smith shared thisOver the last few weeks, I’ve been experimenting with something unexpected: using Cursor not to write code, but to run an entire virtual C-suite. Inside Cursor, I’ve built a team of specialist agents — a CEO, CPO, CTO, CIO, CRO, etc. — each with their own mandate, expertise, and voice. Surprisingly, they behave exactly like real executives, not because they’re trying to please me or be “right,” but because they aim for what high-performing leadership teams always strive for: - Alignment - Clarity - Consistency - Realistic execution planning These agents challenge assumptions, surface risks, call out missing details, push for clearer decisions, and gravitate toward consensus. It doesn’t feel like prompting a model; it feels like managing a team. When placed into a structured collaboration loop — strategy → review → critique → synthesis — the dynamic becomes startlingly real. A recent “board review” inside Cursor showcased this: multiple agents reviewed our go-to-market plan, financial model, and MVP definition. They identified gaps, aligned on priorities, and produced outputs similar to what you’d expect from a senior team preparing for an investor round. What I’m learning is that agents are far more effective when treated as people with roles, responsibilities, and perspectives. Managing this virtual team feels uncannily similar to running an executive workshop. The fuzziness of herding ideas and viewpoints from uncertain sources and nearly aligned motives. For building out an early-stage product strategy or pressure-testing a go-to-market plan, this approach has legs, long ones. The quality, speed, and depth of idea generation, gap analysis and provocative productive argument is something that takes a lot of time and energy to develop in our teams. I am currently open to consulting engagements, particularly around strategy, product development, architecture, and AI-enabled operating models. If this approach resonates or you’d like to explore how a virtual C-suite could accelerate your organization, feel free to reach out. Happy to have the conversation.
-
Phillip Smith shared thisNice one Tom Hill. A fractional CTO hire isn't a budget decision, or a cost cutting measure, it's a way to add value by applying a different lens to your theory of winning.Phillip Smith shared this𝗣𝗹𝗮𝗻𝗻𝗶𝗻𝗴 𝗮𝗻 𝗲𝘅𝗶𝘁? 𝗬𝗼𝘂𝗿 𝗕𝟮𝗕 𝗦𝗮𝗮𝗦 𝘃𝗮𝗹𝘂𝗮𝘁𝗶𝗼𝗻 𝗰𝗮𝗻 𝗿𝗶𝘀𝗲 𝗼𝗿 𝗳𝗮𝗹��� 𝗯𝘆 𝟮𝟬% 𝗯𝗮𝘀𝗲𝗱 𝗼𝗻 𝘆𝗼𝘂𝗿 𝘁𝗲𝗰𝗵 𝘀𝘁𝗮𝗰𝗸! Most founders underestimate how much technical risk translates directly into price. Due diligence teams often apply a 10–30% valuation discount for weak documentation, ageing architecture, or security gaps, according to studies by PwC and Deloitte on M&A deal-breakers. Your CTO’s institutional knowledge is invaluable, but it's also biased. They can explain 𝘸𝘩𝘺 the trade-offs exist, and the buy-side DD team might appreciate your journey and the context behind your architectural choices, but it doesn't reduce the risk on their spreadsheet. A messy codebase, missing test coverage, or unclear IP ownership often means a 10 to 20% haircut or even a delayed or broken deal. At a $50M valuation, that’s an impact of up to $10M. Inversely, tech maturity and scalability can support a 𝟭–𝟮𝘅 𝘂𝗽𝗹𝗶𝗳𝘁 𝗶𝗻 𝗘𝗕𝗜𝗧𝗗𝗔 𝗺𝘂𝗹𝘁𝗶𝗽𝗹𝗲𝘀 for SaaS platforms. That’s the difference between a $50M and a $70M exit. (𝘰𝘳 𝘢 $30𝘔 𝘷𝘢𝘭𝘶𝘢𝘵𝘪𝘰𝘯 𝘥𝘪𝘧𝘧𝘦𝘳𝘦𝘯𝘤𝘦 𝘪𝘧 𝘺𝘰𝘶 𝘤𝘰𝘮𝘱𝘢𝘳𝘦 𝘪𝘵 𝘵𝘰 𝘵𝘩𝘦 20% 𝘥𝘰𝘸𝘯-𝘢𝘥𝘫𝘶𝘴𝘵𝘦𝘥 𝘱𝘳𝘪𝘤𝘦) This is where a Fractional CTO becomes a high‑ROI, pre‑exit investment. Whether you’re 6 months or 3 years out, an independent technical audit helps you see your stack through a buyer’s eyes. 𝗪𝗵𝗮𝘁 𝘁𝗵𝗲𝘆 𝗱𝗼: • 𝗗𝗶𝗮𝗴𝗻𝗼𝘀𝗲 𝗹𝗶𝗸𝗲 𝗮 𝗯𝘂𝘆𝗲𝗿: They stress‑test your architecture, roadmap, and OPS maturity with the same lens DD teams will use to price risk. • 𝗕𝘂𝗶𝗹𝗱 𝘁𝗵𝗲 “𝗰𝗹𝗲𝗮𝗻 𝗱𝗮𝘁𝗮 𝗿𝗼𝗼𝗺”: They prepare due diligence-ready technical documentation, security audits, and compliance mapping that accelerate trust and shorten deal cycles. • 𝗣𝗿𝗼𝘃𝗲 𝘁𝗵𝗲 “𝗽𝗹𝗮𝘁𝗳𝗼𝗿𝗺 𝗽𝗿𝗲𝗺𝗶𝘂𝗺”: They help package your tech as a scalable competitive moat that supports revenue growth, turning tech from a risk into a multiplier. Companies with well‑documented, secure, scalable platforms command higher multiples. Your CTO knows this, but they might be too close to the context to spot all the risks. So in this scenario, it's a partnership. Your CTO runs the business. The Fractional CTO give the independent insight that helps you maximise its sale price. How early are you starting to de‑risk your tech stack ahead of exit? #duediligence #valuecreation #fractionalcto #privateequity #exitstrategy
-
Phillip Smith posted thisHmm, Budget time looming in the UK At what point will we see tax policy target your armies of AI agents? There has always been a tax on work, if Agents escape, how will we fill the ever deepening hole?
-
Phillip Smith posted thisThe speed with which the AI frenzy is taking over business strategy tells us more about how poor we’ve been at execution than it does about the virtue of these new shiny tools. For years, “digital transformation” promised smarter decisions and faster change — but we often ended up with more dashboards than outcomes. Now AI arrives, and leaders rush to declare “AI strategies” without ever having mastered the fundamentals of executing human ones. AI isn’t saving us from our old problems — it’s exposing them, it is an amplifier, a leveraged trade, often without risk management. Real competitive advantage will not come from adopting new tools… but learning to execute better. #Leadership #Strategy #Execution #AI
-
Phillip Smith shared thisA great deal of the blame in the comments here is directed at Deloitte. But buyer beware, clients must do their own due diligence, just as we should all be on our guard against buying arguments that are designed to be convincing. We all need to be pro journalists, and check sources. Deloitte will live and learn. Will you?Phillip Smith shared thisDeloitte will issue a partial refund to the Australian Federal Government after admitting that AI had been used in the creation of a $440,000 report littered with errors, including three non-existent academic references and a fabricated quote from a Federal Court judgment. It’s a headline that lands right at the heart of the transformation happening across the Professional Services industry. AI can now analyse summarise and even simulate insight at scale. But what it can’t yet do is know when to stop. When to question. When to say: ‘this doesn’t seem right.’ For all the talk of automation, this story is a reminder that the value of human advisors isn’t disappearing, it’s being redefined. AI will take thousands of junior roles in Professional Services firms, but senior judgement and quality assurance remain the last line of defence. In an era where a single model can generate a thousand pages of analysis almost instantly, the firms that win won’t just be those that move faster, they’ll be the ones that still think deeply. And this is exactly where the next generation of Partners will earn their keep. The best will become orchestrators, pairing technology’s scale with human discernment. They’ll know how to deploy AI inside the workflow without losing control of the narrative. Because when the model does the work, but the human still owns the outcome, that’s where trust, and value, still live.
-
Phillip Smith reposted thisPhillip Smith reposted thisLaunching 2026 The Mark Long Trust is a new charity founded by Beth Long in memory of her husband, Mark Long, who died in a Spitfire accident in 2024. The Trust provides aviation scholarships for disabled individuals, helping to make flight training more accessible through adapted equipment and tailored support. One scholarship has already been awarded, and more are planned as the programme grows. If you’d like to follow our progress, support the mission, or help spread the word, we’d be glad to have you with us. #MarkLongTrust #InclusiveAviation #Scholarships #ComingSoon #fsdp
-
Phillip Smith shared thisWill we burn the planet down generating AI cat videos? ChatGPT and other AI tools are still in the early-adopter hype phase. What happens when they’re as common as Google Search? The future of AI is much bigger than cats. Inference won’t just generate answers to our questions — it will increasingly do the work. From cranking out content and clickbait, to running business processes, diagnosing disease, or managing risk. If that’s where we’re headed, the right question isn’t: “What’s the carbon cost of one query?” It’s: “How sustainable is AI when it becomes the backbone of human work?” Because that future means: Billions of inferences every second Data centres that never sleep Enormous demand for energy, water, and raw materials The challenge is clear: ✔ Clean, low-carbon power ✔ More efficient hardware ✔ Smarter deployment and scheduling ✔ Governance that keeps pace with scale AI will scale. The real choice is whether it scales sustainably… or recklessly. #ArtificialIntelligence #SustainableAI #TechForGood #FutureOfWork #DataCenters #CleanEnergy #ThoughtLeadership
-
Phillip Smith shared thisLanguage is such an imprecise mechanism for communication. We learn through what we see, hear, feel, and smell. Even the best prose is a very imprecise and fragile abstraction layer. Perhaps it's time to think bigger.Phillip Smith shared this"I'm not so interested in LLMs anymore." One of the godfathers of AI dropped a bombshell: Yann LeCun, the man who helped create the AI revolution, says we're chasing the wrong path. Here's why he thinks we'll NEVER reach AGI through LLMs alone: ↳ Current LLMs need 400,000 years' worth of text to train. ↳ A 4-year-old learns more through 16,000 hours of vision. ↳ The physical world is exponentially more complex than language. His solution? World Models. ↳ Not just guessing the next word. ↳ This is AI that thinks like us: physics, planning, and common sense. While everyone else is busy feeding LLMs more gibberish, ↳ Yann LeCun is doing something entirely different: JEPA. JEPA is Joint Embedding Predictive Architecture. It learns by watching the world, not reading the internet. The wild part? V-JEPA can already spot physically impossible events from just 16 frames of video. ↳ No prompt engineering needed. This isn’t about smarter chatbots. This is about AI that understands reality. For business leaders: if you’re betting everything on today’s LLMs, you might be building the wrong foundations. The future? It will be hybrid, where language meets vision meets actual understanding. Do you think world models will change the game? Share below. ♻️ Repost to help someone in your network. ➕ Follow me, Ashley Nicholson, for tech insights. P.S. LeCun's full presentation is worth watching. Link in comments.
-
Phillip Smith reposted thisReframing bounded context as relationship-centric Agent Scope refreshes an old lens for designing, building and operating enterprise systems. In this model, autonomy, clarity, and resilience emerge not from technical abstraction alone but from aligning technology directly with the relationships organisations exist to serve. #SMEBanking #ArtificialIntelligence #DigitalTransformation #FutureOfBanking #PlayingToWin #AIinFinance #DDDPlatinum Service at Scale: Rethinking AI as the Customer’s Personal ExpertPlatinum Service at Scale: Rethinking AI as the Customer’s Personal Expert
Phillip Smith commented on a post
1mo
We often make the mistake of believing human memory and recall is perfect, and thought is much more than pattern matching. Are we fooling ourselves with our own impressive performance as pattern generators?
-
Phillip Smith liked thisPhillip Smith liked thisBain's Tech Insights Group is looking for a Senior Technologist. We are serving predominantly the Private Equity markets and work on tech due diligence, value creation and full potential projects. I am personally working in this practice now for close to 8 years - it is a high paced and intellectually challenging and rewarding work for some of the best and high profile tech companies in EMEA. This position is working out of our London office.
-
Phillip Smith liked thisPhillip Smith liked thisWhile you were fiddling with your AGENTS.md, your competitor spoke to your customers and stole a march on you. You won't find the value in your markdown files. It's out there. In the real world.
-
Phillip Smith reacted on thisEin weiterer Schritt, um den klinischen Alltag einfacher und effizienter zu gestalten. Ich freue mich sehr über diese Partnerschaft und die Möglichkeiten, die daraus entstehen.Phillip Smith reacted on this🎙️Mehr Zeit für die Pflege - Dedalus HealthCare und voize integrieren KI-Sprachassistent in ORBIS ℹ Dedalus HealthCare und voize bringen sprachgestützte KI-Assistenz ins ORBIS-Krankenhaus-Informationssystem. Pflegekräfte erfassen Patientendaten künftig per Sprache direkt im Moment der Pflege, statt Dokumentation am Arbeitsplatz nachzuholen. Die Lösung adressiert drei zentrale Herausforderungen: Administrative Überlastung der Pflege, Verbesserung der Pflegequalität und Minimierung von Erlösrisiken. 🩺Pflegekräfte stehen täglich vor der Herausforderung, neben hochwertiger Versorgung auch gleichzeitig umfangreiche Dokumentationspflichten zu erfüllen. Die gemeinsame Lösung von Dedalus und voize ermöglicht es, Pflegeinformationen per Sprache direkt am Patientenbett zu erfassen. Die voize KI strukturiert die Inhalte und überträgt sie direkt in ORBIS U. So stehen die Informationen unmittelbar im klinischen Workflow zur Verfügung und können nahtlos im KIS genutzt werden. 💬 „Sprachbasierte KI entfaltet ihren Nutzen nur, wenn sie nahtlos im klinischen Workflow aufgeht“, sagt Winfried Post, General Manager und Vorsitzender der Geschäftsführung von Dedalus HealthCare DACH. „Mit der Zusammenarbeit mit voize verbinden wir modernste KI-Technologie mit den etablierten klinischen Workflows in ORBIS. Dies verbessert die Dokumentationsqualität und unterstützt Pflegekräfte bei ihrer Arbeit.“ 💬 „Krankenhäuser haben zwei dringende Probleme gleichzeitig: Sie verlieren Pflegekräfte, weil administrative Last zu hoch ist. Und sie verlieren Geld durch dokumentationsbedingte Erlösausfälle“, sagt Fabio Schmidberger, CEO und Co-Founder von voize. „Diese Integration löst beide. Weniger Schreibtischarbeit heißt mehr Zeit für Patienten. Vollständige, strukturierte Daten heißt Erlössicherheit und Compliance.“ 🤝 Die Kooperation verbindet die Stärken beider Unternehmen: Während voize die KI-Lösung beisteuert, sorgt Dedalus mit ORBIS für die Einbindung in den klinischen Informationsprozess. Dokumentierte Informationen stehen dadurch nahtlos für alle Berufsgruppen im Krankenhaus zur Verfügung und unterstützen eine reibungslose Zusammenarbeit. AGAPLESION gAG, einer der führenden Gesundheits- und Pflegedienstleister Deutschlands, nutzt voize bereits produktiv in ORBIS. Nach 3 Monaten Pilotierung spart die Integration bis zu einer Stunde Dokumentationszeit pro Pflegekraft und Schicht. 🔗 Weitere Informationen finden Sie unter dem folgenden Link: https://ow.ly/mgHi50ZQ11u #ORBIS #KI #Pflege #DedalusDACHRegion
-
Phillip Smith liked thisI’m glad to share that I’ve joined the Team Topologies Advocate community. I’ve found Team Topologies particularly useful as a practical language for discussing team boundaries, ownership, cognitive load, and the interactions needed to make technology organizations work effectively at scale. I’m looking forward to learning from the wider community, exchanging experiences, and contributing perspectives from my work across engineering leadership, delivery, and organizational design. Thank you to the Team Topologies team for the welcome, and congratulations to Stefania Chaplin, Eduardo Anzai, and Tom Slenders, who are joining the community as well.Phillip Smith liked this🎉 We're thrilled to welcome four experienced practitioners joining the Team Topologies Advocate community. They bring fresh perspectives on organizational design, team dynamics, and technology leadership. Stefania Chaplin is a sought-after international speaker known for making complex technical and human challenges practical, engaging, and accessible. With a background in security and development, she's led multi-million-pound projects and worked with diverse, distributed teams across industries and countries. Her work complements Team Topologies by focusing on what happens between the structures: how people communicate across team boundaries, navigate different perspectives, influence decisions, and exercise judgement in complex environments. Kirill Klimov brings 20+ years of experience across software engineering, engineering leadership, delivery, and organizational design. He helps growing technology organizations design clearer team structures, operating models, and delivery systems so they can scale without losing performance. His work sits at the intersection of engineering leadership, organizational design, and delivery effectiveness. Eduardo Anzai is a digital transformation and technology strategy leader with 25+ years of experience, including 15 years as a trusted advisor to C-level executives across global enterprises. He helps organizations shape business models, technology strategies, and cloud adoption initiatives that balance innovation, business value, and long-term sustainability. Tom Slenders is a product-driven technology leader who helps organizations improve how they design, build, and operate software at scale. He works at the intersection of technology, organization design, and product thinking, with a focus on enabling teams to deliver value sustainably while balancing architectural, security, and organizational constraints. Recently, his work has centered on helping large IT organizations enable software delivery through effective platforms, clear ownership, and well-aligned ways of working. Together, they add even more depth to our growing global network of practitioners helping organizations design team structures and interactions that drive fast flow. Learn more about each advocate: Stefania: https://lnkd.in/d7qVEGAe Kirill: https://lnkd.in/dNMeMpad Eduardo: https://lnkd.in/dfFHryvf Tom: https://lnkd.in/ddCiw-mD Welcome, Stefania, Kirill, Eduardo, and Tom! 🙌
-
Phillip Smith reacted on thisPhillip Smith reacted on thisThe slide in today's Code Craft & AI workshop module that kills your agentic dreams. If we aim to keep the software shippable - you might know it as Continuous Delivery - horizons shrink fast, from "human in the loop" to "human *is* the loop" to "write the code yourself" at high levels of reliability.
-
Phillip Smith liked thisPhillip Smith liked thisOne of the most crucial clarifications in the Team Topologies Second Edition addresses a common misunderstanding: a platform is a grouping of teams, not necessarily a single team. In organisations with more than 40 to 50 people, an internal platform typically requires more than one 8-person team to provide the necessary services, hence the introduction of the term "platform grouping." So while a "platform team" might occasionally refer to a single team, it more often denotes a collection of multiple teams operating within that grouping. This refined understanding highlights the fractal nature of organisations, where self-similar patterns repeat at multiple "zoom levels." A mature platform approach needs to be both fractal and dynamic, evolving as business needs and strategy change. Adidas's digital platform is a great illustration: a logical, high-level grouping of multiple platforms and services, each with its own dedicated teams, rather than a single monolith. Similarly, NAV, the Norwegian Labour and Welfare Administration, runs a small number of coherent internal platforms (application, data, and design system) instead of one cumbersome, catch-all platform. This model keeps flexibility high while keeping cognitive load manageable for consuming teams. The second edition also introduces the concept of a "value stream grouping," generalising this multi-team approach to broader value delivery. Want to go deeper? 📘 Get the book - Order Team Topologies, Second Edition in bulk directly from us. https://lnkd.in/d97TiZea 📊 See it in practice - Explore real-world platform and value-stream transformations, including Adidas, NAV, ING, and more. Read the case studies → https://lnkd.in/dbKJvheU 🎯 Ready to apply this in your organisation? Explore our Enterprise Transformation Package for hands-on support. → https://lnkd.in/dbhHHfxF
-
Phillip Smith liked thisPhillip Smith liked thisDedalus has officially opened its new Irish headquarters in Dublin, marking another step in the healthcare software provider's €10 million expansion programme and long-term investment in Ireland. (Image credit: Dedalus) #healthcare #software #hospitals #Ireland #Europe https://lnkd.in/eGvMzZ4V
-
Phillip Smith liked thisPhillip Smith liked thisi got sick of reading claude-speak and walls of codex jargon. Inspired by some tools being passed around, we made a skill for thisshow-me: a coding agent skill for compact visual representationsshow-me: a coding agent skill for compact visual representations
Experience & Education
Volunteer Experience
-
Wing Adventure Training Officer
Royal Air Force Volunteer Reserve (Training)
- 14 years 5 months
Education
As Devon & Somerset Wings Adventure Training Officer I was responsible for overseeing the safe and effective delivery of Adventure Training activities and expeditions both in the UK and overseas to all units within the two counties, approximately 1000 cadet and 300 adult members of staff. As well as delivering the existing AT programme, I lead an improvement strategy to develop the capabilities of the Wing to deliver expeditionary adventures worldwide.
Previously, as Officer Commanding…As Devon & Somerset Wings Adventure Training Officer I was responsible for overseeing the safe and effective delivery of Adventure Training activities and expeditions both in the UK and overseas to all units within the two counties, approximately 1000 cadet and 300 adult members of staff. As well as delivering the existing AT programme, I lead an improvement strategy to develop the capabilities of the Wing to deliver expeditionary adventures worldwide.
Previously, as Officer Commanding No. 41F Squadron won a National recruiting award in 2011, having implemented a new strategy for growth which saw cadet numbers rise from 12 to 72, and staff from 3 to 9 in a period of 12 months.
Also led a successful and popular three year strategy implementation project to introduce music as a cadet activity to Devon and Somerset Wing.
Organizations
-
BCS
-
Recommendations received
12 people have recommended Phillip
Join now to viewOther similar profiles
-
David Moore
David Moore
With more than 20 years experience, David is skilled at leading and delivering large and complex IT and Business Transformation Programmes.
-
Matthias Funke
Matthias Funke
I work with enterprise customers on their hardest data problems. Proficient in the entire data stack and business use cases.
-
Martin Fourie
Martin Fourie
I help businesses identify where AI and automation will genuinely pay for themselves, then I build them. I work directly with senior management teams to understand how the business really runs, then design, build and deploy the solution myself, from first prototype through to live use and handover.<br><br>Recent work includes an AI email triage system for a PE-backed financial services group, taking an Azure prototype to a live production build on the Microsoft stack. It also includes more than 60 AI and automation workflows for a UK energy supplier, including agentic systems and automated OKR reporting for the executive team.<br><br>My background is in software development and product ownership, so I'm as comfortable discussing commercial value with leadership as I am writing code. Through DesignTurbine, I specialise in secure, compliance-first automation and AI for regulated and data-sensitive businesses, including local models where data can't leave the client's control. I'm just as happy to recommend plain automation or a process change when AI isn't the answer.<br><br>Tools I work with regularly: Power Automate, n8n, Workato, Claude and OpenAI APIs, LangGraph, Azure, Dataverse, SharePoint and Power Apps.<br><br>Open to fractional and contract engagements.<br><br>I hold multiple certifications, including PMP, PMI-ACP, PRINCE2, SAFe Agilist, and PSM.
Explore more posts
Explore collaborative articles
We’re unlocking community knowledge in a new way. Experts add insights directly into each article, started with the help of AI.
Explore MoreOthers named Phillip Smith
5982 others named Phillip Smith are on LinkedIn
See others named Phillip Smith