Day 1
08:15-09:30
Registration & Networking
Start the day by meeting the people you’ll be learning alongside. Early conversations, familiar faces, and a few new connections before things get going.
08:30-09:25
Women in Tech Breakfast
A staple at CTO Craft Con events, this is a space for women in technology leadership to come together, share experiences, and build meaningful connections with others who get it.
09:30-09:40
Welcome to CTO Craft Con
We’ll open the day by bringing everyone together. A quick welcome, a look at what’s ahead, and how to get the most out of the event.
Our Chairperson, Carol Palombini, helps senior technology leaders strengthen executive visibility, strategic influence, and positioning for C-level success. Drawing on her background in psychology, executive coaching, and leadership consulting, she works with tech executives to communicate with impact, build influence across stakeholders, and accelerate career growth.
09:40-10:10
Keynote – Communicating Effectively with Non-Technical Leaders
One of the hardest and least appreciated challenges for a CTO is communicating with, negotiating with, and building trust with non-engineering leaders. There are three independent elements to trust — Motivation, Integrity, and Competence — and this session discusses techniques for demonstrating each one of them with your peers.
We then apply these techniques to three common CTO scenarios: Negotiating Feature / Platform Tradeoffs, Framing a Long-term Technology Investment Strategy, and Managing a Site Incident. You will leave with effective strategies you can apply tomorrow in your work.
10:10-10:35
Debiasing Your Engineering Leadership Decisions
Every significant call you make as an engineering leader has a moment where one path just feels right. But that powerful gut feeling is often a cognitive bias in disguise. And as a leader, you don’t just carry your biases yourself. You amplify them across every team, every architecture review, every technology choice your organisation makes.
This session moves beyond awareness. Drawing on behavioural economics and applied directly to engineering leadership, it introduces a practical five-step checklist for debiasing your decisions: whether you’re setting technical direction, evaluating architectural choices, or governing the growing influence of AI-generated work.
From recognising when cognitive fatigue is driving premature action, to stress-testing the quiet authority bias that AI recommendations now carry, this is a session about making better calls more deliberately, and building organisations that do the same.
10:35-11:15
Morning Recharge
A quick reset before diving back in. Stretch your legs, continue conversations, or meet someone new.
11:15-11:40
The Human Side of AI-Powered Work
The era of AI-first development is fundamentally changing both halves of the engineering organisation. First, we will examine your role as a leader, focusing on the aspects that should never be automated away. Second, we will look at the shifting reality for your engineers as they transition from individual contributors to architects and system orchestrators. Join us to learn what separates high and low expertise with AI, where leaders must lean in, and how to empower your team to exploit AI’s full potential without losing the heart of your organisation.
11:40-12:30
Who Owns Security Now?
AI writes more of your code every week. Your attack surface is growing faster than your security team. And somewhere between the developer, the CTO, and the CISO, nobody is quite sure who is responsible for what.
This panel puts the ownership question directly to the people who have to answer it. How do engineering leaders build security into how teams work, without slowing them down or adding another layer of process nobody follows?
A conversation about accountability, tooling decisions, and where the line sits between security as a function and security as everyone’s problem.
Roundtable – 11:15-12:15
Upskilling, Scaling Teams & Proving ROI/Productivity
Running alongside the main conference, this limited-place roundtable focuses on the leadership and organisational questions shaping modern engineering teams.
Discussions will explore upskilling in an AI-enabled environment, scaling teams sustainably, measuring productivity, demonstrating ROI, and balancing delivery expectations with long-term capability building.
With a small-group, peer-led format, the session is designed to create space for practical discussion, shared experiences, and honest conversations between senior technology leaders facing similar operational and organisational pressures.
12:30-12:55
Ghost Decisions: Accountability, Intent, and the Agentic Organisation
Your agents are fast and the execution layer is largely solved. The bottleneck is your organisation: the decision-making structures and accountability gaps designed for a world where humans did the work.
A ghost decision is what happens when an agent acts without a clear answer. In a human organisation, you’d call a meeting. In an agentic system, it just happens. And when nobody owns the decision, nobody owns the outcome.
Walk away knowing where ghost decisions are being made in your organisation, and how well-defined your organisational intent actually is.
12:55-14:10
Lunch + Networking
Pull up a seat with someone new. This is where conversations open up, ideas get shared, and connections start to stick.
14:10-14:35
Leading Engineering in Startups: The Realities No One Talks About
The startup engineering leadership role looks one way from the outside. It feels very different once you’re in it.
This talk maps a set of recurring problem shapes in startup engineering leadership against the enterprise paradigms people assume don’t apply and the startup myths that say they don’t matter. Then it looks at what changes through an agentic lens and what an agentic solve actually looks like in practice.
Specific, honest and useful whether you’re leading through a startup now or considering the move.
14:35-15:00
Shipping Faster, Trusting Less: Closing the AI Confidence Gap
Every engineering org using AI coding tools has hit the same tension. Velocity is up. PRs ship faster than ever. But confidence in what’s reaching production hasn’t kept up.
The knowledge that maintained quality used to live in people. The senior dev who knew the codebase, the tester who knew the edge cases, the reviewer who caught the subtle stuff. AI coding agents don’t have access to any of that. You get speed without judgment.
This talk covers what the orgs closing that gap are doing differently. How they encode what their best people know into systems agents can act on. How they structure verification as an org-level capability, not a QA task. And what CTOs need to change when individual output goes up but confidence doesn’t follow.
15:00-15:25
Leading with Emotional Intelligence: The Human Edge in an AI-Driven World
The leaders who thrive in this era won’t do it by keeping pace with the technology alone. The capabilities AI cannot replicate, emotional intelligence, self-awareness, the ability to build cultures where people do their best work, are exactly where the advantage lies.
This session introduces “How I Like to Work”: a structured practice developed and tested across product development teams that surfaces what rarely comes up in onboarding or one-to-ones. What triggers someone, how they process information, how they respond to setbacks, what trust and great leadership actually look like to them. One VP of Engineering called it “a shortcut to empathy, alignment, and better teamwork.”
Leave with a practical tool you can bring to your team straight away, and a sharper sense of what human leadership looks like when AI is handling more of the execution layer.
Roundtable – 14:10-15:10
People, Process, and Pipelines: Adapting Workflows and Infrastructure for the AI-Driven SDLC
Running alongside the main conference, this limited-place roundtable brings together senior technology leaders for a deeper discussion on adapting your workflow and infrastructure for an AI-driven SDLC.
When AI can write all the code, we need to take a deep look at both the human and technology sides of software engineering. Have a candid conversation about how your teams work today and how they will work tomorrow, what is changing about how you reward and manage people, maintaining code quality, adopting and operating coding agents, making sure security doesn’t suffer and data/secrets don’t leak, handling the increased load on test/build/CI, and more.
Let’s find out what’s working and what isn’t. Bring your questions and your concerns.
15:25-16:05
Afternoon Networking
A moment to regroup and reconnect. Keep the conversations going with people who are facing the same challenges as you.
16:05-16:30
Everything is Legacy Now: Unlocking tribal knowledge for agents
Twenty years ago Michael Feathers defined legacy code as code without tests; the 2026 version is harsher. Legacy is code without recoverable intent, and by that measure everything your teams have ever shipped qualifies, because the reasoning lives in old meetings and departed heads where no agent can reach it.
This session demos a working semantic layer for software delivery, where tribal knowledge becomes machine-readable as a byproduct of building: specs drafted from real meetings with unknowns flagged rather than guessed, stories traceable to the decisions behind them, and automated drift checks that report when code and intent diverge. That layer is what makes software supportable by agents, and it doubles as the rescue path for the legacy estate you already own.
16:30-17:20
Lightning Talks – People in the Age of AI: Building Teams That Last
AI is changing who does what on your team. Junior developers, curious adopters, reluctant holdouts: the gap between them is widening, and most organisations are making short-term decisions with long-term consequences.
This series of talks looks at what sustainable AI adoption actually requires, from promoting a learning culture to navigating the reality of highly regulated environments where speed is not always possible.
What does your team look like in five years if you get this right? And what does it look like if you don’t?
Roundtable – 16:05-17:05
How I Like to Work: Putting the Human Edge into Practice
Following Michelle’s main-stage session on the human edge in AI-driven leadership, this Deep Dive moves from the bigger leadership question into practical application.
“How I Like to Work” is a structured practice developed and tested across product development teams that surfaces what rarely comes up in onboarding or one-to-ones: what triggers someone, how they process information, how they respond to setbacks, and what trust and great leadership actually look like to them. One VP of Engineering called it “a shortcut to empathy, alignment, and better teamwork.”
In this practical, discussion-led session, you’ll explore the framework for yourself, hear how other leaders approach trust and team dynamics, and leave with a tool you can take straight back to your team.
17:20-17:25
End of Day Wrap Up
Pulling everything together before we head into the evening. What stood out, what to take away, and how to keep the conversations going.
17:30-18:30
Networking Drinks
Wrap up the day together. A relaxed, social end to the day where conversations flow, connections deepen, and the community really comes to life.
Day 2
08:15-09:30
Registration & Networking
Start the day by meeting the people you’ll be learning alongside. Early conversations, familiar faces, and a few new connections before things get going.
08:15-09:15
Tech Leaders Breakfast
Bring a real challenge from your leadership role and leave with fresh perspective on it. As CTOs and senior engineering leaders, we often carry problems that are hard to talk through with anyone our own organisations. This interactive session puts that right.
Over breakfast, you’ll take part in a Troika Consulting exercise: sharing your challenge with a small group of peers, and offering your own experience to theirs in return. It’s a practical taste of the CTO Craft Circles experience – giving you real support, new ideas, and a stronger network within the CTO Craft Community – to start day 2 on solid ground.
09:30-09:35
Welcome to Day 2
Building on the conversations, ideas, and connections from yesterday. A quick look at what’s ahead, and how to make the most of your final day at CTO Craft Con.
Our Chairperson, Carol Palombini, helps senior technology leaders strengthen executive visibility, strategic influence, and positioning for C-level success. Drawing on her background in psychology, executive coaching, and leadership consulting, she works with tech executives to communicate with impact, build influence across stakeholders, and accelerate career growth.
09:35-10:05
Keynote – Owners Not Renters: How We Build an Intelligent Future That Belongs to Everyone
Your AI stack is built on infrastructure you don’t control. Models, platforms, data pipelines: all rented from companies whose interests don’t always align with yours.
Drawing on Mozilla’s open web playbook, this session shows where engineering leaders have real leverage in AI today, from developer tooling to data licensing to model diversity.
Open source AI is closing the gap on closed alternatives. The question is whether your organisation is positioned to take advantage of it.
Leave with a clear framework for identifying lock-in risk in your stack, and a plan for what a more sovereign AI infrastructure looks like in practice.
10:05-10:30
How to Ship Enterprise-Quality Code With AI Agents
AI agents generate working code faster than ever, but consistently verifying it to meet enterprise standards can take as long as writing it by hand.
In this session, you’ll learn how to implement the Agent Centric Development Cycle (AC/DC) – a practical framework for guiding agents with architectural context and coding standards so they produce contextually correct code from the first prompt, verifying their output with deterministic analysis, and efficiently solving found issues by automating remediation before code reaches the PR review.
We’ll walk through the inner loop (real-time verification during generation) and the outer loop (CI-level quality gates and remediation agents), showing how to get reliable, accurate, and consistent results from AI-generated cod
10:30-10:55
The Startup Way: Innovating Within a Corporate Environment
Large organisations kill good ideas slowly. Approval cycles, risk aversion, and competing priorities turn promising initiatives into long-delayed projects or quiet cancellations.
This session walks through how Just Eat Takeaway built and ran startup-style teams inside a global corporate, using real AI initiatives as case studies. A practical framework for fast experimentation, faster delivery, and a clear path from idea to revenue.
Walk away knowing how to structure a team, pitch the model internally, and cut time to market without needing to leave the building.
10:55-11:30
Recharge Break
A quick pause to reset and dive back into conversations that are already flowing.
11:30-11:55
Presentation with Octopus Deploy
Octopus Deploy creates happy deployments, and by extension, happy software teams. Founded in 2012, their vision is for all software teams to look forward to deployment time; to be excited about seeing their changes deployed and used by their customers. They want them to deploy more and more frequently, and to feel 100% confident it will just work.
Session details coming soon!
11:55-12:40
The Hard Calls: Leadership, Missteps, and What You Don’t Say Out Loud
Leading engineering means making decisions with incomplete information, under pressure, about people. Most of those decisions don’t have a clean answer.
Bringing together technology leaders for an honest conversation about the human side of the job: the calls that kept them up at night, the ones they got wrong, and what they did next. No frameworks, no polished retrospectives.
Come with questions you wouldn’t ask in a boardroom.
Roundtable – 11:30-12:30
Reclaim your time, reclaim your leadership
“Time is the scarcest resource and unless it is managed, nothing else can be managed.”
— Peter Drucker
Do you feel that you are perpetually overwhelmed by meetings, emails, and the demands of others? Do you feel like you’ve lost control of your most valuable asset—your time? If you do, then you are not alone and this is the workshop for you.
In this transformative workshop, we will challenge the limiting beliefs preventing you from managing your time. You will gain clarity on the power of managing your time, how to increase your impact and identify areas for change. Additionally, you will develop practical strategies to prioritise what truly matters and lead with purpose
You will leave the workshop with a specific set of actions and experiments for you to take back into your work
12:40-13:05
Quality vs Speed: The Trade-off We Accepted for Years — and Why We Were Wrong
You’ve probably made this call before: reduce QA, ship faster. It feels rational. It might even look like it’s working.
This session is a direct challenge to that logic, built around a real case study. Two business units, one perceived as fast, one as slow. When the data finally came in, the “fast” team had crash rates above Google’s bad behaviour threshold, frequent critical incidents, and no way to measure cycle time. The “slow” team had quality metrics below 0.1% and a delivery cadence that was solid and predictable. The chaos had looked like speed. It wasn’t.
Drawing on DORA, Accelerate, and The DevOps Handbook, this session makes the case that quality and speed move together in high-performing teams. The trade-off framing was always wrong. As leaders, we are responsible for the incentives that keep rewarding the illusion of speed over the reality of it.
13:05-14:20
Lunch + Networking
Less introductions, more depth. Sit down with people you’ve met and take the conversation a step further.
14:20-14:45
Falling Back in Love with Your CTO Role
Three years in, crises resolved, the business rebuilt. And yet.
Lee Provoost found himself at a crossroads familiar to many CTOs but rarely spoken about out loud: the work felt done, the energy was low, and the next move wasn’t obvious. This session is an honest account of what that feels like and what he did about it.
Through conversations with fellow CTOs, Lee found this wasn’t a personal failure. It’s a pattern. And one that’s costly for the organisations that keep cycling through senior tech leaders as a result.
Come with an open mind about what this role asks of you, and leave with a clearer sense of what reigniting your own motivation might actually require.
14:45-15:10
The Last Pull Request: How AI Is Changing the Engineering Team
At iBOOD, pull requests are already disappearing. Trunk-based development, AI-assisted review and tiny autonomous teams have made waiting for approval feel increasingly unnecessary.
This session looks at what happens next as AI becomes part of the team itself. How do roles, ownership and collaboration change when developers spend less time writing code and more time managing intent, context and outcomes?
A practical look at how one engineering team is adapting to AI-native development in real time.
Roundtable – 14:25-15:25
Technology Strategy, Platforms & Engineering Direction
Closing the roundtable programme on day two, this limited-place session creates space for senior technology leaders to discuss the wider strategic and operational challenges shaping engineering organisations today.
Conversations will explore platform strategy, architectural evolution, developer experience, technical decision-making, scaling complexity, operational resilience, and balancing short-term delivery with long-term technology direction.
Built around peer discussion rather than presentations, the format is intentionally small to encourage practical insight sharing, honest conversation, and meaningful exchanges with others leading through similar challenges.
15:10-15:50
Afternoon Break
A final opportunity to connect with a room full of experienced tech leaders. Continue conversations, exchange ideas, and build relationships that last beyond the event!
15:50-16:15
How NOT to Use AI (as a Technology Leader)
Most AI adoption failures aren’t technical. They’re leadership failures: either too cautious to move, or too hasty to replace people once results look promising.
This session tackles both traps. Why fear-driven avoidance costs you real opportunities, and why reckless replacement weakens the very organisation you’re trying to improve.
The real question isn’t whether to use AI. It’s how to adopt it with the right expectations, operating model, and capabilities in place.
16:15-16:40
The Strategy Was Right. The System Still Failed. What CTOs Actually Own.
Most of us are good at articulating the right strategy. Then growth happens. Incidents creep up. Delivery slows without a clear cause. The strategy still looks right on paper, but the system has stopped behaving like the strategy.
This talk is about what’s happening in that gap. Ownership boundaries that quietly erode. Architectural choices that become organisational constraints. Coordination overhead that compounds until it shows up as delivery drift or decisions made too late.
Most problems labelled as execution issues don’t start in execution. They start in decisions about ownership, structure, and sequencing whose long-term consequences were never made explicit.
Leave with sharper signals for catching drift early, and a clearer view of where CTO accountability starts, where it ends, and how to close the gap between intention and reality.
16:40-16:45
Closing Reflections
A final moment to pause and reflect on what’s been shared, learned, and discussed across the event.