Conversations Roadshow by CTO Craft
Berlin, let’s talk tech leadership...
- April 2027
An intimate half-day gathering for CTOs and senior tech leaders to share experiences, explore challenges, and build lasting connections.
What is the Conversations Roadshow?
The Conversations Roadshow is a half-day gathering for senior technology leaders who want practical insight rather than surface-level talks.
While the format remains consistent at each stop — small-group roundtables and peer-led discussion — every event is shaped by its local context. Attendees, facilitators, and discussion topics differ from city to city, ensuring each gathering reflects the challenges and opportunities CTOs are experiencing in that region.
Each session is designed to create space for honest conversation, shared problem-solving, and connections that continue beyond the day.
Small group discussions
12-15 CTOs and senior tech leaders per table, creating space for real exchange.
Peer-led conversation
Interactive roundtables and deep-dive sessions built around shared challenges and experience.
No slides, real conversation
No long keynotes or sales pitches. Just open, honest dialogue and practical insight.
Is this event right for you?
Conversations is built around one thing: the quality of the room.
Peers at similar stages, with similar-shape teams and similar problems on their desks – guided by facilitators who’ve held the role themselves. The conversations work because everyone is operating at the same level, and because someone experienced is steering.
It’s intended for senior engineering leaders who:
- Hold a senior engineering leadership title – CTO, VP Engineering, Head of Engineering, Director of Engineering, or equivalent
- Currently lead an engineering team
- Are in role at a single company, or recently between roles
If that’s you, you’ll get a lot out of it. If it’s not quite, but you think the room is a fit, get in touch.
Past facilitators
Anna McDougall
Mathias Conradt
Andrew Osborne
Rachel Case
Alex Ischenko
Emanuele Giarlini
Dirk Daumann
Steve Brewer
Claus Höfele
Irina Tugui
Anna McDougall
Mathias Conradt
Andrew Osborne
Rachel Case
Alex Ischenko
Emanuele Giarlini
Dirk Daumann
Steve Brewer
Claus Höfele
Irina Tugui
Past Topics
12:00pm – 1:00pm
Arrival and Welcome
Time to meet the other leaders you’ll be learning alongside today. Conversations is built around peer discussion, and this opening space helps surface who’s in the room and what challenges people are bringing with them.
1:00pm – 1:15pm
Welcome Remarks
We’ll start with a short overview of the afternoon and how the Conversations format works. These sessions are built around shared challenges and honest discussion, so we’ll also cover how to engage in a way that makes the experience valuable for everyone involved.
1:15-2:15pm
For each session, you’ll choose from several leadership topics running in parallel.
Join the discussion that best matches what you’re facing today, and take part in a practical conversation with peers who understand the context you’re working in.
Delivery Under Pressure: Making the Trade-Offs That Actually Matter
You’re being asked to deliver faster, with less, and still raise the bar. There’s no longer room for inefficiency – but every shortcut comes with a cost somewhere else.
A series of high-stakes delivery scenarios where every decision forces a trade-off: speed vs quality, autonomy vs alignment, short-term wins vs long-term stability. You’ll be put into small groups, assigned opposing positions, and pushed to defend them – then unpack where each approach holds up and where it breaks down in practice.
Leave with a clearer way to evaluate delivery trade-offs under pressure – including how to articulate those decisions to stakeholders and where to hold the line when everything feels like a compromise.
Claus Höfele - Engineering Leader + Co-Founder @ Build & Lead: Tech Leaders Berlin
Security Without Slowdown: When Speed and Compliance Collide
Engineering teams today are under pressure to move fast, innovate, and deliver – all while navigating growing demands around compliance and cybersecurity. This roundtable explores how leaders can shift the narrative, framing security and compliance as enablers rather than blockers, and creating genuine buy-in by aligning engineering incentives with risk reduction. We’ll also dig into the real tension between speed and regulation – what happens when delivery pressure clashes with compliance requirements, and where teams are tempted to bend the rules. Through practical discussion and shared experiences, we’ll explore how to build a culture where doing the right thing doesn’t slow teams down.
Anna McDougall - Field CTO @ HashiCorp
The Hidden Cost of ‘Working’ Systems: When Legacy Isn’t Broken-but Still Hurting You
For many organisations, legacy systems are the quiet success story of the enterprise stack. They run. They process transactions. They pass audits. They rarely fail loudly enough to trigger urgent intervention. And that is precisely the problem. The most expensive systems in your business are often not the ones that break. They are the ones that continue to function just well enough to avoid scrutiny – while steadily eroding your ability to move, adapt, and compete. This is the hidden cost of “working” systems: not operational failure, but strategic drag.
Rachel Case - Senior Director of Solutions Engineering @ Auth0
2:15pm – 2:45pm
Networking Break
Take time to meet other leaders in the room, follow up on earlier discussions, and start new ones. These informal conversations are often where practical insights and shared experiences surface most naturally.
2:45pm – 3:45pm
For each session, you’ll choose from several leadership topics running in parallel.
Join the discussion that best matches what you’re facing today, and take part in a practical conversation with peers who understand the context you’re working in.
Burnout Is a Systems Failure: Why Your Team Is Exhausted (and What to Change)
Burnout keeps showing up, but the response is usually the same: people are told to manage better, recover more, be more resilient. The work itself rarely gets questioned.
This session looks at burnout as something the system produces. You’ll dig into how work actually flows through your team – how priorities shift, how interruptions land, what gets rewarded – and where those patterns quietly create overload. The focus is on what’s structurally driving exhaustion, not just how it’s experienced.
Through hands-on exercises and shared examples, you’ll map where energy is being drained in your own context and compare it with others facing similar pressures.
You’ll leave with a simple way to spot the biggest sources of burnout in your system, plus one change you can realistically test in your next sprint.
Steve Brewer - Director of Technology @ Healios
Culture Is People: Feedback, Growth, and Who Gets Ahead
Teams rarely feel unfair because of intent – it’s the day-to-day signals that quietly shape who grows and who gets noticed. Feedback lands inconsistently, growth paths feel uneven, and some contributions don’t seem to translate into progression.
This roundtable focuses on those everyday moments where culture is actually made: code reviews, 1:1s, performance conversations, and informal decision-making. You’ll work through real examples with peers to unpack why certain kinds of work- especially “glue work” – get overlooked, why mentorship alone often isn’t enough, and how sponsorship changes outcomes in practice.
We’ll also look at where performance processes tend to break down under real pressure, and what it takes to make progression feel fair without turning it into a heavyweight process.
You’ll leave with practical prompts you can use in feedback and performance conversations to make growth clearer, more consistent, and harder to accidentally bias.
Irina Tugui - Head of Engineering @ Just Eat Takeaway
When AI Writes the Code, Who Verifies It?
AI can generate code faster than ever, but confidence hasn’t kept pace. CTOs are being asked to ship quickly while proving that software is secure, compliant, and reliable in production. The challenge is no longer how to write code faster – it’s how to know what to trust, what to test, and where traditional review processes start to break down.
This roundtable brings technology leaders together to compare the verification strategies they’re using as AI-assisted development becomes part of the engineering workflow. The discussion will explore where deterministic analysis is most effective for structural and security issues, where broader reasoning is needed to identify logical and contextual risks, and how governance, compliance, and sovereignty requirements can be addressed before they become delivery blockers.
Expect a peer-led conversation focused on practical trade-offs, real-world failure modes, and the approaches that are proving resilient in production. You’ll leave with a clearer framework for deciding how different verification methods fit together, where they create the most confidence, and where additional oversight is still required.
Mathias Conradt - Sr. Staff Solutions Engineer @ Sonar
Andrew Osborne - Product Marketing Manager @ Sonar
3:45pm – 4:15pm
Networking Break
Space to step back from the sessions and speak with other CTOs and engineering leaders about what’s resonating so far. An opportunity to deepen connections and continue the conversations informally.
4:15pm – 5:15pm
For each session, you’ll choose from several leadership topics running in parallel.
Join the discussion that best matches what you’re facing today, and take part in a practical conversation with peers who understand the context you’re working in.
The Lonely Seat: The Isolation That Comes with Leadership
Stepping into leadership often means something unexpected: you gain responsibility, but lose the peer group you used to think with. Fewer people to sanity-check decisions, more context you can’t openly share, and a constant pressure to look certain – even when you’re not.
This session explores what that isolation actually feels like in technical leadership roles, and where it comes from in day-to-day practice. Through open peer discussion, you’ll look at how it shapes judgement, decision-making, and behaviour – especially when stakes are high and visibility is low.
We’ll also draw on how experienced leaders stay grounded: not by finding perfect “safe” peers inside their organisation, but by building other ways to test thinking, reduce drift, and avoid making decisions in a vacuum.
You’ll leave with a small set of practical ways to sense-check your thinking and stay connected, without relying on informal support structures that may not exist where you work.
Emanuele Giarlini - Director of Engineering @ MOIA
Rethinking How Teams Ship with Agents
As AI agents become embedded into the way organisations build products, the role of teams is rapidly evolving. This roundtable will explore how responsibilities are shifting from writing code to defining problems, guiding AI, and evaluating outcomes. We’ll discuss how engineering, product, data and design teams can work more effectively in AI-enabled environments, what it means to treat AI as a collaborator rather than just a tool, and the practical challenges of introducing AI-native ways of working into existing organisations. Bring your own experiments and experiences as we compare notes on how teams can adapt and scale in this new era of product development.
Dirk Daumann - CTO/CPO @ Blacklane
The Hands-On CTO Returns: Downshift or the Next Generation of AI-Native Leadership?
For years, the path to becoming a CTO meant moving further away from the code. As organisations scaled, technical leaders were expected to focus on strategy, people, and governance while leaving implementation to their teams. But AI is starting to challenge that assumption.
This session explores whether agentic AI tools are creating a new model of technology leadership-one where CTOs can once again work directly with technology without sacrificing their executive responsibilities. We’ll examine how leaders are using AI to prototype ideas, review architectures, validate product concepts, accelerate delivery, and drive transformation initiatives with a level of speed and involvement that was previously impossible.
Expect an honest discussion about what AI-native leadership looks like in practice, where hands-on involvement creates leverage versus bottlenecks, and whether the most effective CTOs of the next decade will be more technical, not less. You’ll leave with a clearer view of which activities are worth re-engaging with personally, where AI can amplify your impact, and how to balance strategic leadership with direct execution.
Alex Ischenko - Founder @ ExeMatchAI
5:15pm – 5:30pm
Closing Remarks
We’ll close the formal sessions by reflecting on what emerged across the roundtables and the shared challenges leaders are working through right now.
Venue
Skalitzer Str. 85/86, 10997 Berlin, Germany
We’ll be gathering at Spielfeld Digital Hub, an innovative and dynamic co-working space located in the heart of Berlin. With its sleek, modern design and vibrant atmosphere, Spielfeld offers the perfect environment for collaboration and forward-thinking discussions.Located just minutes from Berlin’s city centre, this cutting-edge space fosters creativity and innovation, making it an ideal setting for in-depth conversations and networking with peers. As the day winds down, the relaxed environment continues to inspire meaningful connections — perfect for continuing discussions over drinks.
Pre-registration is now open!
What you can expect from the day:
Networking lunch
Facilitated small-group leadership roundtables
Practical peer discussion on real challenges (no slides, no panels)
Joining a curated room of senior tech leaders
Insights you can take straight back to your organisation
Refreshments throughout the afternoon
Due to the intimate nature of this event, availability will be extremely limited. Pre-registering your interest early will ensure you’re among the first people to grab a ticket.
Can’t wait? Check out CTO Craft Con: Europe
CTO Craft Con: Europe comes to Amsterdam on 29–30 September 2026, bringing together senior technology and engineering leaders from across the region for two days of practical insight, honest discussion and shared experience.
You’ll hear how peers are navigating AI adoption, organisational design, platform strategy and the changing expectations of the leadership role itself, alongside structured roundtables where you can compare approaches with leaders facing similar decisions in different companies and markets.
This is not a traditional conference. It’s a working room for people responsible for engineering organisations today, a space to exchange what’s working, challenge assumptions, and leave with ideas you can apply immediately.
Two days of practical talks and structured roundtables on AI adoption, organisational design, platform strategy and the realities of leading engineering teams today.
Our event partners
London
Berlin
Stockholm
New York
Stockholm
Stockholm