Conversations Roadshow by CTO Craft
Berlin, let’s talk tech leadership...
- 23rd June 2026
- Spielfeld Digital Hub
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 of around 10 or more
- 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.
Your facilitators
Alex Ischenko
Emanuele Giarlini
Anna McDougall
Rachel Case
Suavek Zajac
Steve Brewer
Claus Höfele
Irina Tugui
Agenda
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: Navigating Trade-Offs in Modern Engineering
In today‘s economic environment, delivery matters more because tolerance for inefficiencies is gone. When capital was cheap, companies could afford waste, but that cushion has disappeared. In this roundtable, we’ll explore the real trade-offs behind effective delivery through a series of high-stakes scenarios. Each scenario reflects decisions engineering leaders face today—where optimizing for one outcome inevitably puts another at risk. The session is highly interactive and built around structured debates and small-group discussions. Participants will be assigned opposing positions, challenged to defend them, and pushed to surface where each approach breaks down in practice. Expect a candid, experience-driven exchange with peers—and leave with sharper thinking on how to navigate delivery trade-offs in your own organisation.
Claus Höfele - Head of Engineering @ On
Security Without Slowdown: Winning Engineering Buy-In While Balancing Speed, Innovation & Compliance
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
Leading High-Performing Engineering Teams
This discussion explores what it takes to lead high-performing engineering teams today. Join fellow senior technology leaders to compare approaches to building strong team cultures, navigating change, and making difficult decisions under pressure. Expect an open discussion grounded in real experience, with practical insights from leaders facing similar challenges across their organisations.
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, Not a Personal One
Designing teams that perform without burning people out. Burnout is usually framed as an individual resilience issue, but repeated patterns across teams point to deeper system problems.This workshop treats burnout as an engineering leadership concern, focusing on how work is shaped, prioritised, interrupted, and rewarded. Participants will identify where their systems leak energy and redesign one concrete process or norm to support focus, sustainability, and delivery at the same time.
Steve Brewer - Director of Technology @ Healios
Culture Is People: Feedback, Growth, and Inclusion at Work.
This session explores how company culture is truly built: not through handbooks, but through daily interactions in code reviews, 1-on-1s, and career calibrations. As we navigate the gap between individual growth and leadership accountability, we’ll examine how intentional support systems—like fair metrics and active sponsorship—empower everyone to succeed. This round table moves beyond theory to look at how feedback loops and career paths shape our workplace in practice. Through open discussion, participants will explore the impact of “glue work” on technical milestones, the shift from mentorship to active sponsorship, and how to de-bias performance reviews to prevent stagnation. The aim is not to provide a one-size-fits-all solution, but to create an honest space for shared experiences, peer learning, and actionable insights that drive a more inclusive culture
Irina Tugui - Head of Engineering @ Just Eat Takeaway
Strategy and Structure in a Fast-Changing Environment
This session examines how technology leaders are evolving strategy and organisational structure as the pace of change accelerates. Together with other senior engineering leaders, you’ll compare approaches to scaling teams, responding to rapid innovation, and making confident decisions in increasingly complex environments. Expect an honest discussion grounded in real organisational experience.
The Evolving Role of the Technology Leader
This conversation delves into how the expectations on technology leaders are shifting. Join peers for an open discussion on inspiring teams, creating alignment across organisations, and leading through uncertainty at scale. The conversation will surface real challenges leaders are facing today, along with practical approaches others are using in response.
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: Overcoming Isolation in Technical Leadership
This session explores the often-unspoken challenge of isolation in technical leadership. As professionals transition from individual contributors to leadership roles, they frequently lose peer groups, take on confidential decisions, and navigate complex organizational dynamics. These shifts can create a sense of distance that many leaders experience but rarely discuss openly, even though it can influence how they lead, make decisions, and manage pressure.
Through an open discussion, participants will explore where this isolation comes from, the hidden costs it can have on confidence, decision-making, and long-term sustainability, and the practical ways leaders address it. The goal is not to solve the problem in a single session, but to create an honest space where peers can share experiences, exchange ideas, and leave with one or two practical insights they can apply in their own leadership journeys.
Emanuele Giarlini - Director of Engineering @ MOIA
Rethinking How Teams Ship with Agents
In an 8-week experiment at AirHelp, we brought together people from product, engineering, data, and design under a single role – Shipper – and asked them to build a B2B product end-to-end using AI agents. Coding quickly became the cheapest part of the pipeline. The real leverage shifted to specification and discrimination: defining what to build and evaluating whether the agent actually succeeded. Debugging didn’t disappear; it evolved This roundtable will explore what we learned about scaling AI within a team, how the engineering mindset changes when problem-solving replaces writing code, and what it actually means to treat AI as a co-worker you delegate to and review. We’ll also discuss the practical challenges of introducing AI-native ways of working into existing organisations. Bring your own experiments and experiences – we’ll compare notes.
Suavek Zajac - CTO @ AirHelp
Making Leadership Decisions Under Pressure
This session focuses on how technology leaders are making decisions in fast-moving environments where priorities shift quickly and expectations continue to grow. Join peers to compare approaches to balancing innovation with delivery, supporting teams through change, and maintaining clarity as complexity increases. Expect an open exchange of real experiences, trade-offs, and practical lessons from leaders navigating similar challenges.
Balancing People, Performance, and Priorities
This discussion looks at how technology leaders balance team wellbeing, delivery expectations, and business pressure in fast-moving environments. Join peers to compare approaches to building resilient teams, fostering accountability, and maintaining performance as organisational demands evolve. Expect an open exchange of real experiences, trade-offs, and practical lessons from leaders navigating similar challenges.
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.
6:00pm – 8:00pm
Okta CTO Dinner
Continue the day’s conversation over a good dinner with a small group of fellow senior engineering leaders. A relaxed room with good food and no rush to wrap up. It’s your chance to go deeper with the people you’ve met, pick up threads from earlier in the day, and build the kinds of connections that can to outlast the event itself.
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.
Registration is now open!
What your ticket includes
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 is extremely limited.
Our event partners
Berlin
Stockholm
New York
Stockholm
Stockholm