Conversations Roadshow by CTO Craft
Toronto, let’s talk tech leadership...
- December 8, 2027
- TBC
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.
Session Highlights
Do More with Less: A Root-Cause Autopsy of Pressure on Engineering Teams
If you’re leading an engineering team today, you’ve probably heard some version of the same request: deliver more, deliver it faster, and somehow spend less doing it. It doesn’t seem to matter whether you’re at a startup, a scale-up, or a global enterprise. Different companies, different industries—but the pressure sounds remarkably similar. Why?
In this session, we’re not going to swap war stories or complain about impossible expectations. We’re going to perform an autopsy. Together, we’ll trace where these demands actually come from, why they’re so persistent, and why simply trying to “do more with less” almost never fixes the underlying problem. By the end of the session, you’ll have a practical way to diagnose where pressure is really coming from in your organisation—and a new way to respond before unrealistic expectations become impossible delivery commitments. You’ll also leave with peers facing the same challenges, because the politics of engineering leadership shouldn’t be something we all have to figure out alone.
Christine Miao - Founder @ Technical Accounting
Security when nobody is reading AI code
Most teams are on the path to accepting that a growing share of their code isn’t read by a human before it merges. Review is sampling. Static analysis catches syntax, not intent. Too much code is shipping based on tests and vibes. That might have been survivable when AI was just a chatbot, but now it’s taking real actions: calling internal tools, moving money, touching customer data. Losing the guaranteed human checkpoint is inevitable, so this session addresses what to do about it. What tools and systems mitigate the risk when human review stopped scaling? How do you protect production? And who is accountable when nobody is reading?
David Mytton, Founder & CEO @ Arcjet
Solving for the engineering drift: new approaches to realising AI business value
AI is changing what engineering teams build and how they build it. But what stops that output from translating into measurable business value?
Legacy systems carry years of business rules, operational requirements and institutional knowledge. Meanwhile, AI-generated code creates new demands on review and oversight. How do leaders decide where AI can make a meaningful difference, and what needs to change to realise that value?
Through real case studies and shared experiences, this roundtable will explore where engineering delivery drifts from business goals and the practical steps leaders can take to realign it and increase ROI from their AI coding tools.
Andrei Manolache, CEO & Co-Founder @ DesignVerse
Inheriting Foundations That Are Crumbling
Stepping into a new engineering leadership role rarely means starting with a clean slate. Instead, you’re inheriting legacy systems, undocumented decisions, cultural norms, and technical debt that someone else created – while still being expected to deliver change quickly.
This facilitated roundtable brings together engineering leaders to unpack the realities of inheriting technology and culture. Through peer discussion, participants will explore how to tell what’s actually broken versus simply unfamiliar, how to build trust before making significant changes, and how to weigh the trade-offs of strengthening, evolving, or leaving a foundation alone. By the end of the session, you’ll come away with sharper questions for evaluating what you’ve inherited, and practical perspectives from peers navigating similar situations.
Boomie Odumade - CTO @ GreatNonProfits
Getting Product on Your Side as an Engineering Leader
As an engineering leader, you’re expected to deliver against ambitious business goals – but you can’t do it alone. When priorities clash with your Product counterpart, disagreements over roadmap, capacity, and trade-offs can slow delivery, create frustration, and weaken trust. Building a strong partnership isn’t just a nice-to-have; it’s essential for leading effectively.
This facilitated roundtable explores what it really takes to build a productive relationship with senior Product leaders. Together, we’ll unpack why these tensions arise, share experiences from both sides of the table, and discuss practical approaches for aligning around shared outcomes – even when your priorities don’t naturally match. You’ll leave with ideas for building greater trust, navigating difficult conversations, and working more effectively with your most important cross-functional partner – helping you make better decisions together long after the discussion ends.
Paul Tevis - Leadership Coach @ Middlegame Partners
Leading Through Change You Can’t Fully Explain
Engineering hasn’t moved at this pace in decades, maybe ever. Your team has questions you can’t quite answer yet. How do you lead well when you don’t have all the answers? How do you know you’re making the right call when the ground keeps shifting under you? How do you build trust with a team that can feel the uncertainty even when you’re not naming it out loud?
In this roundtable, we’ll get honest about what it actually feels like to lead through this kind of change, not the version we perform in an all hands. We’ll talk about how to make decisions you can stand behind without full information, how to be transparent about uncertainty without eroding confidence, and what it takes to keep a team’s trust intact when the answers keep changing. Expect a candid, peer-led conversation with leaders navigating the exact same terrain.
Suzan Bond - Founder and Leadership Consultant @ Constellary
When Does Technical Debt Become a Leadership Problem?
Most engineering leaders can name the things they’d fix given a spare quarter, but the hard part is creating the space to fix that tech debt before it causes pain for the business. Software leaders have to justify that investment to stakeholders who ask for visible outcomes and a clear financial return.
This roundtable examines the challenge. We’ll explore how peers have made the case for reducing tech debt when shipping innovation remains the immediate priority. We’ll also examine how AI coding changes the equation: whether it can help teams reduce tech debt or become a reckless accelerant of its growth. Drawing on findings from Sonar’s latest global developer survey, we’ll discuss the current balance between how AI can simultaneously create and help pay down tech debt.
Anirban Chatterjee - Senior Director of Product Marketing @ Sonar
Agenda
9:45am – 10:45am
Women in Tech Brunch
A space for women in tech and engineering leadership to come together, share experiences, and build meaningful connections with others who get the position you’re in.
Invitation only
10:30am – 11:00am
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.
11:00am – 11:15am
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.
11:15am-12:15pm
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.
Do More with Less: A Root-Cause Autopsy of Pressure on Engineering Teams
If you’re leading an engineering team today, you’ve probably heard some version of the same request: deliver more, deliver it faster, and somehow spend less doing it. It doesn’t seem to matter whether you’re at a startup, a scale-up, or a global enterprise. Different companies, different industries—but the pressure sounds remarkably similar. Why?
In this session, we’re not going to swap war stories or complain about impossible expectations. We’re going to perform an autopsy. Together, we’ll trace where these demands actually come from, why they’re so persistent, and why simply trying to “do more with less” almost never fixes the underlying problem. By the end of the session, you’ll have a practical way to diagnose where pressure is really coming from in your organisation—and a new way to respond before unrealistic expectations become impossible delivery commitments. You’ll also leave with peers facing the same challenges, because the politics of engineering leadership shouldn’t be something we all have to figure out alone.
Christine Miao - Founder @ Technical Accounting
Tech
Full details will be announced soon, but this roundtable will explore the realities of technology leadership in today’s fast-moving landscape. Bringing together senior leaders from across the industry, the discussion will focus on scaling teams, navigating rapid innovation, and making strategic decisions in increasingly complex environments. Expect a candid conversation grounded in practical experience, shared challenges, and lessons learned from leaders operating at the forefront of tech.
Leadership
Details are coming soon, but this roundtable will examine what effective leadership looks like in today’s technology sector. Senior leaders will come together to discuss navigating uncertainty, managing organizational change, and building high-performing teams. Expect an open, insight-driven conversation with practical takeaways from leaders shaping the future of tech.
Leadership Wellness
This roundtable will focus on the human side of leadership in high-growth technology environments. Through open discussion, attendees will explore resilience, wellbeing, accountability, and how to sustain high-performing teams under pressure. Expect practical insights and honest perspectives from experienced leaders balancing people, performance, and business priorities.
12:15pm – 1:00pm
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.
1:00pm – 2:00pm
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.
Inheriting Foundations That Are Crumbling
Stepping into a new engineering leadership role rarely means starting with a clean slate. Instead, you’re inheriting legacy systems, undocumented decisions, cultural norms, and technical debt that someone else created – while still being expected to deliver change quickly.
This facilitated roundtable brings together engineering leaders to unpack the realities of inheriting technology and culture. Through peer discussion, participants will explore how to tell what’s actually broken versus simply unfamiliar, how to build trust before making significant changes, and how to weigh the trade-offs of strengthening, evolving, or leaving a foundation alone. By the end of the session, you’ll come away with sharper questions for evaluating what you’ve inherited, and practical perspectives from peers navigating similar situations.
Boomie Odumade - CTO @ GreatNonProfits
Tech
More details are on the way, but this roundtable will bring together technology leaders to discuss the challenges shaping the industry today. From scaling teams and driving innovation to making confident decisions under pressure, the session will offer a practical and honest exchange of ideas, experiences, and lessons learned.
Leadership
Further details will be announced soon, but this session will focus on what strong leadership looks like in modern technology organizations. Leaders will share experiences around decision-making, team performance, and leading through periods of growth and transformation. Expect practical takeaways and thoughtful discussion throughout.
Wellness
This session will focus on the realities of leading people in demanding technology environments. Together, attendees will explore resilience, team wellbeing, and how to create healthy, high-performing cultures while balancing ambitious business goals. Expect candid discussion and practical insights from experienced leaders.
2:00pm – 2:30pm
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.
2:30pm – 3:30pm
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.
Getting Product on Your Side as an Engineering Leader
As an engineering leader, you’re expected to deliver against ambitious business goals – but you can’t do it alone. When priorities clash with your Product counterpart, disagreements over roadmap, capacity, and trade-offs can slow delivery, create frustration, and weaken trust. Building a strong partnership isn’t just a nice-to-have; it’s essential for leading effectively.
This facilitated roundtable explores what it really takes to build a productive relationship with senior Product leaders. Together, we’ll unpack why these tensions arise, share experiences from both sides of the table, and discuss practical approaches for aligning around shared outcomes – even when your priorities don’t naturally match. You’ll leave with ideas for building greater trust, navigating difficult conversations, and working more effectively with your most important cross-functional partner – helping you make better decisions together long after the discussion ends.
Paul Tevis - Leadership Coach at Middlegame Partners
Tech
This executive roundtable will examine the opportunities and pressures facing today’s technology leaders. Discussions will focus on innovation, operational scale, and strategic decision-making in rapidly evolving markets. Attendees can expect a high-value exchange of perspectives, experiences, and practical leadership insights.
Leadership
Designed for senior technology leaders, this roundtable will explore the demands of leadership in complex, fast-paced organizations. Topics will include leading through uncertainty, driving cultural change, and developing resilient, high-performing teams. Expect open discussion and actionable insights from experienced peers across the industry.
Wellness
Focused on leadership resilience and organizational wellbeing, this session will explore how companies can support performance in high-pressure technology environments. Senior leaders will discuss sustainable leadership, accountability, and maintaining engagement during periods of rapid growth and transformation.
3:30pm – 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 – 4:30pm
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.
Our facilitators
Andrei Manolache
Anirban Chatterjee
David Mytton
John Mann
Melissa Young
Naveen Nazimudeen
Paul Tevis
Christine Miao
Boomie Odumade
Suzan Bond
Ready to join the Conversation?
Venue
The Hoxton, Williamsburg
97 Wythe Ave, Brooklyn, NY 11249, United States
We’ll be gathering at The Hoxton, Williamsburg, a stylish and contemporary hotel in one of Brooklyn’s most vibrant neighborhoods. With its thoughtfully designed spaces, relaxed atmosphere, and sweeping views of the Manhattan skyline, it provides the perfect setting for focused discussion and meaningful connection.Easily accessible from across New York City, The Hoxton offers a comfortable and inspiring environment to spend the afternoon in conversation with peers — and to continue discussions over drinks as the day winds down.
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.
Our event partners
