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.
09:30-09:35
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.
09:35-10:05
Keynote – The Quiet Costs of Keeping Things the Same
- Why stability feels safe but often masks the slow erosion of competitive advantage, team capability, and engineering relevance
- How to spot the signs that your org is defaulting to inaction rather than making a deliberate choice to hold steady
- What it takes to build the internal case for change when things are not visibly broken but the direction is wrong
- How to move an organisation forward without losing the trust of the people you need to bring with you
Shawn Mandel, CTO, ex-Parkland, Rogers, Cineplex
10:05-10:30
Fireside Chat – Scaling Culture and Accountability in Distributed Teams
- Why culture becomes fragile as teams grow and spread across locations.
- How leaders reinforce standards and expectations without defaulting to process or bureaucracy.
- The role managers play in translating values into everyday decisions.
- Designing incentive systems that strengthen ownership and uphold high standards.
- Using measurement to reinforce accountability and a culture of high performance.
Farzona Pulatova, VP Engineering, Earnest
10:30-11:15
Morning Recharge
A quick reset before diving back in. Stretch your legs, continue conversations, or meet someone new.
11:15-11:40
11:40-12:25
Presentation – From Slop to Slope: Steering AI Development with Precision
- How AI is actually changing the software development lifecycle in production, including throughput, review load, rework, and defect rates, based on real data and operator experience
- Why increased output does not guarantee better outcomes, and where traditional productivity metrics fail to capture what is really happening
- What distinguishes teams that build durable leverage from those that simply move faster, and how AI maturity evolves as adoption scales
- Practical approaches to AI prompting, review, and workflow, plus a framework for measuring and steering adoption beyond velocity
Stephen Poletto, Field CTO, Span
Panel – Hiring, Retention, and the Changing Shape of Engineering Teams Culture
- Examine what good hiring looks like for engineering roles when technical skills are easier to find than leadership ability, and how the bar has shifted in the last two years
- Explore retention strategies that go beyond compensation, particularly in organisations going through change, integration, or rapid growth
- Discuss how senior leaders are redesigning team structures to reflect new realities around AI, distributed work, and evolving skill requirements
- Share what has actually worked, and what has not, when trying to build teams that can grow with the business rather than just meet today’s needs
Roundtable
11:15-12:15
How Fast is Too Fast?
- A candid conversation about the pace of AI-driven development and where the real limits are. The tools are moving fast. The question is whether your teams, your systems, and your own capacity are keeping up.
- Talk about where you’ve seen acceleration become a liability, whether that’s outages, security incidents, or decisions made without enough human oversight
- Explore how much context switching your engineers can actually handle before speed starts costing more than it saves
- Discuss where you’ve drawn the line on automation, what you’ve decided still needs a human in the loop, and how you’ve made that call
Dwayne Forde, Co-Founder & CTO, Mantle
12:30-12:55
Community Showcase – A CTO’s Guide to Running Meetings That Matter
- Hear why running effective meetings is one of the most underestimated leadership skills, and how poor meeting habits quietly shape team culture.
- Explore the different types of meetings leaders run and attend, and how to structure each one with more intention.
- Learn how to create engaging, inclusive environments that lead to clear, actionable outcomes rather than more follow-up meetings.
Allison McMillan, Fractional VP of Engineering, Tavlin Consulting
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
14:35-15:00
Community Showcase – The Case For Junior Engineers in the Age of AI
- Explain why companies are reducing entry-level hiring by saying AI writes code better, even though this misses the real purpose of junior talent.
- Clarify the difference between coding (machine translation) and engineering (maintaining complex systems), and why human knowledge and institutional memory still matter.
- Show how hiring and developing junior engineers helps sustain a strong organisation over time, because juniors are the pipeline for future senior expertise.
Christine Miao, Founder & Researcher, Technical Accounting
Presentation – Leading Through Uncertainty: Maintaining Momentum Despite Market Disruptions
- Explore the new reality for technical leaders when markets shift fast and entirely new competitive terrain opens up, demanding immediate attention without a clear playbook.
- Examine how to mobilize teams built for execution into entrepreneurial mode while they are still delivering on existing commitments
- Understand why leaders need to actively create space for fast learning cycles, and how casual comments can accidentally shut down the very experimentation the business needs
- How to lead with clarity and purpose to keep teams nimble without creating an environment that fuels chaos and change fatigue
Rob Zuber, CTO, CircleCI
Roundtable
14:10-15:10
What Does It Actually Take to Make Someone Stay?
- A conversation that goes past the usual retention talking points and gets into what senior leaders have genuinely learned about why people leave, and what makes them choose to stay.
- Share the moment you realised compensation and perks weren’t the real issue, and what was underneath it
- Talk about the person you lost that you most regret losing, and what you’d do differently
- Explore what you’ve seen work that surprised you, and what you believed in that turned out to be wrong
15:00-15:25
Presentation – Engineering a High-Performance Feedback Loop
- Develop effective prioritization in a team through coaching and direction.
- Create a goal and outcome-oriented culture to increase psychological safety. Clear expectations improve feedback on assumptions and risk.
- Use signals from team and culture warning and failure modes to address issues early and enhance the feedback loop.
Timothy Ubbens, AVP Engineering, TD Bank
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.
16:05-16:55
16:55-17:00
Lightning Talks – Managing Personal Wellbeing When the Pressure Is On
A series of short, personal talks from senior leaders on what sustained pressure actually looks like at this level, and how they’ve navigated it. No frameworks, no general advice. Just honest accounts of what happened, what changed, and what helped.
- Share what sustained pressure has actually looked like at a senior engineering leadership level, and how it showed up in ways you did not expect
- Reflect on the moment that forced a change, whether that was hitting a wall, making a bad call, or realising something had to give
- Talk through the specific habits, boundaries, or mindset shifts that made a real difference, not what you think should work, but what actually did
Kathryn Hume, CTO, ex-Tangerine, RBC
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.
Roundtable
16:05-17:05
Execution Under Pressure – Why Good Teams Still Get Stuck
- An open discussion on how leaders identify and remove execution bottlenecks, where breakdowns really occur, and how to keep teams performing and motivated when the pressure from markets and boards isn’t letting up.
- Are your biggest execution problems actually technical, or something else entirely? Bring your honest answer.
- Explore how to remove the bottlenecks that are slowing you down without pushing your team past their limit
- Dig into why execution challenges so often come back to alignment, decision making, and prioritisation rather than the technology itself
Bohdan Zabawskyj, Founder, TruNorthCTO
17:00-20:00
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.
18:30-21:30
Infobip Dinner
Day 2
08:15-09:30
Breakfast & Networking
Pick up where you left off. Reconnect with familiar faces, meet a few more, and ease into the day with conversations already in motion.
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.
09:35-10:05
Keynote – What To Do When You’re Measuring It Wrong: A Software Scientist’s Guide to Designing AI Evidence that Actually Helps
- Examine what it takes to build an evidence culture inside an engineering org that can actually keep up with the pace of change, drawing on lessons from open science and developer research
- Explore why treating all developers as identical AI users undermines your insights, and how to approach measurement when every team is running a different experiment
- Understand what science-backed research shows actually moves the needle on team success and technical problem-solving, tested across hundreds of engineering teams
- Design a defensible, evidence-based measurement strategy that reflects the real complexity of how software gets built, rather than defaulting to metrics that look clean but mislead
Dr. Catherine Hicks, Founder & Chief Scientist, Catharsis Consulting
10:05-10:30
Session (To Be Announced)
We’re lining up something special for this slot. Expect a practical, thought-provoking session from a technology leader with real-world experience to share.
10:30-11:15
Recharge Break
A quick pause to reset and dive back into conversations that are already flowing.
11:15-11:40
Presentation – The Quiet Revolution: How CI Became the Operating System for AI-Assisted Development Technology
- Examine why CI/CD, remote development environments, and AI-driven orchestration have become the critical bottlenecks and enablers for AI ROI, and what companies like Stripe and Spotify did differently to make agentic coding work at scale
- Understand how the economics of engineering are shifting as developers move from writing code to orchestrating agents across the full software development lifecycle
- Explore why remote dev environments are becoming the execution layer for agentic coding, and what that means for the infrastructure decisions you are making now
- Learn how CI and stateful flows create the guardrails that make it possible to ship AI-generated code with confidence rather than just speed
Naveen Nazimudeen, Senior Solutions Engineer, Bitrise
Panel – When AI Creates More Management, Not Less
- Examine where AI adoption has added unexpected overhead rather than reducing it, from tool sprawl and governance to the training, integration, and people costs that often get underestimated
- Explore the real impact on teams: how AI is changing the way engineers work, what managers are being asked to absorb, and where the human cost is showing up
- Discuss how senior leaders are making the business case for AI investment when the returns are slower or messier than expected, and what they are telling their boards
- Share what has actually helped: the decisions, structures, and approaches that have turned AI from a source of friction into something that genuinely works.
Melissa Young, SVP Engineering, Vox Media
Kurtis Funai, CTO, Fullscript
Tina Goyal, VP Engineering, Wave Financial
Roundtable
11:15-12:15
From Prompt to Production – How Are You Actually Managing AI-Generated Code?
- A candid conversation about what it really looks like to ship AI-generated code at scale, and the quality, governance, and workflow questions that come with it. Come ready to share what’s working in your org and where you’re still figuring it out.
- Discuss how your review and quality standards have changed as AI-generated code becomes a larger share of what your team ships
- Explore where AI coding tools are genuinely saving time versus where they’re creating new overhead around context, correction, and oversight
- Talk through how you’re thinking about codebase integrity and institutional knowledge as more of the work is done by agents rather than engineers
11:40-12:05
12:05-12:30
Community Showcase – You Think You Are Visionary, Your Team Thinks You Are Confusing
- Examine how big ideas and fast pivots can land as noise, shifting priorities, and confusion for engineers and managers.
- Identify the early warning signs that your communication is creating chaos instead of clarity.
- Understand why capable people stop pushing back when direction feels inconsistent.
- Learn how to communicate vision in a way that drives focused action rather than fatigue.
David Fung, Founder & Executive Coach, Coachful Coaching
12:30-13:45
Lunch + Networking
Less introductions, more depth. Sit down with people you’ve met and take the conversation a step further.
13:45-14:30
14:30-14:55
Community Showcase – Making Leadership VISIBLE: Building Clarity and Trust in Fast-Moving Engineering Teams
- Understand how clarity, trust, and communication shape team performance, alignment, and decision-making.
- Apply the VISIBLE Framework to improve role definition, decision flow, and day-to-day team dynamics.
- Implement simple, repeatable leadership habits that reduce friction, increase focus, and make progress visible across engineering and product teams.
Sheena Yap Chan, Founder, The Tao of Self-Confidence
Presentation – Building Great Engineering Organizations in a Post-AI World
- Examine which leadership skills matter most right now, including judgement, coaching, and systems thinking, and how to separate genuine progress from noise
- Reassess what good hiring looks like when the bar for technical skill has shifted and accountability and critical thinking matter more than ever
- Design team structures and development programmes that keep engineering fundamentals strong as the nature of the work keeps changing
- Explore what high-performing engineering organisations actually look like when the tools, the team, and the business are all moving at the same time
Kirk Gray, VP Engineering, McGraw-Hill Engineering
Roundtable
13:45-14:45
When the Way You’ve Always Led Stops Working
- A candid conversation about the moments that force senior engineering leaders to reassess how they operate. Not a session about frameworks or fixing other people. This one is about you.
- Talk about the moment you realised your default leadership style was no longer serving you or the people around you, and what made it impossible to ignore
- Explore how AI is forcing a deeper identity shift for engineering leaders, not just a change in tools, but a change in what it means to lead a technical team
- Share what you’ve unlearned, what you’re still working on, and what you wish someone had challenged you on earlier in your career
14:55-15:40
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!
15:40-16:05
Presentation – Aligning Engineering Strategy With Business Reality
- Turning high-level company strategy into clear technical priorities teams can act on.
- Navigating conflicting demands from product, finance, and executive leadership.
- Protecting long-term bets when short-term pressure dominates.
- Signals that your engineering strategy is being quietly diluted.
John Kleber, CTO, Buck
16:05-16:30
Community Showcase – AI in the War Room: Lessons from Building Agent-Driven Incident Response
- Examine why more telemetry, dashboards, and data have increased cognitive load without reducing MTTR, and why teams still struggle to answer what broke, how it broke, and how to fix it safely.
- Learn how AI-driven agents were designed and tested to analyse impact, guide root cause workflows, and execute pre-approved remediation steps within defined guardrails.
- Explore how to design the right guardrails, accountability models, and decision flows as agents become embedded in incident response and operational systems.
Rajith Attapattu, CTO, Randoli Inc
16:30-16:35
Closing Reflections
A final moment to pause and reflect on what’s been shared, learned, and discussed across the event.