Agenda | CTO Craft Con: Toronto 2026

Day 1

08:15-9:30

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.

Melissa Young, Fractional CTO

Jennifer Schachter, Senior Software Engineering Manager, Capital One Canada

09:30-09:35

Welcome to CTO Craft Con – Chair’s Opening Remarks

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.

Melissa Young, Fractional CTO

09:35-10:05

Keynote – 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

10:05-10:35

Presentation – From Inheritance to Reinvention: My Story as CTO at PureFacts

You don’t arrive as a new CTO to begin. You arrive in the middle of someone else’s story, and the first job is understanding what you’ve actually inherited before you change anything
A first-person account of moving a real engineering org from overlapping products, delivery friction, and legacy complexity toward platform thinking, a single-version SaaS model, and AI embedded into the product, not bolted on top
Leave with a clearer sense of how to sequence a transformation that has to keep moving while the old system is still running”

Anu Dodda, CTO, PureFacts

10:35-11:00

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

Moderator: Tashuka Shah, Deal Flow, Global Angel Investor Network

11:00-11:30

Morning Recharge

A quick reset before diving back in. Stretch your legs, continue conversations, or meet someone new.

11:30-11:55

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

11:55-12:40

Panel – Hiring, Retention, and the Changing Shape of Engineering Teams Culture

Explore 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
Take a look at 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 – 11:30-12:30

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

12:40-13:05

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

13:05-14:15

Lunch + Networking
Pull up a seat with someone new. This is where conversations open up, ideas get shared, and connections start to stick.

14:15-14:40

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.

14:40-15:05

Presentation – Measuring What Matters Most To Business & Tech

Explore the evolution and practical application of essential metrics to reveal how modern teams can bridge the gap between business outcomes and technical execution.
Cut through the noise of what to measure to understand specifically what matters most
Leverage a usable framework to get to the right measure, every time
Clearly connect what you want to what you measure
See my favourite tools for flow measurement, starting from open source options

Roundtable – 14:15-15:15

This Doesn’t Feel Like Us Anymore: Culture Debt in Times of Change

In times of rapid change—AI shifts, market pressure, reorgs—CTOs are making real-time trade-offs to keep their organisations moving. Decisions get more centralized. Standards flex. Behaviours that wouldn’t normally be acceptable start to slide. Not by accident—but by necessity. These choices don’t just impact delivery—they reshape how teams operate. Over time, they accumulate as culture debt: subtle shifts in trust, accountability, and decision-making that are hard to see, and even harder to unwind.

We’ll explore:

The cultural compromises made under pressure
How those decisions change how teams actually behave and collaborate
Where short-term trade-offs start to redefine the organisation
A candid conversation on the hidden culture consequences of leading through rapid change.

15:05-15:20

Presentation – We Built an Agentic PDLC. Here’s What Actually Happened.

At CTO Craft Con: London, we showed the blueprint: an AI-augmented product development lifecycle where agents handle every stage from requirements through release, with humans reviewing at every gate. We gave ourselves an ambitious timeline to prove it on production features.
Ten weeks later, we’re back with results.
We’ll share the targets we hit, the assumptions that were wrong, and the adjustments we had to make. No theory, just what happened.

Alex Lukashevich, Chief AI Officer, Forte Group

Mike Kinloch, SVP Engineering, Xceptor

15:20-15:55

Afternoon Networking
A moment to regroup and reconnect. Keep the conversations going with people who are facing the same challenges as you.

15:55-16:20

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

16:20-17:05

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

17:05-17:10

End of Day Wrap-Up – Chair’s Closing Remarks

Pulling everything together before we head into the evening. What stood out, what to take away, and how to keep the conversations going.

Melissa Young, Fractional CTO

17:10-20:00

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.

18:00-21:00

CTO Dinner – The AI Productivity Illusion: An Honest Conversation Among Engineering Leaders

Everyone claims 10x, but nobody shows the receipts. Join a small group of fellow attendees for dinner, good food, and a frank discussion about what AI is genuinely accelerating and where it’s quietly creating new problems. These are the kinds of conversations that only happens when the room gets smaller and the agenda disappears.

Dinner host: Ivan Brezak Brkan, DX Director, Infobip

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.

08:15-08:45

Mindful Meditation
Day two kicks off with a moment to pause. Hannah will guide attendees through a short grounding meditation to help you settle in and focus before the day ahead.

Hannah Van Nostrand, Certified Yoga Instructor and Senior Producer, CTO Craft

09:30-09:35

Welcome to Day 2 – Chair’s Opening Remarks
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.

Melissa Young, Fractional CTO

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

Find out 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

Keynote – Can LLMs Generate High Quality Code?

AI tools are quickly becoming key contributors to the output of software engineering teams, but the code they write needs to be reliable, maintainable, and secure. Not all LLMs deliver that.
Issues can also compound, and cause downstream problems. Our deep evaluation of LLMs surfaces their strengths and weaknesses.
Model choice matters: once you know your model’s weaknesses, you can prepare for them rather than be blindsided in production
Pairing AI agents with deterministic analysis lets you manage quality and security risks without giving up the productivity gains that made AI worth adopting

Anirban Chatterjee, Sr. Director Product Marketing, Sonar

10:30-10:55

Presentation – Who’s in the Room?

We spend a lot of energy aligning on goals, but real decisions happen when someone decides who to DM, who to pull into a conversation, and who belongs in the room
Told through real stories: how the mental models leaders carry about what each person contributes are almost always incomplete, and what that costs the organisation
No frameworks, no tidy solution. Just an honest question to take back to your own team

Juan Musleh, Venture CTO, Koru

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 – 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

11:55-12:40

Panel – When AI Creates More Management, Not Less

For many, AI adoption has added unexpected overhead rather than reducing it. We’ll examine challenges 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.

Roundtable – 11:30-12:30

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

12:40-13:50

Lunch + Networking
Less introductions, more depth. Sit down with people you’ve met and take the conversation a step further.

13:50-14:15

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.

14:15-14:40

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.

14:40-15:05

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.

Roundtable – 13:50-14:50

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

15:05-15:40

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 – Chair’s Closing Remarks
A final moment to pause and reflect on what’s been shared, learned, and discussed across the event.

Melissa Young, Fractional CTO