19-20 May, 2026 | Arcadian Loft, Toronto
Need help? events@ctocraft.com

Agenda Snapshot

Here’s an early look at what we’ve got planned.

From hands-on sessions to inspiring keynotes, this agenda snapshot gives you a feel for the conversations and connections waiting for you at CTO Craft Con.

More to be revealed soon!

Keynote

What To Do When You’re Measuring It Wrong: A Software Scientist’s Guide to Designing AI Evidence that Actually Helps

  • Lessons from motivating thousands of developers to participate in open science and what it takes to build an evidence culture that can actually keep up with the pace of change
  • Why treating all developers as identical AI users is destroying your insights, and how to approach measuring AI in an era of a million personalized experiments
  • Science-backed insights for what measurably moves the needle on team success and technical problem-solving, tested with hundreds of tech teams all over the world
  • Why most current AI ROI measurement approaches are misleading, and how to design a defensible, evidence-based strategy that reflects the complexity of real-world software experimentation

Dr. Catherine Hicks, Founder & Chief Scientist, Catharsis Consulting

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

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

Presentation

Leading through uncertainty: Maintaining momentum despite market disruptions

  • The new reality for technical leaders: When markets shift this rapidly, CTOs find themselves acting as product managers by necessity—not because strategy failed, but because factors like AI opened entirely new competitive terrain that demands immediate attention.
  • Bracing for organizational whiplash: How to mobilize teams built for execution into entrepreneurial mode while they’re still delivering on existing commitments—without breaking psychological safety in the process.
  • Creating space for rapid experimentation: Why leaders must actively create space for fast learning cycles while recognizing that casual comments can accidentally become rigid plans that shut down the very experimentation you need.
  • Bridging the gap between opportunity and uncertainty: Your “we get to capture new territory” excitement meets their “we just figured out the last thing” exhaustion—tactics for managing this tension while maintaining velocity.

Rob Zuber, CTO, CircleCI

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

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

Panel

Leading at the Intersection of AI, People, and Business Outcomes

  • Understand how senior leaders balance fast-moving AI change with the day-to-day reality of managing teams.
  • Translate engineering effort into outcomes the business can clearly see, measure, and stand behind.
  • Examine where AI adds unexpected management overhead instead of reducing it.
  • Reflect on decisions that changed how organisations invest time, money, and trust, including the people and process costs that are often underestimated.

Melissa Young, SVP Engineering, Vox Media

Kurtis Funai, CTO, Fullscript

Tina Goyal, VP Engineering, Wave Financial

Irvinder Singh, CTO, The World Bank

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

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 more now, including judgement, coaching, systems thinking, and the ability to challenge hype without blocking progress.
  • Reassess hiring strategies in a market where AI can boost productivity but cannot replace accountability or critical thinking.
  • Explore the future of junior engineers, including how entry-level talent develops when AI handles parts of the craft they once learned through repetition.
  • Design team structures and development programmes that position engineers to use AI productively without eroding core engineering fundamentals.

Kirk Gray, VP Engineering, McGraw-Hill Engineering

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

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