CTO Craft Con: Toronto – Highlights
Our first North American CTO Craft Con was a sell-out!
After full houses in London and Berlin, Toronto welcomed tech leaders from across North America for two days of keynotes, hands-on sessions, and real conversations that went way beyond the slides.
Leaders from startups to enterprises came together to share ideas, swap stories, and remind each other that leadership doesn’t have to be lonely. At the heart of it all? A community built on openness and support.
Conversations that Stuck
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Day 1 - Sessions
Chair’s Opening Remarks
Neeha Curtis, VP Digital Engineering Strategy, Encora
In a high-energy kickoff to CTO Craft’s first-ever North American event, Neeha Curtis, VP of Digital Engineering Strategy at Encora (and former journalist!), sets the tone with warmth, wit, and a healthy dose of real talk about the human side of tech leadership.
“The technical hurdles may be the simple part – it’s the human dynamics that are hardest.”
Whether you’re a startup disruptor or enterprise leader, or somewhere in between, don’t miss this inspiring opener.
Watch the full session and dive into the heart of what makes great tech leadership tick.
Michael Lopp, Founder, Rands in Repose
In his signature blend of wit, wisdom, and a dash of stage magic, Michael Lopp (a.k.a. Rands) opened CTO Craft Con Toronto 2025 with a keynote that was part leadership masterclass, part magic show, and all heart. With a lemon that never existed and a story about Disneyland that hit us right in the feels, Michael made a compelling case: storytelling isn’t just nice to have – it’s essential to effective leadership.
“The moment your audience sees themselves in the story, they stop auditing and start listening. And that’s where the magic happens.”
This session is packed with inspiration, practical insight, and a touch of mischief. Don’t miss the full talk – watch now!
Keynote – Magic and Mouse House: How Storytelling Completes You as a Leader
Keynote – Leading Without the Bloat: Lessons from a Remote-First, High-Growth Team
Lovisa Johansson, CMO, LavinMQ Magnus Landerblom, Lead Developer / Acting CTO, LavinMQ
What happens when you grow fast without the corporate fluff? Lovisa and Magnus from LavinMQ (formerly 84codes) deliver an energizing, behind-the-scenes look at building a remote-first, culture-forward, open-source-driven company—without losing the plot or your people.
“Company culture isn’t something that just happens – you have to care for it like you care for your code.”
Watch the full session for more candid insights, useful tools, and stories that’ll leave you rethinking how you grow your team – without the bloat.
Renata Vaccaro, VP of Financial Operations at Klick Health
Renata Vaccaro brings humor, heart, and hard-won wisdom to the stage in this lively talk about creating cultural alignment across product, customer success, and engineering. With real-world examples (and a hilarious Friends clip), she makes the case that collaboration isn’t just nice to have – it’s essential to team performance and business success.
“Anything is possible with time and money.” – Renata’s mantra for turning roadblocks into conversations.
This session is full of relatable stories and actionable strategies, don’t miss the full video!
Cultural Alignment in Tech: Bridging Product, Customer Success, and Engineering
Over-Indexing on Autonomy as Technical Leaders
Rob Zuber, CTO, CircleCI
Join this candid and insightful session where a seasoned engineering leader dives into the real challenges of hiring for values alignment, managing promotions, and fostering trust within growing product teams. Packed with practical wisdom and a few laughs (plus a lemon-cutting mishap!), this talk will make you rethink how you connect with your people and build stronger, more autonomous teams.
“If not you, then who? If not now, then when?”
Ready to deepen your leadership game and build teams that thrive? Watch the full session for the full story and actionable strategies!
Joel Cumming, CTO, SkyWatch
Melissa Young, SVP Engineering, Vox Media
Bryan McEire, CTO, BoxHub
Sandrine Tremblay, President & CTO, KOLOSTAT
Moderator: Jobin Kuruvilla, Head of DevOps and SM Practice, Adaptavist
In this lively and insightful session, a diverse panel of engineering leaders dives into the art of operating lean teams without sacrificing innovation or culture. From navigating cost-conscious growth to embracing contractors and integrating AI tools, the conversation sparkles with real-world wisdom and authentic experiences. The energy is upbeat, collaborative, and packed with practical advice that resonates across industries.
“AI is not going to take your job, a person using AI is going to take your job.” – a refreshing take on embracing technology as a tool, not a threat.
Curious how to build a lean, motivated, and future-ready engineering team? Watch the full session to catch every insight and story from these industry leaders!
Building Resilient Engineering Teams: Lean Practices in Lean Times
The Unspoken Struggles of Leadership: Running a Company While Life Unravels Around You
James Ciesielski, CTO, Rewind Software Inc.
Join James Ciesielski as he candidly shares the rollercoaster reality of leading a startup while navigating personal turmoil. From sleepless nights juggling growth to confronting his wife’s cancer diagnosis, James opens up about vulnerability, burnout, and the power of leaning on your team when life gets messy.
“If you’re leading right now and life feels like it’s unraveling, you don’t have to pretend it’s not. You can be vulnerable, and you absolutely should seek outside help. It doesn’t make you weak, it makes you real.”
Dive into the full session for a raw, honest conversation that will shift how you think about leadership and human connection in the hardest times.
Lachlan Holmes, CTO, FirstHX
Lachlan Holmes takes us on a lively tour through the rapidly evolving world of AI coding assistants, blending firsthand startup experience with practical insights. From boosting developer speed to navigating the tricky balance of quality, security, and team culture, this talk dives deep into how AI is reshaping software development – sometimes for better, sometimes with new challenges.
“Developers are moving 5 to 10 times faster, not just because AI types code for them, but because it helps them think and experiment differently.”
Curious how to harness AI without losing control? Watch the full session for practical strategies and thoughtful advice from a CTO navigating this brave new coding world.
AI Assistants: Revolutionising Productivity or Adding Complexity?
Innovation at Odds: How Conflict Fuels Great Ideas
Jen Fry, CEO, JenFryTalks
Get ready to rethink conflict with a speaker who’s refreshingly real about drama, feedback, and workplace culture. This session unpacks what healthy conflict really looks like – and how to keep it constructive without the chaos. With humor and straight talk, you’ll learn to spot drama, give clear feedback, and build trust through open communication.
“Words without behaviors are just weapons.”
Ready to turn conflict from a headache into your team’s secret weapon? Dive into the full session to learn how to create a culture where feedback fuels growth and innovation.
Anna Goltsman, CTO, eDynamic Learning
Jump into this lively and insightful session where Anna shares real-world stories from navigating the tricky waters of merging tech teams after acquisitions. Expect a blend of humor, empathy, and practical wisdom as she reveals how “corporate overlords” can transform into trusted collaborators – sometimes with a little help from cats!
“The most human image in the world is the old cat lady… if people see me as human instead of a robot, maybe that’s going to work.”
Whether you’re facing an acquisition or just curious about team dynamics, this session offers plenty of fresh perspectives and practical tips. Watch the full talk to learn how to herd your own cats without the catastrophe!
Herding Cats and Avoiding Catastrophes: Lessons from Team Mergers During Acquisitions
Managing Hybrid Teams: Lessons from Multicultural Tech Hubs
Vahid Zadeh, CTO, Myzone
Neshay Ahmed, CTO and Co-Founder, Wavy
Jen Krieger, VP of Engineering Operations, ex-GitHub
Moderator: Bohdan Zabawskyj, Founder, TrueNorthCTO
In this lively and insightful session, industry leaders dive into the evolving landscape of teamwork – exploring how to balance the irreplaceable spark of in-person collaboration with the flexibility and innovation of remote work. With plenty of real-world stories and practical wisdom, the panel unpacks how to keep teams connected, productive, and trusting, no matter where they’re located.
“Docker did not start in a room, I assure you.” – A powerful reminder that breakthrough ideas often happen beyond traditional office walls.
Curious how to recreate the magic of teamwork in today’s hybrid world? Watch the full session to unlock strategies that will help your team innovate, connect, and thrive — wherever they are.
Stefano Grossi, Founder and CEO of Branco.ai, former CPTO of FreshBooks
Stefano flips the script on the obsession with engineering velocity, sharing hard-earned wisdom from his journey leading teams at FreshBooks and building Branco AI. This session dives into why “moving fast” isn’t enough – real success comes from purposeful direction, team growth, and impact-driven outcomes. Packed with practical insights on aligning vision, fostering feedback, and cultivating a learning culture, Stefano challenges leaders to rethink what high performance truly means.
“Thousands of lines of code without the right direction are completely useless – you might as well have taken a vacation.”
Ready to challenge your assumptions and lead your team beyond speed toward meaningful, lasting impact? Watch the full session to unlock Stefano’s framework for future-proof engineering leadership.
Engineering Velocity Is a Lie: What Really Drives High-Performance Teams
Context, Not Code: AI’s Role in Engineering Flow
Chris Kelly, Director of Developer Experience, Augment Code
Chris Kelly brings his sharp CTO experience and playful “vibe coding” insights to this lively session on how AI is reshaping software engineering, not by replacing us, but by becoming a powerful part of the flow. With a clear focus on context over just code, Chris explores why AI won’t kill coding jobs but will change how we work, and how embracing this shift safely and thoughtfully is key.
“The best code is no code at all – every line is a liability to maintain.” – a powerful reminder that less can be more, even in the age of AI.
Curious how AI fits into your engineering flow? Dive into the full session for a thoughtful, no-nonsense look at coding’s AI future with plenty of practical wisdom and a dash of CTO vibes.
full session to get inspired and start shaping the next era of coding together.
Day 2 - Sessions
Olya Sanakoev, CTO, Rogers Bank
Join Rogers Bank, a savvy tech leader and AI policy enthusiast, as they break down the complex, and often intimidating, world of AI regulation with clarity, wit, and a dash of real-world savvy. This session shines a light on how industries are balancing innovation with compliance amid rapidly evolving global rules, especially through the lens of the EU’s pioneering AI Act.
“Regulation is a reaction to fear – our job is to demystify AI so everyone feels safe, informed, and ready to innovate.”
Ready to cut through the hype and get practical about AI in your world? Watch the full session to join the conversation!
Keynote – The Innovation Frontier: Navigating AI, Privacy, and Consumer Trust
From Backlogged to Backer: How AI Automation Is Transforming IT & R&D
Mojtaba Hosseini, VP Engineering, Zapier
In this lively session, our speaker dives into how automation and AI are transforming everyday workflows – not just for engineers, but for teams across the organisation. With practical stories from IT, post-production, and more, you’ll see how empowering non-tech folks with the right tools saves time, cuts errors, and sparks creativity. It’s about making automation approachable, manageable, and impactful for everyone.
“We’re not just looking for keys under the streetlight, our own department, but also out in the park, where the real opportunities are.”
Curious how these real-world automation hacks can help your team work smarter? Dive into the full session for all the practical tips and inspiring stories!
Mehrsan Javan, Co-Founder & CTO, Sportlogiq
Robin Sutara, Field Chief Data Strategy Officer, Databricks
Melissa DePuydt, Director of Engineering, Medium
Shakti Sinha, CTO, CanadaHelps
Moderator: Neeha Curtis, VP Digital Engineering Strategy, Encora
In this dynamic and down-to-earth conversation, a panel of experienced tech and product leaders dive into the challenges of growing fast-moving organizations. With thoughtful insights and real-world stories, they explore the tricky balance between innovation and operations, the build vs. buy debate, and how to keep your team aligned as you scale.
“Every organisation wants to be good at everything – but the truth is, we have limited resources. Focus on what you’re great at.”
Want the full story? Watch the full session for sharp insights, smart strategies, and plenty of honest lessons learned.
From Startups to Scale-ups: Unique Challenges for Tech Leaders
Beyond Bots: Empowering the Work AI Revolution
Anwesh Rijal, Head of Solutions Engineering, Glean
In this energetic and insight-packed talk, Anwar, CTO at Glean, shares a front-row view into how enterprises are navigating the chaotic, exciting world of generative AI and agents. With wit, practical examples, and a few strong analogies (yes, including one about cereal), Anwar tackles the big question facing tech leaders today: How do we go from hype to real, scalable adoption of AI in the enterprise?
“It’s not a question of if – it’s a question of when. Agents are coming, and we need to be ready.”
Curious how all of this plays out in practice- and what Duolingo, sales teams, and performance reviews have to do with it? Watch the full session to see what’s already possible and what’s coming next.
Shawna Martell, Sr. Staff Engineer, Carta Dan Fike, Principal Engineer and Deputy to the CTO, Carta
Join Carta’s engineering leaders as they dive into their innovative Navigator model- a fresh way to empower senior individual contributors to make decentralised, high-impact technical decisions aligned with company strategy. This session is packed with practical insights on boosting decision velocity, balancing local autonomy with strategic alignment, and evolving your engineering strategy through collaborative feedback loops. Expect thoughtful stories, candid lessons, and a dash of alligator humor to keep things lively!
“A sufficiently senior IC can take their deep understanding of technical details and combine it with a well-informed view of the organisation.”
Curious how this plays out in real life? Watch the full session for stories, advice, and inspiration on making strategy work where the action happens.
Navigators: Decentralizing Decisions and Empowering ICs at Carta
Bootstrapping the CTO: Laying a Foundation for Leadership Success
Dwayne Forde, Co-Founder & CTO, Mantle
In this candid and insightful session, our speaker dives deep into the realities of being a CTO – balancing vision, execution, and team dynamics with a grounded, human touch. Packed with lessons learned from leading large engineering groups, this talk offers practical wisdom on setting a clear vision, fostering ownership, and navigating the inevitable bumps along the way.
“Some belief systems need to be strongly convicted but loosely held.”
If you’re stepping into a CTO role or looking to sharpen your leadership game, this session is packed with actionable insights and real-world anecdotes you won’t want to miss. Dive in and get inspired!
Anne Steptoe, SVP Software Development at Propel Holdings
Anne Steptoe brings her two decades of tech leadership wisdom to the table, unpacking how the QA game has changed- and why modern engineering teams need to embrace a proactive, shared approach to quality. From shifting left in testing, to building powerful CI/CD pipelines, to using observability to catch issues before they escalate, Anne guides us through evolving QA from a final hurdle into an integrated, innovation-driving mindset.
“Quality must be proactive, not reactive – it’s about preventing bugs, not just finding them.”
Ready to rethink QA and boost your team’s velocity without sacrificing reliability? Dive into Anne’s full session and discover how modern QA can fuel innovation while building stronger customer trust.
The New Quality Assurance — Redefining Quality in Modern Engineering Teams
Bridging the Gap: Harmonizing Tech and Product Teams
Daniel Wolfe, CTO, MANDY’S
Get ready for a refreshingly candid and insightful dive into the often-misunderstood relationship between tech and product teams, led by Daniel Wolfe. From his unique perspective as a CTO in a health-food restaurant, Daniel unpacks the challenges of communication breakdowns, misaligned goals, and siloed teams – and shares practical strategies to build a Bridge of Hope that connects these worlds. This talk blends relatable metaphors, real-world examples, and actionable advice to inspire better collaboration and, ultimately, stronger products.
“Harmonising tech and product teams don’t just build better products – they improve the company’s bottom line and make the business more resilient.”
Don’t miss the full session to learn how to bridge the chasm and create a collaborative culture that drives real innovation and customer satisfaction!
Andrew Potapov, Director of Engineering, Leap Tools
Wrap up your day with Andrew Potapov, Director of Engineering at Leap Tools, as he dives into how engineering leaders can go beyond just building teams – they can build careers and sustainable growth frameworks. With nearly two decades of experience, Andrew shares practical wisdom on coaching, career progression, and setting up engineers and managers for long-term success.
“Your job as a leader is not just to build the machine, but build the machine that builds the machine.”
If you’re looking to set up career frameworks that truly empower your engineers and grow your organization from the inside out, don’t miss the full session!
Building Careers, Not Just Teams: A Guide to Performance Management and Career Frameworks
Chair’s Closing Remarks
Neeha Curtis, VP Digital Engineering Strategy, Encora
Neeha Curtis, VP Digital Engineering Strategy at Encora, wrapped up an inspiring two-day CTO Craft event with warmth, gratitude, and a powerful reminder of the strength found in community. Her closing remarks captured the energy of collaboration and continuous learning that defined the conference.
“Having a community of your peers is so incredibly important because these are the people that you can reach out to.”