9 min read

🦔 Rise of the CAIO, AI vs Team Motivation, Handling Skepticism, Rewrites, the New Prioritisation, Employee Burnout: TMW #489

CTO Craft Con: Fintech 2026 - announcing our keynote speakers
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This week's TMW is sponsored by Pensero - giving leaders objective visibility into delivery, quality, and AI impact across the organization.

Hello, hello, hello, welcome to the week!

CTO Craft Con: Fintech 2026 Keynotes

We're thrilled to announce two keynote speakers who are redefining the future of fintech and will be taking the stage for CTO Craft Con: Fintech this November!

Harry Jell, CTO, Yonder, one of the most interesting product stories in UK fintech right now - a rewards credit card growing 3x year-on-year, backed by NatWest, and the first in the UK to blur the line between debit and credit. Harry is building the engineering culture and systems to match that ambition. He’ll be bringing that perspective to the stage in November.

Jennie Woods, VP Engineering, Funding Circle, the UK-listed SME lending platform, where she leads all aspects of product engineering. With broad experience spanning engineering strategy, platform architecture, and cross-functional product delivery, she is currently driving Funding Circle’s shift towards an AI-native product development life cycle. Jennie specialises in translating emerging technology into practical, scalable capability at the intersection of financial services and modern software delivery. She is passionate about building high-performing engineering organisations that are equipped to thrive in an AI-first world.

Join the conversations, you won't want to miss this.

CTO Craft Con: Fintech
Join CTO Craft Con: Fintech in London in Nov 2026 - an intimate, community-centered gathering for engineering leaders to connect, learn through insightful sessions, and build real peer relationships in a supportive environment.

From AI Resistance to Readiness

On Wednesday this week, Carol Palombini and I will be sitting down to discuss how leaders are supporting teams with the rollout of AI in the SDLC, how to support skeptics and resistance to change and how to ensure the culture is ready for the change. If you're facing pushback from your engineers, definitely tune in - there will be time for Q&A!

CTO Craft Bytes: From AI Resistance to Readiness · Luma
AI is changing how product and engineering teams work, but the bigger challenge is often human: trust, mindset, and leadership. In this intimate fireside chat,…

That's it, let's look at some links....

Andy @ CTO Craft

Ps. If you're in an engineering leadership role, you absolutely need to be on top of the latest data on compensation and long-term incentives - have a look at our recent Compensation Report for all the latest insights.

Compensation Survey Report 2026 | CTO Craft
Welcome to the 2026 CTO Compensation Report, presented by CTO Craft and Albany.

CTO Craft Con - Dates for Your Diary

CTO Craft Con: Europe 2026
Join CTO Craft Con Europe 2026 in Amsterdam - an intimate, community-centered gathering for engineering leaders to connect, learn through insightful sessions, and build real peer relationships in a supportive environment.
CTO Craft Con: Fintech
Join CTO Craft Con: Fintech in London - an intimate, community-centered gathering for engineering leaders to connect, learn through insightful sessions, and build real peer relationships in a supportive environment.
CTO Craft | Conversations Roadshow
Each gathering follows the same small-group, peer-led format, but every event is shaped by its local context. Attendees, facilitators, and discussion topics differ from city to city, reflecting the challenges and opportunities CTOs are experiencing in that region.
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AI-enabled engineering organizations need different KPIs

Why AI efficiency and cost visibility matter more than usage.

Lines of code used to measure output. Now they measure how much code you'll have to maintain. When developers generate code in minutes, activity stops meaning anything, and AI amplifies activity faster than any org can validate impact. Dave lays out the five KPIs that actually matter now, including the quality tax: high output with growing instability isn't efficiency, it's deferred cost.

Read more about KPIs

CTO Craft Events Coming Up

See the whole calendar here - not in your city yet? Drop us a line!

Leadership, Strategy & Business

What I got wrong about being a CTO
The job I described on that podcast was only half the job In early 2025, a few weeks into my CTO role, I recorded an episode of the Diary of a CTO podcast with Guy Bevington. The episode was called Leading with Authenticity and I talked about curiosity, about listening before leading, about hiring f
The Four Core Areas of Responsibility for an Engineering Manager
Why do we have engineering managers, really?
The Rise of the Chief AI Officer: Should You Position Yourself as a CAIO?
Happy summer, everyone! Summer is a great time to slow down, reflect, and reassess where you want your career to go next. With AI adoption becoming a board-level priority for many organisations, a new executive title has been gaining attention: Chief AI Officer (CAIO).
So You Want to Fix Your All Hands
I will now explain why at least 50% of your team finds your current All Hands to be a waste of their time. They believe: This is information they can easily

Culture, People & Teams

RDEL #150: How is AI adoption affecting team motivation?
41% of engineering leaders say their teams are less motivated than a year ago, often because creative work is being displaced by the review of AI-generated code.
The Engineer in the Half-Space | Yusuf Aytas
Some engineers do their best work between the lines of ownership, where handoffs, runbooks, dependencies, and missing context decide whether software delivery gets cheaper or more expensive.
When AI Costs More Than the Engineer
Anthropic spends 2.3x payroll on compute. Top software firms spend 0.4x. Three scenarios for where the rest of the market lands by 2029.
AI enthusiasts are in a race against time, AI skeptics are in a race against entropy
Both sides are grappling with a real existential threat, and both sides feel like they are screaming into the void. Here’s how to close the gap and get everyone pulling in the same direction.

Technology, Operations & Delivery

PRs have always been a weak control. AI might finally fix that.
I’ve lost count of the number of times I’ve approved a PR with my only comment being a spelling mistake.
The Rewrite That Actually Worked
Coding agent is a multiplier. Your environment is the exponent.
How to prioritize your backlog when effort is no longer the constraint
How to use learning and reversibility to prioritize work AI can now build cheaply and quickly
The Hidden Cost of Feature Flags
Your team is about to roll out the new AI-powered search feature the board has been pushing for. They put it behind a feature flag and selected a subset of users to take it live in production.

Stress, Wellbeing & Growth

Why I Stopped Arguing With People
I am a software engineer, and I used to enjoy arguing with people for technical correctness. Code reviews, design meetings, mailing-list threads, dinner tables. If someone was wrong, I wanted them to know it, and I wanted them to know exactly why. I collected counterarguments the way I collected patches. I believed that if I just laid out the logic clearly enough, the other person would have no choice but to come around. Truth would win.
How to Prevent Employee Burnout - Toolshero.com
Learn how to prevent employee burnout with practical steps for workload, communication, recovery, recognition and healthier team routines.
Are We Ready for Worsening Employee Mental Health?
On balancing compassion and accountability in America’s growing mental health crisis.
Is Your Attention More Valuable Than Your Time?
After reading this, you’ll understand why protecting your attention might matter even more than managing your time—and how to start doing it today. Productivity Shift: distracted → focused 💗

That’s it!

If you’d like to be considered for the free CTO Craft Community, fill in your details here, and we’ll be in touch!

Campus by CTO Craft: The Go-to Resource for Senior Technology Leaders
Created for CTOs, by CTOs: A transformative learning community for senior technology leaders in startups and scale-ups

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Have an amazing week!

Andy