Topic

CTO Craft

Engineering leadership: teams, culture, incidents, metrics, build vs buy and working with the business.

11 posts
CTO Craftengineering-metricsDORASPACE

Measuring Engineering Productivity in 2025: DORA, SPACE, DX Core 4 and the AI Problem

Every board eventually asks how productive engineering is. I've found the frameworks useful, the pitfalls predictable, and AI assistants have made the whole question harder. Here's how I think about what to measure, who sees it, and what never to do.

18 Mar 2025 · 5 min read
CTO Craftleadershipteamshiring

Two Decades in Tech: What I've Actually Learned About Building Engineering Teams

From writing disaster recovery software at InMage (later acquired by Microsoft) in 2006 to running AI-assisted engineering workflows at Freddie's Flowers in 2025: here's what two decades have actually taught me about building engineering teams.

20 Jan 2025 · 2 min read
CTO Craftproductengineeringleadership

The Working Relationship Between Product and Engineering: A CTO's Perspective

The tension between product and engineering is one of the most commonly cited challenges in tech companies. After 20 years, and a lot of hard-won lessons, here's what I've come to believe about getting this relationship right.

15 Nov 2024 · 3 min read
CTO CraftPenniescharityaward

Winning the Pennies Unsung Hero Award: What Micro-Donations Mean in Tech

In October 2024, I received the Unsung Hero Award from Pennies at their 5th Annual Awards ceremony. This is what micro-donations look like from the engineering side, and why it matters.

20 Oct 2024 · 2 min read
CTO Craftincident-managementon-callpostmortems

Incident Management for Small Engineering Teams: A Practical Playbook

Small teams don't need an SRE department to handle incidents well. They need clear severity levels, an on-call rota people can live with, one person in charge, and postmortems whose actions actually get done. Here's the playbook I use.

8 Oct 2024 · 6 min read
CTO Craftleadershipdistributed teamsoffshore

One Team, Two Countries: Running UK and Offshore Engineering Without 'Us and Them'

Most offshore engineering problems aren't about talent or cost. They're about structure. Here's how I organise UK and offshore engineers into one team: ownership by domain, protected overlap hours, written decisions and fair career paths.

13 Aug 2024 · 5 min read
CTO CraftCTOinfrastructure-reviewstakeholder-management

How to Run a CTO Infrastructure Review That Stakeholders Actually Trust

A platform infrastructure review that produces the right technical answer but fails to bring stakeholders with it is a failed review. Here's the process I use: structured to produce decisions that the board, product leadership, and engineering teams can all trust.

1 Sept 2023 · 4 min read
CTO CraftCTOplatformbuild-vs-buy

Build vs Buy: A CTO's Framework for Platform Decisions

Every CTO faces the build vs buy decision repeatedly. After nearly two decades of making these calls, I've developed a framework that goes beyond the surface-level cost analysis most teams do.

1 Aug 2023 · 2 min read
CTO CraftShopifytransaction-feesplatform-economics

Transaction Fees: The Hidden Cost That Makes Platform Economics Counterintuitive

When teams evaluate SaaS e-commerce platforms vs custom builds, they focus on the obvious costs: subscription fees, development time, staff. The number that actually swings the decision is almost always the one buried in the small print: transaction fees.

5 Jul 2023 · 4 min read
CTO Craftremote-workCOVID-19leadership

The Overnight Shift to Remote: Engineering Leadership During COVID-19

In March 2020, we sent everyone home with 48 hours' notice. Nine months on, here's what we've learned about leading engineering teams through sudden, fundamental change, and what we intend to keep.

10 Dec 2020 · 3 min read
CTO Craftremote-workcultureengineering-teams

Maintaining Engineering Culture When You Can't See Each Other

Engineering culture is built through hundreds of small interactions. When those interactions moved to Slack and Zoom, we had to be deliberate about preserving what made us us.

10 Sept 2020 · 2 min read