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Good Tech Strategy / Bad Tech Strategy — with Anna Shipman 🎙️

Refactoring Podcast — Season 2 • Episode 8

Today's guest is Anna Shipman! Anna is the CTO at Kooth, former Technical Director at the Financial Times, and an accomplished author.

With Anna we talked about her journey in tech and how to develop good technical strategy, drawing from stories and examples from her 20+ years of engineering experience.

🎙️ Episode

You can watch the full episode on Youtube:

Or listen to it on Spotify, Apple, Overcast, or your podcast app of choice.

🔗 Resources

Here are a few articles and resources that were mentioned throughout the interview:

  • A faster — FT’s analysis into how their website speed impacted user engagement and revenue.

  • No next next — focusing on continuous improvements instead of costly, multi-year rebuilds.

  • Building Kooth — stories from bringing mental wellbeing.

  • Anna’s website — an incredible source of inspiration through her blog posts and talks.

🥇 Interview Summary

If you are a 🔒 paid subscriber 🔒 you will find my own summary of the interview below.

It’s the 10-minute, handcrafted takeaways of what we talked about, with timestamps to the relevant video moments, for those who don’t have time to sit through the 1-hour chat.

Here is the agenda:

  • 🗺️ Anna’s Journey (01:21)

  • 🎯 What is Technical Strategy (12:39)

  • 🔄 Evolving Strategy (23:59)

  • 📢 Strategy and Communication (24:43)

  • 🛠️ Creating strategy, in practice (39:35)

  • 📚 Good Strategy / Bad Strategy (45:03)

Let’s dive in 👇

1) 🗺️ Anna’s Journey (01:21)

Anna's path to technology wasn't straightforward.

She studied philosophy and worked in children's book publishing before discovering her interest in tech.

She taught herself JavaScript and CSS, and she eventually decided to pursue a more formal engineering education. As she embarked on a career as a software engineer, she moved through various roles across the whole stack, touching frontend, backend, and infrastructure.

Government Digital Service (GDS) (02:58) 🌍

Anna joined the Government Digital Service (GDS) during a pivotal time when the UK government worked on modernizing its tech infrastructure.

They had a clear mission to bring tech development in-house, with the goal of:

  1. Creating strong strategic know-how, and

  2. Saving costs on external contracts.

One of the highlights of that experience was working on the launch of the website. Anna joined the project when it was in private beta, and contributed to its public launch.

The project aimed to provide a better user experience for citizens, while also reducing internal costs.

Because if its strong mission, GDS was able to attract top talent who were also often willing to take pay cuts.

Transition to Financial Times (05:19) 💼

Anna later moved to the Financial Times (FT) as a technical director, drawn by the purpose of supporting free press, and by the opportunity to work with a leaner team that was more focused on delivery.

The role involved managing a team and delivering critical projects like the website and app, leveraging her leadership experience from GDS.

Role at Kooth (09:04) 🧑‍⚕️

In her current CTO role at Kooth, Anna oversees digital mental health services for children and young people.

Kooth offers self-help content, moderated community forums, and counseling through text-based chats.

Like with FT, and GDS before that, the choice of joining Kooth was significantly influenced by their strong, purpose-driven mission.

2) 🎯 What is Technical Strategy (12:39)

Anna's roles and work have consistently focused on technical strategy. She has always worked on transformative initiatives for the respective organizations, often with a multi-year outlook.

For Anna, technical strategy is about aligning tech efforts with business needs.

A good technical strategy supports the business strategy, driving the company’s goals through effective use of technology.

This alignment ensures that technical work directly contributes to the company’s success.

Anna shared several examples, especially from her tenure at FT and Kooth:

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Refactoring Podcast
Interviews with world-class engineering leaders about writing great software and working well with humans.