The Everyday Agile Podcast podkast

What 20 Years As A CTO Taught Him About AI Compliance: Rob Fawcett

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What does a fractional CTO actually do, and how is it different from being a contractor?


In this episode of the Everyday Agile Podcast, Jac sits down with Rob Fawcett to discuss AI strategy, AI compliance, technology leadership, product development, software delivery, and what it really takes to create value from technology.


Rob shares his journey from project manager and operations leader to CTO, why he chose the fractional CTO model, and why he believes businesses increasingly need experienced technology leadership without necessarily needing a full-time CTO.


We also get into the reality of AI adoption.


The AI hype may be settling down, but organisations now face a different problem: how do they actually govern, manage and embed AI into their businesses?


Rob explains how he turned an AI compliance framework into a SaaS product, why AI needs to be connected to real applications, and why technology should always be designed around the people who use it.


And that's where the conversation moves into product and Agile.


What's the difference between shipping software and creating value?


Why should developers understand the people they're building for?


Why do so many organisations spend thousands on values, principles and transformation programmes but struggle to speak to their actual customers?


And why does Rob believe you should take the technology to the people rather than make the people adapt to the technology?


We also talk about:

• Fractional CTO vs contracting

• AI strategy and AI governance

• AI compliance

• Building AI into products

• SaaS product development

• Product teams and customer empathy

• Software delivery and creating value

• Leadership lessons from good and bad bosses

• Communicating strategy effectively

• Digital transformation

• User research and product discovery

• Technology leadership

• Keeping technology simple

• Connecting strategy, outcomes and outputs

• The difference between shipping and value


Rob also shares two brilliant real-world examples: developing blood-tracking software where usability could literally become a matter of life and death, and a cruise company sending its team onto a ship to watch real customers use its app.


▶︎Connect With Rob

https://www.linkedin.com/in/rfawcett/

https://thehumancto.co.uk

https://www.quantisys.co.uk/

https://aicompliance.uk/


▶︎Tickets for Not Another Agile Conference (22 April 2027, Chester Zoo) are on sale.

https://www.tickettailor.com/events/notanotheragileconference/2178867..


▶︎Our Newsletter:

https://substack.com/@betweenthestandups


⏱️ Chapters

00:00 Meet Rob Fawcett

03:22 From Contractor to Business Owner

04:43 Fractional CTO vs Contractor

05:49 What Does a Fractional CTO Actually Do?

07:22 How to Become a CTO

09:11 AI Strategy & AI Compliance

10:35 Building AI Into Real Products

12:31 Turning AI Compliance Into SaaS

16:07 The AI Hype Is Over

16:52 Lessons From Bad Leaders

21:32 The Real Problem Behind Poor Communication

29:21 Shipping Software vs Creating Value

30:34 Why Product Teams Need Customer Empathy

31:23 What Makes a Great Software Developer?

34:59 The Blood Tracking Software Story

36:42 Stop Making Humans Adapt to Technology

37:12 What Product Teams Can Learn From Cruise Passengers

38:03 Why Companies Overcomplicate Everything

44:04 Rob's Quickfire Business Takes

44:19 The Most Overused Business Phrase

44:35 Take Technology to the People

46:40 The One Thing Every Team Should Know

47:18 Connecting Strategy, Outcomes, Outputs & Problems

48:14 Where to Find Rob


If you work in technology, product, Agile, project management, software delivery, digital transformation or technology leadership, this conversation is for you.


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