Chris Loake, Group CIO at Hiscox: How to Run Towards the Hard Stuff

My Duvet Flip by Jack Parsons

Jack Parsons

Business, Careers

4.2 • 5 Ratings

🗓️ 18 August 2025

⏱️ 36 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Episode Guest:

Chris Loake is the Group Chief Information Officer at Hiscox, where he leads global technology, data, and cybersecurity. With a career spanning finance, banking, and technology, Chris is passionate about resilience, adaptability, and building winning teams.

Episode Timestamps:

0:00 Introduction

0:43 Chris’s first ever podcast

1:17 From paper round to first jobs

2:00 Advice for your first day at work

2:32 From Harvester to accountancy

3:21 Why hating a job can be valuable

3:56 Discovering technology by accident

4:48 Building a first career plan

5:52 How to succeed with “no skills or experience”

6:38 Programming vs leading

7:14 Routes into technology: apprenticeships and bootcamps

8:25 Tech roles that aren’t coding

9:19 What makes someone “super techie”?

9:51 Lessons from technology for life balance

10:43 Building resilience through sport and work

12:03 Why you should never be the fastest in the club

12:26 Work with people who inspire you

13:02 What to ask in a job interview

14:02 Discipline vs motivation

15:21 How to stay disciplined in your career

15:50 Career pivots and lessons learned

17:04 Running towards the hard stuff

17:31 Why failure matters

18:04 The record label failure story

19:00 Why Chris chose business over entrepreneurship

20:28 What makes a true entrepreneur

21:38 Small business vs large business experience

22:46 Go where the people inspire you

23:32 Career pivots vs job hopping

25:00 Landing a first job in tech

25:49 What a Group CIO really does

27:04 How to experiment with new technologies

28:17 Transferable lessons between tech and careers

28:54 CIO vs CTO explained

29:33 The career steps needed for leadership in tech

29:39 Why Chris joined Hiscox

30:47 Technology as a competitive advantage

31:38 Supercharging people with technology

32:44 Why adaptability is the ultimate skill

33:27 From asking two questions to asking 200

34:15 Chris’s invisible success

35:23 Chris’s duvet flip – what gets him out of bed

Episode Partner

Hiscox, a leading international insurer with more than 3,000 employees worldwide. The company is known for specialist insurance solutions and a strong commitment to customer service.

Disclaimer:

The content provided on Duvet Flip is for informational and entertainment purposes only and should not be considered professional advice. The views expressed by hosts, guests, brands or contributors are their own and do not necessarily reflect those of the show's producers, sponsors, or affiliates. The information shared is not a substitute for professional advice, including but not limited to career counseling, financial guidance, legal consultation, or mental health support.

Listeners and viewers are responsible for their own decisions and actions based on the content provided, and Duvet Flip assumes no liability for any outcomes resulting from reliance on the information shared. By engaging with the show, you acknowledge and agree to this disclaimer.

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Transcript

Click on a timestamp to play from that location

0:00.0	Hi, my name is Chris Smoke.
0:01.2	I'm the group chief information officer at Hizcox.
0:03.5	This is my do, I do.
0:04.5	You know, you want to work with people that are better than you
0:07.0	that make you feel a little bit daunted about how you're going to keep up with them. Go and work for a business that inspires you. People that inspire you. Why Hissox? I like to be on a winning team. I feel like Hizcox are a winning team. to work for an organisation you can feel proud of.
0:01.7	They're the ones you have to run towards.
0:03.3	If everyone else is running away because it looks too hard,
0:05.7	that's when you should run towards it.
0:07.0	You have to run towards. If everyone else is running away because it looks too hard, that's when you should run towards it. You have to be motivated, but you have a different stance on it, which I love. Expecting to throw a six to play snakes and ladders. Oh, don't get to play today, it didn't throw a six. It's about discipline, not motivation. What's your duvet flip? You get you out of bed in the morning to flip the dove? Look, I love... I...
0:38.3	Hi, my name is Chris Sloke.
0:40.3	I'm the group chief information officer at Hiscox.
0:46.3	I'm excited, looking forward to meeting him.
0:48.3	I know he's met my boss, so I'm always interested to see how that went as well.
0:53.3	I've had a few different changes of direction over the years and I think it's going to be good fun talking about them. I haven't met Jack before, but I've seen some of the video clips, so I'm expecting a challenging interview. One thing I hope people can take away from episodes is that it's okay to have a career pivot and try something different. Hi Jack, nice to meet you. Let's do this. Let's do this. So Chris, welcome to my duvet flip. How are we? Yeah, very good. Thanks for having me. You're welcome. I want to talk a little bit about your career journey. We're going to talk about a number of things today. Career pivot, your career journey, technology and everything in between. But where did it start for you? You talked about a paper round.
1:27.9	Why did you take out a paper round?
1:29.0	So I was just really keen to start earning money. My parents, they were okay, but they weren't super well off. And it was always really clear if I wanted something, I had to go and work for it myself. And my brother got a paper round when he was 13, and that was the age that you were allowed to start. 13th birthday. I went down to the paper shop and said, can I deliver papers?
1:27.3	And it was it? I stayed there for five years. Wow. And for anyone who's starting
1:49.9	their first job, who may be pivoting into a new job, what is your advice to them? Like, because
1:57.1	first day on a new job, what is your recommendations?
2:02.2	I think just go for it.
2:03.6	I think it's really easy to assume that everybody knows more than you.
2:06.9	And maybe they do on day one, but they won't do after a year or so.
	...

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