Ollie Holden

Enthusiast
DISC Type : i

Chief Information Officer at Intact Insurance UK

Hayling Island, England, United Kingdom

Overview

Ollie Holden is the Chief Information Officer at Intact UK and International, with nearly 30 years of experience leading business transformation. He leverages technology and data to drive change in major organizations and holds a first-class BSc in Mathematics from the University of Southampton.

Outside of his corporate roles, Ollie is passionate about sailing. He is an experienced skipper and has previously participated in the Atlantic Sailing Circuit.

He led the successful transition from a legacy data centre to the cloud at RSA, a major milestone in the companys technological transformation.

Personality Overview

Non-Confrontational

Optimistic

Story Driven

Unlike D or C types, they are convinced more by stories and testimonials.  They prefer to build relationships rather than staying totally transactional. They are generally friendly, so be careful when relying on their word.

Topics They Care About

Business Transformation
His career is defined by leading large-scale transformation programs at companies like The AA and RSA, using technology to drive improved business outcomes.
Data-Driven Strategy
Stated in 2024 that he is ready to "press the accelerator" on RSA's data strategy, highlighting its importance in the insurance industry.
Technology Leadership
A career-long technology executive focused on building strong leadership teams to manage complex change, IT delivery, and digital services.

Media Appearances

CIO interview – Ollie Holden prepares RSA’s Intact future. Featured in Diginomica

See Now

Work History

10-2025
Chief Information Officer at Intact Insurance UK
2-2022 - 10-2025
Chief Information Officer at RSA
11-2017 - 12-2021
Chief Information Officer at The AA
5-2016 - 11-2017
Director Change Capability at Project One
11-2014 - 4-2016
Chief Delivery Officer at TalkTalk

Education

1991 - 1994
1st class BSc(Hons) from University of Southampton
1989 - 1991
Education details unavailable from King George V Sixth Form College, Southport

More Information

Social Presence :

Prographics :

Exp : 10 Location : Hayling Island, England, United Kingdom Job Level : Leadership Designation : Chief Information Officer at Intact Insurance UK
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Insights For Selling To Ollie

During A Call Or A Meeting

DO's

  • Refer to interesting customer testimonials and stress on great customer experience
  • Compliment them about their personality if you get a chance
  • Speak from experience about success that the product has seen with other customers

DONT's

  • Don’t ask too many questions in one go, weave them into the flow
  • Don't be critical or challenge them openly, they can react defensively
  • Don’t be too formal with them, they trust informality more

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Ollie is

  • Relationship and rapport are valuable for them, but so is proven product value.
  • Will you ever get a clear answer from Ollie

  • They will hardly ever say a direct no.

Insights For Deal Planning

    How fast (or slow) will Ollie move?

  • Even when they are constantly engaged, they do not reach decisions quickly.
  • Can Ollie take some risk or not?

  • They can take some low-probability risks if needed.

You And Ollie

Personality Compatibility


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