Simon Legg

Trailblazer
DISC Type : ID

Chief Information Security Officer (CISO) at Hastings Direct

West Sussex, England, United Kingdom

Overview

Simon is the Chief Information Security Officer (CISO) at Hastings Direct, viewing his role as having a "business brain on technology shoulders." He has over 25 years of experience transforming security into a commercial advantage at firms like JLT Group and PRA Health Sciences. People often describe him as a visionary, pragmatic, and dedicated leader.

Outside of his core role, Simon is passionate about evolving the cybersecurity profession. He actively engages in discussions about the future of the industry, mentors others, and champions a collaborative approach to security challenges, believing that strength comes from the community coming together to solve complex problems.

He calls himself the "Anti-CISO," challenging traditional, fear-based approaches to security in favor of being a business enabler.

Personality Overview

Informal

Assertive

Values Relationships

They are more likely to accept new and exciting technologies.  They prefer to ensure that they are in control of the situation. They are not against taking risks and can make tough decisions when required.


Topics They Care About

Business-Focused Security
Emphasizes using information security to solve business problems and create a commercial advantage, rather than acting as a cost center.
Rethinking CISO Role
Advocates for moving beyond the traditional CISO mindset, focusing on enabling the business and articulating security's value over fear and doubt.
AI in Cybersecurity
Discusses how AI will expand the definition of privileged identity and require controls designed for systems, not just humans.

Media Appearances

Hastings Direct Insurance | CybSafe case study. Featured in YouTube

See Now

Work History

9-2019
Chief Information Security Officer (CISO) at Hastings Direct
10-2017 - 6-2019
Group Chief Information Security Officer (CISO) at JLT Group
12-2014 - 9-2017
Information Technology, Risk, Security & Compliance Executive at PRA Health Sciences
12-2014 - 9-2017
Information Technology, Risk, Security & Compliance Executive (CISO / CTO) at PRA Health Sciences
6-2012 - 9-2017
Information Technology Executive at PRA Health Sciences

Education

Education details unavailable from Caterham school
BAHons from University of Sunderland

More Information

Social Presence :

Prographics :

Exp : 17 Location : West Sussex, England, United Kingdom Job Level : Leadership Designation : Chief Information Security Officer (CISO) at Hastings Direct
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Insights For Selling To Simon

During A Call Or A Meeting

DO's

  • Address your competition clearly and confidently
  • Use phrases like ‘your decision will’, ‘you will impact’ etc.
  • Ask them for a lunch or coffee once some rapport has been established

DONT's

  • Don’t hesitate from asking questions or pushing them, but take a friendly approach
  • Do not look like someone who doesn’t know what they are talking about
  • Don’t hesitate from asking them how they truly feel about your product

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Simon is

  • Relationship and product conviction matter equally, followed by a sense of achievement.
  • Will you ever get a clear answer from Simon

  • If they are not convinced, they will say no though in a friendly way.

Insights For Deal Planning

    How fast (or slow) will Simon move?

  • They can make decisions quickly if they develop trust in you and conviction in the product.
  • Can Simon take some risk or not?

  • If necessary, they will be ready to take risks.

You And Simon

Personality Compatibility


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