Simon Legg in

Simon Legg

Login to view DISC.
Chief Information Security Officer (CISO) at Hastings Direct
📍 West Sussex, England, United Kingdom

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.

Read the full overview →
Experience
17 Years
Current Role
Chief Information Security Officer (CISO)
Job Level
Leadership
Location
West Sussex, England, United Kingdom
Personality Overview

How Simon shows up

Communication Style
Decision Approach
Work Preference

Behavioral traits and communication patterns that shape how this person evaluates opportunities, builds trust, and makes decisions in professional settings.

Login to view personality overview.
Priorities

Topics Simon cares 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.
+5 more topics Login to view topics
Career

Work history

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

Media appearances

Hastings Direct Insurance | CybSafe case study. Featured in YouTube
See now
Education
Education details unavailable
Caterham school
BAHons
University of Sunderland
Social presence
in
Behavioral profile

DISC profile (public)

DISC behavioral profile

Dominance, influence, steadiness, and calculativeness scores with guidance on how this person prefers to communicate and decide.

Login to view DISC.

More profiles

Discover additional public profiles from our index.

Unlock the full playbookSee exactly how to sell to Simon. Free, 10 seconds.