Chris Rolland in

Chris Rolland

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Chief Executive Officer at InsureandGo UK
📍 United Kingdom

Chris Rolland is a Group CEO with over 25 years of experience leading PE-backed financial services and insurance companies. An alumnus of Harvard Business Schools executive program, he has a strong track record of driving growth through M&A, digital innovation, and operational excellence. Colleagues describe him as an inspirational and supportive leader.

Outside of his corporate roles, Chris is an avid sportsman with a passion for road cycling, skiing, and scuba diving. His interest in personal and professional growth is highlighted by his completion of high-performance leadership and development programs. He also enjoys traveling.

Unique fact: Chris is motivated by a simple principle, stating he enjoys "working in an industry where I can [look after people]. . . that helps me get up in the morning. "

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Experience
27 Years
Current Role
Chief Executive Officer
Job Level
Leadership
Location
United Kingdom
Personality Overview

How Chris 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.

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Priorities

Topics Chris cares about

Ethical Business
Believes that "doing the right thing" for consumers is a competitive advantage and a core part of his management strategy, a philosophy inspired by his time at American Express.
AI in Insurance
Actively looking to implement more artificial intelligence into the business's daily functions and has served as a judge for the Insurance Times Tech & Innovation Awards.
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Career

Work history

9-2021
Chief Executive Officer
InsureandGo UK
7-2019
BIBA Main Board Director NED and Chairman, Networks and MGA Advisory Board
BIBA
12-2017
Group Chief Executive Officer
InsurEvo
12-2017
Chief Executive Officer
AllClear
5-2015 - 7-2017
Chief Executive Officer
Staysure
In the press

Media appearances

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Education
2016 - 2016
Leadership for Senior Executives Program
Harvard Business School
2001 - 2003
MBA
The Open University Business School
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.

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