Chris Rolland

Visionary
DISC Type : Ds

Chief Executive Officer at InsureandGo UK

United Kingdom

Overview

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. "

Personality Overview

Big Vision Person

Goal-Oriented

Fast But Thoughtful

They exhibit a rare combination of being result-oriented but patient at the same time.  They are very professional in their approach and can weigh multiple perspectives together. Reading between the lines and seeing beyond your words comes naturally to them.

Topics They Care 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.
PE-Backed Growth
Has extensive experience leading and scaling PE-backed businesses, including a recent acquisition by Carlyle Group-backed Ignyte Insurance (NSM) to expand internationally.

Media Appearances

Chris has no verified media appearances

Work History

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

Education

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

More Information

Social Presence :

Prographics :

Exp : 27 Location : United Kingdom Job Level : Leadership Designation : Chief Executive Officer at InsureandGo UK
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Insights For Selling To Chris

During A Call Or A Meeting

DO's

  • During followups, use phone or text if needed, they should be fine
  • Ask them at the end if they see a strong value prop in your product; expect an honest answer
  • Focus on the results that your product produces, expect some strategic questions in return

DONT's

  • Don't get into pricing discussions early on, steer conversation towards proven results
  • Don't focus too much on mutual contacts or bother about other stakeholders, focus on them
  • Don't go over them unless you are left with no other option

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Chris is

  • Strong proof of impact and their conviction will matter the most, but they wouldn't want to act unilaterally either
  • Will you ever get a clear answer from Chris

  • They will say no if they are not convinced but you will have to prompt them.

Insights For Deal Planning

    How fast (or slow) will Chris move?

  • They will want to understand things well but can move fast once they have a clear picture.
  • Can Chris take some risk or not?

  • They have good risk tolerance but are likely to think it through once or twice.

You And Chris

Personality Compatibility


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