Dean Lesslie

Inquirer
DISC Type : dc

Head of Engineering at Hiscox

Copthorne, England, United Kingdom

Overview

Dean is an experienced Head of Engineering at Hiscox, focused on delivering cost-effective digital transformation and change programs. With a background in Oil & Gas and Insurance, he excels at leading teams and aligning technology with business strategy. He holds a HND in Computing Business Systems from Brunel University of London.


During his time at Brook Hunt & Associates, he redeveloped financial models using C#, which enabled the companys first web-based tool.

Personality Overview

Demanding

ROI Conscious

Hard To Convince

They focus on objectivity in a pitch and pay little attention to bells and whistles.  They respond well to confident salespeople. They don’t always try to control the conversation but neither do they like yielding it fully.

Topics They Care About

Digital Transformation
His career is centered on driving digital transformation and change programs to advance a firm's performance across various industries.
Engineering Leadership
Has a clear career progression from lead developer to Head of Engineering, focusing on building and managing strong software teams.
Cost-Effective Strategy
His professional summary emphasizes his ability to provide cutting-edge and cost-effective technology strategies to improve performance.

Media Appearances

Dean has no verified media appearances

Work History

2-2026
Head of Engineering at Hiscox
5-2023 - 2-2026
Head of Software Engineering at Hiscox
10-2020 - 2-2026
Lead Software Engineer at Hiscox
8-2008 - 10-2018
Lead Developer at Wood Mackenzie
9-1998 - 8-2008
I.T. Manager at Brook Hunt & Associates Ltd

Education

1996 - 1998
HND Computing Business Systems from Brunel University of London

More Information

Social Presence :

Prographics :

Exp : 25 Location : Copthorne, England, United Kingdom Job Level : Mid-senior Designation : Head of Engineering at Hiscox
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Insights For Selling To Dean

During A Call Or A Meeting

DO's

  • Be crisp while making the pitch
  • Ask them questions confidently while doing discovery, don’t be apologetic
  • Refer to testimonials from others in similar positions

DONT's

  • Refrain from asking too many questions
  • Don’t try to be an alpha salesperson, give them equal space
  • Don't try too hard to get friendly, let it happen with time

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Dean is

  • Conviction in the product matters to them, followed by proof points and strong testimonials.
  • Will you ever get a clear answer from Dean

  • They may not be very forthcoming, but they will say no if needed.

Insights For Deal Planning

    How fast (or slow) will Dean move?

  • They are neither the fastest decision makers nor the slowest.
  • Can Dean take some risk or not?

  • They can take risks but after weighing up the pros and cons.

You And Dean

Personality Compatibility


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