Simon Gillespie

Evaluator
DISC Type : csd

Country Leader at Kyndryl

Auckland, Auckland, New Zealand

Overview

Simon Gillespie is Kyndryls Country Leader for New Zealand, specializing in complex business turnarounds and IT transformations. A former CEO of NTT NZ and GM at Spark Digital, he is a turnaround specialist who once reversed a decade of corporate revenue decline. Simon is also a Certified Board Member.

Simon has a demonstrated interest in the intersection of technology and high-performance sport. He previously led a partnership to create a "sports smart city, " utilizing IoT and data analytics to measure and enhance athlete performance, showing a passion for data-driven innovation outside traditional corporate environments.

He has set and exceeded more than NZ$1 billion in collective revenue and sales targets throughout his career.

Personality Overview

Fast But Analytical

Thorough Evaluator

Hard To Convince

They focus on the results, but can still be quite procedural and analytical about how to get there  They have a unique set of diverse traits where they are decisive and methodical but can sometimes be extra cautious and skeptical They are not very likely to become strong advocates of your product or service

Topics They Care About

Business Turnaround
His career is defined by leading turnarounds for large organizations, having been headhunted for roles to reverse business decline and drive new growth strategies.
AI-driven Transformation
He frequently posts about leveraging AI for IT operations and business innovation, highlighting Kyndryl's Agentic AI framework as a key enabler for customers.
People-Centric Leadership
He states his leadership approach is centered on people, focused on building optimism and leading by example. A recommendation highlights his ability to build engaged, diverse teams.

Media Appearances

Simon has no verified media appearances

Work History

9-2025
Country Leader at Kyndryl
7-2025 - 9-2025
Career Break
7-2023 - 7-2025
New Zealand Sales Manager at Fujitsu
5-2019 - 5-2023
Chief Executive Officer - NZ at NTT
7-2014 - 5-2019
General Manager, Corporate Customers (Spark Digital) at Spark New Zealand

Education

Simon has no verified education history

More Information

Social Presence :

Prographics :

Exp : 11 Location : Auckland, Auckland, New Zealand Job Level : Mid-senior Designation : Country Leader at Kyndryl
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Insights For Selling To Simon

During A Call Or A Meeting

DO's

  • Showcase your competitive superiority clearly when possible or address it at the minimum
  • Help them weigh the risks by sharing objective proof points instead of anecdotes and examples
  • Keep a professional, business-like approach; especially if you tend to get informal quickly

DONT's

  • Avoid inviting them for any social interactions until you have built some rapport with them
  • Avoid too much small talk, just a few formal pleasantries should be fine
  • Don’t focus on relationship, focus purely on the merit of your product

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Simon is

  • ROI matters the most to them, followed by process and finally proof of results
  • Will you ever get a clear answer from Simon

  • They might hesitate a little, but will go ahead and say no when necessary (or asked)

Insights For Deal Planning

    How fast (or slow) will Simon move?

  • They are unlikely to move very fast, especially when it comes to new products or services
  • Can Simon take some risk or not?

  • They have relatively low risk-appetite and are not very likely to go for something unproven and risky

You And Simon

Personality Compatibility


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