Jessica Gleeson

Wildcard
DISC Type : csi

GM Digital, Data & AI - Businesss & Wealth at Westpac

Greater Sydney Area, Australia

Overview

Jessica leads digital, data, and AI for Westpacs Business and Wealth divisions. Her expertise is in driving customer-centric digital transformations, with previous executive roles at NAB, Suncorp Group, and Commonwealth Bank. She holds a Bachelor of Economics from UNSW and serves on its Information Technology Committee.

She is a vocal advocate for social responsibility, publicly calling for the eradication of hateful narratives. Jessica is passionate about fostering talent and building a strong learning culture, having supported initiatives like internal hackathons and enterprise-wide AI upskilling programs to develop colleagues technical and conceptual skills.

In a 2024 panel on AI, she compared making Generative AI easy to use to someone effortlessly passing you on an electric bike while youre struggling up a hill.

Personality Overview

ROI Driven

Friendly But Slow

Curious But Skeptical

They are often friendly and nice, but can sometimes suprise you with their piercing questions  They typically tend to be late adopters even when they seem friendly and excited about what you have to sell They are unlikely to ever become strong champions even when the conversations are going well; you should focus on cultivating other champions

Topics They Care About

Generative AI Adoption
As an executive at NAB and now Westpac, she leads GenAI strategy and has publicly moderated panels on AI readiness and the future of the technology in banking.
AI Upskilling & Culture
She emphasizes the importance of upskilling, highlighting work with Microsoft's AI Academy and internal programs to build a strong learning culture around data and AI.
Digital Transformation
Her career across Australia's major banks has centered on leading digital transformations that enhance customer experience and drive strategic growth.

Media Appearances

Westpac's new division heads get their teams ready for 2026 tussle. Featured in Australian Financial Review (AFR)

See Now

Work History

12-2025
GM Digital, Data & AI - Businesss & Wealth at Westpac
10-2023
Advisory Member, UNSW Information Technology Committee at UNSW
7-2023 - 12-2025
Executive, Data Strategy GenAI at NAB
2-2021 - 7-2023
Executive General Manager, Customer & Strategy at Suncorp Group
8-2019 - 2-2021
General Manager Digital Banking at Commonwealth Bank

Education

1999 - 2001
B.Economics from UNSW

More Information

Social Presence :

Prographics :

Exp : 22 Location : Greater Sydney Area, Australia Job Level : Senior Designation : GM Digital, Data & AI - Businesss & Wealth at Westpac
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Insights For Selling To Jessica

During A Call Or A Meeting

DO's

  • Focus on immediate action-items rather than the larger goals
  • Be prepared for a lot of questions, answer them objectively
  • Build rapport, it will come handy to handle hard questions later

DONT's

  • Avoid phrases like ‘trust me’, ‘you will just love it’ etc.
  • Do not sound overly eager, modulate your energy levels especially if you are generally enthusiastic
  • Don’t overhype the product/pitch, keep it measured

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jessica is

  • Clear proof of product value matters to them, followed by others' testimonials and rapport.
  • Will you ever get a clear answer from Jessica

  • They are likely to give you a clear answer without taking you around in circles. However, if you share a good relationship, they might not be so forthcoming.

Insights For Deal Planning

    How fast (or slow) will Jessica move?

  • They like to perform full analysis and can take time to make any decision.
  • Can Jessica take some risk or not?

  • They weigh all decisions systematically and are unlikely to take many risks.

You And Jessica

Personality Compatibility


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