Ricardo Rosa

Trailblazer
DISC Type : DI

Non Executive Director at PayInc

Johannesburg Metropolitan Area, South Africa

Overview

Ricardo is an executive with over 25 years of experience, currently leading enterprise commercial engagements at Microsoft Africa. He specializes in AI-enabled transformation and cloud adoption, working with C-suite leaders to align digital strategy with business results. People who have worked with him describe him as having "tremendous business vision" and being a "natural born leader".

Outside of his core technology focus, Ricardo holds certifications in sustainability and accessibility, indicating an interest in driving responsible and inclusive business practices. He follows developments at major technology firms like IBM and engages with insights from global tech leaders like Satya Nadella.

As a non-executive director, he provided strategic oversight during the major rebranding of South Africa’s national payments infrastructure from BankservAfrica to PayInc.

Personality Overview

Informal

Persuasive

Achievement-Oriented

They will bat for you if they come to believe in you.  They like to keep things under control. They are more likely to be open to unproven but exciting technologies.

Topics They Care About

AI Business Value
His current role at Microsoft is focused on helping enterprises achieve measurable business results, from cost optimization to new revenue streams, using AI and cloud technology.
Corporate Turnarounds
His background includes extensive practical experience in turnarounds and restructuring, notably developing strategies for major insurers and banks during his time at PwC.
Board-Level Strategy
He regularly engages with boards and C-suite leaders to align technology investments with core business priorities and long-term market expansion.

Media Appearances

Business Talk – Microsoft's Ricardo Rosa on the second wave of digital transformation. Featured in BusinessTech (South Africa)

See Now

Work History

9-2023 - 11-2025
Non Executive Director at PayInc
9-2021
GM - Microsoft – Enterprise Commercial Director, Africa at Microsoft
7-2019 - 9-2021
Senior Partner - Client and Markets Lead - Advisory Africa at PwC South Africa
6-2017 - 9-2021
Partner and Director - Consulting and Technology Lead Africa at PwC
8-2014 - 5-2017
Chief Executive Officer at Clarendon Transport Underwriting Managers (Pty) Ltd

Education

1988 - 2000
Honor's Degree from University of the Witwatersrand
1986 - 1988
B.Com from University of the Witwatersrand

More Information

Social Presence :

Prographics :

Exp : 35 Location : Johannesburg Metropolitan Area, South Africa Job Level : Senior Designation : Non Executive Director at PayInc
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Insights For Selling To Ricardo

During A Call Or A Meeting

DO's

  • Build a trustworthy relationship while keeping the product center-stage
  • Display high self-confidence and expect them to have a strong personality.
  • Address your competition clearly and confidently

DONT's

  • Don’t force involvement of other stakeholders unless it is critical
  • Do not look like someone who doesn’t know what they are talking about
  • Don’t hesitate from asking questions or pushing them, but take a friendly approach

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Ricardo is

  • Relationship and product conviction matter equally, followed by a sense of achievement.
  • Will you ever get a clear answer from Ricardo

  • If they are not convinced, they will say no albeit in a friendly manner.


Insights For Deal Planning

    How fast (or slow) will Ricardo move?

  • They can make decisions quickly if they develop trust in you and conviction in the product.
  • Can Ricardo take some risk or not?

  • They can take risks if necessary.

You And Ricardo

Personality Compatibility


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